Annapolis Boat Tours
The best out of 20 boat tours in Annapolis - enter dates to check availability
23 ft
Up to 10 persons
Just added to our fleet
Annapolis
Whether you're looking to sail past the historic D.C. monuments, enjoy crabs in Annapolis, or hit the lively waterfronts of Baltimore and Middle River, this versatile 10-seater pontoon is your ultimate ticket to the DMV’s best waterways.
Trips from
US $500
32 ft
Up to 6 persons
4.8
/5
(39 external reviews)
Edgewater (24 min drive from Annapolis)
Step aboard Tight Times Charters, a beautifully restored 1990 Kencraft Challenger Pilothouse, now better than ever after a 2023 upgrade. Departing from Edgewater, this versatile vessel welcomes up to six guests for memorable adventures on the water.
Trips from
US $400
46 ft
Up to 28 persons
5.0
/5
(3 reviews)
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39 external reviews
Edgewater (24 min drive from Annapolis)
Embark on an unforgettable maritime adventure with Hot Pursuit Charter Fishing LLC! Based in beautiful Edgewater, our 1993 Markley Custom vessel is your ticket to an exhilarating day on the water.
"The captain couldn’t have been more accommodating. We booked this boat for a family gathering and celebration of life for a deceased loved one." — Carolyn,
"The captain couldn’t have been more accommodating. We booked this boat for a family gathering and celebration of life for a deceased loved one." — Carolyn,
Trips from
US $450
45 ft
Up to 38 persons
Shady Side (38 min drive from Annapolis)
Experience an unforgettable adventure aboard Bay Hunter Charters, a spacious and well-equipped 45ft Downeast vessel based in Shady Side.
Trips from
US $300
42 ft
Up to 6 persons
Shady Side (38 min drive from Annapolis)
Set sail with Hallocks Grace Charters aboard the stunning 2002 Provincial 42 Downeast, docked in Shady Side, and experience the perfect blend of luxury, comfort, and adventure.
Trips from
US $700
54 ft
Up to 6 persons
5.0
/5
(2 reviews)
Stevensville (19 min drive from Annapolis)
Climb aboard Burton Charters, Inc., a sleek and spacious 2000 Sea Ray 540 Cruiser, and experience the Chesapeake Bay in comfort and style.
"Jim, James and Kimberly were amazing. Everything was perfect…amazing boat, safe and friendly crew and a perfect tour of the lighthouse." — Brandy,
"Jim, James and Kimberly were amazing. Everything was perfect…amazing boat, safe and friendly crew and a perfect tour of the lighthouse." — Brandy,
Trips from
US $2,000
45 ft
Up to 6 persons
Just listed
Arnold (5.7 miles from Annapolis)
Set sail with Annapolis Host & Sailing Adventures aboard a beautifully restored 1987 Hylas 45 Sailing yacht (refit in 2025), departing from Arnold.
Trips from
US $300
35 ft
Up to 6 persons
5.0
/5
(50 external reviews)
Rock Hall (1 hr 17 min drive from Annapolis)
Step aboard Rowe Boat Sportfishing & Excursions, a beautifully restored 1990 Markley Pilot House Downeast, offering the perfect blend of classic charm and modern comfort.
Trips from
US $700
41 ft
Up to 6 persons
Baltimore (51 min drive from Annapolis)
Set sail aboard the Ditch Hag, a beautifully restored 1980 Gene Travers 41ft Chesapeake Deadrise Downeast, based out of Baltimore.
Trips from
US $500
48 ft
Up to 17 persons
4.8
/5
(239 external reviews)
Deale (33 min drive from Annapolis)
Step aboard Lucky Strike Charters, a spacious and stable 2007 Markley 48 Bay boat based out of Deale, perfect for unforgettable group adventures.
Trips from
US $550