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Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$65
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$165
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90
Fishing Charters
Let a captain do the driving while you do the fishing
$90
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.
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!
SD
Shaunak
Chicago's Largest Chartered Catamaran!
Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!
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!