Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Map View

All listings in Chesapeake Bay

Incredible sailboat rentals in Chesapeake Bay, United States.

5.0

(395 Reviews)

Page 2 of 2 • 37 listings

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

New

$400+/hour

Sailing in Annapolis · 13 guests

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

New

$350+/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 Annapolis · 20 guests

Sail the Sea on the Pintita

New

$500+/hour

Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New

$232+/hour

Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New

$400/hour

Sailing in Deltaville · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New

$524+/day

Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New

$298/hour

Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New

$925/day

Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

New

$1,100/hour

Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New

$90/hour

Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New

$250/hour

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0

Snoozed - Active 03 Jun 2025

Sailing Reviews in Chesapeake Bay

Jordan

50ft Catamaran Charter with Water Toys - Annapolis, MD
Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!
DW
Dominique

50ft Catamaran Charter with Water Toys - Annapolis, MD
Amazing experience! Amazing, professional crew! It was very easy to book from the beginning. We had an amazing time! Group of 12.
JM
Josephine

50ft Catamaran Charter with Water Toys - Annapolis, MD
I will charter the boat over, and over again because of their warm hospitality. I will recommend them to everyone
Angela

50ft Catamaran Charter with Water Toys - Annapolis, MD
Amazing! Fun! Professional, Great value for the money paid. One of the best ever! Coming back soon.
EM
Esha

50ft Catamaran Charter with Water Toys - Annapolis, MD
The boat was fabulous, the crew was so attentive, and my family and friends had an amazing time.
CS
Camilla

50ft Catamaran Charter with Water Toys - Annapolis, MD
The crew was very attentive, very friendly and provide us with a great experience!