New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
![New England Fall Foliage Road Trip: Waterfalls and Hidden Gems](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f54e7-5af7-7136-a2ec-b1b3e3c4e675/location752.jpg)
New England Fall Foliage Road Trip: Waterfalls and Hidden Gems Itinerary
Last updated: 2024 Jun 14Historic Boston and Culinary Delights
Morning
Start your day with a delightful breakfast at Mike's Pastry, known for its famous cannolis. Afterward, take a leisurely walk through the picturesque Boston Public Garden.
Afternoon
For lunch, savor the fresh seafood at Legal Sea Foods. Afterward, explore the Freedom Trail on a guided walking tour, immersing yourself in the rich history of the city.
Evening
Enjoy a sophisticated dinner at No. 9 Park, known for its fine Italian cuisine, to end your first day in Boston.
Bedtime
Find amazing hotels in Boston, Massachusetts.
![Visit Boston Public Garden in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/d0/eb/c4.jpg)
4.52Boston Public Garden
Book Now
![Visit Boston Public Garden in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/d0/eb/c4.jpg)
Boston Public Garden
Book Now
![Visit Boston Guided Walking Tour of the Freedom Trail in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/1f5b03dc768c9523.jpeg/21.jpg)
4.85Freedom Trail
Book Now
![Visit Boston Guided Walking Tour of the Freedom Trail in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/1f5b03dc768c9523.jpeg/21.jpg)
Freedom Trail
Book Now
Revolutionary Boston and Harbor Views
Morning
Indulge in a delicious breakfast at Neptune Oyster, famous for its fresh seafood. Afterward, visit the Boston Tea Party Ships and Museum for an interactive tour.
Afternoon
For lunch, experience a traditional New England clam chowder at Union Oyster House, the oldest operating restaurant in the U.S. Then, take a Boston Harbor Cruise to enjoy the city's skyline from the water.
Evening
Dine at Top of the Hub for a memorable dinner with panoramic views of the city.
Bedtime
Find amazing hotels in Boston, Massachusetts.
![Visit Boston Boston Tea Party Ships and Museum Interactive Tour in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/30a0bde098eb21d1.jpeg/21.jpg)
4.75Boston Tea Party Ships and Museum
Book Now
![Visit Boston Boston Tea Party Ships and Museum Interactive Tour in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/30a0bde098eb21d1.jpeg/21.jpg)
Boston Tea Party Ships and Museum
Book Now
![Visit Boston Historical Sightseeing Cruise in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/6233308710ac3db6.jpeg/21.jpg)
4.56Boston Harbor Cruise
Book Now
![Visit Boston Historical Sightseeing Cruise in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/6233308710ac3db6.jpeg/21.jpg)
Boston Harbor Cruise
Book Now
Fenway Park and Brewery Tour
Morning
Start your day with a hearty breakfast at The Capital Grille. Then, embark on a guided tour of the iconic Fenway Park, home of the Boston Red Sox.
Afternoon
Enjoy a beer and lunch at the historic Row 34 before going on a Boston Brewery Tour to learn about the local craft beer scene.
Evening
For dinner, head to Eastern Standard Kitchen & Drinks for a diverse menu in a vibrant setting.
Bedtime
Find amazing hotels in Boston, Massachusetts.
![Visit Fenway Park in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/12/31/df/f1.jpg)
4.19Fenway Park
Book Now
![Visit Fenway Park in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/12/31/df/f1.jpg)
Fenway Park
Book Now
![Visit Boston Fenway Park Guided Ballpark Tour with Options in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/a24eaf4fa0b6176f.jpeg/21.jpg)
4.79Boston Brewery Tour
Book Now
![Visit Boston Fenway Park Guided Ballpark Tour with Options in Boston, Massachusetts](https://cdn.getyourguide.com/img/tour/a24eaf4fa0b6176f.jpeg/21.jpg)
Boston Brewery Tour
Book Now
Literary and Cultural Boston
Morning
Begin your day with a leisurely breakfast at Myers + Chang, known for its Asian-inspired cuisine. Then, visit the Boston Public Library, a haven for book lovers.
Afternoon
For lunch, enjoy the modern French cuisine at L'Espalier. Afterward, explore the Isabella Stewart Gardner Museum, a unique art collection in a stunning setting.
Evening
Dine at Craigie on Main, a renowned restaurant offering a seasonal tasting menu.
Bedtime
Find amazing hotels in Boston, Massachusetts.
![Visit Boston Public Library in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/ae/58.jpg)
4.11Boston Public Library
Book Now
![Visit Boston Public Library in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/ae/58.jpg)
Boston Public Library
Book Now
![Visit Quincy Market in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5a/da.jpg)
4.13Isabella Stewart Gardner Museum
Book Now
![Visit Quincy Market in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5a/da.jpg)
Isabella Stewart Gardner Museum
Book Now
Coastal Charm and Culinary Delights
Morning
Arrive in Portland, Maine, and start your day with a delicious breakfast at Fore Street. Then, take a leisurely walk around the historic Old Port district.
Afternoon
For lunch, savor the local seafood at Eventide Oyster Co.. Afterward, visit the Portland Head Light, a picturesque lighthouse with stunning ocean views.
Evening
Enjoy a memorable dinner at Street and Co., known for its fresh seafood and intimate atmosphere.
Bedtime
Find amazing hotels in Portland, Maine.
![Visit Beacon Hill in Portland, Maine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/63/33.jpg)
4.49Portland Head Light
Book Now
![Visit Beacon Hill in Portland, Maine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/63/33.jpg)
Portland Head Light
Book Now
Scenic Railway and Mountain Views
Morning
Travel to North Conway, New Hampshire, and have a hearty breakfast at Peach's Restaurant. Then, embark on a journey on the Conway Scenic Railroad, enjoying the fall foliage.
Afternoon
For lunch, stop at Delaney's Hole in the Wall, a local favorite. Afterward, take a scenic drive along the Kancamagus Highway, known for its stunning views.
Evening
Dine at White Mountain Cider Company for a farm-to-table dining experience.
Bedtime
Find amazing hotels in North Conway, New Hampshire.
Culinary Exploration and Departure
Morning
Return to Boston and have a leisurely breakfast at Tatte Bakery & Cafe. Spend the morning exploring the Museum of Fine Arts, home to a world-class art collection.
Afternoon
For a farewell lunch, enjoy the Mediterranean cuisine at Oleana. Afterward, take a walk along the Rose Kennedy Greenway, a vibrant park in the heart of the city.
Evening
Conclude your trip with a memorable dinner at Menton, a Michelin-starred restaurant offering a refined dining experience.
Bedtime
Find amazing hotels in Boston, Massachusetts.
![Visit Boston Harbor Islands National and State Park in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/56/5a.jpg)
4.14Rose Kennedy Greenway
Book Now
![Visit Boston Harbor Islands National and State Park in Boston, Massachusetts](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/56/5a.jpg)
Rose Kennedy Greenway
Book Now