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Experience the stories that shaped a nation.
New York City to Boston: From Broadway to the Freedom Trail
Two Cities, One Story | 7 days Starting from $6,672 per Guest
New York and Boston have been in conversation for centuries – rival cities that helped invent America, each with its own accent, attitude, and claim to greatness. This seven-day journey moves between them with purpose: Manhattan’s electric neighborhoods, the Statue of Liberty, a Broadway curtain call, and a pizza-and-gelato walking tour give way to Boston’s cobblestone Freedom Trails, harbor dinner cruise, and a living-history day trip to Plymouth. Two cities, one remarkable week, connected by the fastest train on the Eastern Seaboard and bound together by the story of a nation still being written.
This is a suggested itinerary — we can tailor it based on your group’s interests and pace.
What Our Expert Designer Loves About This Experience?
An Unforgettable 7-Day Private Tour of New York City & Boston
Day One — Arrival in New York City
Your New York adventure begins the moment you land. A private luxury sedan will be waiting inside baggage claim at LGA, ready to whisk you into the city in style — no crowds, no confusion, just a seamless welcome to the Big Apple. All tolls, taxes, and gratuities are taken care of, so you can sit back, take in the skyline, and let the excitement build. Tonight, we’ve secured a coveted restaurant reservation to kick off your trip the right way. This is New York City — and it’s already rolling out the red carpet for you.
Experience Highlights
- Restaurant Reservation
Day Two — Manhattan in All Its Glory
Today is pure New York from start to finish. Your morning kicks off with a private four-hour Manhattan Highlights Tour — South Street Seaport, Times Square, Little Italy, Chinatown — all brought to life by your expert guide in a comfortable luxury vehicle. After lunch, lace up your walking shoes for the NYC Pizza and Gelato Challenge, a delicious four-hour tour through iconic pizzerias and artisan gelaterias with a culinary historian by your side. Cap the evening with the magic of Broadway — orchestra seats, live performance, and that indescribable electricity that only New York’s greatest stages can deliver.
Experience Highlights
- Manhattan Highlights Tour (4 hours)
- NYC Pizza and Gelato Challenge (4 hours)
- Broadway Show
Day Three – Lady Liberty, Ellis Island & Central Park
This morning, your private guide and luxury vehicle take you straight to the ferry for a half-day Statue of Liberty and Ellis Island experience — no lines, no stress, just one of the most iconic journeys in America. Explore the Statue of Liberty Museum and the moving Ellis Island Immigration Museum, where the stories of those who shaped this country come alive. Back in the city, step into the romance of Old New York with a 45-minute private horse-drawn carriage ride through Central Park’s 843 breathtaking acres. This evening, a curated restaurant reservation puts the perfect bow on an unforgettable day.
Experience Highlights
- Half-Day Statue of Liberty & Ellis Island Tour (5 hours)
- Horse & Carriage Ride in Central Park (45 minutes)
- Restaurant Reservation
Day Four – New York to Boston on the Acela
Today, you trade the Manhattan skyline for the charm of New England. A private sedan transfers you to Penn Station, where you’ll board the Amtrak Acela in Business Class — spacious seating, elevated amenities, and sweeping coastal scenery as you travel the iconic Northeast Corridor. Upon arrival at Boston South Station, another private luxury vehicle is ready and waiting to bring you seamlessly into the city. Your first evening in Boston deserves a proper welcome — we’ve arranged a wonderful restaurant reservation so you can settle in, raise a glass, and savor the start of a brand-new chapter.
Experience Highlights
- One Way Train Station Transfer
- Amtrak Acela – New York to Boston
- Restaurant Reservation
Day Five – The Heart & Soul of Boston
Boston doesn’t just tell history — it breathes it. Start your day with a private four-hour sightseeing tour through the city’s oldest streets, visiting the Old North Church, the Boston Massacre site, and the lively Faneuil Hall, guided by a local expert who knows every story worth telling. From there, step back in time on a private Freedom Trail Walking Tour — your costumed guide makes the Revolution feel like it happened yesterday. As the sun sets over the harbor, board the Odyssey for a Premier Dinner Cruise — upscale dining, creative cocktails, and stunning views of Boston Harbor all in one unforgettable evening.
