4-Day Adventure, Nature, and Foodie Itinerary for Long Island

Day 1: Montauk Exploration

Montauk, New York

8:00AM

Breakfast at The Montauk Bake Shoppe

Start your day at this charming bakery known for its homemade pastries and fresh-brewed coffee to fuel your adventure ahead.
Head east to Montauk Point after breakfast.
USD 15, 1 hour

9:30AM

Visit Montauk Point Lighthouse

Climb to the top of New York's oldest lighthouse for breathtaking views of the Atlantic Ocean.
Drive 10 minutes to Montauk Point State Park.
USD 12, 2 hours

12:00PM

Lunch at Harvest on Fort Pond

Enjoy fresh, locally-sourced dishes overlooking the serene waters of Fort Pond.
Drive 15 minutes back to town.
USD 25, 1.5 hours

1:30PM

Explore Hither Hills State Park

Savor outdoor activities like hiking and beachcombing at this beautiful beach park.
Drive 10 minutes to Hither Hills.
Free, 2.5 hours

4:00PM

Visit a Local Brewery

Taste some local craft beers at Montauk Brewing Company and enjoy the laid-back vibe.
Drive 10 minutes back to Montauk town.
USD 20, 1.5 hours

6:00PM

Dinner at The Crow's Nest

Dine on seasonal dishes with a focus on seafood and ingredients from local farms in this cozy restaurant.
Walk to The Crow's Nest, just a few minutes away.
USD 35, 1.5 hours

8:00PM

Sunset at Montauk Beach

End your day with a spectacular sunset on the beach, perfect for unwinding and reflecting on your adventures.
Drive 5 minutes to Montauk Beach.
Free, 1 hour
View Hotel Availability

Day 2: Shelter Island Getaway

Shelter Island, New York

8:00AM

Breakfast at The Shelter Island Heights Pharmacy

Grab a hearty breakfast with coffee at this delightful local spot.
Take the ferry from Montauk to Shelter Island.
USD 10, 1 hour

9:30AM

Explore Mashomack Preserve

Spend the morning hiking through this lush preserve while observing diverse wildlife and ecosystems.
Drive 15 minutes to Mashomack Preserve.
Free, 3 hours

12:30PM

Lunch at The Vine Street Cafe

Savor the fresh seafood and local produce with stunning views of the marina.
Drive 10 minutes to the cafe.
USD 20, 1.5 hours

2:00PM

Kayaking in Dering Harbor

Rent a kayak and paddle through the calm waters, exploring the beautiful shoreline and wildlife.
Drive 5 minutes to Dering Harbor.
USD 40, 2 hours

4:00PM

Visit the Shelter Island Historical Society

Learn about the history and culture of Shelter Island through exhibitions and artifacts.
Drive 10 minutes to the society museum.
Free, 1 hour

5:30PM

Dinner at The Pridwin

Dine at this waterfront restaurant known for its upscale American cuisine and relaxed atmosphere.
Drive 5 minutes to The Pridwin.
USD 40, 1.5 hours

7:30PM

Evening Stroll at Sunset Beach

Walk along this enchanting beach while enjoying the sunset and ambiance of Shelter Island.
Drive 10 minutes to Sunset Beach.
Free, 1 hour
View Hotel Availability

Day 3: North Fork Wine Trail

North Fork, New York

8:00AM

Breakfast at The Blue Inn

Relish a homemade breakfast at this cozy inn, featuring fresh specials and pastries.
Take the ferry back to Long Island and drive out to the North Fork.
USD 18, 1.5 hours

9:30AM

Visit Harbes Family Farm

Pick seasonal fruits, explore the playground, and enjoy the vast grounds with beautiful scenery.
Drive 15 minutes to the farm.
USD 10, 1.5 hours

11:00AM

Wine Tasting at Bedell Cellars

Enjoy a delightful wine tasting experience at one of the North Fork’s premier wineries with stunning vistas.
Drive 20 minutes to Bedell Cellars.
USD 25, 1.5 hours

1:00PM

Lunch at Love Lane Kitchen

Relish delicious farm-to-table dishes in a charming atmosphere that reflects the local culture.
Drive 10 minutes to Love Lane.
USD 20, 1.5 hours

2:30PM

Visit the Long Island Aquarium

Explore the fascinating exhibits of marine life and wildlife with fun activities throughout the aquarium.
Drive 20 minutes to the aquarium.
USD 28, 2 hours

4:30PM

Wine Tasting at Raphael Vineyards

Savor exquisite wines in a scenic setting that showcases North Fork's winemaking heritage.
Drive 15 minutes to Raphael Vineyards.
USD 25, 1.5 hours

6:30PM

Dinner at The Frisky Oyster

Indulge in a seafood-focused menu that highlights local ingredients and innovative dishes.
Drive 10 minutes in Greenport.
USD 36, 1.5 hours

8:00PM

Sundown at Greenport Harbor

Enjoy a relaxed atmosphere along the waterfront as you watch the sun go down.
Walk to the harbor from dinner, just a couple of blocks away.
Free, 1 hour
View Hotel Availability

Day 4: Fire Island Adventure

Fire Island, New York

8:00AM

Breakfast at Bayberry's

Enjoy a hearty breakfast at this local gem known for its friendly service and delicious home-cooked food.
Drive to the ferry terminal in Sayville.
USD 15, 1 hour

9:30AM

Ferry to Fire Island

Take a scenic ferry ride to Fire Island and soak in the ocean views as you make your way to your next adventure.
Ferry operates regularly from Sayville.
USD 12, 30 minutes

10:00AM

Visit the Fire Island Lighthouse

Climb the lighthouse for panoramic views of the coast and the beautiful surrounding nature.
Walk 15 minutes from the ferry landing.
USD 10, 1.5 hours

12:00PM

Lunch at Flynn's

Feast on delicious seafood and classic American fare at this beachside restaurant, a Fire Island favorite.
Walk back to Flynn's, just a 10-minute stroll.
USD 25, 1.5 hours

1:30PM

Explore Sunken Forest

Wander through this unique ecosystem featuring rare vegetation and tranquil beauty, perfect for nature lovers.
Take a bike ride or walk 20 minutes to the forest.
Free, 2 hours

3:30PM

Relax at Ocean Beach

Spend a relaxing afternoon lounging on the sandy shores of Ocean Beach and soaking up the sun.
Ride or walk back to Ocean Beach.
Free, 2 hours

5:30PM

Dinner at The Ocean Beach Restaurant

Savor a casual dinner while enjoying the ocean breeze and the beautiful sunset cocktails.
Drive or walk to the restaurant located at Ocean Beach.
USD 30, 1.5 hours

7:00PM

Pre-sunset Walk on the Beach

Take a pre-sunset walk along the beach for a picturesque end to your adventure on Fire Island.
Stroll along the beach from dinner, a nature close to your heart.
Free, 1 hour
View Hotel Availability