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The Best Boat Tours in Annapolis
Browse, book, and get out onto the water with local experiences.
Suggested Searches
Types of Boats Popular in Annapolis
Sailboats
Set sail with these traditional wind-powered boats
$145-$1,775
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$50-$1,925
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$65-$400
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$350
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$350
Kayaks
Who says you need a motor to have fun on the water?
$425-$450
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$150
Top Boat Tour Locations Near Annapolis
Recent Reviews in Annapolis
EB
Ernest
Private Yacht Charter: On 40ft Regal Commodore
GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.
Abigail
Private Yacht Charter: On 40ft Regal Commodore
Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.
Jordan
50ft Catamaran Charter with Water Toys - Annapolis, MD
Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!
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!
AH
Angela
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!
NC
Nick
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Bill was terrific at helping me learn more about handling a 42' sailboat. I'm trying to get more experience in preparation for taking a bareboat charter, and Bill's experience and mentorship was terrific. I look forward to booking with Bill again in the future.
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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Real reviews from happy Getmyboaters.
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