Ocean Pines Boat Tours

The best out of 29 boat tours in Ocean Pines - enter dates to check availability

Ocean Pines Boat Tours

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Top Boat Tours in Ocean Pines

Ocean Pines: 29 boats available

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25 ft
Up to 4 people
Lost Sailor Guide Service LLC
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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24 ft
Up to 6 people
Magic Bowfishing
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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28 ft
Up to 6 people
Private Luxury Bay Tour (Max 6)
5.0
/5
(9 reviews)
Fenwick Island (6.3 miles from Ocean Pines)
Boat Bayside invites you aboard our award-winning 2023 Axopar 28 Cabin—a sleek Scandinavian masterpiece designed for first-class comfort and high-performance thrills.

"Perfect for our small group, we were looking for a sunset cruise for just us!" —⁠ Annette,
+1
trips from
US $750
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24 ft
Up to 13 people
5 STAR Charters Tours & Taxi
5.0
/5
(6 reviews)
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.

"Not sure ehat to expect, the Sand Bar trip with Capt. Brandon was the highlight of the week." —⁠ Chris,
trips from
US $375
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30 ft
Up to 6 people
Day on the Bay Charters
4.5
/5
(16 reviews)
Ocean City (5.8 miles 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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25 ft
Up to 6 people
Saltwater Adventures Ocean City - Maryland
5.0
/5
(13 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.

"We had a wonderful day in OC! We visited a local sandbar and saw sea birds, horseshoe crabs, and other sea life." —⁠ Jessica,
trips from
US $298
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22 ft
Up to 4 people
A Dare Inshore
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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23 ft
Up to 4 people
Captain Tilly OC Charters – Wedgie²
5.0
/5
(1 review)
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.

"Family had a great crab adventure today!!  Highly recommended!" —⁠ Fran,
+3
trips from
US $200
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28 ft
Up to 6 people
Coastal Guide Service LLC Bay Cruising
5.0
/5
(2 reviews)
423 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.

"Capt and mate were very nice and accommodating." —⁠ Mark,
+3
trips from
US $280
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31 ft
Up to 6 people
Just a toy charter
Ocean City (5.5 miles from Ocean Pines)
Experience the thrill of the open waters aboard Just a Toy, a 2020 Century 3000 Center Console, expertly restored in 2024, and based out of Ocean City.
trips from
US $300

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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