Shady Side Boat Tours
The best out of 21 boat tours in Shady Side - enter dates to check availability
45 ft
Up to 38 people
Shady Side
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 people
Shady Side
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
46 ft
Up to 28 people
5.0
/5
(5 reviews)
Edgewater (21 min drive from Shady Side)
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.
"We booked Don and the Hot Pursuit for a corporate boating event to watch the Blue Angels." — Denise,
"We booked Don and the Hot Pursuit for a corporate boating event to watch the Blue Angels." — Denise,
trips from
US $500
32 ft
Up to 6 people
4.8
/5
(39 external reviews)
Edgewater (20 min drive from Shady Side)
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
48 ft
Up to 17 people
4.8
/5
(242 external reviews)
Deale (10 min drive from Shady Side)
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
45 ft
Up to 6 people
Arnold (15.2 miles from Shady Side)
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 $350
32 ft
Up to 6 people
5.0
/5
(3 reviews)
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159 external reviews
Bozman (1 hr 38 min drive from Shady Side)
Step aboard Screaming Eagle Charters—a classic 2010 Trojan Sportfish ready to show you the best of Neavitt and the Chesapeake Bay! With room for up to 6 guests, this well-equipped vessel is powered by a reliable 380HP Cummins diesel inboard and crui
"We were looking for people who new the area well, and this was the right team." — Leigh,
"We were looking for people who new the area well, and this was the right team." — Leigh,
trips from
US $400
54 ft
Up to 6 people
5.0
/5
(2 reviews)
Stevensville (44 min drive from Shady Side)
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
23 ft
Up to 10 people
Just added to our fleet
Annapolis (9.4 miles from Shady Side)
Cruise the iconic waterways of the DMV in style aboard Floating Kneads Charters – DMV Waterways, a luxurious 2023 Harris Breeze Pontoon designed for unforgettable experiences on the water.
trips from
US $500
35 ft
Up to 6 people
5.0
/5
(50 external reviews)
Rock Hall (1 hr 43 min drive from Shady Side)
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