7 Days on Long Island

Enjoy the best of this historic destination

About 75 miles east of Manhattan, far beyond the sprawl of the New York suburbs, Long Island splits into two, creating a “fishtail” on either side of Great Peconic Bay. The North Fork and the South Fork (jointly referred to as the East End) have evolved very distinctly. Historically, the South Fork has been more popular — especially on July and August weekends! Yet the qualities that originally attracted people to this area can still be found: At times the light is almost transcendent; the local produce remains among the finest in the United States; and there is now a successful and growing aquaculture of oysters. The beaches have fine, whitish sand, and the sapphire-blue water is clean and invigorating.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Visit a historic farmstead 
  • Go antique shopping in Bridgehampton
  • Stop at the famous Montauk Point Lighthouse
  • Hike among the 100-year-old sand dunes
  • Tour the Sag Harbor Whaling Museum
  • Enjoy wine tastings at excellent local vineyards 

Trip Overview

Day 1 : East Hampton
Check into your hotel in East Hampton
Day 2 : Explore historic East Hampton
Explore historic East Hampton
Day 3 : Drive to Amagansett
Walk among sand dunes, visit a famous lighthouse
Day 4 : Explore Sag Harbor
Explore the historic buildings and sites in Sag Harbor
Day 5 : Tour wineries
Visit some of our favorite local wineries and enjoy tastings
Day 6 : Take a cruise
Enjoy a leisurely cruise followed by a picnic lunch, or relax on the beach
Day 7 : Return home
Depart
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Day 1 : East Hampton

Check into The Baker House 1650 in East Hampton or the Topping Rose House in Bridgehampton. To get there, it's easiest to fly into Long Island's MacArthur Airport and rent a car. Alternatively, fly from the Downtown Manhattan Heliport to the East End with New York Helicopter. Either option is more pleasant than driving from New York City, particularly in July and August.

Settle in, have a swim in the hotel pool and refresh yourself with a treatment in the spa.

Walk to dinner at The 1770 House (or drive 15 minutes from the Topping Rose) and dine in either the handsome, casual Tavern or the sophisticated Dining Room.

The Bakers House 1650 in East Hampton
The Bakers House 1650 in East Hampton - The Baker House 1650
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The Baker House 1650

Grand public rooms distinguish this East Hampton Elizabethan-style property from others on the East End.

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Topping Rose House

This charming 22-room inn comprising an 1842 Greek Revival house, a studio and four modern cottages is located in relatively quiet Bridgehampton.

Day 2 : Explore historic East Hampton

Explore historic East Hampton. Stop in the Guild Hall, home to a fine modern art collection, and visit Mulford Farm, a fascinating English Colonial farmstead build in 1630 that was home to 10 consecutive generations of the Mulford family. (Open in July and August.)

Head west to Bridgehampton for lunch at the famous Bobby Van's Steakhouse. Bridgehampton is an excellent town for antique shopping. Browse through the treasures at English Country Home and Lauren Copin Antiques.

Before returning, visit the Channing Daughters Winery. In addition to working with common varietals such as Chardonnay and Cabernet Sauvignon, this winery also successfully experiments with unusual grapes such as Tocai Friulano, Dornfelder and Blaufränkisch. Nearby Wölffer Estate in Sagaponack makes traditional European-style wines.

A bookstore in East Hampton
A bookstore in East Hampton - WalkingGeek/Flickr

Day 3 : Drive to Amagansett

Drive through Amagansett, to Hither Hills State Park, notable for its impressive Walking Dunes, sand dunes that were formed more than 100 years ago. After working up an appetite walking among the dunes, visit the Clam Bar restaurant. Sitting at an umbrella-shaded table with a cup of clam chowder and an impeccably fresh lobster salad roll is pure bliss.

At the far end of the South Fork stands the famous Montauk Point Lighthouse, completed in 1796. Climb the 110-foot tower for stunning views of the coast. If time and energy permit, explore the nature trails near the lighthouse and in adjacent Camp Hero State Park.

Return to East Hampton and enjoy dinner at The Palm, a warmly decorated traditional steakhouse.

Montauk Point Lighthouse in Montauk
Montauk Point Lighthouse in Montauk - Adam Mazza/Flickr

Day 4 : Explore Sag Harbor

Explore the captivating town of Sag Harbor, which is filled with historic buildings from its days as a major seaport. Be sure to visit the fascinating Sag Harbor Whaling Museum.

Lunch in one of the charming restaurants along Main Street, and enjoy some chain-free shopping in the local boutiques. Alternatively, rent a kayak for a couple of hours from Mill Creek Kayaks.

This evening, enjoy dinner at East Hampton Grill

Sailboats on Sag Harbor
Sailboats on Sag Harbor - Gail Frederick/Flickr

Day 5 : Tour wineries

Venture around Great Peconic Bay to the North Fork, home to numerous inviting wineries, many of which feature tasting rooms as well as picnic areas.

Moving from west to east, some favorite wineries include: Paumanok Vineyards, Jamesport Vineyards, Shinn Estate Vineyards, Castello di Borghese, Pellegrini Vineyards, Peconic Bay Winery and Bedell Cellars.

Peconic Vineyard
Peconic Vineyard - Chris Goldberg/Flickr

Day 6 : Take a cruise

Return to Sag Harbor and rent a motor or sailing yacht (complete with captain) for the day. Take a leisurely cruise, and indulge in a romantic picnic lunch.

Alternatively, stay near East Hampton and take a day to relax on the beaches, renowned for their fine, whitish sand and sapphire-blue waters.

Enjoy dinner this evening at The American Hotel in Sag Harbor, which boasts one of the finest wine lists in the world.

The main beach in East Hampton
The main beach in East Hampton - natalieRose/Flickr

Day 7 : Return home

Depart East Hampton and travel home.

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Book This Itinerary

Contact a travel advisor to book your custom itinerary. Fill out the form or call (630) 734-4610.