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03/30/2024 ± 1 day

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All listings in Annapolis

Great sailboat rentals near Annapolis, Maryland.

4.9

(371 Reviews)

Page 1 of 1 • 17 listings

Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0

Superowner

Best of 2023

$390hour

Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0

Superowner

Best of 2023

$138-$150hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

Superowner

$150hour

Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8

$165hour

Sailing in Mayo · 6 guests

The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

5.0

$175hour

Sailing in Rock Hall · 4 guests

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

4.5

$275-$375night

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$400hour

Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0

$2,600day

Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0

$150hour

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New

$400hour

Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New

$175person

Sailing in Saint Michaels · 6 guests

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

5.0

$250-$349hour

Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0

$150hour

Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New

$500-$750hour

Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New

$55person

Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New

$298hour

Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New

$250hour

Top Destinations Nearby

Sailing Reviews in Annapolis

KC
Kevin
April, 2024
Charter 42' Lagoon Catamaran in Annapolis, MD
Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!
KC
Kevin
April, 2024
41' Lagoon Catamaran in Maryland
Captain Jess was fantastic! Great experience!
Ben
August, 2023
41' Lagoon Catamaran in Maryland
Jess was a great captain! We hosted my wife’s 30th birthday party with Jess and it was a great time! His catamaran fit all 12 of us with no problem. He was attentive to the things she wanted to do and was knowledgeable about the area. We had a awesome day on the water with Captain Jess. Would definitely go again!
Alex
May, 2023
41' Lagoon Catamaran in Maryland
Jess was an amazing captain with a gorgeous boat. We had a group of ten women and Jess was so friendly but also gave us our privacy. He offered to take us swimming, but we opted to ride along the bay instead. While it’s an expensive excursion, it’s worth every penny and I will definitely reach out to jess again in the future. I highly recommend!!
Gina
October, 2022
41' Lagoon Catamaran in Maryland
Captain Jess, the catamaran, the outing, the sights, all of it EXCEEDED our group’s expectations (which were already high going in)!! We immediately felt comfortable and secure in Captain Jess upon initial meeting (especially because he quickly outlined safety rules first - green flag!) and the hours out on the water became the highlight of my sister’s bachelorette weekend - we will be forever grateful!
sD
shirley
August, 2022
41' Lagoon Catamaran in Maryland
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!