Travel Dutchess
Spend Christmas in New York on a hosted four-day holiday itinerary—a small-group New York holiday getaway featuring iconic landmarks, hidden gems, incredible dining, Broadway, rooftop views, and festive holiday traditions, all thoughtfully curated by Travel Dutchess.
Ordinary vacations are booked. Signature Experiences are hosted—curated by someone who knows the city intimately and travels alongside you.
Every moment guided in person by Travel Dutchess.
An intimate circle, thoughtfully assembled.
Designed with intention, never off-the-shelf.
Places most travelers never find on their own.
Considered details from arrival to farewell.
Arrive present. Everything else is handled.
New friendships forged over shared, unforgettable moments.
A rhythm of iconic moments and quiet luxuries, unfolding across four unforgettable days.
Private transfers and a rooftop welcome reception (weather permitting) to open the week, followed by a free evening to settle in at your own pace. Cap the night with a Times Square Night Stroll—giant billboards, holiday lights, the Red Steps, and the Broadway district all aglow, with street performers, endless photo opportunities, and the electric excitement of NYC after dark.
An unforgettable evening through New York City's most magical holiday landmarks. Step into the magic of Christmas as we stroll through the heart of Midtown Manhattan. Marvel at the Rockefeller Center Christmas Tree, admire the dazzling Fifth Avenue holiday window displays, explore Bryant Park Winter Village, visit historic St. Patrick's Cathedral, and experience the festive energy that makes New York City the most magical place to celebrate the season.
A leisurely signature brunch to open the day, an open afternoon to explore Manhattan your way, and an evening at your leisure across the city that never sleeps.
Join your fellow travelers for our exclusive Travel Dutchess Signature Brunch at one of New York City's favorite dining destinations. Enjoy delicious cuisine, connect with new friends, and soak in the vibrant energy of the city as we gather for a memorable start to the day.
The afternoon is yours to enjoy. Whether you're shopping, sightseeing, or discovering a hidden neighborhood, this is your opportunity to experience New York at your own pace. I'll be happy to share personalized recommendations and help you plan your afternoon based on your interests—iconic attractions, hidden gems, great shopping, or local favorites.
New York City is one of the world's greatest culinary destinations, where every neighborhood tells a story through its food. From world-renowned Michelin-starred restaurants and celebrity chef dining experiences to iconic neighborhood favorites and legendary street food, every meal is an opportunity to experience the city's incredible diversity. Whether you're celebrating with an unforgettable fine dining experience, enjoying dinner with breathtaking skyline views, discovering an award-winning vegan restaurant, or grabbing a slice from an iconic neighborhood pizzeria, New York offers something for every taste and every budget. Tonight is your opportunity to explore the city your way. If you'd like, you're also welcome to join me for an optional Travel Dutchess Hosts' Dinner at one of my favorite New York restaurants. This relaxed evening is a wonderful opportunity to enjoy great food, connect with fellow travelers, and experience the city like a local. Guests are welcome to join us, with each person paying for their own meal. Discover New York's Culinary Icons:
As your Travel Dutchess host, I'll be happy to provide personalized restaurant recommendations, assist with reservations, and help you discover the perfect dining experience for an unforgettable evening in New York.
A day designed around you—slow mornings, open afternoons, and a magical Brooklyn evening in Dyker Heights.
Start your day at your own pace. Sleep in, enjoy breakfast at a neighborhood café, or revisit a favorite spot from earlier in the trip. This is your opportunity to experience New York like a local and create your own adventure. If I can make one recommendation, make today the day you step outside your comfort zone. Skip the familiar chain restaurants and discover the incredible flavors that make New York one of the world's greatest food cities. You might find your new favorite meal. I encourage you to experience some of New York's iconic and culturally rich foods, including:
The afternoon is yours to enjoy. Whether you're shopping, sightseeing, or simply taking in the city's energy, this is the perfect time to discover what makes New York unforgettable. I'll be available throughout the day to offer personalized recommendations based on your interests—whether you're looking for great food, hidden gems, shopping, museums, entertainment, or the perfect photo spot. Popular ideas include:
As evening falls, we'll journey to Brooklyn's legendary Dyker Heights, where entire neighborhoods transform into dazzling Christmas wonderlands. Stroll beneath millions of sparkling lights, admire elaborate holiday displays, and experience one of New York City's most cherished Christmas traditions before returning to Manhattan with unforgettable holiday memories.
