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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$45-$150
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$325
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$115
Fishing Charters
Let a captain do the driving while you do the fishing
$115
Dennese
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!
BF
Bruce
38-ft Hunter 376 Sailing Adventure in Annapolis
Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!
TM
Tom
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!
BD
Bisola
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Lovely experience, James was really patient and understanding. Boat was clean and had everything we needed. 10/10 experience will definitely book again.
KM
Kelley
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
If you’re looking for a unique and fun way to celebrate a special occasion, or just want to take advantage of the beautiful weather and get out on the water, this is it! I booked a Sunday afternoon trip with friends to celebrate my 36th birthday and it absolutely exceeded my expectations. Captain James was communicative and professional leading up to the trip; he’s a skilled captain and a joy to be around. His catamaran is clean and safe, and equipped with everything you could need, including a sound system and bumpin’ playlist! I will absolutely be booking with him again.
JW
Jessica
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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