sailboat in annapolis

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• Annapolis: 410.263.8234
• Cape Cod: 508.524.9121
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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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Sailing Charters aboard the 'PINTITA' out of Annapolis & Baltimore

Make your next getaway a sailing adventure on the Chesapeake Bay!

Are you planning a birthday or anniversary celebration, planning a proposal, getting married or renewing your vows, or just want to enjoy the Annapolis or Baltimore skyline with a cold beverage while sailing?  Help raise and trim the sails, navigate, man the helm or simply take in the experience and sights while relaxing with a cold beverage. Come see what the allure of sailing is all about. The professional Captain and Crew of the ‘ PINTITA ’ can help make your next adventure a memorable one. 

We are currently booking private sailing charters for up to 20 passengers! 

We ask that you continue to support your local businesses and this Veteran owned small business needs your support and patronage.  Please book your private sailing charter soon for your next friends, family, and or corporate outings.  We are looking forward to harnessing the wind and creating memories with you.

Pla n to join us for the U.S. Navy Blue Angels in Annapolis during Commissioning Week in May, 2024

See our Charters page from the menu above

Call us now to book your getaway:

443-510-5756

The ‘PINTITA’ is perfect for:

Bachelor & Bachelorette Parties

Engagement Proposals

Anniversaries

Alumni Events

Company Events

Team Building

We offer many charters to meet your needs.

The 'PINTITA' Sailboat is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing showers! She is designed to make your outing as entertaining and comfortable as possible.

The PINTITA

Come sail the chesapeake bay..

Join us in Annapolis & Baltimore.  We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards.

Picture Perfect Sailing

• Meet your Skipper

Sail in Annapolis, Book a Sailing Cruise Today

Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits. 

CHOOSE YOUR SAILING ADVENTURE

Sailing options.

With Picture Perfect Sailing, the options are virtually endless!

Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!

Day Sail: come sailing for a few hours

Duration: 3 hours (leaves and returns to Annapolis)

Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

Sunset Sails: come sailing as the sun goes down

Duration: 2.5 hours (leaves and returns to Annapolis)

Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

All Day of Sailing: come sailing on the Chesapeake Bay all day!

Duration: 6 hours (leaves and returns to Annapolis)

Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.

Overnight Sailing: experience sailing and sleeping aboard!

Choose one or two overnights: (leaves and returns to Annapolis)

Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages. 

Double (two) overnights: typically departs at 9am,  one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests.  Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.

The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels. 

What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.

How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.

*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders.  Contact Picture Perfect Sailing for more information and to book a sailing cruise today!

The Sailboat

You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.

With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all! 

Meet your skipper .

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Sailing Charters in Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

Select A Time

1 - 6 people | 3-hour (am/pm) - 2.5-hour (sunset) sailing yacht cruise | 25% deposit, minimum age: 7 years., gratuity not included in pricing.

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• Hour Glass 2.5 Hours
• Users Up to 6 Passengers

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 3 Hours

Morning Sail - Licentia

Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.

Afternoon Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!

Other Times

• Hour Glass 8 Hours

Full Day Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.

Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

"Seriously Fun"

Learn to Sail the Annapolis Way

Adult Sailing Lessons

Youth Sailing Lessons

Join KeelBoat Club

Rent a Sailboat

Evening Sailboat Charters

Try Sailing

Which course is right for me.

I want to be able to operate a vessel I already own or intend to buy.

I intend on renting or chartering sailboats in the future.

I want to explore the art of sailing and am looking for a great experience.

I'm looking to learn at my own pace with personalized private instruction.

Sailing is an Experience to be Enjoyed Over a Lifetime

We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach.

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Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

Annapolis Sailing Charters.

Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Annapolis Sailing Lessons

ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.

If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.

Intro to Sailing

Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.

Private Sailing Instruction

New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.

Learn on your Boat

The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.

ASA Courses

Learn To Sail

Browse our charter fleet.

This modern marvel stands out with sleek lines and a spacious deck layout, ideal for leisurely cruises or adventurous voyages.

American Honey

This state-of-the-art catamaran seamlessly combines performance, comfort, and elegance to provide an unforgettable chartering adventure.

Dos Milagros

Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.

Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

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I want to know about new classes, specials, events and offers from Chronic Sailing.

Life is Just Better on a Boat

sail with us!

Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.

Keep it chronic.

