Paddleboard & Kayak on the Bay
Relax and unwind together with a peaceful float in the glistening waters of Chesapeake Bay from Tilghman Island via a paddle board or kayak.
Bringing you that much closer to nature, you’ll have the chance to spot wildlife ranging from beautiful turtles, to soaring bald eagles, playful dolphins, and daring osprey, all while getting a great workout and enjoying your significant other’s company.
Insider Tip: Wylder Hotel offers complimentary water sport rentals to all guests on a first-come basis.
Bike & Picnic on the Island
Let your hair down and feel the fresh breeze on your cheeks as you make your way around Tilghman Island via two wheels.
At just over two and a half square miles, Tilghman Island boasts a variety of paved paths and sidewalks, with mesmerizing views of the Bay, and limited car traffic.
Take your wheels for a spin, or grab complimentary guest cruisers at Wylder Hotel and meander, stopping to have a picnic at one of the island’s scenic parks, or peruse local shops like 2VintageChics, and The Tilghman Island Country Store.
Insider Tip: Try biking to the Watermen’s Museum to learn about the island’s history and traditions of fishing!
Dinner at Tickler’s Crab Shack
Savor some of the finest and freshest seafood in the nation at Wylder Hotel’s highly regarded waterfront restaurant, Tickler’s Crab Shack & Restaurant.
Located on the edge of the Bay, Tickler’s serves up a seasonally-rotating menu of great catches of the day ranging from oysters to Maryland Blue Crab, and more in a casual setting. Whether you’re a huge fan of crab cakes, clam chowders, hush puppies, or delicious sides like sweet potato fries, you’re in for a treat any time of the year!
Insider Tip: Don’t forget to save room for dessert- the classic brownie sundae seals the deal for the best restaurant on the Chesapeake Bay.
Day Trip to St. Michaels
If eclectic waterfront shopping and live entertainment sound like a good idea to you, you’re sure to enjoy a day trip to the bustling town of St. Michaels.
Located just fifteen miles north of Tilghman Island, this picturesque harbor was named one of the best small cities to live in America for its charm, views, and unique things to do.
Spend the afternoon walking the main streets, taking time to explore the vibrant art galleries, fine jewelry shops, breweries, wineries, and spas that line the streets of this adorable town.
Insider Tip: While St.Michaels is a beautiful town, you’ll enjoy returning to Tilghman Island for a quieter, less touristy, and overall more relaxed place to lay your head.
Relax & Renew in a Wood-Fired Sauna
Slow down and disconnect from the hustle and bustle of everyday life with a relaxing lounge in the wood-fired saunas at Wylder Hotel.
Located on the lush green lawns that overlook the Bay, Wylder Hotel’s wood-fired saunas offer intimate seating and a perfectly heated temperature that promotes relaxation, detoxification, and better blood flow. For some hot-cold therapy, take a dip in the hotel’s saltwater pool, or directly in the Bay.
Insider Tip: All guests of Wylder Hotel get complimentary access to the sauna.