Phone: 508-457-7461
Toll Free: 866-518-6877

Lifestyles of the Rich & Famous

Lifestyles of the Rich & Famous

Enjoy four days exploring the lifestyles of the rich & famous in the scenic Guilded Age playground of the rich, the Gold Coast of Long Island & the Hamptons

Lifestyles of the Rich & Famous

Tuesday, June 25 – Friday, June 28


Enjoy four days exploring the lifestyles of the rich & famous in the scenic Guilded Age playground of the rich, the Gold Coast of Long Island & the Hamptons


DAY 1 - We’ll cruise from New London to the North Fork of Long Island. Enjoy a waterfront lunch (on your own), and then visit one of the North Fork’s many wineries. Visit Duck Walk Vineyard, one of the most well-known names in Long Island wine, for a tour and wine tasting.  We’ll stay for three nights at the Holiday Inn Express & Suites, centrally located in Riverhead, NY.


DAY 2 -  We’ll enjoy a full day touring the Hampton’s charming villages with our local guide, including Southampton, Northampton, Sag Harbor, and Montauk.  We’ll visit the Old Whalers Church and stop at the Montauk Lighthouse & Lighthouse Museum, where you can climb to the top of the Lighthouse for a fabulous three-state view.  In Southampton, we’ll enjoy a delicious 3-course dinner and 12-oz Publick House handcrafted beer.  B, D


DAY 3 - On our “Lifestyles of the Rich and Famous Tour,” we’ll visit Long Island’s Gold Coast to see gorgeous mansions and learn about the famous and infamous people that lived in them. We’ll visit two Gilded era mansions on the Gold Coast. Planting Fields Arboretum State Historic Park, which includes the 67-room Coe Hall Historic House Museum, is an arboretum and state park covering 409 beautifully landscaped acres.  Coe Hall contains many original pieces and furnishings once belonging to the Coe family.  The Tudor Revival mansion is a showcase of artistry and craftsmanship with its wood and stone carvings, ironwork, and stained glass windows.  We’ll tour the mansion and have some time to stroll the gardens before traveling to the palatial Spanish Revival estate that was the summer home of William K. Vanderbilt II, Eagle's Nest. The 24-room Gold Coast mansion is a massive home with a private museum, golf course, boathouse, seaplane hangar and other amenities. After relaxing at the hotel, we’ll enjoy a delicious dinner at the Country House Restaurant, which was once a stage coach stop that hosted meetings of George Washington’s Culper Spy Ring. (B,D)


DAY 4 – On our last day on Long Island, we’ll visit the Long Island Museum.  Set up to resemble a New England Village, with local historic buildings carefully trucked onto the grounds. We’ll start at the Visitor Center for a quick overview and look at the wildfowl decoy gallery. Stop at the magnificent 40,000 square foot Carriage Museum, home to the finest collection of American horse-drawn transportation artifacts in the world, most on permanent exhibition.  You’ll marvel at the scenes depicting life in 19th century New York City, including a “burning” building, and commercial vehicles on bustling city streets. You’ll have time for lunch on your own in the quaint village of Stony Brook, and then we’ll stop at Baiting Hollow Farm Vineyard, where we will not only meet the owners & taste their wines, but we’ll also visit their Horse Haven to learn about their rescue mission and get an up-close look at their beautiful race horses.  We’ll take a look at one of the North Fork’s many farms, Catapano Dairy Farm for a tour of the farm, a fun, interactive goat milking demonstration, and to sample some of their award-winning artisanal cheeses.  You’ll learn how they make their goat and sheep cheeses, and have an opportunity to visit the animals.  You’ll also take home a bar of their pure goat milk soap.  We’ll take the Orient Point ferry to Connecticut and return to the Cape.  (B) 


$ 895 per person, double occupancy, $ 1,110 single occupancy

Departure Times:

Dennis- 7:15 AM
Barnstable- 7:30 AM
Sagamore- 7:50 AM

Return Times:

Sagamore- 9:30 PM
Barnstable- 9:50 PM
Dennis- 10:05 PM


B=Breakfast included

Package Includes:

Three nights at the Holiday Inn Express & Suites

three breakfasts, two dinners

baggage handling

round trip cruise on the Orient Point/New London Ferry

Duck Walk Vineyard tasting

wine tasting and rescue horse tour at Baiting Hollow Winery

full day guided tour of the Hamptons with Montauk Lighthouse

Planting Fields with tour of Coe Hall Mansion Museum

Vanderbilt’s Eagles Nest tour

the Long Island Museum.



Payments and Cancellations

Cash, personal checks & money orders accepted

Visa & MasterCard payments accepted via phone.


$75 per person deposit due upon booking, balance due 45 days prior to tour.  Refundable up to 30 days prior to tour.


Trip Insurance is available for this trip through Travel Insured International for a per person cost of $52   (based on double occupancy rate)


Below is a list of pick-up points available on this tour.

Below is a list of pick-up points available on this tour.

Name Address Contact Details
1 - Dennis Patriots Square, Route 134, South Dennis
On Stop & Shop side, park in lot closest to Rt 134
2 - Barnstable Barnstable Exit 6 Commuter Lot - behind
Burger King, wait at enclosures
3 - Sagamore Sagamore Commuter Lot at base of bridge
on NON Cape side, wait at enclosures
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15 Mill Pond Way, East Falmouth, MA 02536 | Phone: 508-457-7461 | Toll-Free: 866-518-6877