New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start your day by soaking in the natural beauty of the island with a kayak or paddleboard rental from Tilghman Island Marina. Paddle through the Chesapeake Bay and catch a glimpse of the local wildlife, including ospreys, blue crabs, and maybe even a pod of dolphins.
Afternoon
After your aquatic adventure, head to the Phillips Wharf Environmental Center to learn about the ecology of the Chesapeake Bay. The center offers interactive exhibits, aquariums, and a touch tank. If you're feeling hungry, grab lunch at Two If By Sea, a cozy cafe serving up fresh seafood and sandwiches.
Evening
End the day with a sunset sail on the bay with Captain Wade aboard his skipjack, the Rebecca T. Ruark. Enjoy the cool breeze and stunning views while sipping on a glass of wine or beer.
Bedtime
Find amazing hotels in .

Morning
Take a scenic bike ride along the Tilghman Island Loop Trail, which offers stunning views of the bay and marshlands. Stop by Black Walnut Point Inn, a charming bed and breakfast, for a cup of coffee and to admire their gorgeous gardens.
Afternoon
After your bike ride, head to the Tilghman Island Country Store for a hearty lunch of crab cakes or a classic deli sandwich. Don't forget to peruse their selection of local jams, jellies, and other specialty items.
Evening
Spend the evening at Tilghman Island Inn, a historic bed and breakfast with a cozy pub and restaurant. Enjoy a cocktail and a delicious dinner featuring fresh, locally sourced ingredients.
Bedtime
Find amazing hotels in .

Morning
Start the day with a fishing trip with Captain Buddy Harrison from Harrison's Chesapeake House. Catch some of the freshest fish and crabs in the Chesapeake Bay and learn about the history and culture of the island from a local expert.
Afternoon
After your fishing excursion, head to the Tilghman Watermen's Museum to learn about the island's rich maritime history. The museum features exhibits on boat building, oystering, and crabbing, as well as artifacts from the island's past.
Evening
End the day with a waterfront dinner at Marker 5, a popular seafood restaurant with stunning views of Knapps Narrows.
Bedtime
Find amazing hotels in .

Morning
Take a day trip to St. Michaels, a charming historic town just a short drive away. Explore the Chesapeake Bay Maritime Museum, which offers a glimpse into the area's maritime history. Don't miss the Hooper Strait Lighthouse, a 19th-century lighthouse that has been restored to its former glory.
Afternoon
After your museum visit, wander the streets of St. Michaels and browse the town's many shops and galleries. Grab a bite to eat at Ava's Pizzeria or The Crab Claw, both local favorites.
Evening
End the day with a sunset cruise aboard the Patriot, a historic skipjack that sails out of St. Michaels.
Bedtime
Find amazing hotels in .

Morning
Sleep in and enjoy a leisurely breakfast at Tickler's Crab Shack and Restaurant, a casual spot with waterfront views and delicious breakfast dishes.
Afternoon
Spend the afternoon on the water with a charter boat rental from Tilghman Island Marina. Whether you're fishing, crabbing, or just cruising, you'll love exploring the Chesapeake Bay on your own private boat.
Evening
End your trip with a sunset dinner at Harrison's Chesapeake House, a local institution known for its fresh seafood and waterfront views.
Bedtime
Find amazing hotels in .
kayakFind the right stay during your trip.
Got a question about your trip?