sailboat rental maui

Private Boat Charters on Maui

(808 ) SEA-MAUI

Maui's #1 Boat Charter company

5 STAR VESSELS / 5 STAR SERVICE

Event Planning

Sea Maui offers 2 sailing catamarans which operate from Ka'anapali Beach daily. Our private boat charters are completely customizable. We offer snorkeling trips, sunset sailing, weddings, memorial sails and more! Full catering and open bar included on all trips.

We offer private charters to fit any budget. Both of our vessels can accommodate up to 48 passengers and have the capabilities to provide amazing snorkeling tours, sunset sails, wedding events and more. Priced from $1,200 an hour, we offer the most competitive pricing for large vessels on Maui.

We offer a wide range of services to make each sail a perfect experience for you and your guests. All trips are fully catered by renowned Executive Chef Joey Macadangdang and every sail includes an open bar. We can also provide live entertainment, floral arrangements, transportation and more! 

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2435 Ka‘Anapali Parkway, Lahaina, Hawaii 96761, United States

(808) 732-6284

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Maui Yacht Charters

Sail the majestic maui coastline aboard your own luxury sailboat yacht charter.

Explore Our Maui Fleet

Fountaine Pajot Bahia 46

Lagoon 440 Fly Bridge

Excess 12 – 39’

Beneteau Oceanis 50

Beneteau Oceanis 48

Nautor Swan 46

Visit one of the luxury spa resorts on Kaanapali beach.

• See “tons” of frolicking Humpback whales.
• Snorkel, sunbathe, fish, surf, sail, swim, relax.
• Maui, Lanai and Molokai, short sails between islands.
• Fishing is great and we know the most amazing snorkel spots.
• Lahaina is a historic whaling town, beautiful art galleries, wonderful upscale restaurants.

Sailing Maui and Oahu is a weather friendly option for Winter.

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Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.

What our customers say...

The Busy Boater

Exploring boating from a renter's perspective

Boat Rental Destination: Maui, Hawaii

Yes, you can rent a boat in Maui. There are options for sailing, fishing, paddling, jet skiing and cruising on the second largest and second most populated island in Hawaii.  Let’s see what it takes to get our on the water in someone else’s boat here.

What’s Good

• Very accessible from US, especially the Western States.
• It is an island, surrounded by water, with incredible natural beauty
• High level of tourism means room for niche opportunities
• Lack of traditional hazards to navigation found elsewhere

What’s Not

• The surf and rocky shore do not lend themselves well to inexperienced boaters
• Rough, and often unpredictable conditions limit your ability to go out
• The industry is focused on high volume tours that deliver on low expectations

Boating Conditions in Maui

Maui is a small island in the middle of the Pacific Ocean. It can be subject to violent surf conditions as swells build up over thousands of miles before reaching the shore and being compressed onto the beaches. Like other islands in Hawaii, the ‘lee’ shore (downwind) on the East, and Northeast side tends to be the most protected from weather (both wind and rain). This is where you’ll find most of the resorts, boat rentals, and charters.  On this side of the island, you’ll usually find manageable waters once you get out of the surf a hundred or so yards offshore. 

The weather is calmer in the morning. So, the earlier you can plan to start, and end, your day, the better.  And by early, I mean, plan on being back on shore between 11:00am and 1:00pm as the wind and surf start to pick up. The weather is pleasant year-round, benefiting from the moderating effect of all that ocean water. Winter is wetter than Summer, but you’ll still be able to find sunshine most days on that ‘lee’ shore.

Things to do on a Boat Rental in Maui

Snorkeling at molokini crater.

Molokini is a partially submerged volcanic crater about 3 miles off the Southwestern coast of Maui. There’s an abundance of coral inside the crater and the entire area is a protected wildlife sanctuary. The walls of the crater serve as a breakwater to calm the waters inside and minimize flow of ocean currents. All of this makes for some incredible snorkeling and bird watching. Some will even say this is the best snorkeling in all of Hawaii. You can only access Molokini Crater by boat.

Snorkeling at Turtle Town

Maluaka Beach, which is back on Maui directly East of Molokini, hosts an abundance of sea turtle activity. This area is referred to as ‘Turtle Town’. To access this area, you can:

• Swim out with snorkel gear from the beach
• Take a tour boat from one of the marinas to the North
• Paddle over from Wailea using a rental kayak, paddleboard, or outrigger canoe.

For the paddling option, head to Hawaiian Ocean Sports in front of the Grand Wailea hotel or Wailea Scuba Surf Paddle in front the Fairmont Hotel. Both offer hourly rentals and tours with a two-mile paddle down to Maluaka. Standup Paddleboards are great for Turtle Town because you can really get a clear view into the water while standing on your board. However, tandem kayaks and outrigger canoes are better for storing gear and snacks. They’re also a bit safer out in the ocean in case one paddler gets tired.

This is an adventure that needs to be completed in the morning. The rental companies in Wailea will stop allowing paddlers to depart by noon on most days as the wind and surf start to pick up.