- Captain Shawn

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Rent the best Annapolis sailboats

• Sailboat Rentals
• Maryland Sailboat Rentals

Our top sailboat rentals

Annapolis, MD

Sailing Charter - Sunset Cruises, Learn to Sail, and Family Fun Time!

Oxon Hill, MD

Beautiful Sailing Catamaran with Captain

46' Catamaran Charter with Water Toys - Annapolis, MD

Boston Whaler Harpoon 5.2 Sailboat

Edgewater, MD

Excellent Chesapeake sailing onboard Windsnap

Experience sailing in the heart of Annapolis md

DOS MILAGROS - Beneteau Oceanis 45

Sail away on Equus, a properly maintained, well appointed cruiser

Stable, comfortable & fast - sleeps 8 w/4 baths!

New Yacht Charter

LANI - Leopard 42' Catamaran Sailboat

Sailing Vessel (S/V) DreamCatcher

ESCAPE--Leopard 43’ Sailing Catamaran

46' Sailboat Landfall cruiser plenty of rooms!!

Washington, DC

Luxe Champagne Cruise - Set sail from the Wharf DC

Solomons, MD

"Hallelujah" Beneteau Oceanis 350 Sailboat

Custom Sailing Charters - 44’ Catamaran

Cruise the Potomac on a Lagoon 380 Catamaran

How to rent a sailboat in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for sailboat rentals

Top sailboat rentals reviews in Annapolis, MD

Sailing Charter -...

Birthday well spent! I couldn't ask for anything better. Best captain ever, fast response and great people all...

Excellent...

Another great day on the water! This is our second time out on Windsnap, sailing un-captained this time. Everything...

46' Catamaran...

Amazing boat, perf for our bachelorette party of 9. Put simply, it was just a total blast. And cutest seafaring dogs...

I had an incredible time on the 50' catamaran! It offered ample space for everyone, including those less comfortable...

We couldn’t have asked for a better charter experience, Captain Deren and the entire crew were excellent!

My first Boatsetter booking was an excellent experience. I was a bit apprehensive about how this site worked, but...

Beautiful Sailing...

Awesome experience! I booked James' boat for my girlfriends birthday, and it was a wonderful time. James was very...

Boat rocked. Would follow wherever you dock.

ESCAPE--Leopard...

Six perfect hours on the Chesapeake with a great Capt Dauby and crew of Julie and Justin. 18-20kt breeze made sailing...

Boat was in great shape and we had a fun day on the water.

The boat was awesome - plenty of room and lots of fun things to do.

Experience...

My wife and I had an amazing time with Alberto and his wife. Their sailing knowledge and hospitality were such a joy...

Sailboat Rentals in Annapolis, MD

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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: $ - $, 8 sailboat rentals & charters in annapolis, md.

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:

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

Annapolis, MD could be the perfect boating playground for you

Planning a sailing vacation in Annapolis? Enjoy the freedom of the open water on a private yacht charter from Sailo. Rent a boat from a couple of hours to a full day, to really explore Maryland from Annapolis. With a licensed captain driving your boat rental with, you’ll be able to relax and discover those hidden gems with your friends or family. Prefer to skipper your yacht rental? Use our advanced filters to find your perfect bareboat charter on Sailo!

Our premium inventory of Annapolis, MD private sailboat charters

We’ve been asked many times if a sailboat rental is a good choice to explore Annapolis, MD from the water. With more than 27 charters rented every day during the season, our answer is YES, you’re set for an amazing experience when you rent a sailboat in Annapolis! Our boats are available with or without captain, with prices starting at $250 per day, depending on the boat type you choose. Browse, find, and book in minutes the best sailboat for you in Annapolis, MD!

Learn how to find the right boat for great yachting experiences

Wondering how to find the best charter for a memorable experience on the water in Annapolis, MD? We have created a set of advanced filters to help you navigate easily our database of Annapolis boat rentals and yacht charters, and find the one for you. First pick a start date and then choose your trip duration. You can go for an extraordinary of 2, 4 hours or full day experience. Next, select the number of guests, the type of boat and the price range you are comfortable with. The crew filter helps you narrow down the results to the boats with the captain included in the price, or bareboats that you’ll captain yourself. Choose the boat you want in Maryland, to view more pics, read description and reviews. Message the owner if you have any questions or continue with your booking request.

How much does it cost to charter a yacht in Annapolis, MD?

