Winter Magic New York: A NYC Urban Adventure (Dec 2026)

Overview

Winter Magic New York: A NYC Urban Adventure (Dec 2026)
New York, NY, USA
Dec 4 - 10, 2026
Group size: 1 - 8
Expedition Sisterhood
$4,499
Deposit: $900

About this trip

🎄 Winter Magic in New York: A NYC Urban Adventure (Dec 4-10, 2026) 


Step into the magic of New York City at the most festive time of year. This 7-day, women-only urban adventure brings together iconic sights, heartwarming holiday traditions, and intimate group moments — all carefully curated and guided by Christine Baldwin of Expedition Sisterhood.


Based in the heart of Times Square at the Sheraton, each day balances must-see experiences with hidden gems and cozy gatherings. You’ll ferry to the Statue of Liberty, wander through festive Chinatown and Little Italy, marvel at the Rockettes Christmas Spectacular with a behind-the-scenes tour, stroll Central Park and Fifth Avenue’s glittering window displays, and toast the season at beloved local spots from Sarabeth’s to Her Name is Han.


Afternoons invite you to discover art at The Met and the Museum of Broadway, savor European pastries in hidden cafés, and shop at winter markets or unwind with live jazz at Lincoln Center. 


With guided highlights and time to explore at your own pace, this trip celebrates the joy of discovering NYC together — without the stress of planning.


What’s Included: All breakfasts and dinners (plus most lunches), entry fees, guided tours, shuttles from LGA, and Christine’s personal guidance throughout.


Your only homework: pack your scarf, your curiosity, and your holiday spirit. ✨


Note: Itinerary subject to change based on weather, availability, or group needs. All meals, entry fees, shuttles, and guiding included unless otherwise noted.


✨ LIMITED SPOTS AVAILABLE – ONLY EIGHT SPOTS TOTAL!
This winter adventure is designed for women seeking connection, delight, and the timeless wonder of Christmas in the Big Apple — together.


Full itinerary and pre-arrival guide will be sent after booking, along with a waiver and guest preference form. All guests must return a signed waiver to finalize participation.

Booking, Grace Period & Cancellation

💰 Payment Plan – NYC Holiday Tour (December 2026)

To reserve your spot, a 20% deposit is collected through WeTravel at checkout. This deposit holds your space on this small-group experience. 

  • Deposit (20%) due upon booking (non-refundable after the grace period)

  • The remaining balance will be split into equal monthly payments, due on the 9th of each month, with final payment due by October 9, 2025

  • Some components of the trip—like Broadway show tickets, Rockettes reservations, and private      tours—may become non-refundable once purchased. You’ll always be notified in advance if any part of your itinerary is affected.

  • Full terms will be included on your invoice and guest agreement and waivers.

Expedition Sisterhood will always do its best to resell unused tickets and issue partial refunds when possible, should plans change unexpectedly.


🌿 Grace Period

Guests may cancel within 7 calendar days of booking for a full refund, including the deposit — as long as the waiver and guest agreement have not yet been signed.


Once the waiver is signed or the 7-day window has passed (whichever comes first), the deposit becomes non-refundable, and the cancellation terms below apply.


This grace period ensures you have time to fully review the experience and ask any questions before finalizing your commitment.



❗Cancellation Policy   

  • The 20% deposit is  non-refundable after the grace period.

  • Cancellations made more than 60 days before the trip may be eligible for a partial refund, depending on what has already been paid or reserved on your behalf.

  • Cancellations within 60 days of the trip are non-refundable, unless your spot can be filled by another guest.

We believe in transparency and fairness. If you need to cancel, we’ll work with you to resell your spot whenever possible and minimize your financial loss.

What's included

Pre-trip Support

Guest forms, waivers, travel tips, and full itinerary sent after booking. Christine will assist with logistics and arrival plans.

Lodging

Six nights at the Sheraton Times Square. Shared or private rooms with 2 beds. Central, safe, and walkable location near Broadway and Fifth Avenue.

