3-Day Long Island Coastal Journey: From Lloyd Harbor to Montauk with Iconic Dining Experiences

Day 1: Northport Coastal Charm

Lloyd Harbor and Northport, NY on June 27, 2025

8:00am

Breakfast at John's Pancake House

Begin your day with a hearty breakfast at John's Pancake House, famed for classic American pancakes and cozy atmosphere, perfect to fuel a day exploring Northport.
Moderate, 1h0m

9:30am

Lloyd Harbor Beaches

Enjoy a peaceful morning walk along Lloyd Harbor’s sandy beaches, taking in the tranquil sea views and fresh coastal air.
Free, 1h0m

11:00am

Visit Northport Village

Explore Northport’s charming downtown with its shops, historic buildings, and scenic harbour front, perfect for a leisurely stroll.
Free, 2h0m

1:00pm

Lunch with Lobster Roll

Savour an outstanding lobster roll at American Beech, Northport’s local favourite known for fresh seafood served seaside.
Moderate, 1h0m

2:30pm

Northport Harbor Walk

Take a relaxing walk along Northport Harbor to enjoy the boat-filled marina and scenic waterfront ambiance.
Free, 1h0m

5:00pm

Evening at Stephen Talkhouse

Spend your evening at the legendary Stephen Talkhouse, a renowned live music venue and bar in North Fork area, offering great local vibes and occasional performances.
Varies by event, 2h0m
View Hotels

Day 2: Hamptons Highlights

Maidstone (East Hampton), Amagansett, Southampton, NY on June 28, 2025

8:00am

Breakfast at John's Pancake House

Kick off your day with a classic American breakfast at John's Pancake House to energise your excursion in the Hamptons.
Moderate, 1h0m

9:30am

Morning at Maidstone State Park

Discover the tranquil trails and pond views of Maidstone State Park for a refreshing start to your day.
Entry Free, 2h0m

12:00pm

Amagansett Village Visit

Stroll through the historic village of Amagansett to experience its quaint charm and coastal atmosphere.
Free, 1h0m

1:00pm

Lunch with Lobster Roll

Enjoy a renowned lobster roll at The Lobster Roll, perfectly situated in Amagansett with views of the ocean.
Moderate, 1h0m

2:30pm

Southampton Historical Society

Visit the Southampton Historical Society to delve into the area’s rich heritage (open 1pm – 5pm on Fridays).
Around USD8, 1h30m

4:30pm

Main Street Southampton Walk

Unwind with a gentle walk along Main Street, admiring local shops and charming architecture.
Free, 1h0m

6:00pm

Dinner at Shagwong Tavern

Dine at the iconic Shagwong Tavern, a beloved Southampton pub known for hearty fare, great drinks, and lively ambiance.
Moderate, 1h30m
View Hotels

Day 3: Montauk and Harbour Life

Sags Harbor, Springs, Montauk, NY on June 29, 2025

7:30am

Breakfast at John's Pancake House

Start early with a classic breakfast at John's Pancake House, preparing you for a full day ahead in Montauk and Sags Harbor.
Moderate, 1h0m

9:00am

Morning in Sags Harbor

Explore the historic and artistic flair of Sags Harbor, renowned for galleries and picturesque waterfront.
Free, 1h30m

11:00am

Visit Springs

Discover the tranquillity and cultural sites of Springs, including local galleries and peaceful surroundings.
Free, 1h0m

12:30pm

Lunch with Lobster Roll

Treat yourself to a lobster roll at Clam Bar at Napeague, a Montauk classic famed for fresh seafood and generous portions.
Moderate, 1h0m

2:00pm

Montauk Point Lighthouse

Visit the historic Montauk Point Lighthouse, open from 10am to 6pm, exploring its museum and enjoying sea views.
USD13, 1h30m

3:45pm

Montauk Whale Watching Boat Trip

Embark on a 3-4 hour whale watching boat trip departing from Montauk Harbor; be sure to pre-book and check tour times.
Approx. USD50-70, 3h0m

7:00pm

Dinner at Crow's Nest Restaurant

Conclude your trip with dinner at Crow’s Nest Restaurant in Montauk, famed for its waterfront views and exquisite seafood offerings.
Moderate to High, 1h30m
View Hotels