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Sail Away Catamarans

Celebrate or relax in style on a private yacht charter

Charter a luxury catamaran yacht for a few hours, days or weeks.

Enjoy the scenic views, sailing yacht charter amenities and the adventure that lays ahead for you and your guests. Our experienced captains provide local knowledge and nautical skills to ensure a safe and fun experience for everyone. We can’t wait to have you aboard!


Charters available in these beautiful destinations

Thomas Point Shoal Lighthouse

Key West, FL

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The Abacos, Bahamas

Virgin Islands

U.S., British & Spanish Virgin Islands

St. Vincent & Grenadines

St. Vincent & The Grenadines

Make your special occasion a one of a kind experience.

Charters for Special Occasions

Our mission at Sail Away Catamarans is to provide you and your party a one of a kind experience. Chartering a private yacht is a fun and decadent way to celebrate birthdays, weddings, anniversaries and retirements. Or get the gang together for a family trip, bachelorette party, or a corporate event. Our experienced charter agents are standing by to help make your event a memorable one.

Book Today and Set Sail


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One of our specialists will call and review your booking with you as your date nears. Let’s go sailing!

"Can not recommend Sail Away Catamarans enough! I was planning a bachelorette party with 12 girls and they could not have been more accommodating. They were very responsive, reasonably priced and the day of went off without a hitch! ...the boat was just beautiful! All the girls had wonderful things to say and a great time!

Our Most Popular Itineraries

Sunset cruise on the bay, so maryland: crab feast + sail, overnight in annapolis or saint michaels, custom itinerary, book your sailing charter now.

Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

boat docked at a restaurant in Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

  • This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
  • Invite up to 12 guests for half or full-day private yacht charters.
  • She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
  • With a 5 ft draft, Muse can navigate secluded coves and anchorages.
  • A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
  • Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

  • Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
  • Accommodates up to 12 guests for half or full-day private yacht charters.
  • Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
  • Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

  • The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
  • With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
  • Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
  • Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
  • Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

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326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

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catamaran charter annapolis


Private day-charter on our catamaran for bachelor/bachelorette parties, birthdays, anniversaries, company functions or any other occasion.

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New Model Charter Yachts In Annapolis, MD

Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home. Come charter with us and discover the Waypoints difference.

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Catamaran Charter Annapolis - Catamaran Rentals

Top-rated yacht charters in annapolis - preselected yacht rentals:.

Catamaran Saona 47 for hire in Port Annapolis Marina

Catamaran Saona 47 for hire in Port Annapolis Marina

  • Saona 47 [Yacht Price incl. Taxes]
  • Barbeque Grill
  • Outboard engine for dinghy
  • Yacht Insurance
  • Bahamas charter tax
  • Final cleaning
  • Damage waiver
  • Cancellation insurance
  • Virgin Islands Search and Rescue (VISAR)
  • Cruising tax
  • Fuel (for outboarder)
  • Maryland Amusement Tax
  • VAT or sales tax

Catamaran Astrea 42 for charter in Annapolis

Catamaran Astrea 42 for charter in Annapolis

  • Astrea 42 [Yacht Price incl. Taxes]
  • Dinghy with engine

Catamaran Lagoon 50 for rent in Port Annapolis Marina

Catamaran Lagoon 50 for rent in Port Annapolis Marina

  • Lagoon 50 [Yacht Price incl. Taxes]
  • Cockpit cushion
  • Tourist tax
  • Transit log
  • Charter certificate
  • Administration fee
  • Fuel (for dinghy engine)
  • Charter package (Final cleaning, Bed linen, Towels, Kitchen gas, Dinghy with engine, Starter package, Damage Waiver)

Cat Bali 4.4 for rent in Annapolis

Cat Bali 4.4 for rent in Annapolis

  • Bali 4.4 [Yacht Price incl. Taxes]
  • Starter Package

Cat Elba 45 for hire in Annapolis

Cat Elba 45 for hire in Annapolis

  • Elba 45 [Yacht Price incl. Taxes]

Catamaran Bali 4.8 for rent in Annapolis

Catamaran Bali 4.8 for rent in Annapolis

  • Bali 4.8 [Yacht Price incl. Taxes]

TOP Yacht Charters - Yacht Rentals

  • Catamaran Charter North Atlantic Ocean
  • Catamaran Charter United States of America
  • Catamaran Charter US Atlantic Coast
  • Catamaran Charter Chesapeake Bay
  • Catamaran Charter Maryland

Catamaran Rental in Annapolis, United States

Book a catamaran in annapolis.