Meals

All breakfasts, dinners, and most lunches included. Local restaurants, cozy cafés, and group meals. Dietary needs accommodated. Alcohol not included.

Entry Fees

All tickets included - including but not limited to: Statue of Liberty/Ellis Island, Rockettes, The Met, Museum of Broadway, and two Broadway shows, tours and other program items. No surprise fees.

Transportation

Shuttles from LGA, plus all group subway and transit costs. No car needed — all local travel is coordinated and supported.

Taxes, Tips & Other Fees

All required NYC taxes, service fees, and group gratuities are included in your trip price. No added costs or surprise charges — it’s all built in.

Special Experiences

Backstage tour at Radio City, live jazz, iconic meals, and unforgettable group moments — designed just for Expedition Sisterhood.

Trip Support & Community

Led by Christine — a Montana-based travel adviser. Enjoy a small group of like-minded women and personalized support with packing, logistics, and connection.

What's not included

Airfare

Flights to and from New York City (LGA) are not included. Guests are responsible for booking their own travel based on advised times to meet shuttles.

Market Priced Food

Meals include a generous allowance, but guests pay out of pocket for items marked "market price" or significantly beyond the entrée range.

Alcohol

Expedition Sisterhood does not provide alcohol. Guests may purchase drinks separately at meals where alcohol is available.

Daily Tab for Extras

Extras like alcohol, upgraded entrées, or optional desserts are tracked on a personal tab. Tabs are settled directly with Christine at the end of each day.

Day 1 - December 4

Day 1 - December 4 image

✨ Arrival & Welcome to NYC

Guests will arrive in New York City by mid-afternoon and travel to the Sheraton Times Square via group shuttle, with pickups at LaGuardia Airport scheduled for approximately 12:30 PM and 3:30 PM. Upon arrival, everyone will check in, settle into their rooms, and begin getting to know their travel sisters.


That evening, the group will stroll together to Carmine’s Times Square for a hearty, family-style Italian welcome dinner — filled with laughter, warm conversation, and festive holiday flavors.


This first night will offer a gentle introduction to the city and one another, setting the tone for a joyful and connection-filled week ahead.

Day 2 - December 5

Day 2 - December 5 image

🗽 Liberty, Memory & Broadway

The first full day in New York City will begin with breakfast at the hotel before the group heads downtown to Battery Park. From there, guests will board the 9:00 AM ferry for a meaningful visit to the Statue of Liberty and Ellis Island, including pedestal access and time to explore the exhibits at both historic sites.

After returning to Manhattan, guests will enjoy lunch on their own from nearby street vendors (budgeting $15–20), followed by a quiet visit to the 9/11 Memorial reflecting pools. Museum entry will be optional.


The afternoon will continue with a colorful cultural stroll through Chinatown and Little Italy, where bubble tea, fresh cannoli, and espresso will be included — along with time for photos and a bit of browsing. After a brief rest and change back at the hotel, the group will gather for a fresh, local dinner at Westville Hell’s Kitchen.


The evening will conclude with the group’s first Broadway show, offering a magical theatrical experience to close out the day.

Day 3 - December 6

Day 3 - December 6 image

🎄 Rockettes, The Met & Holiday Magic

The morning begins with a walk to Radio City Music Hall for the 10:00 AM Rockettes Christmas Spectacular, followed by a behind-the-scenes tour of this legendary venue (both included).


From there, the group will walk to Café Un Deux Trois for a charming midday meal, then visit the peaceful beauty of St. Patrick’s Cathedral, with time to light a candle or take photos.


The afternoon will include a visit to The Metropolitan Museum of Art, where guests can explore world-class exhibits and holiday highlights at their own pace. Dinner will follow at Sarabeth’s Upper East Side, a cozy favorite known for its warm hospitality.


To end the evening, guests will enjoy a festive walk through Midtown to admire Fifth Avenue’s holiday windows and the twinkling lights of the Rockefeller Center Christmas tree before returning to the hotel for a well-earned rest.

