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All listings in Maryland

Incredible sailboat rentals in Maryland, United States.

5.0

(359 Reviews)

Page 1 of 2 • 27 listings

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$138+/hour

Instant Book

Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0

Superowner

Best of 2025

$800/hour

Instant Book

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0

$325/hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

$150/hour

Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0

$150+/hour

Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

5.0

$150+/hour

Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0

$250+/hour

Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0

$400+/hour

Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0

$250+/hour

Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0

$185/hour

Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0

$150/hour

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/hour

Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0

$1,100/hour

Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0

$325/hour

Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0

$150+/hour

Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New

$250+/hour

Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New

$350/hour

Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New

$232+/hour

Sailing in Annapolis · 13 guests

Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

New

$350+/hour

Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New

$100/hour

Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New

$400/hour

Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New

$280/hour

Instant Book

Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New

$298/hour

Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New

$90/hour

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Sailing Reviews in Maryland

Lisa

38-ft Hunter 376 Sailing Adventure in Annapolis
Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.
Kasie

38-ft Hunter 376 Sailing Adventure in Annapolis
Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.
Bobby

38-ft Hunter 376 Sailing Adventure in Annapolis
We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!
ES
Emil

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Capt. Joe gave us a wonderful afternoon! He is friendly, knowledgable, and fun! The boat is perfect for cruising around the Bay. Lots of space to lay out and clean facilities downstairs. An excellent value!
LP
Laura

38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!
AS
Abhishek

Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!
Great trip. Capt Bill and his crew provided us with an amazing time aboard their vessel.