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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$170-$785
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$500
Kayaks
Who says you need a motor to have fun on the water?
$125-$325
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$150
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
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!
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!
AP
Andrea
38-ft Hunter 376 Sailing Adventure in Annapolis
Here’s what I have for a review for our incredible day on the Bay. Feel free to add or make Our experience with Captain Alberto was nothing short of amazing. From start to finish, he was incredibly kind, extremely knowledgeable, and highly professional. We not only enjoyed breathtaking views of the Chesapeake Bay, but we also had the opportunity to learn a great deal about the physics of sailing—thanks to Captain Alberto's expertise. One of the highlights of our trip was when Captain Alberto allowed us to take turns at the helm. It was an exhilarating experience to steer the boat under his guidance, making us feel like true sailors. His patience and clear instructions made it easy for us to confidently handle the boat, adding a personal and interactive element to the voyage that we greatly appreciated. The weather couldn’t have been more perfect, with clear skies and gentle winds that made for a serene and enjoyable trip. The views were extraordinary, offering us a stunning panorama of the Bay that we'll never forget. But what truly made this experience exceptional was Captain Alberto himself. His warm personality and deep understanding of sailing were the phenomenal icing on the proverbial cake. We highly recommend sailing with Captain Alberto. Whether you're a seasoned sailor or a complete novice, you're guaranteed to have an unforgettable experience!
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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