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Experience the stories that shaped a nation.
Boston Culinary 5-Day Itinerary
Available Year Round - Starting from $2642 per guest
Get ready to taste your way through Boston and beyond with this flavorful, story-rich getaway. From a lively North End food tour filled with Italian classics to a private pub crawl through historic taverns, each day serves up something deliciously different. Sip cocktails on an elegant dinner cruise, walk the decks of the Boston Tea Party Ships, and even sneak in a spooky-sweet sightseeing trip to Salem. Whether it’s your first bite or your fiftieth visit, this journey blends iconic history with unforgettable meals—turning every forkful into part of your travel story. Come hungry, leave inspired.
What We Love About This Experience
“I love this itinerary because guests don’t just eat—they connect with the city through its flavors. From hand-rolled pasta in the North End to toasting history in the city’s oldest pubs, this one is a foodies dream!”
Eric Derr
FIT Experience Designer
“What I love most about this itinerary is how it layers culture, cuisine, and storytelling. It’s not just sightseeing—it’s experiencing DC through all five senses.”
Shamira Clark
FIT Experience Designer
“I love how this trip blends food and history. From tossing tea to toasting in old pubs, it’s all about flavor and fun—with plenty of surprises along the way.”
Mary Eggert
FIT Experience Designer
Embark On An Unmatched Journey Of A Lifetime
Our expert team has put together a sample itinerary designed to inspire your next vacation – and we’re all about customizing it to match your interests, budget and schedule for a genuine local experience. Looking to add a tour, include additional transportation, extend your hotel stay or include a unique touch? Our Experience Designers are here to make it all happen for you!
This is a suggested itinerary – we can customize based on your preferences.
Day 1 - Your Ride Awaits
Your luxury experience starts when you’re met inside the airport with a smile by your friendly driver – who’ll be holding a sign with your name on it.
Day 2 - Tea Leaves & Tiramisu
Start your Boston story at the Boston Tea Party Ships & Museum, where interactive exhibits and dramatic reenactments bring the city’s revolutionary roots to life.
Next, dive into the North End—Boston’s beloved Little Italy—for a guided food tasting tour. Savor traditional bites and sweet treats as your guide serves up delicious history with every step.
The evening is yours to explore. Whether it’s a waterfront stroll or a cozy corner table for two, the city offers countless ways to wrap up the day.
Day 3 - Spells & Sips
Venture beyond the city for a private sightseeing tour of Salem, where colonial history and witchy folklore intertwine. From charming streets to centuries-old stories, it’s a journey that surprises at every turn.
Back in Boston, hop aboard your luxury vehicle for a historic pub crawl led by a lively local guide. You’ll raise a glass in the city’s oldest taverns—each pint poured with a side of Revolutionary-era tales.
We’ll take care of dinner reservations tonight, so all you need to do is show up hungry.
Day 4 - Choose Your Own Boston
With the day wide open, follow your own path—wander Beacon Hill, shop on Newbury Street, or hit a museum or two. It’s your chance to explore what speaks to you.
In the evening, step aboard the Odyssey Premier Dinner Cruise. As the city skyline twinkles, you’ll enjoy gourmet cuisine, live entertainment, and a front-row seat to Boston’s harbor magic.
Day 5 - Until We Meet Again
When your unforgettable experience in Boston comes to an end, you’ll be met at your hotel by your driver for your private transfer back to the airport via luxury vehicle.
Four Seasons Hotel Boston
Discover the enchantment of New England in Boston’s historic heart. Nestled in Back Bay’s iconic brownstones, Four Seasons Hotel Boston offers a prime spot for city exploration. Steps from major attractions, wander the Freedom Trail, indulge in Newbury Street’s shopping or unwind in rooms with stunning views of the Public Garden, Beacon Hill and the State House’s golden dome. Perfect for experiencing “America’s Walking City” in style.
Amenities
- Restaurant
- Fitness Center
- Valet Parking
- Concierge
- Indoor Pool
- Bar
Fairmont Copley Plaza Boston
$$$$$
Embrace luxury and elegance at the Fairmont Copley Plaza in Boston. A downtown landmark since 1912, this 5-star hotel epitomizes the city’s rich history and sophistication and offers 383 individually decorated guest rooms and suites, each one designed with a classic appeal and sophisticated details. Situated in the historic Back Bay, steps from Fenway Park and the Boston Public Library it embodies the quintessential Fairmont style, balancing modern amenities with a nod to Boston’s heritage.
Amenities
- Restaurant
- Fitness Center
- Valet Parking
- Concierge
- Wi-Fi
- Bar
Boston Harbor Hotel at Rowes Wharf
$$$$$
Discover the beacon of Boston Harbor, where the iconic 60-foot archway heralds a hospitality experience unrivaled in its class. This Forbes Five-Star and AAA Five Diamond urban resort combines timeless beauty with modern elegance. In the heart of Rowes Wharf, your waterfront sanctuary offers rooms where comfort and design meet. Gaze at the bay’s gentle waves and the radiant downtown glow. Here, every detail is crafted for the discerning traveler. Your luxurious adventure awaits – come and shine!
Amenities
- Restaurant
- Fitness Center
- Indoor Pool
- Concierge
- Valet Parking
- Bar
Inclusions
- Roundtrip Airport Transfers to Boston via luxury vehicle including bottled water, driver gratuity and inside meet & greet upon arrival
- Boston Tea Party Ships & Museum
- North End Italian Food Tasting Tour
- Salem Private Sightseeing Tour
- Private Historic Boston Pub Crawl with Round Trip Transportation
- Odyssey Dinner Cruise
- Restaurant Reservation Concierge Service
*Gratuities for the tour guides are not included.
*Hotel accommodations available for an additional charge.
More Information
- This experience is offered year-round, seven (7) days a week.
- You can customize the starting location of your Boston tours to fit your schedule.
- All stops, timing and inclusions of the tours are dependent on traffic and weather conditions.
- Want to see something specific? We love to personalize our tours to suit your specific interests and passions!
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Quotes From Our Travelers
“American Stories Travel turned our family’s Boston trip into a learning adventure. With their expert tour guides – it wasn’t just about seeing the historic sites – it was about feeling a deep connection to America’s roots. They really made history come alive in a way that inspired our children.”
2023 - E.G.
“Walking Boston’s Freedom Trail with our private guide from American Stories Travel truly felt like a VIP journey through American history. Not only did he tell us little-known facts – he also gave us some great recommendations about where to eat dinner that evening.”
2023 - F.C.
“When we were in Boston we did the private Harvard Campus walking tour organized by American Stories Travel. It was super informative and really put into perspective what makes Harvard so special. We got to see more than just the main sights – we learned about it’s history and what it’s really like to be a student there.”
2023 - L.S.
“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.
“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.
