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All listings in Maryland

Incredible sailboat rentals in Maryland, United States.

5.0

(367 Reviews)

Page 1 of 2 • 26 listings

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$100+/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

$425/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 · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

$400+/hour

Sailing in Essex · 6 guests

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

5.0

$150/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 Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0

$1,100/hour

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/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 Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New

$400/hour

Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New

$100/hour

Sailing in Washington · 6 guests

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

New

$280/hour

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

ML
Martha

50ft Catamaran Charter with Water Toys - Annapolis, MD
We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!
CR
Chawin

38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.
AP
Andrea

38-ft Hunter 376 Sailing Adventure in Annapolis
This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!
Elisabeth

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️
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.