Annapolis, MD yacht charters for daily trips are available at an average of $1100 per day. Cheaper boats (sometimes with no captain included) may be rented for $250. Our Annapolis premium charters may have price tags up to $6500, with crew, fuel, docking fees and other extras added to your budget.

Essential safety tips for recreational boating

Whether you’re renting a boat with captain or you choose a bareboat, always keep in mind this basic safety guidelines:

• if you rent a captained charter, always pay close attention to your captain
• walk slowly and never run onboard as you can easily slip and fall overboard
• be mindful of stairs and hatches (never step on them)
• if you go swimming, floating or paddling, stay away from other boats even if they are anchored or moored
• pay attention to the other group members and make sure that everybody is accounted for at all times

Because we love the ocean

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:

• Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
• Eco-friendly sunblock can help prevent damage to marine life
• buy local and sustainable food products

However long you’re sailing for, a little goes a long way.  Read more about responsible boating.

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Located on the Annapolis Waterfront – Premier Sailboat Dealer for Catalina Yachts & Com-Pac Yachts & True North Power. Serving the Chesapeake Bay & Mid-Atlantic Region

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Featured Boats

2000 Tartan 3500

Price: $125,000

Annapolis, Maryland

2016 Catalina 385

Price: $270,750

Edgewater, Maryland

1998 Catalina 400

Price: $140,000

2000 Hunter 410

Price: $118,000

Baltimore, Maryland

2021 Hanse 508

Price: $696,000

2024 Catalina 355

Price: Request Price

2024 Catalina 425

2024 Catalina 445

2025 True North 34 Outboard Express

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Your trusted full-service boat buying experts.

• Since our establishment in 1953 by Lawrence Hartge in Annapolis, MD, we have been proudly serving boating enthusiasts on the stunning Chesapeake Bay with exceptional service and unparalleled expertise.
• Lawrence Hartge, a visionary and passionate boater, laid the foundation of our company with a simple yet powerful mission: to offer a full-service boat buying experience that surpasses expectations.
• His dedication to the craft and his love for the Chesapeake Bay set the tone for our company's values, which we continue to uphold to this day.
• Over the years, we have become synonymous with excellence in the Mid-Atlantic region.
• Whether you're a seasoned sailor or a first-time buyer, we understand the unique needs and preferences of our customers, and we strive to match them with the perfect vessel.
• Our extensive selection of boats caters to all tastes and budgets. From sleek powerboats to classic sailboats, we offer a diverse range of options that will suit any boating enthusiast.
• Whether you're looking to buy, sell, or simply enhance your boating experience, we are here to make your dreams a reality.
• Come visit us and tour our boats at Pier 7 Marina in Edgewater, MD.

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48 S River Rd S, Edgewater, MD 21037

(410) 267-8181

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Sailing Season is Here. Join Us for a Sail!

2 Hour Public Sailing Cruises

“My husband and I sailed with you on last Saturday evening’s sunset cruise…we were with our dear friends who were celebrating their 25th anniversary. We all had such a wonderful time! Candidly, I was a bit apprehensive, having never sailed before and not knowing what to expect, but I will definitely be back! We all will. Thanks again, so much, for a wonderful adventure.”

Marieanne H.

“We love sailing on the Woodwind and Woodwind II; It is part of our summer plans every year, especially when family comes from out of town. The crew is always fun and professional and each sailing is a new adventure!”

The Paulsons Urbana, Maryland

Woodwind sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Each trip is unique. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.

On our cruises you will see:

• United States Naval Academy
• Annapolis Harbor
• Chesapeake Bay
• Scenic views of Annapolis skyline
• Severn River

Depending on the wind direction and speed, you may see:

• Chesapeake Bay Bridge (we may even go underneath)
• Thomas Point Lighthouse
• Kent Island
• Regattas competing in the Bay
• Ospreys and other local birds
• Watermen checking their catch

The 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels. Our bar is stocked with wine and beer, including a nice selection of local craft beer.

Have a group of up to 16 passengers?

You can get your tickets further in advance and be welcomed aboard first. Click here to learn about our group sailing packages on public cruises.

Weekday sunset sails include the following events or entertainment:

History Mondays

A guided tour exploring the history of the area, the Chesapeake, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.

Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most.  Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from April 27 through August 31. 100 other sailboats also race in the Wednesday Night Regatta. Wednesday’s are the nights to Party Like A Sailor.

Thursday, Friday, Saturday, and Sunday

There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve up your favorite beverage as you relax watching the sunset over the city skyline.

