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High quality excursions along the Potomac River

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Memorable Excursions

Memorable yacht charters that will last a lifetime

About MD Yacht Charters

Amazing excursions, a lifetime of memories.

MD Yacht Charters is a luxury yacht chartering company serving residents, tourist, and a host of professional clientele in the Washington Metropolitan area since 2013. We take great pride in creating amazing and high quality excursions along the Potomac River in DC, Maryland and Virginia for small intimate groups.

Our team of trained professionals will ensure that you and your friends have an experience that will last a lifetime.

private yacht charter maryland

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Our team at MD Yacht Charter is committed to ensuring you have a memorable charter experience with us always. 

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Classic Sail Charters

Classic Sail Charters

Private sailing charters in maryland, choose your location, annapolis, md.

May - October

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West River, MD

  • Most Popular!

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!

  • Users Up to 6 Passengers
  • Hour Glass 2.5 Hours

Your Dream Adventure Awaits

Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way. is required. 

Charters Feature

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Sunset Cruises

Daily Sails

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Weekend Cruises

Milestone Celebrations

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Marriage Proposals

Family Adventures

Check-out what our Guests say about us! ★★★★★

Capt. Nate & Payton were great! We did an engagement shoot on the boat and they were unbelievably helpful. They were extremely accommodating to the photographer and worked to position the boat perfectly as the sun was setting. Siena is a beautiful boat and the west river is idyllic. Can't recommend enough.

Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him.

My fiancé and I are both from New England and grew up by the water, so we knew we wanted a nautical setting for our engagement photos. We had a fabulous time with Classic Sail Charters on the beautiful Siena! Captain was so helpful in offering to angle the boat this way and that for better light and even raising or collapsing sails. We'll definitely be back!

My husband I along with our two grown children (in their 30's), had a wonderful day with decent wind in July sailing at times to 15 knots! Captain Tony was accommodating and friendly. He had a variety of snacks and beverages on board and encouraged participation in sailing the boat as well as relaxing in the sun or shade! We will definitely do this again and we're thinking of also offering this as a gift to my parents who also love to sail.

This past Friday, we joined Capt. Tony aboard the Licentia for an afternoon sailing the Bay. We had a great afternoon sailing and motoring (we lost the wind) around the Bay and through the Annapolis Harbor. Capt. Tony is very knowledgeable, friendly, and helpful. He has loads of sailing experience and all enjoyed his sea stories. Would we go again? Absolutely - planning a trip for next May.

Four of us sailed with Captain Tony on 2 different trips - one afternoon and one morning. Both days were fantastic and relaxing and lovely. The 2nd trip we lost the wind eventually so motored around the Bay and Annapolis and Tony gave us some history and stories. He is delightful and skilled and we had a terrific time. We will definitely plan another trip one of these day.

Island Chill Yacht Charters

Chesapeake Boat Cruises

  • Night Owl Party
  • Raft-Up Party!
  • Friend-Ships
  • Birthdays!!!
  • Anniversary
  • Bachelorette
  • Mother’s Day
  • Father’s Day
  • Blue Angels USNA
  • Memorial Day
  • Island Celebrations
  • Natural History
  • Chesapeake History
  • Fishing Trips
  • Aqua Creative Studios
  • Team Building
  • 43′ sailboat
  • 34′ Powerboat
  • 20′ Bow-rider
  • About ICYC-CBYC
  • How to Book
  • (410) 212-4476

Island Chill Yacht Charters -- Choose the wave!

2-Boat Party - Powerboat and Sailboat

WIth Birthday Celebration Package

Welcome Aboard, 2024!

Island chill yacht charters (icyc), & chesapeake bay yacht charters (cbyc), 'to bring people together to create memories and  strengthen friendships & family connections', new location : 'the marina', 1444 shore drive, edgewater, md 21037 (map), email: [email protected]; [email protected].

Booking portal opens March 15th

Call 410-212-4476 for reservations.