Lanai is a sparsely populated island 9 miles West of Maui. You can get there from Maui by ferry, or on a private boat rental. Hulopoe Bay on the South side of Lanai is known for its snorkeling. It tends to be less crowded than Molokini. You can get here on a boat rental, charter boat or even take a ferry for $60 round trip.

Lanai also has some breathtaking underwater caves called the Cathedrals. However, this requires scuba diving to appreciate.

Whale Watching

More than half of the world’s humpback whales spend winter in Hawaii where they birth and nurture their calves. So, the months of January and February in Hawaiit make for some of the best whale watching anywhere. On Maui last January, it seemed like we could look out on the water in any direction for a minute or so and see the spray from a blowhole. Taking a private boat rental or charter out to the waters off Maui will give you a better chance at seeing them up close.

Boat Rental and Charter Options in Maui

Paddling rentals on maui.

Most of the resorts in Maui have a modest equipment rental facility on the beach.  About half of those rent stand-up paddleboards (SUPs) and sea kayaks.  Many hotels also have one or two outrigger canoes that go out in small groups.  We saw tour groups in sea kayaks and outrigger canoes about a mile off-shore.

Paddling in Maui consists of paddling out to sea on a short route and back to the beach.  There are no navigable rivers, or much in the way of paddling destinations. However, this is a great way to get a bit of distance from the beach to snorkel.

Beach parking on Maui can be hard to find, so its best to look for a boat rental service within walking distance from your hotel.  If you do rent from an outfitter that requires you to drive, be sure to ask if they can arrange free or validated parking at the hotel they operate from. Otherwise, you could wind up driving in circles hunting for an open parking space on the street or in public parks.

I also recommend waiting to reserve/commit until you are on the island.  This equipment has a high degree of availability, and the websites are in no way indicative of what you’ll find on the beach on a given day. 

Sailboat Rentals on Maui

We found one Hobie Cat sailboat rental on Maui at the North end of Ka’anapali at West Maui Sailing School .  To take this small catamaran out, you need to go with an instructor.  The lesson costs $85, plus $25 for each additional person. Unfortunately, they only have one instructor, and for two years now we’ve been told he is out for several weeks with a back injury.  We went by the outfitter to find out more. They do indeed have a Hobe 17 Getaway sailing catamaran with roller furling jib on a beach dolly.  However, it seems the ‘sailing school’ has evolved into a primarily a beach rental similar to all the others with the sailboat gathering vegetation.

There is also an outrigger sailing canoe available for tours in Wailea. This trimaran departs from the beach in front of the Fairmont Hotel.  While it appears to be a very sea-worthy vessel, the sailing rig itself is rather small.  So, it could be a fun adventure, but likely not on the same order as a Hobie Cat.

Maui Day Boat Charters

The vast majority of visitors to Maui will find their way onto the water by day boat charter. There are a very wide variety of boats and tour types to choose from.

Snorkel/Sunset Cruises

Beach catamarans of 50-60 feet board on the Ka’anapali beach at the Whalers Cove Mall, along with a number of Rigid Inflatable Boats (RIBs) of varying sizes.  There are kiosks where the mall meets the beach to book a charter.  The beach cats give you more opportunity to bask in the sun. However, the RIBs will get you to a destination and back much faster. Private charters are available for $1,300 per hour and up, including food and beverage. Sea Maui also has a monohulled sailboat for up to six people that goes for $1,300 for two hours.

A few downsides to note: I’ve never seen a single charter catamaran on Maui with its sails. So, if you are looking to sail, you may be disappointed. Sea Maui’s monohull, on the other hand, I have seen sailing. Many of these boats also looked uncomfortable crowded.  So, if you aren’t an extreme extrovert, be sure to ask about capacity limits before booking a tour.

There are also a number of larger tour boats that leave from harbors in Lahaina and Kiehei. Maalaea harbor in Kihei is more convenient from Wailea, while Lahaina is near the Ka’anapali resorts.

If you take a snorkel cruise, you’ll probably be pitched on renting a west suit or vest to stay warm in the frigid waters.  We went to Molokini on a cloudy day in January.  It was a little chilly for my taste, and I hate cold water, but I didn’t think a vest was necessary.   I recommend bringing a ‘rash guard’ which is a swim shirt or moisture wicking athletic shirt to keep your torso a bit warmer. A pool noodle is also a great accessory to bring along; it helps you sit higher in the water so you can take breaks and stay a bit warmer in the sun.

Deep Sea Sportfishing Charters

A number of fishing charter boats leave from harbors in Lahaina and Kiehei,. Price for a shared boat start at $200-$400 per person for 2-8 hours of fishing. If you’ve got a group, most companies also offer private charters. As with most of our boating recommendations in Hawaii, go as early as you can for calm water. Even if you don’t get sea-sick, your charter is much less likely to get cancelled or cut short in the morning. Read about our charter with Finest Kind Sportfishing here .

