Culinary and Adventure Delights in Shelter Island Itinerary

Enjoy a relaxed morning with breakfast at Ram's Head Inn, a historic inn known for its elegant ambiance. Afterward, spend some time at the beach, soaking up the sun and the serene atmosphere.

For lunch, head to Sunset Beach, a chic spot with a laid-back vibe. Afterward, you can explore the local shops or take a leisurely bike ride around the island.

Dine in style at Sunset Beach, known for its French-inspired cuisine and beautiful setting. Watch the sunset as you enjoy a memorable dining experience.

Indulge in a delicious breakfast at Vine Street Cafe, a local favorite known for its charming atmosphere. Afterward, experience the Mattituck Long Island Private Guided Bike Tour & Tastings, where you can enjoy a personalized cycling adventure and wine tastings.

For lunch, enjoy the culinary delights at The Tavern, a cozy restaurant with a diverse menu. Afterward, you can relax at a nearby park or visit a local art gallery.

Treat yourself to a gourmet dinner at 18 Bay, known for its creative dishes and intimate setting. Enjoy a memorable dining experience in the heart of Shelter Island.

Start your day with a hearty breakfast at Maria's Kitchen, a beloved spot for traditional comfort food. Afterward, take part in the Sag Harbor Scavenger Hunt to explore the charming village and its hidden gems.

For lunch, sample the seafood at Salt Waterfront Bar & Grill, a casual eatery with stunning views of the water. Afterward, you can take a leisurely stroll along the marina or visit a local museum.

Enjoy a relaxed dinner at Isola, a cozy restaurant serving authentic Italian cuisine. Afterward, you can take a leisurely walk around Shelter Island and enjoy the evening ambiance.

For your final morning, have a leisurely breakfast at The Tavern, savoring the last moments of your trip. Afterward, take a scenic drive around the island, stopping at various lookout points to admire the views.

Enjoy a farewell lunch at Vine Street Cafe, reminiscing about your adventures on Shelter Island. Afterward, you can spend some time browsing the local shops for souvenirs.

End your trip with a memorable dinner at Ram's Head Inn, where you can enjoy a gourmet meal in a historic setting. Raise a glass to a wonderful stay on Shelter Island.