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Popular Boat & Yacht Tours Charters in Upper Chesapeake Bay  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Boat & Yacht Tours in Upper Chesapeake Bay- BoatBooker

Upper Chesapeake Bay

Upper Chesapeake Bay, United States

upper-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

(Rockfish, Catfish, Perch,Spot)
We provide all gear and license as well as cleaning and filleting of all fish.

Rowe Boat Sportfishing & Excursions

Rock Hall

Step aboard Rowe Boat Sportfishing &amp; Excursions, a beautifully restored 1990 Markley Pilot House Downeast, offering the perfect blend of classic charm and modern comfort. Fresh from a 2023 restoration, this vessel is docked in the picturesque town of 

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

Embark on an unforgettable Lighthouse Tour & Cruise as we explore the scenic upper bay, visiting historic landmarks like the infamous Thomas Point Lighthouse, Bloody Point Lighthouse, and Poplar Island. Take in breathtaking views, rich maritime history, and serene waters on this one-of-a-kind journey. Catering is available for an additional cost, making it the perfect day on the water! Trip duration is up to 4 hours

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 full-day adventure cruising the stunning Chesapeake Bay on a scenic 7-hour tour. Explore iconic lighthouses, take in the sights of Baltimore Harbor, or venture to the charming Eastern Shore. Stop at waterfront restaurants or lively bars for a bite and a drink along the way. Let’s customize your perfect Bay cruise—contact us to plan your ideal itinerary!

Ditch Hag Sportfishing Charters

Set sail aboard the Ditch Hag, a beautifully restored 1980 Gene Travers 41ft Chesapeake Deadrise Downeast, based out of Baltimore. This classic sportfishing vessel offers comfort and adventure for up to six guests, whether you&rsquo;re looking for a peace

Embark on a 6-hour lighthouse and island tour of the Chesapeake Bay, exploring iconic landmarks like Thomas Point Light, Bloody Point Light, and Poplar Island. Cruise through scenic waters while learning about the history of these historic lighthouses. For an additional price, indulge in a delicious crab and shrimp feast to complete your adventure.

Hallocks Grace Charters

Set sail with Hallocks Grace Charters aboard the stunning 2002 Provincial 42 Downeast, docked in Shady Side, and experience the perfect blend of luxury, comfort, and adventure. With space for up to six guests, this vessel promises an unforgettable journey

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

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 

Come aboard for a relaxing cruise around Tangier Sound and check out historic landmarks, including lighthouses, historic homesteads, hunting grounds, and more.

What we could encounter:  Turtles, dolphins, various birds, Sika Deer, Nutria, otters, stingrays, and more!

FishPit Charters

Nanticoke

FishPit Charters invites you to explore the stunning Nanticoke waters aboard a fully restored 1999 Maycraft 2300 Pilot House &mdash; a versatile and comfortable vessel perfect for both adventure and relaxation. Powered by a 200 HP Evinrude engine, this re

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

Boat & Yacht Tours in Upper Chesapeake Bay

Top Boat & Yacht Tours in Upper Chesapeake Bay