Maui Private Powerboat Rental (bareboat)

The one private boat rental opportunity we found on Maui without a captain (aside from paddling) was through Aloha Outdoors . This is the only true ‘ bareboat ‘ option we’re aware of on the island. Aloha Outdoors rents a fleet of three Glacier Bay 2240 SXs at the Kihei Boat ramp, just north of Wailea. These 23′ power catamarans are available for 2 to 6 hour intervals.

Powerboat Rental Checkout

On the day of our private boat rental, we arrived at 7:45am for an 8:00am reservation. There was one other group ahead of us, but we were out on the water by 8:30am. There was one dock hand with two trucks, so I assume some of the staff live close by. He did note they were currently short staffed. 

The dock hand talked to us about our boating experience and shared the challenges unique to the area, discussed today’s forecast and reminded me several times that it is my decision to go out and come back, and nobody else’s.  He encouraged us to go down and take a look at the inlet before we made a final decision to go out.  Then he filmed a short video of me acknowledging my responsibility for the rental boat and my crew.

Coming and Going from the Dock

He puts the boat at the dock and sends us on our way.  The marina is absolutely the most challenging that I’ve ever navigated.  It has a huge rocky sea wall that keeps the water calm at the ramp and dock…although when the surf picks up the water can splash over the wall!  The space around the docks and the rocky breakwater is relatively tight, and since it is the only recreational ramp in the area, it is relatively busy.  It wasn’t congested, but there was a constant pace of boats coming in and out. 

Once you are off the dock and turned around without hitting the rocks, you head for the end of the sea wall where you make a hard left and head straight out to sea.  There are four very tall, well marked buoys to guide you in an out. 

The challenge though is on the way back.  Since you’ve been out for a few hours, the sea has picked up with larger swells than when you left.  Coming in, you’ll have a following sea with the swells at your stern breaking to surf before you reach the inlet.  The boat master warned us of the condition before we left and again over the phone when we called for a return pickup. 

You have to time your re-entry across two concepts:

• Wait for a lull in the sea as big waves usually come in sets, then when the sea state has calmed
• Position your boat behind a swell with ample space before the next swell behind your boat. 

Out on the Water

If you come in on top of a swell, it will push your boat uncontrollably toward the shore and into the rocks as you try to turn into the inlet.  Once you safely get to the buoys and make your turn, you’ve gotta put the hammer down and get that boat behind the rocky breakwater before the next wave crashes.  Then, once in the marina, quickly slow the boat to avoid the docks, traffic, and sea wall.  As we discovered, the show isn’t over at that point.  Calm your nerves, regain your fine motor skills, and idle back and forth until you have a clear dock space.  Then, be gentler than you’ve ever been before coming into the dock: rather than a wooden dock or a wooden dock covered in tires or fire hose, your dock is made of concrete and rebar!

Once you are away from the shore, there really isn’t much in the way of navigation hazards to worry about. The bottom drops off quickly so there’s no running aground. There isn’t much boat traffic on this side of the island (the main port is on the East side of Maui), no crab pots, and no rivers emptying logs into the seaway.

If you want to snorkel in Molokini, take the 7am start.  There are two buoys for recreational boats in the crater. Remember that arrived at 7:45am? There were two boats putting in when we arrived that we watched heading out. After we launched at 8:30am we headed directly to Molokini. When we arrived, the two recreational buoys had been picked up by the two boats we watched depart at 7:45am! So, we would have had first dibs at 7. 

There are also a number of commercial buoys available that you can use after 10:30. There are plenty there, so you’ll likely have no trouble finding a free one. However, you have to dive or get in the water and maneuver your boat hook to get the rope, which is about 8′ deep, and then thread the line from your boat.  It can be done, but some combination of rough conditions, inexperienced crew, and a crowded crater might have you rethinking it.

While Molokini is the most obvious destination for a boat rental on this side of Maui, the state maintains a number of mooring balls throughout the area with their locations recorded here.   The charter company will tell you, and I agree, the anchor really should only be for emergencies out here because of the coral and harsh conditions, so these will be your only practical options for ‘stops’.

The charter company will rent fishing gear for $85 per pole and the boat is definitely set up for it.  Hawaii does not require a fishing license, so there’s no additional cost or paperwork to do this.

The whale watching is unbeatable if you are out during January or February.  We had to stop our boat three times for whales that came within 100 yards of our boat while cruising around.  We saw lots of breeches and felt surrounded the entire time on the water.

What to Expect in the Rental Boat

These boats have been taken in and out of a rough saltwater harbor and fished on by renters for many years, and that’s how they look.  They’re stained, rusted, and faded.  The rub rails are well used, and the fabric is well worn.  However, our boat was mechanically sound and it was obvious that Aloha Outdoors looks after the boats very well.  So, it isn’t a plush cream puff for filming rap videos, but it has a comfortable seating layout and room for fishing.  The rental company limits your group size to six. Six adults will have plenty of room to stow their gear and stretch out on this boat.

