Caswell-Massey Holiday 2024 Sweepstakes
The $100k New York Shopping Spree GIVEAWAY
Enter to win your dream New York City Jet Set Shopping Spree, worth $100,000. Stay at the finest hotels, eat at the best restaurants in the world, and shop the highest-end luxury brands all in the the City of Dreams.
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Turn the Big Apple into Your Playground
Suggested Itinerary
Here’s a week-long itinerary for a luxury shopping vacation in New York City during the holiday season. Enjoy the festive atmosphere and indulge in some of the best shopping experiences the city has to offer!
Day 1: Arrival and Upper East Side Shopping
- Morning: Arrive in NYC and check into your luxury hotel (consider The St. Regis or The Peninsula).
- Afternoon: Stroll down Madison Avenue. Visit high-end boutiques like Chanel, Prada, and Louis Vuitton.
- Evening: Dinner at The Modern, a Michelin-starred restaurant at the Museum of Modern Art (reserve in advance).
- Night: Enjoy a walk through the festive window displays at nearby Bergdorf Goodman.
Day 2: Fifth Avenue and Holiday Lights
- Morning: Breakfast at Sarabeth’s on Central Park South.
- Late Morning: Shop along Fifth Avenue. Visit iconic stores like Saks Fifth Avenue and Tiffany & Co.
- Afternoon: Lunch at Nobu (reservations recommended) and continue shopping at the flagship stores.
- Evening: Catch the holiday lights display at Saks Fifth Avenue, then enjoy dinner at Carbone in the West Village.
Day 3: SoHo and Nolita
- Morning: Brunch at *Balthazar* in SoHo.
- Afternoon: Explore SoHo’s trendy boutiques and designer shops (visit places like Isabel Marant and A.P.C.). Don’t miss the unique stores in Nolita.
- Evening: Enjoy a cocktail at The Blond in the 11 Howard Hotel, followed by dinner at Beauty & Essex.
Day 4: Brooklyn and DUMBO
- Morning: Head to Brooklyn and enjoy breakfast at Butler in Williamsburg.
- Late Morning: Explore local boutiques and artisanal shops in Williamsburg.
- Afternoon: Walk to DUMBO for stunning views of Manhattan and shop at local brands. Stop by Jane’s Carousel for a scenic view.
- Evening: Dinner at The River Café with spectacular views of the skyline.
Day 5: Luxury Department Stores
- Morning: Breakfast at The Palm at the Plaza.
- Late Morning: Spend the day at Bloomingdale’s and Saks Fifth Avenue for exclusive holiday promotions.
- Afternoon: Lunch at Saks’ Café and continue shopping for high-end brands.
- Evening: Attend a Broadway show (book tickets in advance) and grab dinner at Le Bernardin afterward.
Day 6: Fashion and Art
- Morning: Breakfast at Cafe Sabarsky in the Neue Galerie.
- Late Morning: Explore the Upper West Side and visit boutiques along Columbus Avenue.
- Afternoon: Visit The Met for a cultural break, then shop at The Shops at Columbus Circle.
- Evening: Dinner at Masa (if you’re a sushi lover, reservations are essential) or at Per Se for a special tasting menu.
Day 7: Final Day and Departure
- Morning: Enjoy a leisurely breakfast at your hotel.
- Late Morning: Last-minute shopping in Times Square or revisit favorite spots for any final purchases.
- Afternoon: Check out and have lunch at *The Grey Dog*.
- Departure: Head to the airport and make sure you leave with plenty of time to spare before your flight departs. (NYC traffic is no joke).
Tips:
- Make reservations for popular restaurants and shows in advance.
- Consider using a personal shopper service for an elevated experience.
- Take advantage of holiday events like ice skating at Rockefeller Center or visiting the Christmas markets.
Enjoy your luxurious holiday shopping adventure in NYC!