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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$785
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$60-$245
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$75-$500
Kayaks
Who says you need a motor to have fun on the water?
$75-$325
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$280
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$350
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$150
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!
George
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)
SW
Stacie
38-ft Hunter 376 Sailing Adventure in Annapolis
Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!
Cliff
38-ft Hunter 376 Sailing Adventure in Annapolis
I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing
AM
Aleisha
38-ft Hunter 376 Sailing Adventure in Annapolis
BOOK WITH CAPTAIN ALBERTO!! I mean this was the BEST thing experience I had all summer. He accommodated our needs, let us have fun, and taught us soo much during the process. Captain Alberto just had the best hospitality that I’ve seen in a long time. As a first-time boat goer, he made me feel so comfortable and welcomed! I will definitely be back and will rebook with captain Alberto. I mf you are looking through boat options and stumble on this, this is your sign to book with him!
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!