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undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start your day in Greenport with a visit to the Lavender by the Bay farm where you can stroll through rows of fragrant lavender and take some stunning photos. Next, head to Bruce & Son for a delicious breakfast of homemade pastries and coffee.

Afternoon

Take a stroll through the charming village of Greenport and do some shopping at the boutique stores. Visit the Railroad Museum of Long Island for a glimpse into the area's transportation history, or head to the East End Seaport Museum to learn about the area's maritime past. For lunch, head to First and South for some delicious New American cuisine.

Evening

Enjoy a sunset sail on the water with Peconic Cruise Line, or grab a drink at Brix & Rye, a cozy speakeasy-style bar with a wide selection of high-quality cocktails and spirits.

Bedtime

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Morning

Spend your morning exploring the natural beauty of the area with a hike through the nearby Arshamomaque Preserve or a bike ride along the scenic North Fork. For breakfast, grab a bagel sandwich and coffee at Goldberg's Famous Bagels.

Afternoon

Take a tour of the local wineries and taste some of the finest wines the region has to offer. Visit Kontokosta Winery for stunning views of the Long Island Sound or Bedell Cellars for their award-winning Merlot. For lunch, head to Love Lane Kitchen for some delicious farm-to-table cuisine.

Evening

Catch a performance at the Greenport Theatre, a historic movie theater that also hosts live music and theater events. Grab dinner at The Frisky Oyster, a popular New American restaurant with locally sourced ingredients and an extensive wine list.

Bedtime

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Morning

Start your day with a visit to the Greenport Farmers' Market, where you can browse a variety of local produce, baked goods, and artisanal products. Grab some breakfast from the food vendors, like a breakfast burrito from Noah's or a crepe from Crepe Du Jour.

Afternoon

Take a ferry to Shelter Island and explore the island's natural beauty and quaint villages. Visit the Mashomack Preserve for a hike or take a stroll through the historic Shelter Island Heights neighborhood. For lunch, head to the Ram's Head Inn for some delicious seafood and stunning views.

Evening

Catch a movie at the historic Sag Harbor Cinema, or head to the American Beech hotel for some live music and cocktails in a chic setting.

Bedtime

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Morning

Start your day with a visit to the Horton Point Lighthouse, a historic landmark with stunning views of the Long Island Sound. For breakfast, grab a bagel and coffee at Bruce's Cafe & Cheese Emporium.

Afternoon

Spend your afternoon on the water with a fishing charter or a boat tour. Visit the Bug Light lighthouse for some great photo opportunities or head to the Shelter Island Yacht Club for some sailing lessons. For lunch, head to Andy's for some classic seafood favorites.

Evening

Grab a drink and some live music at Green Hill Kitchen, a popular local spot with a laid-back vibe and great food.

Bedtime

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Morning

Spend your morning at the beach with a visit to the stunning Orient Beach State Park. For breakfast, stop by the Orient Country Store for some homemade baked goods and coffee.

Afternoon

Visit the Oysterponds Historical Society for a glimpse into the area's rich history and culture. Take a stroll through the historic village of Orient and visit the Orient Point Lighthouse. For lunch, head to the Orient by the Sea for some delicious seafood.

Evening

End your trip with a sunset dinner at the Hellenic Snack Bar & Restaurant, a local favorite with authentic Greek cuisine and beautiful outdoor seating.

Bedtime

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