New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate Boston Sports and Sightseeing Adventure Itinerary

Last updated: 2024 Jun 14

Sports and Sea Adventures in Boston

Morning

Start your day with a hearty breakfast at the iconic Mike's Pastry, known for its delicious pastries and Italian treats. After breakfast, head to the historic Fenway Park for a guided ballpark tour and immerse yourself in the rich history of the Boston Red Sox.

Afternoon

For lunch, enjoy fresh seafood at Row 34, a popular spot for oysters and craft beer. Afterward, embark on the Boston Harbor Sunset Cruise to enjoy the beautiful views of the city from the water.

Evening

Conclude your day with a dinner at Legal Sea Foods, a Boston classic known for its seafood dishes. After dinner, you have the option to attend a Boston Red Sox Game at Fenway Park and experience the electric atmosphere of a live baseball game.

Bedtime

Find amazing hotels in Boston, Massachusetts.

4.19
Fenway Park
Book Now

4.27
Boston Harbor Sunset Cruise
Book Now

Historic Boston and Culinary Delights

Morning

Enjoy a leisurely breakfast at The Capital Grille before starting your day with a Boston Freedom Trail Small Group History Walking Tour. Explore the significant historical sites along the trail and learn about the city's role in the American Revolution.

Afternoon

For lunch, savor the flavors of Italy at Neptune Oyster, known for its fresh seafood and lobster rolls. Afterward, visit the Boston Tea Party Ships and Museum Interactive Tour to relive the famous event that sparked the revolution.

Evening

Indulge in a fine dining experience at O Ya, a renowned Japanese restaurant. After dinner, take a stroll around Faneuil Hall Marketplace and enjoy the street performances and bustling atmosphere.

Bedtime

Find amazing hotels in Boston, Massachusetts.

4.91
Boston Freedom Trail Small Group History Walking Tour
Book Now

4.75
Boston Tea Party Ships and Museum Interactive Tour
Book Now

Maritime Adventures and City Views

Morning

Start your day with a delicious breakfast at Top of the Hub, where you can enjoy panoramic views of the city. After breakfast, set out on a Boston Whale Watching Catamaran Cruise for a chance to see these majestic creatures in their natural habitat.

Afternoon

For lunch, head to Union Oyster House, the oldest operating restaurant in the United States, and enjoy a traditional New England meal. Afterward, take a Boston Duck Tour The Original and World-Famous to explore the city by land and water.

Evening

Dine at Toro, a popular Spanish restaurant known for its tapas and lively atmosphere. After dinner, take a romantic Boston Harbor Champagne Sunset Sail from Rowes Wharf and watch the sun set over the water.

Bedtime

Find amazing hotels in Boston, Massachusetts.

4.58
Boston Whale Watching Catamaran Cruise
Book Now

4.65
Boston Duck Tour The Original and World-Famous
Book Now

Academic and Cultural Immersion in Cambridge

Morning

Cross the Charles River to Cambridge and enjoy a delightful breakfast at Craigie on Main, a local favorite. Afterward, take a Cambridge Explore Harvard University on a Student-Led Tour to learn about the history and traditions of the prestigious institution.

Afternoon

For lunch, experience the Mediterranean flavors at Oleana, known for its innovative cuisine. Afterward, visit the Massachusetts Institute of Technology (MIT) and explore the campus on a Massachusetts Institute of Technology Public Tour.

Evening

Dine at Eastern Standard Kitchen & Drinks, a brasserie-style restaurant with a vibrant atmosphere. After dinner, take a leisurely walk around Harvard Square and soak in the intellectual energy of the area.

Bedtime

Find amazing hotels in Boston, Massachusetts.

4.57
Cambridge Explore Harvard University on a Student-Led Tour
Book Now

4.33
Massachusetts Institute of Technology (MIT)
Book Now

Salem Witch Trials and Haunted History

Morning

Enjoy a final breakfast at Myers + Chang, a beloved spot for Asian-inspired dishes. After breakfast, take a day trip to Salem and start with a Salem Witch Museum Admission Ticket to learn about the infamous witch trials.

Afternoon

For lunch, try the legendary pizza at Santarpio's Pizza, a local institution. Afterward, explore the Salem, MA History and Hauntings Guided Walking Tour to uncover the dark and mysterious past of the town.

Evening

Conclude your trip with a memorable dinner at No. 9 Park, a fine dining restaurant known for its exquisite cuisine. After dinner, participate in the Salem Boos and Brews Haunted Pub Crawl for a spooky and entertaining end to your journey.

Bedtime

Find amazing hotels in Boston, Massachusetts.