With only a limited number available in the beautiful Annapolis , hiring a catamaran is a fantastic way to spend your next sailing adventure on the eastern American coastline. Book online with and enjoy the sights of the picturesque Chesapeake Bay and surrounds.

Catamarans are often the first preference for larger groups of sailors, as they are designed for space and comfort. The catamaran has 2 hulls and as a result, a better stability as a result of even weight distribution. In combination with a low lying deck, the catamaran is an ideal option for families with younger children or those who experience seasickness.

Whilst Yachtico endeavours to continue to provide fantastic quality boats and improve the amount of catamarans available in Annapolis, you may also wish to consider hiring a sailing boat in this city or check out other locations in the United states where catamarans are available for hire.

For catamaran rental in Annapolis , check out the great boats we have on offer below and book online today to ensure you get the boat you are seeking in this beautiful destination.

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Boat & Catamaran charter in Annapolis  - Yacht Rental

Boat & Catamaran charter in Annapolis - Yacht Rental

Annapolis yacht rental.

Annapolis, often christened as “America’s Sailing Capital,” is a jewel of the Chesapeake Bay, drawing sailing enthusiasts from all over the globe with its deep-rooted maritime traditions and spectacular waterways. As the pulse of Maryland’s nautical world beats in this historic city, Yachting.Rent stands at the forefront, providing unparalleled yacht rental experiences that capture the essence of Annapolis’s maritime grandeur.

Nestled on the banks of the Severn River and a stone’s throw away from the vast expanses of the Chesapeake Bay, Annapolis offers an intricate tapestry of sailing adventures. From navigating the calm waters of the river, with the United States Naval Academy as a backdrop, to venturing into the open bay, every journey here tells a story. Yachting.Rent’s meticulously curated fleet of yachts is designed to cater to these diverse narratives. Whether you’re seeking a romantic sunset sail past the iconic Thomas Point Shoal Lighthouse or embarking on a multi-day exploration of the bay’s myriad coves and estuaries, our yachts serve as your trusted vessel. Each yacht in our collection is maintained to the highest standards, ensuring not just safety but also an unmatched level of comfort and luxury. As the historic buildings of Annapolis fade into the horizon and the bay opens up, the luxury of our yachts and the expertise of our crew ensure that your journey is as captivating as the destination.

Yet, it’s not just about the yachts; it’s about the experience. Yachting.Rent understands that every sailor or group of travelers has a unique vision for their Annapolis adventure. As such, our team, deeply entrenched in the local sailing community, offers personalized itineraries. Maybe you wish to anchor in a secluded bay, feasting on Maryland’s famed blue crabs as the sun dips below the horizon. Or perhaps, you dream of docking at one of the bay’s historic towns, soaking in the local culture before setting sail again. Our local expertise ensures that your voyage is sprinkled with these unique moments, turning a simple yacht rental into an unforgettable Annapolis story.

In essence, Yachting.Rent is more than just a yacht rental service in Annapolis. We are your partners in crafting nautical tales, steeped in the rich maritime legacy of Maryland. With the sails hoisted high and the Chesapeake Bay beckoning, we invite you to embark on an Annapolis journey where every wave, every gust of wind, and every horizon is a testament to the timeless allure of sailing. Join us, as we set sail, write stories, and celebrate the spirit of Annapolis, one yacht voyage at a time.

Daniel Goldman

CEO of Yachting.Rent

Boat & Catamaran charter in Annapolis

Bali 4.4 - 3 + 1 cab. - Apollo - 2022

Bali 4.5 – 4 + 2 cab. – Adria Chicha – 2017

Lagoon 450 F - 4 + 2 cab. - Shiva - 2018

Lagoon 450 F – 4 + 2 cab. – Shiva – 2018

Lagoon 42 - 4 + 2 cab. - Eleni - 2023.

Lagoon 42 – 4 + 2 cab. – Hanselli – 2024

Lagoon 42 – 4 + 1 cab. – pirelli – 2024.

