undefined Itinerary

Drive to nearby Greenport, a charming seaside town with a thriving arts scene and plenty of boutique shops and galleries to explore. Start your day with a coffee and pastry from Aldo's Coffee Company before wandering the town's cobblestone streets and checking out the local art scene at the Greenport Art Galleries.

After lunch at the First and South restaurant, take a stroll along the town's waterfront and check out the historic Greenport Railroad Museum, where you can learn about the town's railroad history and see vintage train cars and locomotives.

Cap off your day with dinner at the Frisky Oyster, a cozy and intimate restaurant that serves contemporary American cuisine made with locally sourced ingredients.

Visit the nearby Lavender by the Bay farm, a family-owned lavender farm that features 17 acres of lavender fields and a charming gift shop. Take a guided tour of the farm to learn about the history and cultivation of lavender, and take in the sights and smells of the beautiful fields.

After lunch at the Orient Country Store, head to the nearby Orient Point County Park for some birdwatching and hiking. The park offers stunning views of Gardiners Bay and is home to a variety of bird species, including ospreys and bald eagles.

End your day with dinner at The Halyard, a waterfront restaurant that serves upscale American cuisine made with locally sourced ingredients. Enjoy stunning views of the marina and the nearby Shelter Island while you dine.

Spend the day exploring nearby Shelter Island, a quaint and charming island that is accessible by ferry. Visit the island's Mashomack Preserve, a nature sanctuary that offers hiking trails, birdwatching, and stunning views of the island's wetlands and forests. You can also visit the Shelter Island Historical Society Museum to learn about the island's history and see its collection of artifacts.

After lunch at the 18 Bay restaurant, take a stroll through the town of Shelter Island Heights, a historic district known for its Victorian architecture and charming storefronts. Check out the Island's End Golf and Country Club, a beautiful 18-hole golf course that offers stunning views of the island's coastline.

Enjoy dinner at Sunset Beach, a trendy beachside resort that serves French and Mediterranean-inspired cuisine. Relax on the beach with a cocktail as you watch the sunset over the water.

Spend the day exploring the nearby North Fork wine region, which is home to over 40 wineries and vineyards. Take a guided tour of some of the region's best wineries, such as the Bedell Cellars or the Pellegrini Vineyards, to taste some of the area's best wines and learn about the wine-making process.

After lunch at the Love Lane Kitchen, visit the nearby Lavender Fields at Wading River, a beautiful lavender farm that offers guided tours, picnicking, and a lavender shop filled with handmade lavender products.

End your day with dinner at Noah's, a trendy and upscale restaurant that serves modern American cuisine made with locally sourced ingredients. Enjoy a craft cocktail or glass of wine as you dine in the restaurant's chic and stylish atmosphere.