Island Chill Yacht Charters (ICYC) creates the 'Relaxing Excitement of the Islands' on our Chesapeake Bay sail and powerboat private cruises for Families, Friends and Couples. We're conveniently located in historic Londontowne in Edgewater, close to Washington D.C. & Baltimore, and just 6 miles south of Annapolis - the 'Sailing Capital of America!' We're the perfect venue for hot summer days and chill sunsets. Celebrate Birthdays, Anniversaries, Bachelorette Parties, Corporate Retreats - add our 'Sail-E-Bration' special occasion decoration packages! National Holidays and Special Events too. Chose our 43'-sailboat (Therapy), or either our 34'- (Irie Vibes)  or 20'-bow-rider (Tallawah) powerboats to cruise along the shores of the South and Rhode Rivers, the magnificent Chesapeake Bay as well as get close to the Thomas Point Shoal Lighthouse. At anchor, enjoy swimming, paddle boards, floating lily pad; sun, beaches, sand bars and islands; even kayak and fishing options too. Endless possibilities - endless fun!

Chesapeake Bay Yacht Charters (CBYC) focuses on Specialty and Storyteller cruises - full of Captain John Smith, historic landmarks, President George Washington, lighthouses, pirates, birds, striped bass, wildlife, blue crabs, ospreys and Chesapeake Bay habitats. You'll be an active participant on Storyteller   charters - it's like you are Sir David Attenborough and Ken Burns for a day! There's also Family and Friends Fishing Charters as well as Full Moon Rising trips. Aqua Creative Studios is a great venue for photo and video shoot productions. We even offer exciting opportunities to Crew on Therapy on Windy-Day sailboat expeditions too! 

  • Irie Vibes :  34' Powerboat ( 6-Guests)
  • Therapy :  43' Sailboat (6-Guests)
  • Tallawah : 20' Powerboat (4-Guests)
  • Half-Day : am or pm (2h, 3h or 4h)
  • All Day (am/pm; pm/Sunset (7.5 h)
  • Sunset  (2.5 h)
  • Night Owl Parties
  • 2-Boat Party , Up to 12-Guests
  • Custom Cruises
  • Kids-Adolescents
  • Romantic Couples

Special Occasions:

  • Anniversaries
  • Mother's Day - May 12th
  • Father's Day - June 12th
  • Decoration Packages

National Events:

  • Blue Angels
  • Island Heritage Days

Corporate Events:

  • Team-Building

Chesapeake Bay Yacht Charters:

  • Storyteller - Natural History
  • Storyteller - Chesapeake History
  • Family and Friends Fishing Trip
  • Windy Day Sailboat Adventure

Aqua Creative Studios:

  • Destinations

Reservations:

  • Marina Location (Maps)

So, click the links to see excursion options and what to expect. Call with questions or just go ahead and book our Half-Day, Full-day and Sunset cruises for Families, Adolescents and Kids, Friend-Get-Togethers and Couples Getaways. We're ideal for Special Occasions – Birthdays, Anniversaries, Bachelorette Parties and Graduations (each with add-on 'Sail-E-Bration' Decoration Package options). We're a private and exclusive charter company, so we're happy to customize your cruise! Call us. Catering options too. We also offer Corporate Retreat and Reward packages. We celebrate National Events: Memorial and Labor Day, July 4th fireworks, Mother's Day, Father's Day, Jamaica Day, Canada Day and honor the Blue Angels display over the Naval Academy during Commencement Week in Annapolis. Book early! We also have special 2-and 3-Boat combinations for up to 12- and 16-Guests for Special Occasion celebrations. Some bookings need you to call us directly (410) 212-4476 to give time to organize. Our Aqua Creative Studios are an innovative venue for music video shoots, fashion photo presentations, video features and personal portfolios - we even have equipment: drones, cameras, models and photographers too. So, no travel hassles, no airport chaos, no traffic, no lines, no exorbitant gas prices - just an all fun-adventure-party. 

