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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

Day Two – “North Fork” ~ Vineyard tours and Wine Tasting & Long Island Aquarium

Enjoy breakfast at the hotel before meeting our guide for a day of sightseeing and exploring the “North Fork”. Tour through charming villages and seaside communities as well as visit the Southhold Historical Society. Mid-day enjoy free time for lunch on own in one of the area’s charming villages. This afternoon we’ll explore the North Fork’s wine region. Recently named one of the ‘Top Ten Wine Regions in the World’ by Wine Enthusiast magazine, we’ll enjoy visits to two of Long Island’s wonderful vineyards followed by a wine tasting! Tonight, enjoy a private dinner at the Long Island Aquarium following by VIP ‘after hours’ access to the Aquarium!

Meals: Breakfast, Dinner

Day Three – “South Fork” ~ The Hamptons, Sag Harbor, Whaling Museum & Montauk Point Lighthouse

Enjoy breakfast before meeting our guide for another day of sightseeing touring the “South Fork”.  Tour 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.  We’ll also enjoy a stop at one of America’s “top 10 beaches” and visit Sag Harbor, once a bustling port town where whalers of all nationalities converged.  Enjoy some free time to stroll up Main Street and visit its old-time storefronts, antique shops and enjoy lunch on our own. This afternoon, we’ll continue touring and visit Sag Harbor Whaling Museum and learn about local history as you walk through exhibits housed in a 19th-century mansion.  Continue on to Montauk Point State Park for a visit to Montauk Point Lighthouse, commissioned by George Washington in 1792.  Tonight, enjoy another delicious dinner.

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)