The twin Yamaha outboards with almost 3,000 hours both ran, started, stopped, and shifted without complaint.  The boat has full redundancy with separate fuel and electrical systems for each engine, giving you a strong margin of safety should anything go wrong.  The only thing not working on our boat was one of the fuel gauges; but we had confidence in fuel in the other tank and I’ve never trusted a marine fuel gauge anyway.

You can read more about our experience with the boat here .

What to bring on a Private Powerboat Rental in Maui

Bring food, plenty of drinking water, reef safe sunscreen and ginger ale. If the weather picks up, you could be out longer than you expected before it is safe to come in. So be prepared for that with appropriate provisions.  While the catamaran hull handled the chop incredibly well, it did have quite a bit of side-to-side roll.  Busy Boater Jr experienced his first bought of sea sickness out here. Ginger ale or ginger snaps can help settle a stomach at sea. Consider having any crew that might get seasick take Dramamine. We also brought a pair of binoculars, as none are provided with the boat rental.

What kind of Skills and Experience do You Need to Rent a Private Powerboat on Maui?

Renting a powerboat on Maui without a captain is definitely not for an inexperienced crew and may not even be suitable for many experienced lake boaters.  Being confident handling a powerboat in rough seas and navigating an unfamiliar coastline with a GPS is a is a must. Aloha Outdoors does offer the option to go out with an instructor. This would be a fantastic opportunity to get some rough water experience for future adventures.

How Much Does the Powerboat Rental Cost?

Currently, the least expensive rental option is $695 for five hours. Last year, before they ran into a staffing shortage, they offered shorter trips for as low as $295. You’ll also be charged for fuel at the end of your charter, based on what you’ve used. We were out for about 4 hours, and they estimated we used 15 gallons of fuel and charged us $4.85 per gallon for $72.75 in fuel. That price was in line with the pumps in the area. With tax, our total 5-hour charter charge was $817.56.

The website says there is no insurance available for these charters. However, when we booked, there was an offer of $100 per $1,000 of coverage. That seemed pretty steep, so we decided to roll the dice.

Parking is free at the Kihei Boat Ramp; there seemed to be an adequate amount, but we were there on a weekday.

If you can, book your reservation at least a week ahead of your trip to the island as they do fill up. 

Jet Ski Rentals on Maui

Maui Water Sports rents jet skis on the beach in Ka’anapali for $99 for 45 minutes plus $50 for an additional rider. No experience is necessary to take this tour. Jet Skis handle rough water very well for a number of reasons, and these rentals leave from a floating dock, so its east to maneuver in and out. There’s a big caveat though: you can’t rent jet skis during whale season (December 15 through May 15).

Unless you are with a child that is too young to take their own ski, I highly recommend riding alone. For the most part, jet skis are a lot more fun with one person: they will go faster with less weight, and you’ll feel more comfortable making quick turns and doing sweet jumps without a passenger that’s less able to anticipate what’s coming. On older jet skis, it was fun to put a passenger on the back and try to throw them off. However, newer jet skis are so big and stable that you have to be moving so fast and violently to throw someone off, it gets dangerous.

Public Service Announcement: one of jet skis’ best attributes is also their Achilles heel: they’re easy for inexperienced riders to operate. Many inexperienced riders the world over head out without an understanding of the rules of the road, or respect for fellow boaters. This has led to Jet Skis being banned in certain waters and implementation of licensing requirements in others. When you Jet Ski, please keep a lookout in all directions for other boats and give others plenty of room to operate. Be mindful of your wake; it can ruin a peaceful day on the water for paddlers and other small boats.

Boogie Boarding on Maui

One of the simplest ways to enjoy the waters of Hawaii is with a boogie board. You can rent these on the beach, but we bought ours for $12.99 at the grocery store. They also sell this same model at the ABC Store for $14.99, along with some larger, slightly more expensive models. This is also one alternative that favors the afternoon, since you’ll be looking for some bigger surf to ride those waves.

More recently, we rented a boogie board from Boss Frogs in Lahaina. $25 got us a larger, sturdier board for the full week that we returned on our way to the airport. This is a great place to rent all kinds of gear for the beach, by the way.

Getting to Your Maui Boat Rental

The main airport on Maui, OGG, offers daily direct flights from all major cities on the US West Coast. There are also flights from a few Canadian cities, O’Hare and JFK.  Outside of those areas, you’ll get here by connecting through the West Coast, or Honolulu, on the nearby island of Oahu. 

OGG is a very easy airport to access. Security lines are short and rental cars are within walking distance of the terminal. 

A rental car is usually the best option to get around the island of Maui because most resorts and boating destinations are 30+ minutes from the airport, and attractions are spread out far enough that walking or taking public transportation is not very practical.  Hotels here charge the price of about three margaritas plus tip per day for valet parking, but self-parking is often available free of charge.

Further Reading

Be sure to check out Busy Boater adventures on the islands of Oahu and Kauai .