ICYC and CBYC are unique on the Chesapeake Bay. We'd love to welcome you aboard. 

Please Review: Booking/Reschedule/Cancellation/Refund Policy - Safety Policy - Weather Policy - Motion Sickness Policy - Smoking/Lighters/Vaping Policy - Alcohol/Food Policy - Bathroom/Down-Below Policy - Black-Soled Shoes Policy - FAQs

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Therapy (Up to 6 guests)

private yacht charter maryland

Irie Vibes ( Up to 6 guests)

romantic-sunset-cruise-charter-annapolis-chesapeake-bay-maryland-thomas-point-light-house-south-river-maryland-boat-charter-rental-baltimore-yacht-captain-sailboat-powerboat-12-twelve-people-overnight-bed-breakfast-annapolis-boat-rental-no-captain

Tallawah (Up to 4 guests)

private yacht charter maryland

2-Boat Raft-Up (Up to 12 guests)

Therapy waits patiently for Spring.....

private yacht charter maryland

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MD Yacht Charters

MD Yacht Charters is a luxury yacht chartering company serving residents, tourist, and a host of professional clientele in the Washington Metropolitan area since 2013. We take great pride in creating amazing and high quality excursions along the Potomac River in DC, Maryland and Virginia for small intimate groups.

Mapped location of MD Yacht Charters

  • Celebrations
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See the Titanic

A captivating journey through the life and legacy of the Titanic, featuring objects and personal artifacts.

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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!

Destinations

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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Select a Yacht or Itinerary

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

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Submit Request

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

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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.

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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: $ - $, annapolis boat rentals: private yacht charters md.

Charter this amazing Jeanneau Sun Odyssey 410

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

Rent a Boat Charter in Annapolis, Maryland with Sailo!

Looking for a boat rental Annapolis, MD? Let's start choosing the right private yacht rental in Annapolis, MD - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.

How to rent a boat in Annapolis, Maryland?

Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!

A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena boat charters and Solomons Island boat rentals .

Sailo concierge team is here to help you rent the perfect private boat charter in Annapolis to go sailing in Maryland. To ask for more details or request special arrangements on your private yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.

Annapolis, MD could be the ideal yachting playground for you

Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.

Top private boat rentals in Annapolis, MD

Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat rentals in Annapolis, MD . Another great choice is a catamaran rental in Annapolis, MD . Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters in Annapolis . Maryland is an excellent place to enjoy a party, so discover our party boat rentals in Annapolis, MD for 13+ guests in Annapolis and see for yourself.

How to find a boat charter in Annapolis, Maryland?

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 boat rental in Annapolis, MD, 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 Annapolis boat charter with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis yacht 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 charter in Annapolis, MD for a day?

Annapolis boat rentals prices vary significantly. You can find great budget friendly private yacht rentals in Annapolis, MD 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.

Can I pay in installments for my Sailo Annapolis boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly yacht charters in Annapolis, MD. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Responsible boating guidelines

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

Popular locations to rent a boat in Maryland

  • boat rental St Michaels, MD
  • boat rental Cambridge, MD
  • boat rental Baltimore, MD
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Yacht Charter Maryland - Yacht Rentals Maryland

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

Yacht Sun Odyssey 389 for rent in Annapolis

Yacht Sun Odyssey 389 for rent in Annapolis

  • Sun Odyssey 389 [Yacht Price incl. Taxes]
  • Barbeque Grill
  • 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 Saona 47 for hire in Port Annapolis Marina

Catamaran Saona 47 for hire in Port Annapolis Marina

  • Saona 47 [Yacht Price incl. Taxes]
  • Outboard engine for dinghy

Yacht Dufour 430 available for charter in Port Annapolis Marina

Yacht Dufour 430 available for charter in Port Annapolis Marina

  • Dufour 430 [Yacht Price incl. Taxes]

