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Page 1 of 1 • 24 listings
52
Baltimore
Maryland
55
Annapolis
Maryland
8
Selby-on-the-Bay
Maryland
120
Washington
District of Columbia
30
Arlington
Virginia
7
Oxon Hill
Maryland
13
Fort Washington
Maryland
165
Potomac River
United States
10
Cape May
New Jersey
8
Wildwood
New Jersey
8
Lake Anna
Virginia
209
Chesapeake Bay
United States
8
Long Beach Island
New Jersey
7
Berkeley Township
New Jersey
17
Toms River
New Jersey
11
Brick
New Jersey
17
Brielle
New Jersey
8
Belmar
New Jersey

Rudolf
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Charles and his wife are amazing people who went above and beyond to offer us an amazing sailing experience all while teaching us about the various aspects of boating life. Book them for your next adventure, you won’t be disappointed.
CM
Caleb
2020 Misty Harbor Pontoon (Tritoon) for 12 people in Annapolis Area
Immaculate boat. Phillip communicated quickly, consistently, and clearly. His boat is well maintained and runs well. We were eight adults and three children and had plenty of space to sit. Beautiful day on the Chesapeake Bay left us wanting a longer trip next time!
CT
Catherine
Private Captained Annapolis Harbor Cruise – Sunrise, Sightseeing, Sunset
Stephen was a very professional and accommodating tour guide! We had a lovely time exploring some of the inner coves on Annapolis on the dinghy that you wouldn’t be able to see on foot. Stephen was very timely and communicative—answering any questions you may have and making sure you have a great experience. If you’re looking for an excursion just to get on the water, I would highly recommend!

Susan
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
This was a perfect sailing experience. The boat is immaculate, comfortable and beautiful. Captain Joe is incredibly knowledgable and fun! Everyone should get a chancw to experience this!!!!
BF
Barb
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Highly recommend sailing with Captain Charles on the Optimystic! Was like hanging out with an old friend. Beautiful boat and fun time!
JB
Jada
42ft Party Yacht Best of Baltimore 2024-25 Winner!
Captain Brian was amazing! He was so helpful, professional, and made sure everything went smoothly for me and my guests. The weather was perfect, and he was very accommodating to make sure we had the best experience possible. We had so much fun out on the water! I truly appreciate how easy and enjoyable he made the whole trip. It was such a fun and memorable experience I’m definitely looking forward to booking again and would absolutely recommend anyone to book with him.