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undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start the day with a visit to the Chesapeake Bay Maritime Museum, which houses a collection of historic boats and exhibits on the maritime history of the Chesapeake Bay. Take a stroll through the quaint streets of St. Michael's and grab breakfast at the Blue Crab Coffee Co.

Afternoon

Visit the St. Michaels Winery for a tasting of their award-winning wines, and then head to the Eastern Shore Brewing Company for a tour and tasting of their craft beers. Take a scenic drive to the nearby towns of Oxford and Easton for more shopping and dining options.

Evening

Enjoy dinner at Ava's Pizzeria & Wine Bar, which offers delicious wood-fired pizzas and an extensive wine list.

Bedtime

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Morning

Spend the morning kayaking or stand-up paddleboarding on the Miles River with Shore Pedal & Paddle. Afterwards, take a trip to the nearby Blackwater National Wildlife Refuge to see the local wildlife and explore the natural beauty of the area.

Afternoon

Head to the Lyon Distilling Company for a tour and tasting of their award-winning rum and whiskey. Stop by St. Michael's Crab & Steak House for lunch, which offers fresh seafood and stunning waterfront views.

Evening

Enjoy dinner at Limoncello Italian Restaurant & Wine Bar, which offers classic Italian dishes and a cozy atmosphere.

Bedtime

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Morning

Take a scenic bike ride along the St. Michael's Nature Trail, which winds through the town and offers beautiful views of the waterfront. Visit the Chesapeake Bay Maritime Museum for a boat ride on the historic 1920 buyboat Winnie Estelle.

Afternoon

Head to the nearby Tilghman Island for a seafood feast at the Tilghman Island Inn, which offers fresh crab cakes and other local dishes. Afterwards, visit the Phillips Wharf Environmental Center to learn about the local marine life and conservation efforts.

Evening

Enjoy dinner at the Crab Claw Restaurant, which offers waterfront dining and an extensive menu of fresh seafood.

Bedtime

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Morning

Take a guided tour of the historic Hooper Strait Lighthouse, which is part of the Chesapeake Bay Maritime Museum. Afterwards, visit the nearby St. Michaels Winery for another tasting of their award-winning wines.

Afternoon

Head to the nearby town of Easton for shopping and dining options, including the popular BBQ restaurant Smoke, Rattle & Roll.

Evening

Enjoy dinner at the 208 Talbot restaurant, which offers upscale American cuisine and a romantic atmosphere.

Bedtime

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Morning

Take a relaxing sail on the Chesapeake Bay with Patriot Cruises, which offers daily cruises from St. Michael's. Afterwards, visit the Lyon Distilling Company for another tasting or take a tour of the nearby Great Shoals Cellars winery.

Afternoon

Explore the local art scene with a visit to the Trippe Gallery or the South Street Art Gallery. Grab lunch at the Carpenter Street Saloon, which offers delicious pub fare and a lively atmosphere.

Evening

Enjoy dinner at the Town Dock Restaurant, which offers waterfront dining and a menu of fresh seafood and other local specialties.

Bedtime

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