Yacht Sun Odyssey 440 available for charter in Port Annapolis Marina

Yacht Sun Odyssey 440 available for charter in Port Annapolis Marina

  • Sun Odyssey 440 [Yacht Price incl. Taxes]

Sailing yacht Jeanneau 58 for rent in Port Annapolis Marina

Sailing yacht Jeanneau 58 for rent in Port Annapolis Marina

  • Jeanneau 58 [Yacht Price incl. Taxes]
  • Skipper (food not included)

Catamaran Astrea 42 for charter in Annapolis

Catamaran Astrea 42 for charter in Annapolis

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

Sailing boat Jeanneau 51 for rent in Port Annapolis Marina

Sailing boat Jeanneau 51 for rent in Port Annapolis Marina

  • Jeanneau 51 [Yacht Price incl. Taxes]

Motor yacht Jeanneau NC 33 available for charter in Port Annapolis Marina

Motor yacht Jeanneau NC 33 available for charter in Port Annapolis Marina

  • Jeanneau NC 33 [Yacht Price incl. Taxes]

Yacht Dufour 390 Grand Large for rent in Annapolis

Yacht Dufour 390 Grand Large for rent in Annapolis

  • Dufour 390 Grand Large [Yacht Price incl. Taxes]

Sailing yacht Catalina 45 for charter in Rock Hall

Sailing yacht Catalina 45 for charter in Rock Hall

  • Catalina 45 [Yacht Price incl. Taxes]

Sailing yacht Catalina 425 for hire in Haven Harbour Marina

Sailing yacht Catalina 425 for hire in Haven Harbour Marina

  • Catalina 425 [Yacht Price incl. Taxes]

Sailboat Oceanis 37 for rent in Rock Hall

Sailboat Oceanis 37 for rent in Rock Hall

  • Oceanis 37 [Yacht Price incl. Taxes]
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Boat Rentals in Maryland, U.S

Home state to the Chesapeake Bay, Annapolis and the city of Baltimore - Maryland in the United States is fast becoming a popular destination for boating. With a selection of sailing boats, catamarans and motorboats available to book online with Yachtico.com . Not to mention you can start your dream vacation in Maryland at a fantastic price.

Located on the Central-east coast of the United States, Maryland is home to stunning scenery and has a great sailing infrastructure. The port of Annapolis is by and large the location to charter from if you are looking for a sailing vacation and avoiding the commercial ships. The beautiful Chesapeake Bay is a favourite amongst sailors, with a diverse natural enviornment and plenty of opportunities to enjoy a fresh catch.

From Maryland, you can charter your sailing boat, catamaran or motorboat in either direction of the American east coastline. To go north, sail south-east around Delaware and venture up to New Jersey as far as New York City for a unique adventure in the big apple. Alternatively, cruise south and discover the bays and ports of Virginia through to Virginia Beach before returning to Maryland.

Whatever you choose to do, Yachtico.com is here to make sure you have a great boating vacation. Check out our great selection and book online today to begin your next trip!

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Rent the best Annapolis luxury yacht charters of 2024

  • Luxury Yacht Charters
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Top Annapolis luxury yacht charters

Rent a Marquis Yachts cruiser in Washington, DC near me

Washington, DC

Luxury Private Yacht at National Harbor MGM

Rent a Meridian Yachts motor yacht in Washington, DC near me

Luxury DC Yacht Charter

Rent a Cruisers Yachts cruiser in Washington, DC near me

Beautiful time for DC Potomac Cruisin’!