As our unforgettable holiday experience comes to a close, enjoy one final breakfast with your fellow travelers before departing. Reflect on the memories you've made, the friendships you've formed, and the magic of experiencing New York City during the most wonderful time of the year.
Whether you're heading home with a camera full of photos, new friendships, or inspiration for your next adventure, we hope you leave with memories that will last a lifetime.
New York City isn't just one of my favorite destinations—it's a place that has shaped my life. I had the privilege of living in New York for more than 15 years, and during that time I fell in love with its energy, diversity, creativity, and endless opportunities for discovery.
I believe travel changes you. Every journey expands your perspective, introduces you to new people, and creates memories that stay with you long after you return home. Travel reminds us that there's always more to learn and experience.
While many people dream of traveling the world, not everyone has the opportunity to visit dozens of countries. That's one of the reasons I love New York so much. There is no other city quite like it. In just a few days, you can experience the flavors, traditions, neighborhoods, and cultures of people from around the globe—all without ever leaving one city. From Little Italy and Chinatown to Harlem, the Lower East Side, and neighborhoods influenced by cultures from every continent, New York offers a truly global experience.
My passion is creating thoughtfully curated trips that go beyond checking attractions off a list. I want you to experience New York through the eyes of someone who knows and loves the city—whether we're admiring the Rockefeller Center Christmas Tree, strolling through Bryant Park Winter Village, enjoying incredible dining, discovering hidden gems, or taking in breathtaking skyline views from a rooftop.
When you travel with Travel Dutchess, you're not just booking a vacation. You're joining a hosted experience where the details are thoughtfully planned, the itinerary is intentionally curated, and every moment is designed to help you create lasting memories.
I can't wait to welcome you to the city that changed my life.
Let's experience New York differently.
Three nights in a carefully selected Manhattan hotel.
Meet your fellow travelers while enjoying an elegant welcome reception with breathtaking skyline views.
Experience the excitement of Times Square illuminated by millions of lights while capturing iconic New York photos.
A guided Day One evening through Midtown's most magical landmarks—the Rockefeller Center Christmas Tree, Fifth Avenue holiday windows, St. Patrick's Cathedral, Bryant Park Winter Village, and Radio City Music Hall.
A beautifully curated brunch at one of New York City's favorite restaurants.
Visit Brooklyn's famous holiday neighborhood filled with spectacular Christmas displays.
Gather one last time over a relaxed morning breakfast before departures, celebrating the weekend together in an elegant New York setting.
We'll navigate the city together during our planned group activities.
A special keepsake to begin your New York holiday adventure.
Travel with an experienced New York host who has lived in the area for over 15 years and has carefully curated every experience.
Airfare is not included in the package price.
To provide you with the greatest flexibility, guests are responsible for booking their own airfare. Upon request, Travel Dutchess is happy to assist you in selecting or booking flights that best align with the group's arrival and departure schedule, ensuring you don't miss any of our signature experiences.
Our goal is to make your travel experience as smooth and stress-free as possible from the moment you arrive in New York City.
Experience New York City during its most magical season through a thoughtfully curated hosted journey designed to create unforgettable memories.
Reserve your space with 25% down — $499.75 — and divide the remaining balance into three monthly payments of $499.75, charged automatically to your card on September 15, October 15, and November 15.
Final payment is due November 15, 2026. Nothing is charged after the final installment.
Share a room with a travel companion or fellow guest.
Private accommodations based on hotel availability.
