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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
Sailboats
Set sail with these traditional wind-powered boats
$150-$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
Danika
Charter 44' Orana Cruising Catamaran In Deale, Maryland
We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!
JH
Jennifer
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!
AN
Ashley
Experience the Serenity of Sailing SV Magic
We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!
GE
Gerard
Experience the Serenity of Sailing SV Magic
Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.
WC
Whitney
Experience the Serenity of Sailing SV Magic
We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!
WB
Winnie
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!
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!