Saxdor 320 GTO - Kali - 2022

Saxdor 320 GTC – Olivia – 2022

Saxdor 320 gto – kali – 2022.

catamaran charter annapolis

Why Choose Us

Yacht charter in Annapolis

Annapolis, a city woven with maritime tales and Chesapeake Bay adventures, beckons to all who yearn for the rhythmic dance of the waves and the thrill of the open sea. At the heart of this storied nautical landscape, Yachting.Rent emerges as the premier yacht charter service, bringing unparalleled sea voyages tailored to capture the quintessential Annapolis experience. With us, chartering a yacht isn’t just about renting a boat; it’s an invitation to be part of Annapolis’s age-old maritime tapestry, all while ensconced in luxury.

Centuries of naval tradition flow through the waterways of Annapolis. From its historic harbor, echoing tales of tall ships and old-world voyagers, to its proximity to the sprawling Chesapeake Bay, Annapolis is a sailor’s dream. Recognizing this, Yachting.Rent has meticulously assembled a fleet of yachts to match the grandeur of these waters. Our charter yachts, each echoing a blend of luxury and performance, are equipped to navigate both the serene stretches of the Severn River and the vast expanses of the bay. Whether you’re envisioning an intimate sunset sail, a spirited regatta with fellow sailors, or a leisurely exploration of Maryland’s coastal towns, our yachts stand ready. And with our experienced crew at the helm, every technicality is handled, allowing you to immerse in the journey fully.

But what truly sets Yachting.Rent apart is our commitment to curating unique Annapolis sea adventures. We understand that chartering a yacht is more than just a transaction; it’s about crafting memories. Maybe today, you’d want to drop anchor by the Thomas Point Shoal Lighthouse, indulging in a gourmet meal aboard as the lighthouse stands sentinel against the twilight. Tomorrow, you might decide to trace the routes of historic sea battles, all while our crew regales you with tales from yesteryears. Or perhaps you’d fancy a voyage to the quieter parts of the bay, where time seems to stand still. With Yachting.Rent, your charter becomes a canvas, and every wish, every whim, becomes a brushstroke, painting your perfect Annapolis story.

In entrusting your yacht charter needs to Yachting.Rent in Annapolis, you’re choosing more than a service. You’re choosing an experience, a journey back in time, and an adventure that stretches forward into the horizons of the Chesapeake Bay. With the wind as our guide and the legacy of Annapolis as our muse, we invite you aboard. Let’s chart waters less traversed, let’s breathe in stories whispered by the winds, and let’s discover Annapolis in its purest, most enchanting form, one yacht charter at a time.

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About Annapolis

Why is Annapolis a good sailing destination?

Annapolis, often heralded as the “Sailing Capital of the U.S.,” sits on the Chesapeake Bay’s shimmering shores, a veritable nexus of maritime history and modern-day seafaring. The city’s rich naval heritage, combined with its unique geographical offerings, makes it not just a good, but an exceptional sailing destination. Yachting.Rent, having sailed these waters and listened to their whispered tales, offers insights into why Annapolis is a sailor’s dream come true.

Firstly, Annapolis’s historical significance is unrivaled. Founded in the 17th century and home to the U.S. Naval Academy, the city breathes history with every tide. Sailors navigating these waters don’t merely skim the bay’s surface; they voyage through time, retracing the paths of ancient mariners, naval fleets, and explorers of yore. The city itself stands as a testament to its maritime roots, with cobblestone streets leading to historic docks and age-old taverns. Every corner of Annapolis tells a tale, and sailors get to be a part of this ever-unfolding narrative. With the Chesapeake Bay’s sprawling expanse acting as the backdrop, Annapolis becomes more than just a sailing point; it becomes a portal to bygone eras.

But history is just one facet of Annapolis’s allure. The natural charm of the Chesapeake Bay and its tributaries offers varied sailing experiences suitable for both novices and seasoned sailors. From the calm, mirror-like inlets perfect for leisurely day sails to the bay’s vast stretches that challenge and thrill, Annapolis offers diverse nautical landscapes. Wildlife enthusiasts can spot herons, ospreys, and even the occasional dolphin. Fishermen can drop a line in pursuit of the bay’s famed blue crabs and rockfish. And when the sun sets, painting the sky in hues of gold and crimson, sailors find countless secluded coves to anchor for the night, lulled to sleep by the gentle Chesapeake waves.

Yachting.Rent recognizes that beyond history and nature, what truly elevates Annapolis as a sailing destination is its vibrant community. The city plays host to numerous sailing events year-round, from regattas that see sleek racing yachts slicing the waters to boat shows showcasing the latest in marine innovation. Annapolis is where old-world charm meets modern maritime advancements, and sailors, whether they’re looking for camaraderie, competition, or simple solitude, find their calling here.