Rent a Skipperliner Boats mega yacht in Essex, MD near me

Luxury parties on Maryland party boat

Rent a Endeavour Cat cruiser in Annapolis, MD near me

Annapolis, MD

Sail on the Pintita

Rent a Leopard catamaran in Annapolis, MD near me

ESCAPE--Leopard 43’ Sailing Catamaran

Rent a Sea Ray Boats cruiser in Washington, DC near me

50' Sea Ray Luxury sport Yacht

Rent a Sea Ray Boats motor yacht in Washington, DC near me

VIP Yacht Charters, LLC - Let the adventures begin

Rent a Leopard catamaran in Edgewater, MD near me

Edgewater, MD

LANI - Leopard 43' Catamaran Sailboat

Rent a Other cruiser in Edgewater, MD near me

Sailing Vessel (S/V) DreamCatcher

Rent a Cherry Blossom  other in Washington, DC near me

Cruise in Comfort: Our Authentic Riverboat in Washington for 300 pax!

Rent a Lagoon catamaran in Edgewater, MD near me

STARZ - 2018 Lagoon 42 (3 Cabin / 3 Head)

Rent a Beneteau other in Annapolis, MD near me

DOS MILAGROS - Beneteau Oceanis 45

Rent a National Elite mega yacht in Washington, DC near me

Elevate Your DC Experience: Our Topside Deck, for up to 150 Guests!

Rent a Odyssey DC commercial in Washington, DC near me

A Night of Elegance Awaits: Your Evening on the Water for 600 pax!

Rent a Spirit of Mt. Vernon commercial in Washington, DC near me

"Savor exquisite dining with Washington's scenic backdrop.

Rent a Miss Christin commercial in Washington, DC near me

Create unforgettable memories in Washington, DC.

Rent a Spirit of Washington commercial in Washington, DC near me

Experience DC's spectacular views at sea for Up to 464 Pax!

How to rent a luxury yacht charters in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of luxury yacht charterss.

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.

Boating with Boatsetter

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 luxury yacht charters

Miami

Top luxury yacht charters reviews in Annapolis, MD

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VIP Yacht...

Captain Rod and Myra did an awesome job at making our event so special. Amazingly, they were able to operate during...

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Beautiful time...

Our celebration of my daughter's 50th birthday aboard the boat, A Blast, could not have been more perfect! The...

I booked this boat for my friends bachelorette trip and it was the highlight of the weekend! There is a big speaker...

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LANI - Leopard...

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I had a great time for my birthday on “A Blast”. I was worried about the weather and it possibly raining but there...

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Hands down great boat and great Captain

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We had a fun evening with friends aboard the beautiful A Blast! Prior to the outing, my questions were promptly...

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Luxury DC Yacht...

I actually read all the reviews before booking this boat for my wife’s Birthday and guess what, all the 5 star...

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This was my 2nd time renting the Good Vibes Charter and we are already planning to do it again next year! The yacht...

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ESCAPE--Leopard...

My party and I had an awesome time! The original boat we booked was having trouble and Cap Shawn accommodated us with...

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STARZ - 2018...

Shawn was very accommodating and responsive. The boat was perfect; clean, plenty of functional space for me to host...

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had the best time!! The captain was amazing, the group had so much fun. Would definitely do it again and 100%...

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Luxury Yacht Charters in Annapolis, MD

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private yacht charter maryland

Yacht Charters on the Bay by Watermark

private yacht charter maryland

Enjoy private yacht charters for elegant and fun occasions – corporate, social, weddings and more – from the Inner Harbor on climate-controlled yachts.

  • Air Conditioned
  • Hosts Crab Feast
  • Walk to Water Taxi
  • Music Venue
  • Banquet Hall / Catering Venue
  • Entertainment Venue
  • Events Venue
  • Family Friendly
  • Group Activities
  • Groups Welcome
  • Non-Smoking
  • Preferred Catering List
  • Outdoor Event Space
  • Step-on Guide Service
  • Ticket Sales
  • Outdoor Seating Available
  • Brochures & Guides Available
  • Group Dining
  • Private Dining
  • Will Buyout
  • Alcohol Served

Meetings & Convention Services

  • Special Event & Party Planners
  • Boat Cruises
  • Historic Sites

Tours & Sightseeing

Catering & event facilities.

