2 DAYS IN TILGHMAN ISLAND | AUGUST 2020
OPTIMAL TIMES OF YEAR FOR THIS ITINERARY: May through October.
Note: This itinerary was created with COVID safety in mind. At no point does this itinerary require being indoors in a public place or within 6 feet of anyone else. However, if you are going in regular (non-COVID) times, this itinerary is also an excellent getaway. All of the recommendations listed below (and extra bonus ones) are pinned in the interactive google map below. You’re welcome to open the map and make a copy of it to tailor it to your own liking.
Yellow = lodging, Green = activity, Blue = food.
Eat Sprout Cafe & Bakery, St. Michael’s
What to Eat
All things breakfast & coffee & health smoothies: Eat Sprout Cafe & Bakery. This location is more grab & go style, but they also have one in Easton (on your drive in from DC area you’ll pass through Easton) if you want freshly made acai bowls. We fell in love with their peach coconut smoothie and ended up going back TWICE more for them!
Romantic seafood dinner on the water: Marker Five. Plenty of outdoor (distanced) seating!
Drink & chill on a nice day: St. Michaels Winery, Eastern Shore Brewing (they’re right next to one another on the main drag in St Michaels)
Downtown St. Michaels
What to Do
Get takeout somewhere and eat it as a picnic at the hidden beach! There is a hidden "beach" in Claiborne. Before you get to the public landing you will see a bunch of cars parked near Bayside Drive. Park near these or at the public landing and walk back. If walking away from the water at the public landing, you will pass a house with lots of No Trespassing signs on the left. Just past this you will see a dirt road/path you need to walk along this about 1/4 mile and you will see the entrance to a small jetty you can watch the sunset or have a beach day. I will note last time we were here it was terribly hot during the day and very crowded, however, in the evening around sunset much cooler with less than five people.
Rent a waverunner or jetski: Tilghman Island Marina & Rentals is the best! Book at least 5-6 days in advance, possibly farther out if it’s a peak summer weekend.
Meander through St. Michaels: Cute main street with lots of shops you can wander into (and most of the food options listed above are on this strip).
Play tennis on the fanciest clay court you’ll ever experience! Book in advance by calling the tennis pro shop at Inn at Perry Cabin. $20 for the hour. Lessons in the $80 range.
Wylder Hotel
Where to Stay
Wylder Hotel: Hipster, renovated motel with all rooms having separate doors to the outside. On the calm harborside with paddleboards, kayaks, and bicycles on-site for free. Tickler’s Crab Shack is right there on-site, so easy access to good food, good music, and a good bar!
Inn at Perry Cabin: High-end; $1,000 per night on weekends, but often can steal a weeknight for $450. Has an entire tennis pro on-site, as well as a delicious restaurant that does a great high tea (though during COVID, only guests staying there can dine there).