In summary, Annapolis, with its blend of history, nature, and community, stands as a beacon for all things maritime. It’s a place where every sail hoisted becomes a part of a larger narrative, every nautical mile traveled is a story, and every sailor, a storyteller. At Yachting.Rent, we’ve been fortunate to be a part of this grand tapestry, and we invite you to set sail, discover, and be enchanted by the myriad wonders of Annapolis, Maryland.

catamaran charter annapolis


catamaran charter annapolis

What Choose

Sailing boat or Catamaran, what to sail in Annapolis

Choosing the right vessel for your sailing adventures in Annapolis, Maryland, is essential to ensuring an unparalleled maritime experience. Annapolis, steeped in naval history and nestled on the expansive Chesapeake Bay, presents varied sailing terrains and experiences. At Yachting.Rent, we understand that your vessel is more than just a means of transportation—it’s your companion on the waters. To assist you in making the best choice, let’s delve into the advantages of sailing boats versus catamarans in the context of Annapolis’s unique maritime environment.

A traditional sailing boat, often characterized by its single hull and deeper draft, offers an authentic nautical experience. These vessels, deeply ingrained in Annapolis’s maritime heritage, are perfect for those looking to immerse themselves in the city’s rich sailing traditions. The mono-hulled design allows for a closer connection to the water, letting sailors feel each wave and current. It offers an adrenaline-pumping experience, especially when heeling in stronger winds, making it a preferred choice for purists and thrill-seekers. Moreover, with the Chesapeake Bay’s deeper areas and open waters, sailing boats can harness the wind’s power and provide exhilarating speeds. They are also ideal for competitive events and regattas that Annapolis is renowned for.

Catamarans, on the other hand, have gained immense popularity in recent times, and for good reasons. With their twin hulls, catamarans provide unmatched stability, making them a preferred choice for families and those new to sailing. They almost entirely eliminate heeling, ensuring a more relaxed and comfortable journey. The wide deck space on catamarans is perfect for sunbathing, lounging, or hosting larger groups, turning your sailing trip into a floating social gathering. Additionally, the shallow draft of a catamaran makes it ideal for exploring the Chesapeake Bay’s numerous coves, inlets, and secluded beaches. With their increased buoyancy and stability, catamarans can also anchor closer to the shore, allowing for easy access to Annapolis’s picturesque landscapes and waterfront attractions.

At Yachting.Rent, we recognize that choosing between a sailing boat and a catamaran is often a reflection of personal preferences and the kind of experience one seeks. Those yearning for a nostalgic and more tactile connection with the waters might gravitate towards traditional sailing boats. In contrast, those seeking luxury, stability, and space might find catamarans more appealing. Regardless of your choice, Annapolis’s vibrant maritime culture, coupled with the Chesapeake Bay’s varied sailing terrains, promises an unforgettable journey.

In conclusion, whether you’re tracing the routes of ancient mariners on a mono-hulled beauty or exploring hidden coves on a spacious catamaran, Annapolis offers the perfect backdrop for every maritime tale. Yachting.Rent is here to ensure that your sailing experience in Annapolis is tailored to your preferences, ensuring memories that last a lifetime. Sail forth, and let Annapolis’s waters narrate their stories to you.

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Check out sailing destinations by regions.

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  • Annapolis, Maryland
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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, catamaran rentals in annapolis, md, no boats found, to see more results try changing your dates, moving the map, or removing your filters.

Annapolis, MD

boating guide

In addition to the best offers we have for boat and yacht charters in Annapolis, MD, see also options available for rent in these nearby locations:

  • 21 boat rentals in Annapolis, MD
  • 21 boat rentals in Parole, MD
  • 21 boat rentals in Highland Beach, MD
  • 21 boat rentals in Arnold, MD
  • 21 boat rentals in MD
  • 21 boat rentals in Edgewater, MD
  • 21 boat rentals in Riva, MD
  • 21 boat rentals in Severna Park, MD
  • 10 boat rentals in Stevensville, MD
  • 21 boat rentals in Shady Side, MD

Renting a boat is the perfect way to explore Annapolis, MD

Rent a yacht in Annapolis to see this stunning location like you’ve never seen before. With a private boat rental from Sailo, you and your family or friends will have the freedom to discover some of the most beautiful parts of Maryland. Whether you choose a sailboat, catamaran or a motorboat, you are in for a thrilling, romantic and unforgettable adventure aboard your private yacht charter.