​​​ Kainani Sails

​ makai adventures, choosing to sail with us means you are choosing to support a locally owned and family operated business that employs  full-time maui residents, many of whom have lost their homes. we appreciate you #lahainastrong.

Private Sailing Charters & Relaxing Sunset Sails ...   Departing from the sand of Ka'anapali Beach  CUSTOM SNORKEL SUNSET SAILS AVAILABLE! CALL: 808-495-1001

Set sail in the calm, leeward waters of Lahaina, Maui and enjoy an unobstructed view of a Maui sunset aboard a private yacht. Relax on the bow or participate in sailing!

Maui Private Charters

Breaching Whale

Maui Boat rental, relax for the day aboard a private yacht, Maui Sailing Charters

Click on the pictures to view more!

Booking during Whale Season?

Add an hour to your tour for extra time to look for Humpback Whales. More time means more opportunity to see these amazing animals who visit Hawaii during the months of December - mid April.

Sunset Sail

 3 hours, or more.

Enjoy a peaceful, unobstructed view of a Hawaiian sunset aboard your own private yacht. We'll hoist the sails around 4pm and sail until the sun sets. The yacht is yours. Bring your significant other, family, or friends! Relax as we sail in the calm waters of Lahaina.  The West Maui mountains really light up when the sun starts to go down- a view best seen from the water. This is also a great option for romantic proposals, ash scatterings, celebrations of life, and an opportunity to enjoy time on the water.

​ Departures from Ka'anapali Beach

Generally 3 hours before the sun sets,

times vary slightly throughout the year

Rate: $475  per hour, includes private boat with captain and crew, snorkeling gear, basic beverages, and an antipasto  pupu  platter. Does not include alcoholic beverages, towel service or suggested gratuity of 18-25%. Gratuity can be added onto your credit card at the end of the trip, or your crew will gladly accept cash.

What makes a Maui sunset special?

Maui County consists of the Hawaiian Islands of Maui, Molokai, and Lana'i. We get to make the most of what every sunset has to offer- from changes in the clouds, to the colors of the mountains, and yes, we even get to see the "green flash" when we're lucky! Every sunset has something amazing to offer, even during the times of year when it dips behind the island of Lanai. When you are on Maui be sure to take some time to not only soak in the sun, but enjoy a sunset as well. 

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Description

Taking a family holiday sailing with kids can be a magical experience and create lasting memories that they will recall for a lifetime. From island hopping to fun cruising a sailing vacation is a great adventure for everyone in the family.

If you have a model preference, make sure to note that in the reservation notes, while we can’t guarantee that particular brand or model, we will try our best to find it for you .

About the product

• Safe sailing for all ages
• The average weight of 8,845 pounds

Note: We do not deliver boats.

Product specifications

Model | 2013, 2015, 2018, 2019 Oceanis 31 Capacity | 8 Length | 31′.8″ Beam | 11.11″ Draft | 5.1′ Furling Jib | Yes Cabins | 2 Canvas | Bimini Winches | Manual

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Frequently asked questions

The following info will help you clarify certain questions you have about renting Sailboat from Cloud of Goods.

Yes. Sailboat rentals in Maui available via Cloud of Goods. You can make a reservation and have your Sailboat rental delivered to you in Maui

Sailboat rentals available via Cloud of Goods in Maui now. We have a range of Sailboat rental models from popular brands to fit to your needs. Simply make a reservation online on CloudofGoods.com and one of our local rental shop partners in Maui will meet you with your Maui Sailboat

Pricing depends on your Maui delivery location and many other factors. Best way to find the exact Sailboat rental pricing in Maui is to add the Sailboat model you want to online shopping cart and fill out the details on the checkout page to get a price quote for Sailboat rental & delivery in Maui

EXPLORE MAUI

Sail trilogy, explore our maui snorkeling tours.

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SUNSET SAIL

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Our Story is a tribute to the dreamers and visionaries: Though our family’s legacy began in the 1920’s, it wasn’t until 1969 that a fateful shipwreck in SE Alaska changed the course of our future. After the disaster, Captain Eldon Coon and his wife, Jeannette, sold everything they had and used the proceeds, with help from their children, Jim, Rand, and Pattie, to build a 50′ sailing…

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Sea Monkey is Maui’s Premier

Luxury private charter, re-opening mid january, awaiting the arrival of our brand new vessel, you can book a tour on our parent company, blue water maui by clicking here., check our calendar, recommended tours.