Day 4 - December 7

Day 4 - December 7 image

🎷 Cathedrals, Culture & Jazz

Day 4 will begin with the group taking the subway uptown for morning pastries and warm conversation at the Hungarian Pastry Shop, a beloved local café. From there, guests will walk to the awe-inspiring Cathedral of St. John the Divine for a private group tour and quiet time in the garden.


The group will then head back toward Midtown for a classic New York lunch at Café Luxembourg. The afternoon will be open for personal exploration, with optional visits to the American Museum of Natural History (included), a peaceful stroll through Central Park, or simple rest time at the hotel.


In the evening, the group will gather for dinner at Loi Estiatorio, a refined Greek restaurant known for heartfelt service and memorable flavors. The day will end on a high note at Dizzy’s Club, where guests will enjoy live jazz and skyline views — a rhythm-filled close to a meaningful day.

Day 5 - December 8

Day 5 - December 8 image

🌉 Brooklyn Views & Final Curtain

After breakfast, Day 5 begins with the group traveling by subway to Brooklyn Promenade and DUMBO, where guests will enjoy sweeping skyline views, cobblestone streets, and photo-worthy moments at every turn. Lunch will be served at Seamore’s, a laid-back seafood spot known for fresh flavors and coastal comfort.


Guests may choose to walk across the iconic Brooklyn Bridge before returning to Manhattan for an afternoon of discovery at Chelsea Market and a scenic stroll along the High Line.


That evening, the group will dine at Joe Allen Restaurant, a legendary Broadway bistro beloved by performers and theater fans alike. The night will conclude with the group’s second Broadway show — a grand finale to this theater-filled NYC journey.

After the show, guests will return to the hotel to reflect on a week filled with joy, connection, and unforgettable memories.

Day 6 - December 9

Day 6 - December 9 image

🎭 Broadway Museum, Free Time & Farewell Dinner

Day 6 will begin with breakfast at the hotel followed by a visit to the vibrant and immersive Museum of Broadway, where guests will explore an interactive journey through theater history (entry included).


The rest of the day will be open for guests to explore New York City at their own pace — whether solo, in pairs, or as part of a small optional outing. Christine will check in the night before to help coordinate plans based on group interests and comfort levels.


Suggested adventures will include The Museum of Modern Art (MoMA), a stroll through the Bryant Park Holiday Village, a visit to Grand Central Terminal, or afternoon tea at The Plaza. Guests may also choose to wander Central Park and enjoy quiet corners like Bow Bridge or Strawberry Fields.


Lunch will be on your own, with flexibility to dine alone or with fellow guests. That evening, the group will gather one last time for a farewell dinner at Her Name is Han, a warm and soulful Korean kitchen that captures the heart of the city. Guests will return to the hotel for a final night of reflection and rest — hearts full and feet (probably) tired.

Day 7 - December 10

Day 7 - December 10 image

✈️ Departure Day

On the final morning, guests will enjoy one last breakfast at the hotel before preparing for departure. Room check-out will be required by 11:00 AM, and group shuttles to LaGuardia Airport (LGA) will run as needed between approximately 5:00 AM and 11:30 AM, based on individual flight schedules.


The group trip will officially conclude by 1:00 PM, with Christine available through that time to assist with final shuttle coordination and farewells.


This final day will offer a gentle close to a magical week — filled with hugs, full hearts, and one last glimpse of the city that never sleeps… until next time.

Map of the trip locations

A. New York, NY, USA

New York, NY, USA

About your organizer

Expedition Sisterhood offers small-group trips for women who crave meaningful connection, culture, and adventure. Led by a Montana-based guide with a passion for storytelling, our experiences blend nature, history, and community into unforgettable journeys. Whether you’re walking through Yellowstone, wandering NYC, or exploring hidden gems, we handle the logistics—so you can travel with purpose, laugh freely, and feel fully alive.

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