Curious about your options for renting a catamaran in Annapolis, MD?

Are you looking for a catamaran to rent in Annapolis, MD? We’ve got your covered with a total of 27 waiting for you at the dock. Available with or without captain, these amazing charters are the best way to enjoy the coastal scenery during the day, a breathtaking sunset or a day full of fun in the water with family or friends. Rent a private catamaran charter in Annapolis and get ready for a great experience in the waters of Maryland.

Amazing yachting experiences happen on the right boat. Search for it now!

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day rental in Annapolis, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a boat with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht in Annapolis, MD for a day?

Boat charter prices in Annapolis, MD vary significantly. You can find great budget friendly rentals starting from €250 for a daily trip. Luxury or party yacht rentals for the day can cost up to €6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

If I rent a yacht on Sailo, will I get insurance coverage?

Yes, all Sailo boats available for rental have insurance: sometimes included in the price, other times available to buy as mandatory extra.

Together we protect our oceans

However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:

  • Take your rubbish home
  • Use eco-friendly sunblock
  • Avoid single use plastic

Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle.  Read more about responsible boating.

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Darling Charters Annapolis

Welcome aboard darling, a classic lobster yacht built on martha’s vineyard.

catamaran charter annapolis

Perfect for those early risers, or for when you have an action packed day and want to fit it all in.

catamaran charter annapolis

Harbor Cruise

catamaran charter annapolis

This cruise will make you feel like a local and discover all that Annapolis has to offer from the water.

catamaran charter annapolis

Sit back and enjoy this cruise around the harbor, and watch as Annapolis lights up with the setting sun.

Wedding on the water photo

Special Event

We are pleased to speak with you to design a unique day on the water.  We think we are the ultimate way to arrive at your special event or wedding , spectator boat for a regatta, or celebrate that special occasion with your friends, family or clients. Contact us to find out how we can bring that added classic elegance to your next event.

A married couple on the darling charters vessel

Blog Posts ‍

What to bring, what to wear , refreshments, cancellation policy, departure & arrival, terms and conditions, the fine print, testimonials.

“The prettiest boat in Annapolis"

"Wonderful captain, conversation, sights, boat & charcuterie board! ‍ I would do it again!

“ l loved being out on the water on a beautiful August afternoon. It was the perfect way to entertain three of my close friends. We enjoyed Champagne, sunshine and a guided tour of Annapolis area creeks and the Chesapeake Bay. We all agreed that our time on the picnic boat was greatly enhanced because of our captain Alexandra"

About the Boat

Darling is a 1973 Wasque 32 (pronounced “Way-squee”) named after Wasque point on Martha’s Vineyard.  She is a much loved classic and one of only 50 built by Martha’s Vineyard Boatworks.     Based on the lobster boat hulls of Maine, she was designed to be a fishing boat for the often challenging waters around the Vineyard and Buzzards Bay. As result she is a seaworthy vessel, cruising smoothly on the near full length keel. Darling had a major refit in the early 2000s that included the hard top and a new engine, and has continued to be upgraded to keep her in great shape. She is a very sea worthy design and also provides a wonderful open cockpit - the perfect setting for your next cruise.

Darling Charters Boat Cruising In Annapolis Maryland

Founded by two lifelong sailors, we wanted to share our love of the water with you and provide the ultimate way to experience Annapolis! ‍ When we found Darling it was love at first sight - book your cruise today to find out why!

Cute Lab Dog Looking Right

46ft Catamaran Charter Annapolis, 4 hrs

catamaran charter annapolis

  • Paddle boards & water floats
  • Dock Street, Dock St, Annapolis, MD 21401, USA Meet us in the downtown city dock to get get onboard
  • Not wheelchair accessible
  • Near public transportation
  • Most travelers can participate
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This is a private tour/activity. Only your group will participate
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Stephanie L

46ft Catamaran Charter Annapolis, 4 hrs provided by WindSong Charters


  • Bowthruster
  • Furling mainsail
  • Fully battened mainsail
  • Electric toilet

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Annapolis. MD YACHT CHARTERS, USA / United States

12 Knots offers crewed and bareboat yacht charters in Annapolis. MD, USA / United States. You may choose the right boat for you from 13 yachts listed on the web site. Click on the one you like to make an easy reservation for your sailing vacation in Annapolis. MD.Rates start from €3,675 per week.