Aloha and Welcome aboard the Sea Monkey

Our luxurious private vessel is in lahaina harbor on maui, hawaii  our bespoke boat tours will take you on an unforgettable journey through some of the most spectacular sights that the pacific ocean has to offer., experience a unique blend of luxury and adventure as you explore maui's pristine coastline and crystal-clear waters on board our distinguished vessel, sea monkey. our private boat tours offer an exclusive and tailor-made experience that is personalized to your preferences. whether it's a private snorkeling tour, whale watching, or sunset tour, our expert crew will ensure an unparalleled experience for you and your group….all with aloha., with cutting-edge catamaran hull technology, sea monkey is designed to offer a smooth and comfortable ride so that you can sit back, relax, and take in the breathtaking views of maui's natural wonders. our private tours allow you to fully immerse yourself in the local culture and enjoy a more intimate experience with your group. our knowledgeable crew will provide you with insider information about the island, its people, and its unique history., discover the magic of maui as you snorkel in pristine coves teeming with vibrant marine life. get up close and personal with majestic humpback whales as they breach the surface of the ocean. take in the stunning hawaiian sunset with your loved ones as you cruise across the pacific waters., at sea monkey, we pride ourselves on delivering the ultimate luxury experience with unmatched hospitality, service and aloha join us for an unforgettable adventure that you will cherish for a lifetime..

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Rent a Boat in Hawaii with Sailo!

Enjoy a one-of-a kind experience on the water in Hawaii with your own private Sailo yacht charter. Whatever your sailing style; from experienced skipper, fishing fanatic or thrill seeker, to those who just want to relax on deck with your family or friends, you’ll be spoiled for choice. Rent a boat in Hawaii with Sailo for a memorable day trip or a sailing vacation to remember.

Our premium Hawaii private boat rentals inventory

Step aboard your private yacht charter in Hawaii, with a choice over 2 boats to rent from Sailo. We offer a selection of boats for all tastes, including sailboat rentals in Hawaii . You can also choose from Maui catamaran rentals . Want to see Hawaii in style? Choose from one of our motor yacht charters in Hawaii on Sailo.If you’re looking to host a party or a reception for more than 13 guests, you’ll also find party boats in Hawaii in Hawaii, for a truly memorable event.

How to rent a yacht in Hawaii (HI)?

Sailo offers beautiful Maui yacht rentals at various price points in Hawaii. Use our advanced filters to narrow your search by date, group size, and trip duration: 2 hrs, 4 hrs or full day boat charters in Hawaii. You can also choose the type of boat (sailboat, motorboat, catamaran) you want and go even further and look for a particular length, manufacturer and model. The price filter will help you see the available Maui boat rentals within your budget and the crew option is useful when you want to see boats with a skipper/captain included or only bareboats. Do you see a yacht charter in Hawaii that you would like to rent? Click on it to go to the next page to read more about it, see more photos, send a direct message to the owner to ask more questions or start creating your booking request right away!

How much does it cost to rent a yacht in Hawaii?

You can charter a boat in Hawaii for a day, for an average of $1100. The average price for a weekly Maui boat rental is $3500. Your total budget for a boating trip in Hawaii depends on many factors such as: trip duration, if captain and crew are included in the price or their cost have to be paid separately, fuel cost (which could be significantly higher on a motorboat compared to a sailboat) and other extras you choose to customize your experience in Hawaii.

What is Sailo’s cancellation policy?

As long as the booking request hasn't been accepted by the Maui boat charter owner, the renter can cancel the request without any charge. If the renter cancels after the booking request has been accepted, the booking will be subject to the terms of the cancellation policy in place for each boat. The renter should check the cancellation policy with the boat owner, as some of the professional operators have specific cancellation policies which supersede that of Sailo. Whenever a boat owner doesn't have a specific cancellation policy, Sailo's Standard Cancellation policy will apply.

Tips for responsible boating

If you’re looking to explore our beautiful planet, a yacht charter in Hawaii is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:

• Don’t disturb coral or sealife
• Take your trash home (and don’t throw anything in the sea)
• Respect the locals and their customs wherever you go

Read more about responsible boating.

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Maui Boating - All You Need to Know BEFORE You Go (2024)

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Private Boat Charters & Rentals

Top-rated activities for maui.

Lanai Island Guided 4x4 SUV Sightseeing Trekker Tour with Maui to Lanai Ferry

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Maui Nui Sunset Luau on Kaanapali Beach with Open Bar at Sheraton Resort

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Small-Group & Private Maui Whale Watching Tour - Amore Boat Charter [Dec-Mar]

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Traveler's photos.

Latest reviews of Private Boat Charters & Rentals

Loved this tour.

Mahalo to the tour guides on this fabulous day, heading over to Lanai is so awesome.

Best trip ever!!!!

Im sorry but this was the best American boat experience ever. When they say open bar they mean it! Great staff, great experience, food icing on the cake this should be 200 per person!!!!!!

No sunset and it sprinkled for 2 mins so the musician hardly played any songs. .

No sunset and it sprinkled for 2 mins so the musician hardly played any songs. . Maybe two. Another passenger Took pic of him drinking alcohol and not playing. We picked Tuesday for the MUSIC Also, we were not made a ... more ware the food was available. My husband walked over and saw it available. Couldn’t have been much better experience. Wouldn’t recommend.

Incredible views, incredible crew!

