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Tour Itinerary

4 days / 3 nights

Day One – Welcome to Long Island! ~ Visit to Old Westbury Gardens

Welcome to Long Island! This island stretches 125 miles from the bustling city of Manhattan to the tranquil Montauk Point Lighthouse.  Here we’ll discover quaint villages, cultural treasures, boutique shopping, pristine beaches and exceptional vineyards. Experience the lifestyle of Long Island’s famous residents: Jerry Seinfeld, Billy Joel, Calvin Klein, Martha Stewart and more! This afternoon, well enjoy a visit to Old Westbury Gardens, listed on the National Register of Historic Places, is the former home of the Phipps Family.  This magnificent Charles II-style mansion is nestled amid 200 acres of formal gardens, landscaped grounds, woodlands, ponds and lakes.  Later, we’ll arrive to our Long Island hotel for a relaxing three night stay! Take some time to relax and freshen up before enjoying a delicious dinner tonight.

Meals: Dinner

Optional Add On:  High Tea at Old Westbury Gardens 

Day Two –  Sag Harbor, Whaling Museum & Award Winning Vineyard Wine Tasting

Enjoy breakfast before embarking with your local Guide for a wonderful day of touring and tasting! Begin with a historic tour arriving to the village of Sag Harbor once a bustling port town where whalers of all nationalities converged. Visit Sag Harbor Whaling Museum and learn about local history as you walk through exhibits housed in a 19th-century mansion. Then enjoy time to stroll up Main Street and visit its old-time storefronts, antique shops and enjoy lunch on our own. This afternoon, cross over to the ‘North Fork’ and named one of the ‘Top Ten Wine Regions in the World’ by Wine Enthusiast magazine where you’ll visit to one of Long Island’s award-winning vineyards for a wine tasting!  Enjoy a planned dinner this evening at one of the area’s popular restaurants.

Meals: Breakfast, Dinner

Day Three – The Hamptons, Montauk Point Lighthouse & Dinner at Long Island Aquarium with Private VIP ‘After Hours’ Aquarium Access

After breakfast, meet your local guide for another delightful day of sightseeing through ‘The Hamptons’; the summer playground of the rich and famous consisting of chic seaside communities where today’s most well-known celebrities own summer homes. Enjoy some time in Southampton to visit the charming shops and eateries before setting off for a drive along ‘billionaire lane’ where Wall Street execs, CEOs, and celebrities alike, live in multimillion-dollar mansions along this famous beachfront stretch and visit one of America’s “top 10 beaches.”  Continue to Montauk Point State Park for a visit to Montauk Point Lighthouse, commissioned by George Washington in 1792.  Tonight, enjoy dinner at the Long Island Aquarium along with private ‘after hours’ VIP access to the Aquarium!

Meals: Breakfast, Dinner

Day Four – “Gold Coast” ~ Mansion tour & Depart for home

Enjoy breakfast this morning before we check out and tour along the “Gold Coast”. The turn of the century through the 1930’s, the North Shore was a virtual Who’s Who of High Society. From the Astor’s to the Vanderbilt’s, this was THE place to be for some of the most notable Americans.  Also, F Scott Fitzgerald’s famous historical novel, The Great Gatsby, was inspired by one or more of Long Island Gold Coast Mansion’s! Enjoy a tour of the grandest of them all – Oheka Castle! Later, we bid Long Island farewell and depart for home.

Meals: Breakfast

Tour Inclusions

  • Three night’s accommodations
  • Three breakfasts
  • Three dinners
  • Three days professional tour guide service
  • Admission to Old Westbury Gardens
  • Drive past homes and estates of the rich and famous
  • Tour the “North Fork”
  • Admission to Southold Historical Society
  • Visit two Vineyards for tour and tastings
  • Evening admission to Long Island Aquarium
  • Tour the “South Fork”
  • Stop at one of America’s “top 10 beaches”
  • Visit to Sag Harbor
  • Visit ‘the Hamptons’
  • Admission to Sag Harbor Whaling Museum
  • Admission to Montauk Point Lighthouse & Museum
  • Free time in Long Island’s quaint villages
  • Admission to Oheka Castle
  • Hotel taxes; meal taxes and gratuities
  • Luggage handling (one piece per person)