1 Day in Boston + Itinerary

One day in Boston isn’t a lot of time, but don’t fear, you can still explore a lot in this short amount of time in this very walkable city. In our 7 Day New England Road Trip, we had only 1 day in Boston, so Teddy and I were determined to make the most of it. Below you’ll find how we spent our time, with our home base in the Back Bay area of Boston. To maximize our time, we stayed in the same hotel for 2 nights, getting in late one evening, having the full day in Boston, and then leaving the following morning. If you’d prefer, you could always stay outside of Boston and take a Subway into the city. I’ve done this before on other trips to Boston and it just means you have an earlier wakeup.

Stop 1: Boston Public Garden

We talked here from the Back Bay area. This was one of my favorite stops in all of Boston on our trip. While I’d been here a few times before over the years, it’s just beautiful every visit. There’s flower gardens, swan boats, bridges, and large old trees. It’s large enough of an area that it isn’t really packed, though a lot of people are there in the mornings. Spend about 15 minutes to 1.5 hours in the area.

Stop 2: Beacon Hill

This is an easy walk from the Public Gardens. It’s a historic neighborhood and has some of the most beautiful architecture. If you’ve been to Alexandria, VA or Old City and Society Hill in Philadelphia, it is very similar. There’s a few little shops you can stop in, but for the most part it’s just residences that you can admire from the historic streets. Budget about 30 minutes to admire the home in the area.

Stops 3-15: Freedom Trail (About 2 Miles one way)

The Freedom Trail will be the majority of your day. You can either book a tour or follow it on your own. If you do it on your own, you can pay $10 and follow the Freedom Trail app. You’ll start at Boston Common, which is right next to the Boston Public Gardens. If you follow this route, it’s about 2.5 miles one way.

You’ll know you’re on the “right” path because there are bricks in the sidewalks as well as markers showing various stops. You can read about each stop here.

• Boston Common
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel
• Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Boston Massacre Site
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

Along the trail, you’ll find opportunities to stop for a snack, coffee, or lunch. Along our route, we grabbed coffee and pastries early in the morning near the Old South Meeting House and we grabbed lunch at Quincy Market.

Stop 16: Subway to Your Hotel

By this time, it’s usually afternoon and you’re ready to relax for a bit. If you have a hotel in town, this is a great opportunity to take the subway back to the hotel and take a little nap. If you don’t have a hotel in town, find a cafe or spot with a view to sit down and relax.

Stop 17: Dinner in Back Bay or in the North End

Grab dinner in the Back Bay area where there are quite a few restaurants, or in Little Italy on the North End of Boston. I’ve eaten in both areas. If you’re headed to a Red Sox Game, check out the Back Bay since it’s most convenient. If you don’t have set plans in the evening, check out the North End. The vibe in Little Italy is lovely, especially during the evening.

Stop 18: Boston Red Sox Game (Seasonal), Concert, Show, or Ballet

If you’re there during the summer, you may be able to swing going to a Boston Red Sox Game, even if you don’t like baseball. I don’t really follow baseball and in my 4 trips to Boston, on two of them I’ve been to the stadium because it’s that iconic. If you’re not into baseball or would rather just do something else, check out another show or concert in the area like the Blue Man Group, Hamilton, or the Boston Ballet. I’ve been to each of those three and have loved them all, though they’re quite different. Enjoy the lights of the city as the sun goes down and savor the rest of your day in Boston!

We are not huge city people, so 1 day in Boston was enough for us. If you love the city, plan a few extra days in the area so you can do even more!