charter sailboat annapolis

Sailing Season is Here. Join Us for a Sail!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

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Make your sailing experience a memorable one! Sail away with us!

Private Chesapeake Bay Charters ……….. Like No Other ………..

A sunset cruise, a romantic dinner, a family excursion, a wedding proposal….. Seas the Bay will help you design your special day in Annapolis.

A sunset cruise, a romantic dinner, a family excursion, a wedding proposal….. Seas the Bay will help you design your special day in Annapolis. Book Now

Seas the Bay Sailing

Sailing Charters in Annapolis MD on the Chesapeake Bay

We are a family-owned and operated company based in Annapolis Maryland, offering private sails for any occasion on Southerly, our 54 ft. Irwin. From three-hour day cruises to sunset dinner sails, to wedding proposals and photo shoots, we can customize your sailing charter for an on-the-water experience to remember.

We ensure you and your guests will fully enjoy your time on the water in historic Annapolis, and are committed to a fun, unique, memorable and safe experience!

Experiences on the Chesapeake Bay

Three Hour Private Charter

Enjoy a fun-filled day on the water, or an evening sail with the breathtaking Annapolis sunset

from $425 / person

Special Event Photo Shoot

Share unforgettable experiences with those you love

In addition to our regular afternoon and sunset sails on the Bay, we offer custom charters. We are passionate about sailing and will design a charter for you.

You deserve to be pampered. Schedule a charter today and let Seas the Bay help you relax! See and experience Annapolis and the Chesapeake Bay like you never have before.

Book your charter today by clicking the “Book Now“ button to see and Experience…

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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.

• Most Popular!
• 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.

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.

• Chesapeake Bay Itineraries
• Key West Itineraries

Chesapeake Bay

• Virgin Islands
• St. Vincent & The Grenadines
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• Meet Your Captains
• Charter Management
• Sailing Lessons

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!

Destinations

Charters available in these beautiful destinations

Key West, FL

The Abacos, Bahamas

U.S., British & Spanish Virgin Islands

St. Vincent & The Grenadines

Make your special occasion a one of a kind experience.

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

Select a Yacht or Itinerary

Search for the yacht or find an itinerary that best fits your event.

Submit Request

" Book Now " to submit your preferences and make your payment. You will receive a confirmation number & email.

We Will Review

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

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

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

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Charter a Boat

Spend multiple days and nights on-board your private yacht, or just a few hours to watch the sunset. Bring your own snacks & drinks or have a meal delivered or catered on-board. Arrive in style at your favorite dock bar. Go for a swim or just relax and enjoy the view.

We want you to have your perfect day on the Bay, whatever that means to you. That's why we've come up with a variety of itinerary options to choose from. Have something specific in mind? Just ask!

Charter Itineraries

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.

Annapolis Dinner Cruise

A romantic getaway or a casual evening with friends and family. We’ll serve dinner from a downtown restaurant or have your meal catered on-board.

Half Day Sail

Only have time for a shorter day on the water? No problem! Plenty of time to fit in a swim, take in amazing views or enjoy a cocktail on-board or at your favorite dock bar.

Full Day Sail

It’s the ultimate day on the water! Spend a full 8 hours exploring the northern Chesapeake Bay aboard one of our luxury catamarans.

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.

Ready to sail with us?

Get in touch to book one of our itineraries or discuss something special for your cruise.

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• Annapolis: 410.263.8234
• Cape Cod: 508.524.9121
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Private Sailing Charters

When you charter the Liberté, you pick the day, the time of day, the number of hours, who’s onboard, the music, the food and what you’d like to drink from our bar (no b.y.o.b.). If it rains on the day of your parade, there’s no charge on the boat or the bar. We will also make an effort to get your catering canceled if you won’t be taking your party elsewhere. We can try to reschedule your sail or if you prefer, we will refund your deposit.

Each cruise is unique and we strive to make it just the event you envisioned, be it a lively cocktail party, a formal wedding or just a casual afternoon on the water.

Birthdays, anniversaries, graduations, reunions and retirements are all great reasons for a grand event. Having it aboard the Liberté makes it even more special. Adding a theme can further enhance the experience and fun. After all, it is your party!

Music, food, beverages and attire can be blended to suit the mood. Consider a casual “steelbeach” party with reggae music and rum punches. A 1920’s theme brings to mind snazzy clothes and jazz with cocktails and hors d’oeuvres. Of course, there’s also the ever-popular pirate theme. If you can dream it, we can probably make it happen, for a party you and your guests will never forget. The Liberté has a stereo with a large c.d. collection of all genres of music, or feel free to bring along your iPod or your own c.d.’s.

Food is an important part of the planning. We offer a wonderful catering menu in Annapolis and work with some fine food purveyors in Cape Cod, serving everything from casual appetizers to full dinners. You may prefer to bring your own, use your own caterer or go potluck. Boxed or bagged lunches are a comfortable option as well. We have a full beverage bar onboard (no b.y.o.b.) and can work with your theme to expand the libation options.

Get In Touch Now

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Private Daily Charters

- including “learn to sail” options, - corporate events, - blue angels and usna graduation week, - spring and fall boat show sails, - wednesday night race viewing, - engagement photos, reservations, sail the chesapeake on a 47 foot sloop out of annapolis, maryland with your charter hosts rick and annette, half day, full day and evening sails plus special events.

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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Bareboat Sailing Charters on the Chesapeake Bay