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Massachusetts, United States

Boston

Give it two days: the Freedom Trail and North End one day, Back Bay museums and Fenway the next. Below: 2 sights, 2 activities and 1 outdoor spot, plus how Boston fits into a longer trip.

Plan Boston with friendsBrowse 9 places
Boston, Massachusetts, United States
Places
9

2 See · 2 Do · 1 Outdoors · 3 Eat · 1 Drink

Curated routes
1

Boston to Portland

Best season
May – Oct

from our route notes

Warmest month
July

28°C / 82°F avg high

Coolest month
January

1°C / 34°F avg high

Wettest month
October

about 123 mm rain

Climate: NASA POWER 2001–2025 averages.

Things to do in Boston

9 places from our curated routes, grouped by what you will do there. Each one has its own page with the address and full notes.

See

2 sights worth building a day around in Fenway.

  • Isabella Stewart Gardner Museum in BostonPhoto: Federal Bureau of Investigation · Public domain
    See

    Isabella Stewart Gardner Museum

    Art collection displayed around a Venetian-style courtyard.

    Tip Free if your name is Isabella.

    • Fenway
    • $$
    • 2 hr
  • Museum of Fine Arts, Boston in BostonPhoto: ajay_suresh · CC BY 4.0
    See

    Museum of Fine Arts, Boston

    Encyclopedic art museum with strong American and Impressionist galleries.

    • Fenway
    • $$$
    • 3 hr

Do

2 activities for when the group wants to do more than look across Downtown and Fenway.

  • Freedom Trail in BostonPhoto: Ingfbruno · CC BY-SA 3.0
    Do

    Freedom Trail

    2.5-mile red-brick line past 16 Revolutionary-era sites.

    Tip Start at Boston Common and finish in Charlestown.

    • Downtown
    • Free
    • 3 hr
    • Morning
  • Fenway Park in BostonPhoto: Rick Berry · Public domain
    Do

    Fenway Park

    Baseball's oldest ballpark (1912); take a tour or catch a game.

    Tip Ballpark tours run year-round.

    • Fenway
    • $$$
    • 3 hr
    • Apr–Sep

Outdoors

1 outdoor spot for fresh air in Back Bay.

  • Boston Public Garden in BostonPhoto: Gaby Azeem · CC0
    Outdoors

    Boston Public Garden

    Victorian garden with the swan boats and lagoon next to the Common.

    Tip Swan boats run spring to early fall.

    • Back Bay
    • Free
    • 45 min

Eat

Where we would book a table in Boston across Faneuil Hall and North End.

  • Union Oyster House in BostonPhoto: Seasider53 · CC BY 4.0
    Eat

    Union Oyster House

    America's oldest operating restaurant (1826), serving oysters at a raw bar.

    • Faneuil Hall
    • $$$
    • 75 min
    • Lunch
  • Neptune Oyster in BostonPhoto: Thong Le · Google
    Eat

    Neptune Oyster

    Small North End oyster bar famous for its hot buttered lobster roll.

    Tip No reservations; arrive before opening.

    • North End
    • $$$
    • 75 min
    • Weekday lunch
  • Regina Pizzeria in BostonPhoto: Keith Lennop · Google
    Eat

    Regina Pizzeria

    The original 1926 North End pizzeria serving thin, charred pies.

    • North End
    • $
    • 45 min
    • Dinner

Drink

Our picks for a drink in Boston in Charlestown.

  • Warren Tavern in BostonPhoto: Upstateherd · CC BY-SA 4.0
    Drink

    Warren Tavern

    Charlestown tavern from 1780 near the end of the Freedom Trail.

    • Charlestown
    • $$
    • 60 min
    • Evening

How to fit Boston into a trip

Boston is stop 1 of 3 on our Boston to Portland route. Follow it as-is or lift Boston into your own plan.

Getting here and onward

Distances are straight-line estimates between destination centers, not road distances.

Boston month by month

Average daily highs run from 1°C / 34°F in January to 28°C / 82°F in July. October is the wettest month, with about 123 mm of rain. Outlined months fall in the best season on our routes.

Average daily highs, NASA POWER 2001–2025 averages. Boston weather and the best time to visit →

Near Boston

8 other destinations from our guides within about 250 km (155 mi), measured in a straight line.

Boston questions, answered

How many days do you need in Boston?

Our route notes suggest 2 days in Boston. On our Boston to Portland route it is stop 1 of 3 in a 5-day trip. The listed visit times for our 9 places add up to roughly 16 hours, before travel between them, so you will need to choose.

What is Boston best known for?

Give it two days: the Freedom Trail and North End one day, Back Bay museums and Fenway the next. Standouts on our list: Isabella Stewart Gardner Museum (Art collection displayed around a Venetian-style courtyard); Museum of Fine Arts, Boston (Encyclopedic art museum with strong American and Impressionist galleries); Boston Public Garden (Victorian garden with the swan boats and lagoon next to the Common).

When is the best time to visit Boston?

Our Boston to Portland route is best May – Oct. NASA POWER 2001–2025 averages put the warmest highs in July (28°C / 82°F), the coolest in January (1°C / 34°F) and the most rain in October (about 123 mm).

What are the best things to do in Boston?

Start with Freedom Trail, Boston Public Garden, Isabella Stewart Gardner Museum, Museum of Fine Arts, Boston and Fenway Park. Our guide lists 9 places in all, from 2 sights, 2 activities, 1 outdoor spot, 3 places to eat and 1 bar or café.

Where should a group eat in Boston?

Our picks: Union Oyster House (Faneuil Hall); Neptune Oyster (North End); Regina Pizzeria (North End). No reservations; arrive before opening (Neptune Oyster).

What is near Boston?

The closest destinations in our guides are Downtown Boston & the Waterfront (about 0 km / 0 mi), South Boston & Castle Island (about 4 km / 2 mi) and Portsmouth (about 83 km / 51 mi). Distances are straight-line estimates, not road distances.

Plan Boston with your crew

Open the Boston to Portland route in TripsCircle, invite friends with a link, settle which of these 9 places make the cut with a quick poll, then split costs and share one packing list.

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