Experience Highlights
- Discover Boston Private Sightseeing Tour (4 hours)
- Freedom Trail Walking Tour (1.5 hours)
- Odyssey Premier Dinner Cruise (2.5-3 hours)
Day Six – A Journey Back to Plymouth
Step even further back in time today with a full-day private excursion to Plymouth. Your expert guide and luxury vehicle whisk you from Boston to Plimoth Patuxent Museums, where you’ll explore a living 17th-century Pilgrim village, board the legendary Mayflower II, and stand before the iconic Plymouth Rock. Your Heritage Pass unlocks immersive exhibits honoring both the Pilgrims and the Wampanoag people, whose history here spans over 12,000 years. History isn’t just observed today — it’s truly lived. Back in Boston for the evening, a special restaurant reservation awaits to close out this remarkable day in style.
Experience Highlights
- Day Trip to Plimoth Patuxet from Boston (8 hours)
- Restaurant Reservation
Day Seven – Farewell to Boston
All great adventures must come to a close, but this one ends exactly as it began — in comfort and style. Your private luxury sedan will be ready and waiting to transfer you from your hotel to Boston Logan International Airport, with all tolls, taxes, and gratuities included. As you head home, take a moment to look back on seven extraordinary days — the energy of New York, the soul of Boston, and memories that will stay with you long after the journey ends. Until next time.
Lotte New York Palace
Price Starts at $$$
In the heart of the action, Lotte New York Palace stands proudly on Madison Avenue at 50th Street, with commanding views of St. Patrick’s Cathedral and Rockefeller Center. A stone’s throw from world-class shopping, Broadway theaters, museums, and fine dining, this hotel is a cornerstone of culture. The Villard Mansion, part of the hotel’s storied architecture, holds a place on the National Register of Historic Places and is recognized as a treasured landmark of New York City.
Hotel Amenities
Amenities
- Restaurant
- Fitness Center
- Spa
- Concierge
- Wi-Fi
- Bar
Hotel Location
Fairmont Copley Plaza Boston
Price Starts at $$$
Embrace luxury and elegance at the Fairmont Copley Plaza in Boston. A downtown landmark since 1912, this 5-star hotel epitomizes the city’s rich history and sophistication and offers 383 individually decorated guest rooms and suites, each one designed with a classic appeal and sophisticated details. Situated in the historic Back Bay, steps from Fenway Park and the Boston Public Library it embodies the quintessential Fairmont style, balancing modern amenities with a nod to Boston’s heritage.
Hotel Amenities
Amenities
- Restaurant
- Fitness Center
- Valet Parking
- Concierge
- Wi-Fi
- Bar
Hotel Location
More Information
- This experience is offered year-round, seven (7) days a week (Plimoth Patuxet available mid-March to November only).
- This itinerary can begin in either New York City or Boston.
- You can customize the starting location of the tours to fit your schedule.
- All stops, timing, and inclusions of the tours are dependent on traffic and weather conditions.
- Broadway show selections vary by season and availability. Specific shows cannot be guaranteed.
- Cost of meals not included (unless otherwise noted).
- Hotel accommodations available for an additional charge.
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Quote from Our Travelers
“I’ve always been a Wall Street enthusiast, but the private tour of the Financial District that American Stories Travel set up for me was eye-opening. There was so much happening there that I had no idea about – from the past to present day. I didn’t go in expecting to learn anything new – but boy did I!”
2025 - Z.K.
“As foodies, the customized culinary tour in Boston was a game-changer. American Stories Travel’s guide was super knowledgeable. We not only ate good but we learned a lot about the history of the city as we walked from one tasting to the next.”
2023 - T.W.
“The private sunset harbor cruise arranged by American Stories Travel was the highlight of our Boston trip. Seeing the city from the vantage point of the Boston Harbor is a magical memory we’ll hold dear.”
2023 - M.K.
“The family-focused itinerary from American Stories Travel was a game-changer. The kid-friendly activities they planned for us were spot on. My children especially loved the scavenger hunt at the American Museum of Natural History – which we loved because it was fun and educational!”
2025 - M.S.
“We were in New York for our anniversary and American Stories Travel made it our best one yet! The magical horse and carriage ride through Central Park ending with a gourmet picnic – which was a surprise for my wife – made it extra special! We already agreed we are using them for our next anniversary.”
2026 - F.S.
