Springtime in the Hamptons & Manhattan

Gold Coast Mansions & Musicals

  • Date

    May 11-16, 2026 | Mon / Sat – 6 Days

  • Location

    Riverhead | Southampton | East Hampton | Cove Neck | Old Westbury | Times Square

Overview

Experience late spring as it flows into the summer in the Hamptons—known for its rich history, extravagant homes, and over 3,000 acres of vineyards! A guided tour will lead you through East Hampton Village, crowned one of America’s most beautiful villages. Sip wine along the North Fork Wine Trail, home to over forty wineries! Visit Long Island’s most extravagant estates the illustrious Gold Coast Mansion. Tour the 127-room OHEKA Castle, whose halls once echoed with the sounds of lavish Roaring Twenties parties, and the famed formal gardens of Old Westbury Gardens.

New York City has always been a city of superlatives: the tallest, trendiest, biggest, and best. It’s also one of the world’s most dynamic destinations. The skyline seems to be forever evolving, and exciting new restaurants and shops continuously pop up in every neighborhood. First-time and frequent visitors alike will experience variety at every turn! Join us in the heart of spring for New York City’s best, including three nights at the Marriott Marquis Times Square, just steps from the theatres, top restaurants, and world-class shopping. The bright spot, however, is always Broadway—and we’ve got your tickets! 

HIGHLIGHTS INCLUDE

  • Explore the Hamptons with a local expert
  • Enjoy lunch & tour at OHEKA Castle 
  • See Cooper’s Beach & Billionaire’s Row
  • Free time in Southampton & East Hampton 
  • Tour Old Westbury Gardens 
  • Savor a local wine tasting
  • Tickets to two Broadway musicals
  • Experience a New York City Ballet performance 
  • Visit Central Park & the New York Historical Society

PACKAGE INCLUDES

  • Roundtrip commercial air from Indianapolis to New York, New York
  • Escorted
  • 5 nights accommodations
  • 4 Breakfasts
  • 2 lunches, 2 dinners
  • Farewell Brunch
  • Sightseeing and admissions per itinerary
  • Ground transportation
  • Hotel baggage handling

NOTE: This itinerary includes activities where moderate walking is required.

Mon, May 11: Fly to New York. Enjoy a Welcome Lunch and tour OHEKA CASTLE, the centuries-old French-style chateau that was—and still is today—the second-largest private residence ever built in America. During the Gilded Age of the 1920s, the owner, Otto Hermann Kahn, used the 109,000-square-foot, 127-room estate as a summer home where he hosted lavish parties and regularly entertained royalty, heads of state, and Hollywood stars. Continue up Long Island and check in to Hyatt Place Long Island/East End for two nights. Enjoy the evening free for dinner on your own. (Meals: Lunch)

Tue, May 12: Following breakfast, meet up with your local guide, a long-time resident of Southampton, and tour through the south fork of the Hamptons. Stop at Coopers Beach and drive down Billionaire’s Row awash with the homes of Wall Street billionaires as well as celebrities such as Calvin Klein and Ian Schrager. Spend some time in the village of Southampton, encountering the rich history of New York’s oldest English settlement and the shopping district with its charming boutiques! Enjoy lunch and some free time here before exploring East Hampton Village, considered one of America’s most beautiful villages. Return to the hotel and freshen up before a wine tasting and dinner. (B,D)

Wed, May 13: After breakfast this morning, check out of the hotel and transfer to Centerport, home of the Vanderbilt Museum and Planetarium. The estate, known as Eagle’s Nest, served as the summer home of William K. Vanderbilt II, the great-grandson of Cornelius Vanderbilt. Then head to Old Westbury Gardens for a tour of the famed formal gardens. Completed in 1906 by the English designer, George A. Crawley, the magnificent Charles II-style mansion is nestled amid 200 acres of manicured landscaping, woodlands, ponds, and lakes and is listed on the National Register of Historic Places. Enjoy an included lunch before waving goodbye to the Hamptons as you make your way to the “city that never sleeps.” Check into the Marriott Marquis Times Square in Manhattan for three nights. Have dinner as you please before joining the group to see a Broadway Musical! (B,L) 

Thu, May 14: Today is yours to enjoy! Spend the morning and afternoon as you please in the Big Apple. Shop, visit a museum, or explore the city. Tonight, gather with the group to see another Broadway Show. (B) 

Fri, May 15: After breakfast, head to Central Park for a horse-drawn carriage ride around the park. Traverse the park just as New Yorkers would have in 1858—the first year the park was open to the public! Then head to the New York Historical Society, New York’s first museum founded in 1804. In the evening, see the New York City Ballet perform All Bach, inspired by the music of composer Johann Sebastian Bach. (B,D)

Sat, May 16: Check out of the hotel and savor a special Farewell Brunch before transferring to the airport for your flight home. (BR)

Hyatt Place, Long Island/East End. Located on the Peconic River, this waterfront hotel features a full-service marina and convenient location to the Hamptons. Highlights: in-room coffee/tea maker, refrigerator • complimentary WiFi Internet access • restaurant • bar • indoor and outdoor pools • fitness center.

New York Marriott Marquis. Conveniently located in the heart of the theatre district and Times Square, with entertainment and restaurants just around the corner. Highlights: high-speed Internet access (fees apply) • four restaurants, including The View Restaurant, the only revolving rooftop restaurant in NYC • fitness center.

Pricing

  • Package with Air*
  • Double P/P – $4,299
  • Triple P/P – $4,029
  • Single – $5,119
  • Land Only
  • Double P/P – $4,029
  • Triple P/P – $3,759
  • Single – $4,849

*Subject to change due to fuel surcharge

Documents Required: Valid U.S. government issued REAL I.D.