Rent a Boat in Annapolis. MD: 13 Available

Sun odyssey 389 sailboat charter (2018).

39 North - 0

Rent a boat Jeanneau NC 33 (2018) in Annapolis. MD

Knot Home - 0

Sailboat Sun Odyssey 440 - 3 cab. (2018) for rent in Annapolis. MD

Summer Salt - 0

Dufour 430 - 3 cab. sailboat charter (2021)

Opportune Moment - 0

Rent a boat Jeanneau 53 - 3 cab. (2018) in Annapolis. MD

Recovery Room - 0

Sailboat Jeanneau 58 (2017) for rent in Annapolis. MD

Padraigin II - 0

Fountaine Pajot Astrea 42 - 3 + 1 cab. catamaran charter (2021)

Serene Blue - 0

Rent a boat Fountaine Pajot Astrea 42 - 3 + 1 cab. (2024) in Annapolis. MD

Serenity Now - 0

Catamaran Lagoon 50 - 6 + 1 cab. (2022) for rent in Annapolis. MD


Fountaine Pajot Saona 47 (Quintet) - 3 + 1 cab. catamaran charter (2019)

Dark Star - 0

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Frequently Asked Questions about yachting in Annapolis. MD

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catamaran charter annapolis


Yacht Tours & Charters Boca Raton & Annapolis

November 1st - May 31st

Sail Annapolis Chesapeake Bay

June 1st - October 31st

Webone About

We have several packages to choose from

Whether you’re planning a family outing, a bachelorette party, a birthday celebration, or even a wedding, our tailored packages ensure that your special occasion will be celebrated in style against the backdrop of the beautiful sea.

For those seeking a more immersive experience, our 4-day liveaboard course offers hands-on sailing instruction, allowing you to master the art of sailing while living aboard our luxurious catamaran.


Captain & Crew included

All charter packages include Captain & Crew

Host an Event

Host your event on a Yacht

Windsong Fleet

Check out our legendary yachts.


SV Too Short - Book Now


Leopard 58 - COMING SOON


Leopard 48 - COMING SOON


Lagoon 52 - COMING SOON

Check our current packages, special charter offers.

Select pricing plan to get more

catamaran charter annapolis

4 Day Liveaboard Course

Learn what it takes to be a Liveaboard Sailor!

  • ✓ Sailing techniques
  • ✓ Navigation equipment
  • ✓ Special technique and strategy
  • ✓All meals provided
  • ✓ Certification

4 Day Course


Application Form

catamaran charter annapolis

Standard Sailing Course

Learn the sailing basics !

  • ✓ Professional equipment
  • ✓ Lunch provided
  • ✓ Course Material

Standard Pack

catamaran charter annapolis

Sailing Vacation

All-inclusive three day Sailing vacation

  • ✓ Snorkel equipment
  • ✓ Paddle Boards & Floats
  • ✓ All meals and drinks

Premium Vacation


Premium Pack

Overhead view of Catherine Marie

Catherine Marie

Elegant private yacht charters & rentals in annapolis, baltimore, and on the eastern shore.

Whether you’re hosting a large corporate function, a birthday celebration, or an elegant wedding reception , Catherine Marie is one of the grandest yachts available at Yacht Charters on the Bay℠ by Watermark®. Used for private charters in the Annapolis, Baltimore and Eastern Shore area, she has three decks for your dining and dancing pleasure. The first and second decks are enclosed and climate-controlled for your cruising comfort, while the spacious top deck offers some of the best views on the Chesapeake Bay.

View Catherine Marie’s Floor Plan

Catherine Marie’s Spacious Deck Features

Catherine Marie’s spacious main deck features expansive table-height windows for unobstructed views, rich mahogany paneling, and a full-service bar. The second deck includes a lounge with a handsomely appointed mahogany bar and custom-carved built-in seating complete with bistro tables, chairs, and ottomans. Double doors open to the covered aft deck, which is perfect for music and dancing. The top deck is fully open with patio-style tables and chairs and the most amazing views of the Chesapeake Bay.

Catherine Marie top deck

Each Proposal is Customized to Your Event

Each private yacht event at Yacht Charters on the Bay℠ by Watermark®  is unique. We tailor your event to meet and exceed your individual party needs. Contact us today  to begin discussing how our exclusive yacht rentals can make your next event unique and remarkable in every way. We make planning your next event easy, down to the smallest detail!

Schedule an Event

catamaran charter annapolis

Reserve Catherine Marie


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