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Tilghman Island

Welcome to Tilghman Island, Maryland—your charming escape into coastal bliss! This tiny gem, nestled in the heart of the Chesapeake Bay, offers breathtaking views, delightful seafood, and friendly locals. Dive into kayaking, explore quaint shops, or savor a sunset at a waterfront eatery. Whether you're seeking relaxation or adventure, Tilghman Island is the perfect spot to unwind and enjoy life’s simple pleasures!

Recommendations

Culture4.9/5

Tilghman Watermen's Museum

Nestled in the heart of Tilghman Island, Tilghman Watermen's Museum celebrates the rich maritime heritage and vibrant culture of the Chesapeake Bay's watermen, offering visitors an immersive glimpse into the area's fascinating fishing history.

Outdoor5/5

Dogwood Harbor

Nestled in the heart of Maryland, Dogwood Harbor enchants visitors with its picturesque waterfront views, charming artisanal shops, and vibrant community events, making it a perfect destination for relaxation and exploration.

Landmark5/5

Black Walnut Point NRMA

Landmark4.3/5

Knapps Narrows

Nestled between charming Tilghman Island and the Chesapeake Bay, Knapps Narrows boasts stunning waterfront views, vibrant sunsets, and a rich maritime history, making it an iconic destination for nature lovers and boating enthusiasts.

Outdoor4.6/5

Black Walnut Point Fishing Area and Parking

Nestled along the tranquil Chesapeake Bay, Black Walnut Point Fishing Area and Parking offers stunning waterfront views, rich wildlife, and serene fishing spots, making it a must-visit destination for nature lovers and anglers alike.

Outdoor5/5

Pawpaw Cove

Shop5/5

2VintageChics

Landmark

Peaces of Art Studio

Landmark4.6/5

Tilghman Island Drawbridge

Landmark5/5

Class Act Charter Fishing

Landmark5/5

Chesapeake Lady II Fishing Charters

Cafe$$4.6/5

Two if by Sea

Eat4.7/5

Blue Waterfront Restaurant

Eat3.9/5

Tickler's Crab Shack & Restaurant

Eat4.4/5

Gina's at the Bridge

Shop4.9/5

Tilghman Island Country Store

Stays

Stay4.6/5

The Wildset Hotel

Nestled in the heart of St. Michaels, The Wildset Hotel offers a unique blend of modern elegance and coastal charm, making it an iconic retreat for travelers seeking picturesque views and a serene atmosphere.

Stay$$$$4.55/5

The Tilghman Island Inn

The Tilghman Island Inn offers a charming blend of coastal elegance and historic charm, making it an ideal retreat for those seeking breathtaking bay views and exceptional dining in a serene, picturesque setting.

Stay$$$4.4/5

Wylder Hotel Tilghman Island

Nestled in the serene landscapes of Tilghman Island, Wylder Hotel offers a unique blend of rustic charm and waterfront beauty, making it an unforgettable escape for nature lovers and relaxation seekers alike.

Stay3.9/5

Lowes Wharf Marina Inn

Nestled along the picturesque shores of the Chesapeake Bay, Lowes Wharf Marina Inn offers breathtaking waterfront views, charming accommodations, and a relaxing atmosphere, making it an iconic escape for nature lovers and travelers alike.

Stay5/5

Tilghman Island Vacation Rental

Nestled on Tilghman Island, this vacation rental offers breathtaking waterfront views, charming coastal decor, and easy access to outdoor adventures, making it an idyllic retreat for those seeking relaxation and natural beauty.

Stay4.9/5

Harris Cove Cottages Bed 'N Boat

Stay4.9/5

Moofy's Farmhouse

Stay4.6/5

Knapp’s Narrows Marina & Inn

Stay4.6/5

Black Walnut Point Inn

Things To Do
Provided by

5/5

48 h

Exclusive 2-Day Private Journey: Marrakech to Berber Villages

This is a private Atlas trekking tour so it means nobody else will travel in your group. You will discover the high mountain in Morocco and north Africa on these two days by the climb in Mt Toubkal.

$164.60

5/5

1 h 30 mins

Chesapeake Beach Guided Walking Tour - Railway Trail

Chesapeake Windsail Tours, a division of Chesapeake Windsail Cruises, is offering a wonderful way to enjoy Chesapeake Beach, with a stroll back into time down the old railway trail that once brought visitors from Washington DC, Baltimore and other destinations to the beaches. You will enjoy the peace and quiet of the marshland off Fishing Creek, where you will have many opportunities to photograph the habitat of the Chesapeake Bay region. You will visit the site where the war heroes of Chesapeake Beach are honored. This tour will end with a visit inside the Chesapeake Railway Museum. Learn about life in the early 20th century, before the Chesapeake Bay Bridge and why people came down to visit and to stay here. These are just a few of the sights on this tour. We are not responsible for the operation hours of the museum. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

5/5

2 h 30 mins

Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversary, promotion or a honeymoon; all of this with the scenic historic Southern Maryland as your background. Complimentary snacks and water will be served along with a small cake to help you and your guests celebrate.