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Crime and Public Safety | Burning boat on Severn River blocked from…

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Crime and public safety | painting the end zones | photos, crime and public safety, crime and public safety | burning boat on severn river blocked from crashing into community pier by annapolis firefighters, eyewitness says.

Emergency operators received a call at 4:09 p.m. about a boat on fire near Round Bay and the Linstead-On-The-Severn neighborhood by Sullivan Cove.

The caller said the fire started in the engine compartment and all passengers were safe and accounted for, said Anne Arundel County Fire Department spokesperson Don Clime.

Land units and three county fire boats were deployed, Clime said, as was Annapolis Fire Boat 36, which was the first to arrive.

Defense attorney Peter O’Neill, who lives in Linstead, noticed white smoke on the water from his riverside home. He said the sheer amount of it, pulsing from the back of the vessel, caught his eye.

Soon, however, the smoke turned dark, and O’Neill watched as the boat was overwhelmed with flames. He said he could smell fiberglass burning from his house.

It wasn’t long before the Annapolis fire boat arrived on the scene, O’Neill said.

By the time the city firefighters made it to the vessel, the current had begun to steer the burning boat toward the shore, where the Linstead community pier sits. The long pier, which is available to residents of the neighborhood’s 154 homes, has boat slips and ramps. There’s also a designated swimming area and a diving board, the lawyer said.

Watching from his house, O’Neill could envision a “catastrophe,” a spreading fire along the pier and its resting, tied-up boats.

However, the firefighters on Annapolis Fire Boat 36 were able to maneuver around the burning vessel and position themselves in between the flames and the pier like a “wedge,” the attorney said.

Using their fireboat, city firefighters were able to redirect the burning vessel away from the pier as they fought the blaze.

“The way they handled the situation was just a reflection of their level of skill and professionalism,” O’Neill said.

No civilians or firefighters were injured during the incident, according to the Anne Arundel County Fire Department. The department said it did not have information on the type of boat, the number of people onboard, or how they escaped.

Clime said Annapolis Fire Boat 36 was the primary responder to Saturday’s fire and that by the time their boats had arrived, the situation was largely neutralized. A third boat called in from Shady Side also turned back.

According to Hunter Dortenzo, a spokesperson for the state Natural Resources Police, the boat, once extinguished, was towed to a marina in Crownsville, south of where the incident took place. The name of the boat and who owns it is unclear.

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7 things to do in Annapolis: Maryland Renaissance Festival royalty ready for opening day

Oh, the burden of royalty at the Maryland Renaissance Festival .

The king and queen of England were headed to Aberdeen. It was Renaissance Faire Night at Ripken Stadium, where the Single-A IronBirds were ready to play the Greenville Drive.

Actors Fred Nelson and Laurie Simonds were game for the appearance, sporting 30 pounds of brocade, ruffles and lace to promote the opening of their make-believe realm on Saturday.

Noblesse oblige.

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“The pitch itself was horrible,” his majesty wrote in an email afterward. “The costume definitely restricts shoulder movement, and the ball bounced once before the plate. … Didn’t matter. We all had great fun.”

The fall festival takes place on weekends from Aug. 24 through Oct. 20 and, after almost 50 years, remains a singular event on the Maryland entertainment calendar. It is held at 1821 Crownsville Road in Annapolis.

The fair is a series of scripted plays and shows set across 10 stages — even the jousting is part of the pageant. But it’s also an outdoor festival at a 19-acre pretend village called Revel Grove that’s held over nine weekends. Crowds are entertained by some 200 performers, from actors and musicians to stunt artists and jousters.

Vendors sell the ordinary (think bubble wands) and the exotic (think leather and swords). Visitors can munch on sausage or cheesecake on a stick or gnaw on smoked turkey legs, then wash it down with the honey wine known as mead.

Nelson is in his 22nd year as the oft-wed Henry. This is Simonds’ 18th season, including four as Lady Seymour and the last two since her character became queen. Forty-six professional actors surround them, including state Del. Heather Bagnall as Lady Thomasin Templeton.

“We are in character and, obviously, we’re wearing heavy costumes and it’s very hot out there. So, it can often be a very physically demanding performance,” Nelson said. “And we are all doing that together. It’s kind of like going to hell and back together. We are a tight unit based on what we all do together.”