Every detail of this experience has been personally curated by Travel Dutchess. From hand-selected accommodations and unforgettable holiday experiences to restaurant recommendations and insider tips, you'll enjoy New York City through the eyes of someone who knows and loves the city.
This isn't simply a trip—it's a hosted experience designed to help you create lasting memories while discovering New York like a local.
Join a small group of travelers for an unforgettable holiday experience filled with iconic sights, festive traditions, incredible dining, and meaningful connections.
11 places remaining
5 of 16 places reserved. This is a small, hosted group by design.
November 15, 2026
All balances are due by November 15, 2026. Reserve early to spread your payments across the full plan.
Reserve with a deposit →Reserve with 25% down and spread the balance over three monthly payments, or settle in full today. Every payment is processed securely by Stripe.
So you can plan with clarity, the following are not part of the package price:
Secure your spot with a deposit and settle the balance through three manageable installments.
Installments are charged automatically to the card on file. Custom schedules can be arranged upon request.
Because this is an intimate, small-group experience, cancellations are handled with the following guidelines:
Travel insurance is strongly encouraged to protect your investment against unforeseen circumstances.
A few essentials to ensure a seamless holiday experience:
By reserving your spot on a Travel Dutchess Signature Experience, you acknowledge and agree to the following:
For any questions, please reach out directly — we're here to guide you every step of the way.
Stories from travelers who have joined a Travel Dutchess Signature Experience.
“Pam made our New York trip absolutely unforgettable! From the moment we arrived, every detail was taken care of. Her knowledge of the city is incredible—from Broadway tips to hidden restaurants and photo spots we never would have found on our own. We simply relaxed and enjoyed every moment. I'm already planning my next trip with Travel Dutchess!”
“I've been to New York before, but experiencing it with Pam was on another level. She knows all the hidden gems and perfectly balances the iconic attractions with unique local experiences. Her hospitality made everyone feel welcome, and her positive energy kept our group laughing the entire trip.”
“Pam's love for New York is contagious! She shared fascinating stories about the city, recommended amazing places to eat, and made sure we never wasted time standing in long lines or wondering what to do next. It felt like exploring the city with a trusted friend who knows all the best spots.”
“Traveling with Pam was completely stress-free. She thought of everything before we even had to ask. From the hotel and Broadway to incredible restaurants and those little hidden places that make New York so special, every experience was carefully planned. If you want more than a vacation—if you want memories you'll never forget—book with Pam!”
“Pam truly takes the stress out of traveling. From the moment we arrived in New York, every reservation, recommendation, and detail was already taken care of. We didn't have to worry about transportation, where to eat, or what to see. All we had to do was enjoy the city. Her knowledge and hospitality made this one of the best vacations I've ever had.”
“What sets Pam apart is her passion for New York. She doesn't just take you to the famous attractions—she shares the stories behind them and introduces you to hidden gems that most visitors never experience. It felt like exploring the city with a close friend who knew all the best places. I laughed, made lifelong memories, and can't wait to book another Travel Dutchess trip.”
Your New York holiday includes three nights in a hand-selected Manhattan hotel, a welcome reception, the Travel Dutchess signature brunch, a farewell dinner, the Dyker Heights Christmas lights experience, a Times Square night stroll, group transportation during hosted activities, and a welcome gift.
Free planning notes from a host who spends every December in Manhattan.
A realistic day-by-day plan for four December days in Manhattan — the tree, the windows, Broadway, Brooklyn lights, and the meals in between.
Read guide · 9 min read
December in Manhattan means 20,000 steps a day in 35-degree wind. Here is exactly what to bring — and what to leave home.
Read guide · 6 min readEvery holiday light display worth your evening in New York — and the hour to arrive at each one so you are not standing in a crowd.
Read guide · 7 min readJoin the interest list and I'll send the itinerary, holiday planning notes, and a heads-up before the last spots go.
No spam. Just this trip and future Signature Experiences.
Join the inaugural Travel Dutchess Signature Experience and create holiday memories you'll treasure for years to come.