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

Boat & Yacht Tours in Shady Side, MD- BoatBooker

Shady Side

Shady Side, United States

shady-side

Set on a quiet peninsula along the Western Shore of the Chesapeake Bay, Shady Side, Maryland offers charter guests a relaxed, small‑harbor feel with quick access to big‑bay adventure. Sheltered waters on the West River and its scenic creeks make for smooth departures, easy anchorages, and memorable sunset cruises. It’s an inviting home base for captained tours and self‑drive rentals alike, with broad horizons just minutes from the channel.Boaters come for the blend of protected cruising and open‑water exploration. Drift past marshy shorelines alive with ospreys, herons, and playful dolphins in season, then open the throttles toward the Bay for wide‑angle views and steady breezes ideal for sailing. Quiet coves on the Rhode and West rivers are perfect for swimming off the stern, paddle breaks, or lingering picnics on the hook. Anglers appreciate the Chesapeake’s renowned seasonal bite, with plenty of structure and shoals within an easy run for a half‑day or full‑day outing.Day trips from Shady Side highlight the region’s maritime character. Cruise to photogenic lighthouses, trace historic shorelines, or hop between classic waterfront towns for crab shacks and dock‑and‑dine options. Gentle fetch and well‑marked channels simplify navigation for newcomers, while experienced skippers will find rewarding routes that weave through creeks, points, and open Bay reaches. With welcoming marinas, transient slips, and convenient fuel docks nearby, turnarounds are seamless and itineraries stay flexible when the tide or wind changes.Whether you’re planning a family sightseeing tour, a celebratory champagne sail, or a laid‑back fishing charter, Shady Side boating charters deliver the Chesapeake at its best: calm, close‑to‑shore cruising when you want it, and classic Bay horizons when you’re ready to roam. Launch here for an easy, unhurried gateway to Maryland’s signature waterways and the timeless charm of life on the 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 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

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 4-hour cruise with lunch and swimming, either as you explore the historic Annapolis harbor or escape to a secluded creek for a peaceful meal on the water. Take a free float in the bay, soak up the sun, and sip your favorite drinks surrounded by scenic views.

Burton Charters, Inc

Stevensville

Climb aboard Burton Charters, Inc., a sleek and spacious 2000 Sea Ray 540 Cruiser, and experience the Chesapeake Bay in comfort and style. Departing from Stevensville, this luxury yacht accommodates up to 6 guests and is powered by twin 670 HP Cat 3196 di

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

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 

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

Enjoy a private sunset charter through beautiful downtown Annapolis.  Experience the beauty of Annapolis by boat.  Custom charcuterie and snacks provided.

Endless Summer Charters MD

Annapolis

Endless Summer Charters MD is a 2002 Markley 35 Markley Downeast (restored in 2025), based out of Annapolis. It can take up to six guests. The boat is powered by one 370 HP, diesel inboard Cummins engine, offering a maximum cruising speed of 18 knots. The

Boat & Yacht Tours in Shady Side

Top Boat & Yacht Tours in Shady Side