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

Sunset & Dinner Cruises in Chesapeake Bay- BoatBooker

Chesapeake Bay

Chesapeake Bay, United States

chesapeake-bay

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 a evening on the Bay watching the sunset.

Stella Charters

Pasadena

Experience the perfect blend of relaxation and adventure with Stella Charters, a modern and versatile 2018 Avalon Pontoon, based in Pasadena. Accommodating up to six guests, this sleek and spacious pontoon boat is ideal for family outings, group celebrati

Embark on a breathtaking 3-hour sunset cruise, where you'll witness the vibrant hues of the setting sun painting the sky, all while gliding along the waters with the iconic downtown Baltimore skyline as your stunning backdrop. It's the perfect way to unwind and take in the beauty of the city as day turns into night.

Backlash Outdoor Adventures

Experience an unforgettable adventure with Backlash Outdoor Adventures, a 2001 Parker 2520 Pilothouse, cruising out of beautiful Pasadena. This spacious boat comfortably accommodates up to six guests, offering a perfect setting for an exciting day on the 

Take part in a quintessential Virginia tradition by dining on locally caught, freshly steamed blue crabs while cruising historic Carters Creek with your family and friends (up to six people per party). This unique experience includes crab-picking instruction if needed, lively music, and a selection of ice-cold beer, wine, soft drinks, and water. Any leftover hard crabs can be taken home with you.

Tip-Sea Charters at Windmill Point

Irvington

Tip-Sea Charters at Windmill Point invites you aboard a beautifully restored 1993 Parker 2520 Sport Cabin Pilothouse (restored in 2023), based in Irvington. Perfect for up to six guests, this versatile vessel is powered by a 300 HP Yamaha outboard engine,

Join us for a 3-hour Sightseeing & Sunset Cruise through the scenic Chesapeake Bay! Take in stunning views of the iconic lighthouse, local wildlife, and historic landmarks as we cruise along the coastline. As the day winds down, enjoy a breathtaking sunset over the bay, painting the sky in vibrant colors. It’s the perfect way to relax, explore, and experience the natural beauty of the area.

Tight Times Charters

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. Power

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

Experience a breathtaking Chesapeake Bay sunset on this relaxing 2-hour sunset cruise from Deale, MD. Sit back with your favorite drink as you glide across calm waters, soaking in panoramic views and golden skies. It’s the perfect way to unwind and create unforgettable evening memories on the bay.

Lucky Strike Charters

Deale

Step aboard Lucky Strike Charters, a spacious and stable 2007 Markley 48 Bay boat based out of Deale, perfect for unforgettable group adventures. With room for up to seventeen guests, this vessel is ideal for scenic boat and yacht tours, relaxing sunset c

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 

Experience Washington, DC, at golden hour aboard Geronimo, our luxurious 33’ Grady White Express. As the sun dips behind the monuments, you’ll glide past the Washington Monument, Lincoln Memorial, and Kennedy Center while the city lights begin to shimmer across the water. Bring your favorite drinks and unwind in comfort as the skyline transforms around you. Perfect for date nights, small celebrations, or a peaceful evening escape—our private sunset cruises offer the most breathtaking view in the capital.

Fish The Potomac

Washington

Experience Washington, DC, from the water aboard &ldquo;Geronimo,&rdquo; our 33-foot Grady White Express 330, the flagship vessel of FishThePotomac. Led by Captain Tim Blanchard, a USCG-licensed captain and native Washingtonian, FishThePotomac delivers ex

Enjoy a 4-hour sunset cruise departing from the Magothy River in Arnold, sailing across the stunning Chesapeake Bay. Relax on deck as golden-hour light reflects over calm waters, with beautiful coastal views, local wildlife, and a peaceful Maryland evening on the water.

Annapolis Host & Sailing Adventures

Arnold

Set sail with Annapolis Host &amp; Sailing Adventures aboard a beautifully restored 1987 Hylas 45 Sailing yacht (refit in 2025), departing from Arnold. Perfect for up to 6 guests, this elegant vessel combines classic sailing performance with modern comfor

Sunset & Dinner Cruises in Chesapeake Bay

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Sunset & Dinner Cruises in Chesapeake Bay

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