We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$210-$945
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$150-$400
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$65-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$600
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$600
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$105
Kayaks
Who says you need a motor to have fun on the water?
$65
DC
Donte
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!
Marie
38-ft Hunter 376 Sailing Adventure in Annapolis
We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!
Sam
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.
MR
Matt
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!
hg
hunter
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!
DD
Danuta
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!
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
Read Article
October 03, 2022
Read Article
August 12, 2021
Read Article
July 19, 2021
Read Article
December 30, 2019
Read Article
December 26, 2019
Read Article