We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

Find Sailing Charters Near You

4.9(Average of 4,092 reviews in this area)
Get set to boat with the GetMyBoat Guide to sailing
1 - 24 of 240 listings
Sip and Sail D.C.Sailing in Potomac River · 6 guests

Sip and Sail D.C.

New
$700hour
SpeedBoat | $275 Hr | 10 PeopleEvents in Potomac River · 10 guests

SpeedBoat | $275 Hr | 10 People

New
Superowner
$275hour
22' Sea Ray Powerboat for 6 people in Washington, District of ColumbiaPowerboats in Potomac River · 6 guests

22' Sea Ray Powerboat for 6 people in Washington, District of Columbia

5.0
$155hour
Regal 36ft Luxury Yacht | $350 | 7 peopleEvents in Potomac River · 7 guests

Regal 36ft Luxury Yacht | $350 | 7 people

New
Superowner
$350hour
Double Deckers Boat | $450 HR | 14 PeopleEvents in Potomac River · 14 guests

Double Deckers Boat | $450 HR | 14 People

New
Superowner
$450hour
Brand new Bayliner DX2200 Boat Rental in Baltimore, MarylandPowerboats in Potomac River · 8 guests

Brand new Bayliner DX2200 Boat Rental in Baltimore, Maryland

5.0
$200hour
"Imi Ola" Seawind 1260Events in Potomac River · 12 guests

"Imi Ola" Seawind 1260

5.0
Superowner
$716hour
Seawind 1260 Cruising Catamaran Rental in Little Harbour, BahamasSailing in Potomac River · 6 guests

Seawind 1260 Cruising Catamaran Rental in Little Harbour, Bahamas

5.0
$1,200day
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Severna Park MarylandEvents in Potomac River · 12 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Severna Park Maryland

New
$1,100hour
Charter this 42ft Sailboat in Edgewater, Maryland for upto 6 persons and sail on beautiful Chesapeake Bay and beat inflation.  Same prices this year as last!!Sailing in Potomac River · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for upto 6 persons and sail on beautiful Chesapeake Bay and beat inflation. Same prices this year as last!!

5.0
$150hour
Charter 44' Orana Cruising Catamaran In Deale, MarylandSailing in Potomac River · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
41' Lagoon Cruising Catamaran in Maryland, United StatesSailing in Potomac River · 12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

5.0
Superowner
$349hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USASailing in Potomac River · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
$150hour
Cruising Monohull Sailing from Downtown Annapolis! Sunsets, daysails and stargazing!Sailing in Potomac River · 6 guests

Cruising Monohull Sailing from Downtown Annapolis! Sunsets, daysails and stargazing!

New
$250hour
Beneteau 41ft Sailing Charter in Annapolis, MarylandSailing in Potomac River · 8 guests

Beneteau 41ft Sailing Charter in Annapolis, Maryland

5.0
$200hour
Annapolis Sailing a 34' Beneteau Sloop! SEVERN RIVER & Chesapeake BAYSailing in Potomac River · 6 guests

Annapolis Sailing a 34' Beneteau Sloop! SEVERN RIVER & Chesapeake BAY

5.0
$150hour
Get away for a day or weekend! Charter 44' Catalina Sailboat!Sailing in Potomac River · 6 guests

Get away for a day or weekend! Charter 44' Catalina Sailboat!

5.0
$490day
34ft Sailing Yacht in Annapolis, MarylandSailing in Potomac River · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
Sailing Charter with USCG Licensed CaptainSailing in Chesapeake Bay · 6 guests

Sailing Charter with USCG Licensed Captain

5.0
$899day
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, MarylandSailing in Chesapeake Bay · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United StatesSailing in Chesapeake Bay · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.5
$220night
Charter 41ft S/Y Selina II Sloop in St. Michaels, MarylandSailing in Chesapeake Bay · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$349hour
Sunset Champagne Cruise on the Chesapeake BaySailing in Chesapeake Bay · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$399hour
41’ Bristol Sailboat Charter in Solomons Island, MDSailing in Potomac River · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90hour

Top Destinations Nearby

Local Sailing Reviews

  1. AW
    Alan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Perfect for a few hours or the whole day. The captain made it easy as he knew all the trick of the area so we just needed to sit back and enjoy or man the helm to steer Down wind is the perfect time for light fair and another beverage. We will keep Capt Albert on our short list if we want to get away for an after noon Thanks Alberto

  2. VF
    Vanessa
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We loved our day with Alberto and Grace! A great boat, and such a fun outing on the water. Even with lighter wind today, we had an amazing time. Alberto was helpful and responsive in our initial communications and planning. We would absolutely head back out with Captain Alberto again. Thank you!

  3. Janessa
    Janessa
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    We had a wonderful experience chartering Jim’s sailboat over Labor Day weekend. Jim was very accommodating, walking through the boat with us and making sure everything was in great shape before we began our charter. We sailed from Rock Hall to Annapolis and back, spending two nights aboard Icarus. His upgrades to the boat really helped make it easier to sail and more comfortable to relax in, and Jim was always readily available if we had any questions. Could not recommend this more highly, and we don’t think there’s a better charter out there for the price in the Chesapeake.

  4. sD
    shirley
    41' Lagoon Cruising Catamaran in Maryland, United States

    We were so lucky with the weather to enjoy a beautiful sunset birthday cruise. Captain Jesse was easy going and the boat was equipped and easy to set up with the food we brought. We were a party of 10 ladies ages 40-84y. It was smooth sailing and fun!

  5. MC
    Matthew
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto and his wife were super hosts for us today. We had a wonderful time, it was easy to get to and on the boat, got to pull some lines and steer the boat. Good stories and sailing pointers as well! It was a beautiful day with the right amount of sun and wind! Best way to celebrate my 40th Birthday! thanks so much Capt!

  6. JD
    Jamie
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Alberto and his wife were absolutely awesome with our sailing experience. Even in bad weather they made the best of it!!

Boating Guide - Sailing

Set sail with GetMyBoat - enjoy a sailing charter.

Hit the open water in style on a sailing charter. Sailing charters with a professional captain are a relaxing way to get on the water and travel by wind power. A sunset sailing cruise, cocktail cruise, or other sailing adventure can make for the perfect experience on a lake or the ocean. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. GetMyBoat has all types of sailing charters and you can build a custom itinerary to plan the sailing holiday of your dreams. From hourly, half-day, full-day or overnight sailing excursions, you are sure to create memories that will last a lifetime.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Things to consider when booking a sailboat rental or charter.

  • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
  • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
  • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

GetMyBoat has 240 listings for Sailing experiences in this location with 4,092 reviews.

Search Sailing