Actors have spent weeks memorizing lines for the year 1537 — Simonds uses an app — but also perfecting the skill of staying in character while walking through a village crowded with onlookers and plotlines. Because, whether it’s kids or adults, people want to engage with the walking, talking fantasy players.

“I love to let them talk about who they are and what makes them want to be in Revel Grove and they see the magic that we create,” Simonds said. “You sort of lose yourself in that too — that, ‘Oh, hey, this is real for them.’ And I’m glad that I get to help be a part of that.”

Going to the festival can be like sticking your head in a Renaissance blender, a bewildering mix of funny hats, pointy shoes and shouting fools. You can wander, but it pays to make a plan by using the changing list of shows and the map on the website.

“You can’t see it all in one day,” Simonds said. “I don’t even know if you could see all of it in a whole weekend. But if you’ve never been there, you’re going to be walking into a very immersive, real life, actual structured building environment.”

Jousting? Yes. Music in the pubs? Yes. Magic? Up to you. Jacques Ze Whipper? His 3.4 million Instagram followers might be on to something.

View this post on Instagram A post shared by Jack The Whipper (@jacqueszewhipper)

And if you decide to come back, you won’t be alone.

“I have noticed people coming up to me with their kids and introducing them to me,” Nelson said. “And I come to find out, over the course of the conversation, that the reason that they wanted to introduce their child to me is because they themselves came up to me and played with me when they were children.”

General admission tickets are $26, with discounts for children, seniors and groups. The show does sell out to avoid overcrowding. Prices go up Sept. 14, when the weather usually cools and the crowds swell.

Here are other things to do in the week ending Thursday Aug. 29.

City Dock moves

7 p.m. Thursday

City Dock in Annapolis will be closed for months starting this fall if a city plan to transform it into a climate resilience project stays on schedule. So grab all the time there you can.

Fitness business Moms in Motion presents a waterfront dance workout class at Susan Campbell Park just in time for sunset. $20.

Summer movie

7 p.m. Friday

It’s funny just how many bad movies Nicolas Cage has made. Good ones, too. Sure. But the World War II flick “USS Indianapolis: Men of Courage,” though based on a true story, probably isn’t one of the good ones. Rotten Tomatoes viewers give it just 30%.

Hear me out on this. What can save a meh movie from oblivion? Watching it outdoors in the fading days of summer!

SOFO, a group of merchants along South Forest Drive (get it?), will show the 2016 film in the Bay Ridge Plaza parking lot. The evening starts with music at 7, with food and drink for sale. The movie begins about 8:30. Parking is limited. Bring your own chairs. Free.

Guitar hero

6:30 and 9:30 p.m. Saturday

It can be hard to pick a show from the stream of Rams Head on Stage acts. But a sure sign of a talent worth catching is two performances in one night.

Marcus Miller is a New York-based bass guitarist, songwriter and producer who’s worked with jazz legends including Miles Davis and Herbie Hancock. He’s also a politically aware activist honored by UNESCO, which produced the 2020 get-out-the-vote concert, Lift Every Voice and Sing. The Annapolis shows come at the tail end of his summer tour promoting his funk/R&B collaborative album “Basement Party.”

Tickets are $55 plus taxes and fees.

Wet dog kinda day

11 a.m.-2 p.m. Sunday

The end of summer means it’s time to get your dog wet.

The Anne Arundel County SPCA’s annual Puppy Plunge is a fundraiser where dogs get a chance to get in the water at Camp Letts in Edgewater. There will be music, food, drinks and merchandise. Admission is $10 per car.

Down by the River

11 a.m.-3 p.m. Sunday

Anne Arundel County continues its waterfront park open houses at Quiet Waters Park.

The River Days Festival include rides aboard the tour boats Miss Anne 1 and 2, music, games, crafts, face painting, food trucks, and activities by local environmental organizations and county agencies. Registration required. Free.

Last chance

7:30 p.m. Tuesday

It’s your final night to catch Classic Theatre of Maryland’s outdoor summer production, “The Miser.”

Moliere’s farce takes place in the beer garden at Reynold’s Tavern. Tickets are $55-$75 plus taxes and fees, and do not include dinner or drinks.

Rick Hutzell

[email protected]

Rick Hutzell is the Annapolis columnist for The Baltimore Banner. He writes about what's happening today, how we got here and where we're going next. The former editor of Capital Gazette, he led the newspaper to a Pulitzer Prize for coverage of the 2018 mass shooting in its newsroom.

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