Ocean Pines Boat Tours

The best out of 32 boat tours in Ocean Pines - enter dates to check availability

Ocean Pines Boat Tours

32 boats available

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Top Boat Tours in Ocean Pines

Ocean Pines: 32 boats available

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Listing image
Pilothouse silhouette
25 ft
Up to 4 people
5.0
/5
(1 review)
Bishopville (15 min drive from Ocean Pines)
Set sail with Captain Skip Maisel for an unforgettable cruising experience along the breathtaking waters of Fenwick Island and Ocean City! Whether you're looking for a relaxing day on the water, scenic coastal views, or a customized cruise to explore

"We could not have asked for a better experience. This was our first time using BoatBooker and our captain was incredible." —⁠ Maureen,
+1
trips from
US $400
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Aluminum fishing silhouette
24 ft
Up to 6 people
Ocean Pines
Magic Bowfishing is a rugged and versatile 2020 Long Beach Custom Boats 2480 Aluminium Fishing vessel, perfectly designed for action-packed days on the water in Ocean Pines.
+1
trips from
US $500
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Bay boat silhouette
28 ft
Up to 6 people
5.0
/5
(4 reviews)
Fenwick Island (6.3 miles from Ocean Pines)
Step aboard the ultimate "SUV of the Seas" for an unforgettable private charter tailored entirely to your group! Boat Bayside is a stunning 2023 Axopar 28 Cabin—a sleek, award-winning Scandinavian masterpiece that perfectly blends modern l

"We had an incredible time on the boat ride. The captain was absolutely amazing, friendly, professional, and made everyone feel comfortable throughout the trip." —⁠ Hawanatu,
+1
trips from
US $649
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Skiff silhouette
24 ft
Up to 13 people
5.0
/5
(1 review)
Ocean City (5.1 miles from Ocean Pines)
Discover Ocean City from a whole new perspective with 5 STAR Charters Tours & Taxi! This spacious 24 ft USCG-inspected Carolina Skiff can comfortably accommodate up to 13 guests, making it perfect for families, friends, or group outings.

"Captain Brandon gave us a wonderful boat trip and was very accommodating with our family." —⁠ Kathleen,
trips from
US $375
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Center console silhouette
25 ft
Up to 6 people
5.0
/5
(9 reviews)
Ocean City (18 min drive from Ocean Pines)
Welcome aboard "Saltwater Adventures" with your host Capt. Tony Battista. The boat is a custom 25' center console that was built right here in West Ocean City and was launched in 2017.

"The captian was very friendly making us all comfortable immediately." —⁠ Bryanna,
trips from
US $298
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Pontoon silhouette
30 ft
Up to 6 people
4.4
/5
(12 reviews)
Ocean City (21 min drive from Ocean Pines)
Join us for an unforgettable day on the water, where every moment is designed to create lasting memories.

"I normally don’t leave reviews unless an experience is either exceptionally good or exceptionally bad, and thankfully this one falls into the first category." —⁠ Kennedi,
trips from
US $275
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Bay boat silhouette
22 ft
Up to 4 people
5.0
/5
(1 review)
Ocean City (17 min drive from Ocean Pines)
Experience the ultimate adventure on the water aboard the 2017 Bulls Bay Bay Boat, fully restored in 2025 and based out of Ocean City.

"Captain Dennis was early and assisted me in getting to the marina." —⁠ Jeff,
+4
trips from
US $300
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Panga silhouette
23 ft
Up to 4 people
Ocean City (5.2 miles from Ocean Pines)
Step aboard the “Wedgie²”, a 2007 Panga Marine Marquesas based in Ocean City, captained by Chris Tilghman.
+3
trips from
US $200
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Center console silhouette
28 ft
Up to 6 people
5.0
/5
(1 review)
398 external reviews
Ocean City (17 min drive from Ocean Pines)
Set sail on a memorable adventure aboard the Coastal Guide Service LLC Bay Cruising, a 2001 Dusky 28 Center Console based out of Ocean City.
+3
trips from
US $280
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Pilothouse silhouette
40 ft
Up to 6 people
4.9
/5
(146 external reviews)
Ocean City (17 min drive from Ocean Pines)
Fish Finder Adventures LLC invites you to an unforgettable day on the water aboard a classic 1986 Gary Davis Custom Pilothouse.
trips from
US $650

Frequently Asked Questions about Boat Tours in Ocean Pines

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Boating in Ocean Pines

Discover Ocean Pines, Maryland, a laid‑back gateway to smooth, scenic waterways perfect for relaxed cruising and family‑friendly adventures. With calm inshore conditions and tree‑lined channels, Ocean Pines boating charters are ideal for first‑time renters, multigenerational groups, and anyone seeking easygoing time on the water without the ocean swells.

From sunrise outings to golden‑hour returns, you’ll enjoy gentle routes that wind past quiet shorelines and bird‑rich marsh edges. Anglers appreciate the sheltered waters for light‑tackle action, while leisure‑seekers favor pontoons for picnics, sandbar stops, and photo‑worthy views. Kayak and paddle craft lovers find glassy stretches for unhurried exploring, and small powerboats make it simple to cover more ground in a single trip.

Close to the energy of nearby beach towns yet blissfully peaceful on the water, Ocean Pines offers an inviting mix of convenience and calm. Well‑placed launch points, fuel docks, and transient slips make planning straightforward, and protected conditions mean more cruising time and fewer weather delays. Whether you’re mapping a short loop with kids or a longer day of casting and cove hopping, routes are intuitive and rewarding.

Choose Ocean Pines boating charters for smooth sailing, easy navigation, and coastal charm—an accessible destination where relaxed itineraries, wildlife spotting, and memory‑making moments come naturally. It’s the perfect starting point for boaters who want the shore’s best views without the hurry.

What people said about boating in Ocean Pines

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How people rated boat trips in Ocean Pines

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Nearby Boating Destinations

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