Absolute must do while in Maui. We saw several whale pods, mama whales showing their young how to wave, and excellent views of the coastline and Molokai. The crew and captain were fantastic, high energy, knowledgeable, a ... more nd kept the drinks flowing. Food was pretty good, definitely go with the short rib! The catamaran was pristine and well maintained. Instructions for boarding and exiting were easy to understand. I cannot express enough how much the 3 of us enjoyed this tour. We keep saying it was an epic day. So memorable and enjoyable.

Awesome time

Amazing service from the 3 crew members Nick, Paul and Phil. We saw a lot of whale activity in the evening. The drinks kept flowing and the food was much better than expected. Would definitely do another trip like this.

A fantastic trip!

Best excursion during our week in Maui. The reviews were spot on about Sea Maui. The captain and crew were outstanding. You won’t be disappointed.

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The Best Boat Rentals in Maui

Browse, book, and get out onto the water with local captains and boat owners., our favorite boat rentals in maui.

5 (48 reviews)

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the United States

Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull

Private Custom Charters - Sanity Snorkel Vessel

1/2 Day Snorkel Trips To Lanai From Kaanapali Beach

Fountaine Pajot 46 catamaran

Brand New 60’ RIB Charter Maui Hawaii

24ft Blue Glacier Bay 2240 SX Renegade Rental in Kihei, Hawaii

Sunreef 62 catamaran

49 tour, snorkel, whale watch catamaran

Suggested searches, types of boats popular in maui.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

$200-$6,400

Set sail with these traditional wind-powered boats

$475-$6,400

Explore local waters with a boat rental dedicated to sightseeing and exploration

Get off the boat and into the water with offshore snorkeling trips

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

• Fishing Charters

Let a captain do the driving while you do the fishing

Most Popular Yacht Rentals in Maui

Private Snorkeling and Sailing Charter

24ft Glacier Bay 2240 SX Renegade Rental in Kihei, Hawaii

Recent reviews in maui, shaman february, 2024.

The service and the communication was amazing I felt very special like my desires were met. I saw that the captain went out of his way to make sure we were happy. 😃 I do not write reviews but I will for them. Thanks for a gift and experience I will not forget .

dan January, 2024

From start to finish was seamless experience - Keahi was on point with locations for snorkeling and was blessed by the Whale gods with some amazing breaches, and should have paid extra for the sunset- can’t wait to use them again next time we are back

Michael November, 2023

Everything was great. We took a sunset cruise and the weather was perfect. The captain and first mate were wonderful, and the communication to make it happen was awesome. Prayers they will be able to continue after the fire. They make you feel like O’hana.

Steven August, 2022

Best time ever! We have been to Maui many times. This was the first time we had a private charter and we are glad we did. The boat, crew and itinerary were great. We enjoyed snorkeling part of the time and sailing part of the time. Seeing the sea turtles and fish were highlights. Everyone was so helpful.

Andy March, 2022

The 2 person crew of Keahi is outstanding. They are welcoming, professional, and delivered exactly as communicated. If you are considering a sail/snorkel in Maui with one of the big commercial outfits, you should definitely consider Keahi instead. You will not be disappointed! Captain Marty even found us at a restaurant after the sail to return a left-behind pair of shoes!

pam March, 2022

From the initial correspondence, Ali, the booking agent, was super helpful and responded to emails ultra quick. The information and directions (where to park, how to get to the boat) provided before hand were super helpful. Once we got on the boat, we were completely catered to. We were looking for something "chill and relaxing," and that's exactly what we got. We snorkeled with the turtles and then sailed around spotting whales and dolphins. Thank you Marty and Kass for an awesome trip!

Top Boat Rental Locations in the United States

Miami , Florida

945 listings

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272 listings

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Awesome, so you’ve decided to rent a boat with us now, to finish, just select your date, time and options and we’ll be seeing you on the water.

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Book Now. Aloha Outdoors’ has joined forces with the U.S. Coast Guard to help promote its new public safe boating outreach initiative – “You’re in Command.” This initiative encourages all recreational boaters to take responsibility for their actions on the water. So, as a boat owner or operator, you are responsible for your safety and the safety of your passengers.

Firstly, all you really need to operate safely and legally on state and federal waters is boater education to get on the water as soon as possible. Then you can complete a boating license safety course on boat-ed.com with minimal time and effort. As well as with the comfort that comes from knowing you are taking a course that is officially approved by the agency responsible for boating safety in your state. With Boat Ed, you can complete an online boating safety course at your own pace and on any device. So, All courses are mobile-ready, which means that completing your course can be fast, easy, and entirely at your convenience.

