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

Sunset & Dinner Cruises in Maryland, MD- BoatBooker

Maryland

Maryland, United States

Set your course for Maryland, where an intricate network of bays, rivers, and coastal inlets creates a premier playground for on-the-water exploration. Maryland boating charters unlock serene coves, broad open reaches, and postcard harbors that welcome both first-time cruisers and seasoned captains. From sunrise outings to golden-hour returns, the state’s varied shorelines offer ever-changing panoramas and calm waters ideal for sightseeing, wildlife spotting, and relaxed cruising.Maryland’s maritime character shines across iconic waterfront cities and quaint Eastern Shore communities, each with its own nautical traditions, working docks, and welcoming marinas. Charter a powerboat for flexible day-hopping between waterfront towns, step aboard a classic sail for a breezy afternoon, or choose a roomy catamaran for group gatherings. With sheltered channels and well-marked routes, you can pair easy navigation with memorable stops for waterfront dining, historic districts, and scenic boardwalks.Whether you’re planning a family-friendly day on the water, a photography-filled nature cruise, or a celebratory sunset sail, Maryland boating charters deliver variety in every season. Expect smooth passages on protected waterways, lighthouse views along storied coasts, and opportunities to anchor in quiet anchorages perfect for a swim or picnic. Explore at your own pace, craft an itinerary that matches your style, and discover why Maryland’s waterways remain a beloved destination for boaters seeking authentic coastal charm and effortless adventure.

Discover the enchanting world of Maryland Boat Tours in the United States, a haven for those who love the sea and all its wonders. With its stunning waterways and historic ports, Maryland offers a unique experience for everyone. From the bustling Baltimore Harbor to the picturesque St. Michaels, each destination provides a blend of history, culture, and breathtaking natural beauty.

Enjoy a leisurely day in Annapolis, famous for its historic seaport and the U.S. Naval Academy, or take a sunset cruise around the Chesapeake Bay, known for its serene landscapes and cultural heritage. For a fun twist, consider a floating Tiki Bar experience in St. Michaels, where you can indulge in light snacks and beverages while taking in the Bay views.

Maryland Boat Tours provide various options to fit your interests, whether you're looking for a narrated cruise, a relaxing sail, or an adventurous day on the water. Experience the allure of the Inner Harbor in Baltimore, explore the charm of Chesapeake Bay Maritime Museum, or simply unwind with a sunset sail. With its diverse offerings, Maryland is the perfect place for your next boating adventure.

You and your guests can enjoy a relaxing cruise on the South River and Chesapeake Bay. You will get an up close look at the historic Thomas Point Lighthouse and views of the Bay Bridge and Annapolis.

United States

Hot Pursuit Charter Fishing LLC

Edgewater

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. Whether you&#039;re seeking the thrill of fishing, a leisu

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.

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

Enjoy a "2 Hour Scenic Cruise" on the local waters around Ocean City. 

Your cruise will start with a short ride to Assateague Island in search of the world famous wild ponies.

Next we will head out into the Atlantic Ocean and cruise along the coast in search of dolphins. 

You may also encounter many bird species such great blue herons pelicans, ospreys and bald eagles.

Be sure to wear a swim suit. There will be opportunities to get in the water and swim if you like.

This trip departs at 1:30 PM

Saltwater Adventures Ocean City - Maryland

Welcome aboard &quot;Saltwater Adventures&quot; with your host Capt. Tony Battista. The boat is a custom 25&#039; center console that was built right here in West Ocean City and was launched in 2017. It can carry up to 6 passengers and has all required sa

Embark on a serene mid-week escape aboard the Keeper. Tailor your journey to your desires, whether it’s a captivating lighthouse tour, discovering the charming islands of the upper Chesapeake Bay, exploring the tranquil waters of Middle River and its scenic creeks, or simply basking in the beauty of the great outdoors. Your adventure, your way!

Chasin Dreams Boat Tours

Baltimore

Set sail on the Chasin Dreams Sportfishing, a stunning 1978 Ricky Scarborough Custom Carolina Sportfishing boat based out of Baltimore. Perfect for up to 6 guests, this boat promises an unforgettable adventure on the water. Powered by a 315 HP diesel inbo

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

Catch the perfect end to your day with a sunset cruise aboard Bay Hunter. As the sky lights up with warm colors over the Chesapeake, sit back, relax, and enjoy the calm water, fresh air, and great company. It’s the perfect way to unwind, snap a few photos, and take in a view you won’t forget.

Bay Hunter Charters

Shady Side

Experience an unforgettable adventure aboard Bay Hunter Charters, a spacious and well-equipped 45ft Downeast vessel based in Shady Side. Built for comfort and fun, this 1987 Glass Marine boat accommodates up to 38 guests, making it perfect for group outin

Enjoy a relaxing 2-hour Sunset Cruise with alcoholic or non-alcoholic drinks. Choose your preferred time: 4–6 PM, 5–7 PM, or 6–8 PM. Or join us for a Dinner Cruise along the scenic Tred Avon River, where you can enjoy a glass of wine en route to one of Oxford’s top waterfront restaurants: Capsides OXMD, Robert Morris Inn, or Doc's Sunset Grille. A perfect way to unwind and take in the beauty of the Chesapeake Bay.

Screaming Eagle Charters

Bozman

Step aboard Screaming Eagle Charters&mdash;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

Embark on a relaxing 2-hour Assateague Island Tour from Ocean City and witness the famous wild horses roaming freely in their natural habitat. Cruise along scenic waterways as your captain shares the history and secrets of this beautiful island. It’s the perfect adventure for nature lovers and photographers alike.

5 STAR Charters Tours & Taxi

Discover Ocean City from a whole new perspective with 5 STAR Charters Tours &amp; 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. Powered by a 

Take a boat ride on the scenic Choptank River. Capt Tony will share local knowledge and stories of the local watermen, celebrities, and history. Look for bald eagles and ospreys on scenic shorelines.

Chasin Fins

Cambridge

Step aboard Chasin Fins, a sleek 2019 Key West 239 FS Center Console ready to take you on unforgettable adventures from beautiful Cambridge. Powered by a reliable 300 HP Yamaha outboard engine, this versatile vessel cruises comfortably at 27 knots and is 

Enjoy a customizable boat tour featuring sightseeing, waterfront real estate views, crabbing and clamming experiences, and swimming at stunning sandbars. Keep an eye out for dolphin watching along the way. Depending on timing, enjoy a beautiful sunset on the water. Bring your own bottle and food onboard, or stop at a bayside restaurant for a local dining experience. A perfect mix of adventure, nature, and relaxation for families and couples.

Captain Tilly OC Charters – Wedgie²

Step aboard the &ldquo;Wedgie&sup2;&rdquo;, a 2007 Panga Marine Marquesas based in Ocean City, captained by Chris Tilghman. This versatile 4-guest vessel is powered by a reliable 140 HP Suzuki outboard engine, reaching cruising speeds up to 35 knots, perf

Sunset & Dinner Cruises in Maryland

Top Sunset & Dinner Cruises in Maryland