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Massachusetts, USA

Boston

Colonial history, Ivy-League charm, and Fenway on a summer night.

Best time: May – October

Sample Itineraries

Three ways to see Boston.

These are sample plans to spark ideas. Every trip is fully customized to your travel style, budget, and dates.

3-Day Boston Weekend

A quick, high-impact weekend in Boston.

Fly BOS · T · Walk

Day 1 — Arrival & city highlights

Places
  • Freedom Trail
  • Fenway Park
Sights & experiences
  • Walk the Freedom Trail
  • Red Sox game at Fenway
Food to try
  • Cannoli at Mike's Pastry

Day 2 — Neighborhoods & culture

Places
  • Harvard Square
  • Beacon Hill
Sights & experiences
  • Harvard campus tour
  • Whale-watching day trip
Food to try
  • Lobster roll at Neptune Oyster

Day 3 — Slow morning & signature moment

Places
  • North End
  • Boston Common
Sights & experiences
  • Walk the Freedom Trail
Food to try
  • Clam chowder at Union Oyster House

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