Translate: Home | FAQ'S | Contact Us
corner corner
Old Town Trolley Tours logo Boston's best sightseeing tour
box shadow
arrow Boston Attractions
arrow Cool Things to Do
arrow Things to Do with Family
arrow Things To Do In The Fall
arrow Things To Do In Spring
arrow Boston Historic Sites
arrow Reasons to Visit Boston
arrow See Boston in One Day
arrow Things To Do In Winter
arrow Boston American History
arrow Boston Neighborhoods
arrow Boston Hidden Gems
arrow Boston Museums
arrow Public Garden Guide
arrow Boston Common Guide

Boston map Inner Harbor

View our tour map including stops and attractions throughout the city.
> Go to Boston Map

more arrow
January July
February August
March September
April October
May November
June December
take our quiz challenge

Test Your Knowledge
and You Could Win!

Take our fun quiz for a chance to win discounts and prizes. > Go to Trolley Quiz

more arrow
boston tea party tickets on sale now

Buy your Boston Tea Party Ships & Museum tickets online and reserve your spot today! Museum now open.

More on Boston tickets
Boston chocolate tour

Join us for a flavorful afternoon as you sample chocolate creations from some of the finest culinary landmarks in Boston.
> Go to Boston Chocolate Tour

more arrow
Old Town Trolley decoration

How to See Boston in 2 Days

Old Town Trolley decoration
boston harbor
"Here's a recommended itinerary from our travel planners at Historic Tours of America"

Your friends who have traveled here might say you need more than 2 days in Boston to see all the best attractions, but many of the attractions only require 30 minutes to an hour for a tour. This means that you can easily visit 5 Boston attractions per day and still have time for 3 leisurely meals; and we all know how important it is to eat the great food in Boston! Here’s a recommended itinerary from our travel planners who know all the shortcuts.

old state house and trolley
Old State House

Day 1- The Freedom Trail & Shopping

9:00am start: The first stop on the tour is located close to Faneuil Hall, Quincy Marketplace, and Long Wharf. So you can start the morning by grabbing breakfast at North 26 and walk by the marketplace on your way to the wharf.

Stop #5- The Freedom Trail

Hop off and visit the Old State House, Boston Massacre Site, Old South Meeting House, and Kings Chapel Burying Ground. These are all great attractions along the Freedom Trail and many of them are free. The Old State House is the oldest public building in Boston and was where the Declaration of Independence was first read to the people of Boston on July 18, 1776. You can see everything here in about 90 minutes or less.

Stop #7- Shopping & Lunch

Walk down the famous Marlborough and Newbury streets, go shopping, visit Copley Square, relax in Boston Common and have a great afternoon. You’ll also want to stop at Cheers for lunch and a beer with Norm!

Re-Board at Stop #15

family throwing tea at museum
Boston Tea Party Ships & Museum

Ride through the Seaport District en route to stop #17 at the Boston Tea Party Ships and Museum for a 1 hour tour and reenactment of the event that started the American Revolution. Stop in at Abigail’s Tea Room for a spot of tea and pastry. Finally, take the last trolley back to the depot and stroll on over to the North End for dinner at Trattoria Il Panino.

Day 2- Ballparks, Universities, & More

9:00am start: Depending on what hotel you’re staying at will depend on the closest trolley stop to hop on. You’re going to want to shoot for one of the stops between # 5 and #10.

Stop #12- Fenway Park

Walk around the area or just pass by on the trolley and enjoy the view.

Stop #13- Harvard, Cambridge, & M.I.T

Take 90 minutes to walk around campus and marvel at all the historic buildings and libraries. On to stop #15, where you’ll get to see more of the Freedom Trail like Park Street Church, The State House, Granary Burying Ground, the Make Way For the Ducklings statue in Boston Common and Beacon Hill.

At this point, you will have seen many of the major Boston attractions on your list and it would be time to have some lunch and take the afternoon to visit some of the attractions we have not checked off . As you can see, if you plan your itinerary correctly, you can easily see all of Boston in 2 Days. Taking the Old Town Trolley Tour is like taking a trip through history. You will be delighted to see so many places where so many significant events in America’s past took place and to be able to do it all in just 2 days!

corner corner

Historic Tours of America, ® 201 Front Street, Key West, Florida 33040
Copyright © Historic Tours of America, ®

Old Town Trolley Tours and Transportainment are registered trademarks of Historic Tours of America® and Ghosts & Gravestones, Frightseeing and Boston's Original Chocolate Tour are registered service marks of Historic Tours of America®