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Popular Sunset & Dinner Cruises Charters in Assateague Island  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sunset & Dinner Cruises in Assateague Island- BoatBooker

Assateague Island

Assateague Island, United States

assateague-island

Enjoy 2 relaxing hours on the water. Make it a booze cruise, a dolphin-watching trip, or whatever you’d like. Tell us what you'd like to do.

United States

Day on the Bay Charters

Ocean City

Join us for an unforgettable day on the water, where every moment is designed to create lasting memories. Whether you&#8217;re in the mood for a lively daytime booze cruise, a serene sunset sail, or a festive evening tour of Christmas lights on the bay, w

Explore the bay aboard the Stella Marie..

Running Tide Charters

Step aboard Running Tide Charters and experience Ocean City like never before! This versatile 2001 World Cat 246SF Center Console is built for both adventure and relaxation. Accommodating up to six guests, it&rsquo;s powered by dual 150 HP Yamaha outboard

Enjoy a relaxing sunset cruise through the beautiful back bays, visiting local hotspots after the rush. Unwind as you take in the evening views, and if desired, dinner drop-offs can be arranged through the captain.

A Dare Inshore

Experience the ultimate adventure on the water aboard the 2017 Bulls Bay Bay Boat, fully restored in 2025 and based out of Ocean City. Perfect for up to four guests, this sleek vessel is powered by a powerful 150 HP Suzuki outboard engine, allowing you to

No need to fight the crowd and sand in your shoes. Come out and enjoy the exhilarating Ocean City Air Show from the boat! Depending on weather conditions and guests' preferences, you can experience the spectacular event from the ocean, the back bay, or the sandbar. 
What to Bring
--BYOB feel free to bring your own beverages (NO GLASS PLEASE)
--Food/snacks
--Towel
--Small cooler. There is a cooler on board; you are welcome to use
There is only one slot available per day due to show times, so don't miss out

Coastal Guide Service LLC Bay Cruising

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. Perfect for groups of up to six guests, this sleek vessel offers both comfort and performance, powered by a 300 HP

Experience Ocean City’s beauty on a sunset cruise with Nanticoke Outfitters! Enjoy calm waters, breathtaking views, and a relaxing ride through scenic back bays. Perfect for families, couples, or friends, our private small group cruises offer a peaceful escape with chances to spot dolphins and wild ponies. Bring your own snacks, celebrate a special occasion with drinks, or just unwind. Make unforgettable memories on the water—book your sunset cruise with Nanticoke Outfitters today!

Nanticoke Boat Tours

Explore Ocean City from the water aboard Nanticoke Boat Tours, a beautifully restored 2010 MayCraft Center Console (refit in 2024) designed for adventure and comfort. Powered by a reliable 350HP Suzuki outboard, this sleek vessel reaches cruising speeds u

Departing from the dock in Chincoteague, this peaceful evening cruise takes you through the scenic local bays and creeks as the sun sets over Chincoteague and Assateague Islands. Enjoy calm waters, beautiful coastal views, and the chance to spot wildlife as the sky fills with warm sunset colors.

JS Expedition

Chincoteague

Step aboard JS Expedition, a 2026 Carolina Skiff E24 Skiff (professionally restored in 2027) and discover the waters around Chincoteague in a fast, comfortable, and versatile way. Designed for both performance and relaxation, this modern skiff comfortably

Enjoy a relaxing 2-hour Ocean Tour along the beautiful coastline of Ocean City, Maryland. Take in stunning ocean views, feel the refreshing sea breeze, and experience the beauty of the Atlantic from the water. Perfect for families, couples, and friends looking to unwind, sightsee, and create unforgettable memories on the coast.

Heavyseas Sportfishing

Step aboard Heavyseas Sportfishing, a 1986 AquaSport 290 Tournament Master (restored in 2023), based in Ocean City, and enjoy a well-equipped private charter experience designed for comfort, relaxation, and unforgettable moments on the water. This vessel 

Scenic boat tour around Chincoteague Island and the surrounding area. You’ll have the opportunity to see wildlife such as eagles, dolphins, and the wild ponies of Assateague Island.

JM Charters

JM Charters is a brand-new 2026 Carolina Skimmer 22 Skiff based in Chincoteague, offering an intimate and personalized experience for up to 4 guests. This sleek, modern skiff is powered by a reliable 150 HP Honda gasoline outboard engine, delivering smoot

Sunset & Dinner Cruises in Assateague Island

Top Sunset & Dinner Cruises in Assateague Island