We use cookies to improve your browsing experience.
And dolphins make us happy. Find out more about our cookies policy here.
Sailboats
Set sail with these traditional wind-powered boats
$140-$490
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$150-$450
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$840
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$840
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$400
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$200
NW
Nicole
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!
Noelle
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
My group and I had an amazing time! If you’re looking to have a great experience make sure to book with Captain McCoy. The boat was very clean. Getting on board was simple and finding the dock was easy. Also enjoyed stopping in the middle of our trip to just enjoy the weather and laying out on the front of the boat. I’d definitely book again!
KC
Kevin
Charter 42' Lagoon Catamaran in Annapolis, MD
Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!
Ben
41' Lagoon Catamaran in Maryland
Jess was a great captain! We hosted my wife’s 30th birthday party with Jess and it was a great time! His catamaran fit all 12 of us with no problem. He was attentive to the things she wanted to do and was knowledgeable about the area. We had a awesome day on the water with Captain Jess. Would definitely go again!
Alex
41' Lagoon Catamaran in Maryland
Jess was an amazing captain with a gorgeous boat. We had a group of ten women and Jess was so friendly but also gave us our privacy. He offered to take us swimming, but we opted to ride along the bay instead. While it’s an expensive excursion, it’s worth every penny and I will definitely reach out to jess again in the future. I highly recommend!!
Gina
41' Lagoon Catamaran in Maryland
Captain Jess, the catamaran, the outing, the sights, all of it EXCEEDED our group’s expectations (which were already high going in)!! We immediately felt comfortable and secure in Captain Jess upon initial meeting (especially because he quickly outlined safety rules first - green flag!) and the hours out on the water became the highlight of my sister’s bachelorette weekend - we will be forever grateful!
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
December 11, 2019
Read Article
August 24, 2023
Read Article
April 10, 2020
Read Article
December 30, 2019
Read Article