Curator’s statement
At The Private Traveller, I specialize in curating bespoke travel experiences that blend luxury, culture and unforgettable moments. My USA travel itinerary blogs, featuring Boston and New York, highlight iconic destinations and world-class hotels like the Four Seasons Boston, The Plaza and Equinox Hudson Yards. Each itinerary is thoughtfully crafted to offer unique activities, exclusive perks and seamless experiences. With a passion for detail and a commitment to excellence, I bring your dream holiday to life.
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Day 1-3: Boston
Begin your luxury USA adventure in the historic city of Boston, where charm, culture and sophistication converge. Staying at the Four Seasons Hotel Boston, you’ll enjoy a prime location overlooking Boston Common. The hotel offers both a tranquil retreat and easy access to the city’s vibrant attractions. Whether strolling along the Freedom Trail, admiring the art collections at the Museum of Fine Arts or indulging in Italian treats in the North End, Boston brims with experiences that capture the spirit of New England.
The Four Seasons Boston blends timeless elegance with exceptional service, making it the ideal base for your stay. With its indoor pool, world-class dining and proximity to the city’s most iconic landmarks, this hotel ensures every moment of your visit is unforgettable. Boston in the festive season, with its twinkling lights and cozy atmosphere, sets the tone for an extraordinary holiday itinerary.
Day 4-8: New York, The Plaza
No trip to New York during the holidays would be complete without a stay at the iconic Plaza Hotel. This legendary property, located at the corner of Fifth Avenue and Central Park South, is synonymous with luxury and timeless elegance. From its stunning Beaux-Arts architecture to its celebrated Palm Court, home to the city’s most famous afternoon tea, The Plaza exudes glamor and charm.
During the festive season, The Plaza transforms into a magical winter wonderland, providing the perfect backdrop for holiday memories. Whether you're marveling at the tree at Rockefeller Center, ice-skating in Central Park or enjoying a quiet moment by the hotel’s Christmas displays, The Plaza offers a quintessential New York experience that feels straight out of a classic holiday film.
Day 9-11: New York, Hudson Yards
In the heart of Manhattan’s newest neighborhood, Hudson Yards, the Equinox Hotel redefines luxury with its emphasis on wellness, innovation and modern sophistication. This sleek property is the perfect choice for travelers seeking a holistic approach to luxury. Offering state-of-the-art fitness facilities, a tranquil spa and an outdoor pool with panoramic city views.
Staying at Hudson Yards also means you’re steps away from some of New York’s most exciting attractions, including The High Line, The Edge Skydeck and The Vessel. The hotel’s chic interiors and commitment to wellness make it a standout destination. Its location in this dynamic district ensures you’re always at the center of the action.
Day 12-13: Brooklyn, New York
For a change of pace, head across the East River to Brooklyn and check into The William Vale, a modern retreat in the heart of Williamsburg. This architectural gem offers stunning views of the Manhattan skyline and a vibrant neighborhood filled with boutique shops, artisanal eateries and local culture.
With its spacious rooms, private balconies and rooftop bar, Westlight, The William Vale blends luxury with Brooklyn’s creative spirit. Relax in the barrel saunas at the Winter Spa or enjoy a quiet dinner while soaking in the city’s twinkling skyline from a unique vantage point. The William Vale offers a fresh perspective on New York’s charm, perfect for a more laid-back yet luxurious experience.
Day 14-15: The TWA Hotel at JFK Airport
End your journey on a high note with a stay at the iconic TWA Hotel at JFK Airport, a masterpiece of mid-century design brought to life by Eero Saarinen. This architectural wonder offers a nostalgic yet modern experience, complete with a rooftop infinity pool overlooking the runways and a fully restored Lockheed Constellation airplane turned cocktail lounge.
The TWA Hotel isn’t just a place to stay — it’s an experience in itself. Explore the meticulously preserved terminal, enjoy a drink in the retro Sunken Lounge or indulge in a meal at the Paris Café by Jean-Georges. Perfect for aviation enthusiasts and design lovers alike, the TWA Hotel provides a fitting finale to a luxurious USA itinerary, blending history, innovation and timeless style.
Need to know
Planning travel itineraries is something I truly enjoy. This 15-day holiday adventure began simply with the idea of spending Christmas in New York and experiencing the magic of The Plaza Hotel during the festive season. Inspired by a TV program we’d seen about the hotel — though it was more focused on Thanksgiving brunch — we knew The Plaza would be a spectacular place to celebrate the holidays. However, wanting to travel before Christmas Day and stay through New Year, it felt like too much time to spend in just one location. To make the trip more dynamic, I started exploring nearby destinations to create a multi-center holiday.
The plan took shape with the decision to fly directly to Boston, where we’d spend a few days soaking in its historic charm and festive atmosphere. From there, we’d take the train down to New York, with The Plaza as our first stop. For New Year, a British Airways agent suggested a quieter evening in Brooklyn, watching the Manhattan fireworks from across the water. Having stayed in Brooklyn before at 1 Hotel Brooklyn Bridge, we decided to try something different this time. The William Vale, with its incredible views of Manhattan, seemed like the perfect fit.
Another bucket-list destination for me has always been the TWA Hotel at JFK Airport. With our return flight departing from there, it made perfect sense to book at least one night to experience its iconic design and unique atmosphere. This left a few days between Christmas and New Year, and we realized we didn’t want to spend the entire time at The Plaza. Hudson Yards, a neighborhood we hadn’t explored since its redevelopment, offered an exciting new perspective on Manhattan. The Equinox Hotel, with its modern luxury and wellness focus, was the perfect choice to round out the itinerary. And just like that, the trip was complete!
If you would like to read up in more detail about this Holiday itinerary, and find out all the things that I have planned for our visits to both Boston and New York at Christmas and New Year, you can find them here:
Luxury Winter Itinerary: Boston and New York with Iconic Hotels and Seasonal Highlights - Part 1
Exploring New York: A Luxury Holiday Itinerary Featuring Iconic Hotels and Unique Experiences Part 2
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Dave Gillan
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