Maui Boating is your source for great ocean recreation. Whether you’re staying at the Aston Maui, Grand Wailea, Wailea Marriot, Waldorf Astoria, Maui Hilton, Andaz Maui at Wailea, Four Seasons Maui, Wailea Beach Resort, Motage at Kapalua, Honua Kai Resort, World Mark Kihei, Diamond Resorts Ka’anapali, Royal Lahaina Resport, Wailea Beach Villas, Ka’anapali Beach Club, Maui Beach Vacation Club, Aston Ka’anapali Shores, Papakea Resort,

Castle Paki Maui, Sands of Kahana, Palms at Wailea Maui by Outrigger, Wailea Ekahi Village, The Kulakane, Makena Surf Resort, Kealia Resort, Kahana Village Vacation Rentals, Kahana Villa, Kihei Surfside Resort, Napili Kai Resort, Lahaina Shores Beach Resort, The Maui Escape, Napili Sunset, Kamaole Sands, Maui Sunset, Maalaea Surf Resort, Wailea Elua Village, Hana Kai Maui Resort, Luana Kai Resort, Kihei Akahi or the Wailea Ekolu Village, we have a great activity for you.

Booking Military Discount

An unparalleled selection of accommodations to suit any lifestyle, taste or budget. Similarly, from full-service resorts and stylish boutique hotels to condominium retreats and affordable lodging. So you can count on finding the perfect fit for any traveler, family or group. Likewise, Hawaii is a great place to relax and play. The ocean is a wonderful escape for all those that wish to see a new perspective of the Hawaiian Islands.

So, you can rent a boat with our quality boat rental options and hire a charter boat for your fun day on the water. Our opinion, Don’t buy a Boat when you can rent a boat on Maui. Obviously, This is a great alternative. You can enjoy your boat rental with Fishing Gear, Sea Scooters, Snorkel Sets, BBQ Grill Rental, and other Ocean Recreation. So Take a vacation and rent a boat on maui and get your photographer to capture the moment when you have a great day on maui. Maui Activities are available but make sure to to make the right choice. Book your boat rental today.

Maui Boat Tours & Private Boat Charters

We are limiting our capacity to 60% to provide greater comfort and continue delivering some of the best boat tours on Maui .

Book your trip

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Book today and get special online price for daily tours!

Please fill in the information below and we will contact you soon. Mahalo!

A MESSAGE FROM THE CEO

I am proud to announce that we are the first passenger tour company limiting the guests we serve to 60% of our US Coast Guard capacity to support sustainable tourism and elevate your ocean adventure. With this new business model, we continue to build on 40 years of unsurpassed guest service, inspired by a renewed commitment to enhancing your time with us. Read the full statement regarding limited capacity

Leilani is a 50ft Uniflite power vessel

Well-known for being solid boats, Uniflites are respected seagoing yachts. Leilani is perfectly designed for Hawaiian waters and features added amenities for your comfort. Her spacious main cabin provides perimeter seating and shelter from inclement weather and there is always plenty of space as she operates at a limited capacity. There are large windows with plenty of air flow and forward of the main cabin is a private restroom.

Please note: Your safety is our number one priority! Fortunately, Mother Nature nearly always cooperates, and we do go to Molokini and Turtle Town. On days of inclement weather, our Expert Captains reserve the right to select alternate locations where the conditions are safe and offer the best overall conditions.

EXPLORE PARADISE

The adventure of a lifetime awaits you

We are your guides for fun and adventure, while providing exceptional service and amenities. Experience the incredible beauty of whales, dolphins, turtles, Molokini Crater and Turtle Town. Take in the breathtaking underwater world and immaculate views. The memories you make with us, will not be soon forgotten.

ACTIVITIES DESTINATIONS

EVERYONE IS INVITED

EPIC EXPERIENCE

Molokini snorkel tour

Memories not soon forgotten. If you know where to go, you’ll find them!

IT'S YOUR DAY

Private boat charters

Booking a Maui charter with your family and friends, or business associates on a Hawaii corporate incentive trip is always a great idea. When guests book a Maui boat tour with Leilani, they always find that quality, consistency, and providing a remarkable Hawaiian adventure are at the top of our list. Leilani is an ideal choice for private and small group Maui whale watching tours, Hawaii snorkel tours, and Maui wedding charters.

About charters

Maui whale watching

Sunset dinner cruise

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Wedding cruise

The Best Snorkeling Spots

Over 40 Years of Experience

Visiting Hawaii, and exploring her waters is a must-do activity in Maui. Visitors from around the world travel to Hawaii to experience many things including marine life viewing, nature, history, culture, and adventure. One of the best ways to experience the Hawaiian Islands is on a Molokini snorkeling tour . With the gorgeous Pacific Ocean, and views of Maui’s outer island before you — magic always happens. For over 40 years, Leilani has excelled in providing exceptional service, and quality consistently. The experience on our vessel offers a wonderful glimpse into Hawaii’s paradise.

Molokini Snorkel Tour

MAUI WHALE WATCHING

See the North Pacific Humpback

If you’re visiting Maui during the Winter months (December-March), consider booking Leilani for a Maui whale watching adventure. It’s a great occasion to see the North Pacific humpback whales flourishing in their natural environment. Guests can watch humpback whales gracing the ocean’s surface with behaviors like breaching, fluke dives, pectoral slaps, head lunging and more. 

Maui Whale Watching

Reserve your exclusive private charter today!

Call 808 242 0955 for pricing or Send request and we will call you back!