  • Banquet Facilities
  • Crab Feast Friendly
  • In-House AV
  • Number of Event Rooms: 2
  • Banquet Capacity: 149
  • Reception Capacity: 149
  • Preferred Catering
  • Step-On Guide Services
  • History & Heritage
  • Guided Tours

Transportation

  • Water Transportation

Related Listings

Cool Breeze Sailing Charters llc

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Lady Sarah

Lady Sarah is a custom-built power catamaran designed to escort your guests with style and speed.

Built-in booth seating on the first deck and wide-open spaces on the top deck give you flexible use of the available space. The enclosed, climate-controlled main deck of Lady Sarah features rich tones of dark blue leather and cherry accents, built-in booths for comfortable seating, and a fully stocked bar. The partially covered upper deck has built-in bench seating around the perimeter, as well as comfortable tables and chairs in the center. It’s a beautiful place to enjoy the scenic views of the Chesapeake Bay.

View Lady Sarah’s Floor Plan

Wide-Open Spaces with a Great View

Rainbows can be seen from the deck of Lady Sarah

Reserve Lady Sarah

Gift Certificates - The gift of adventure!

Sail Selina II

Private Dinner Sail

Enjoy a three-course dinner and open bar aboard our yacht with this private dinner sail!

Quick Details

  • Users Occupancy: 4 People Max.
  • Calendar Availability: Daily
  • Anchor Vessel: Clean & Safe

A Private Dinner Sail Charter from St. Michaels

Dine with the wind in your hair on our 44-foot mahogany and brass-adorned yacht! It has plenty of space on deck for a table set with linens and china.

Your private dinner cruise will be catered by the finest restaurants in the area. On this sailboat charter you’ll get to enjoy your choice of Chesapeake Bay crab cakes, mussels, scallops, all kinds of seafood as well as award-winning steaks and lamb. Along with a three-course meal, this sunset cruise also includes an open bar of hand crafted local brewery beers, international wines, or champagne.

Please call for more information so we can properly accommodate your sailboat charter on your personalized private yacht dinner.

If you aren’t planning to spend the night we are only 90 minutes from Philadelphia, Baltimore and Washington D.C. & just 60 minutes from Annapolis.

  • Chevron down What's Included

The following items are included in your dinner sail:

  • Private charter, up to four guests
  • Three-course gourmet dinners
  • Beer, wine, Champagne, bottled water, soda
  • Binoculars, sunscreen, sunglasses
  • Rain jackets, hats, blankets
  • Free parking, seven days a week

Related Sail Boat Tours

  • Calendar Daily
  • User All ages
  • Users 6 People
  • Hour Glass 2 Hours

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

  • Hour Glass Full Day

Full-Day Private Sail

Join us for a full day of sailing (8 hrs) on this boat tour that includes a mini-tour of the St. Michaels harbor before cruising along the Miles River and discovering its hidden coves enjoying the views and wildlife of Chesapeake Bay.

  • Most Popular

2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized boat tour!

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    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 ...

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  10. Event, Wedding and Corporate Yacht Charters

    Add a unique experience to your corporate event and ask us for a full day on the bay trip to St. Michaels, a lighthouse cruise with a live narrator, or cruise with Francis Scott Key. Whether it is cocktails and hors d'oeuvres or a full crab feast on the top deck, a private yacht charter will become your most popular event. Explore Corporate Events

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    Maryland's best chartered yacht vendor offering private charters, wedding yacht charters, corporate and special events. Request a quote for your next event. Watermark. Directions & Parking 410-268-7601 Search. Close Toggle navigation. ... MD, and destination cruises to St. Michaels, Maryland, we work with the region's best vendors to plan ...

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  23. Private Dinner Sunset Cruise

    A Private Dinner Sail Charter from St. Michaels. Dine with the wind in your hair on our 44-foot mahogany and brass-adorned yacht! It has plenty of space on deck for a table set with linens and china. Your private dinner cruise will be catered by the finest restaurants in the area.