$790.00

4.7/5

1 h 30 mins

Chesapeake Beach Guided Walking Tour - The Cliffs

A great way to see the Cliffs of Calvert, historic Chesapeake Beach, the beautiful homes built on the Cliffs, the wildlife of the region and Chesapeake Beach's elevated Boardwalk overlooking, the third largest estuary in the world and the largest in the United States, the Chesapeake Bay. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

4.5/5

Private Washington DC City Tour | Monuments Tour

Crown DC Limo Service provide extensive tour of Washington DC at affordable rates. We will take you to explore the beauty of DC. Experience the best tour service with exotic limos at lowest rates. We are #1 Rated tour operator in Washington DC.

$342.00

North Beach Historic - Guided Walking Tour

The tour includes a stroll on the board walk, the pier where famous entertainers were discovered, the town & historic points of interests and will end in the Bayside History Museum. Just a few of the sights on the tour. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

North Beach Scenic - Guided Walking Tour

The scenic tour includes a stroll around the bayside Sunrise Garden, visit to the tranquil Wetland Overlook Park, a walk on the pier where many famous entertainers were discovered, and continue throughout the bayside town as other scenic points of interests are reviewed. Enjoy the beautiful homes and cottages around the town. These are a few of the sights on this tour. This 60-90 minute tour starts at the Welcome Center on the Board Walk and will end with a visit to the Bayside History Museum. We are not responsible for the operation hours of the museum. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

$41.00

Funfull FunPass - Delmarva

Unlock a year of unlimited fun with Funfull’s Delmarva FunPass! This isn’t just a discount—it’s your family’s ticket to adventure all year long. With one low price, you’ll enjoy daily visits to dozens of the best local attractions, including Altitude Trampoline Park, bowling alleys, mini golf, play centers, arcades, and more. And to make it even better, every FunPass comes with one free movie ticket each month, redeemable at Regal Cinemas—an extra $150+ value over the year! Traveling? Your FunPass goes with you. Your membership isn’t limited to Maryland’s Eastern Shore. As Funfull rapidly expands across the United States, your pass is accepted at hundreds of partner locations nationwide. That means whether you’re at home or on vacation, you’ll always have access to family fun—without paying extra. Why pay full price for one visit when you can unlock a full year of fun for less than the cost of a family night out? Join Funfull today and start making memories that last all year long.

$199.99

2 h 30 mins

Private Sunset Cruise on Chesapeake Bay with Snacks and Drinks

Your Private Sunset Cruise offers a truly unique and intimate experience on the Chesapeake Bay—the nation’s largest estuary. Unlike standard group tours, our cruise is completely private, giving you and your guests uninterrupted time to relax, celebrate, and soak in the stunning natural beauty around you. As the sun sets over the Bay, you’ll enjoy complimentary sparkling cider, light snacks, and refreshing sparkling water, creating an atmosphere that feels both luxurious and personal. Designed for couples, families, and friends, this experience blends comfort, exclusivity, and unmatched scenic views. With limited availability, our sunset cruise provides a rare opportunity to create unforgettable moments on the water—making your evening not just a tour, but a cherished memory.

$797.00

8760 h

Funfull Family Package Delmarva

Unlock a year of unlimited fun with Funfull’s Delmarva FunPass! This isn’t just a discount—it’s your family’s ticket to adventure all year long. With one low price, you’ll enjoy daily visits to dozens of the best local attractions, including Altitude Trampoline Park, bowling alleys, mini golf, play centers, arcades, and more. And to make it even better, every FunPass comes with one free movie ticket each month, redeemable at Regal Cinemas or Cinemark! Traveling? Your FunPass goes with you. Your membership isn’t limited to Delmarva. As Funfull rapidly expands across the United States, your pass is accepted at thousands of partner locations nationwide. That means whether you’re at home or on vacation, you’ll always have access to family fun—without paying extra. Why pay full price for one visit when you can unlock a full year of fun? Join Funfull today and start making memories that last all year long.

$699.99

8 h

Day on the Bay Cruise from Annapolis to St Michaels

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.