Boston City Break • View Itinerary
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Boston, Massachusetts,
Boston Public Garden
Boston Harbour Cruise
View Boston Sign next to window
The Prudential Building sign seen from inside View Boston
Beacon Hill, Boston
Harvard Street Sign Boston

Boston City Break

4 day City Break – from £359

With flights from £809

Explore Boston’s enchanting cobblestone streets. Walk in the footsteps of revolutionaries, take in sweeping skylines and follow the Freedom Trail through the city’s storied past. As one of America’s oldest and most historic cities, Boston is yours to discover at your own pace.

  • Follow the iconic red-brick Freedom Trail
  • Step aboard the world’s oldest commissioned warship
  • Try a New England lobster roll or clam chowder at Quincy Market
  • Cruise the harbour on a sightseeing tour
  • Take in the city from up high at View Boston Observation Deck

Your Itinerary

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You can customise this itinerary by adding extra nights or destinations. Just let us know what you would like to do

Boston Public Garden

Day 1 – Welcome to Boston

Boston is a compact, walkable city with an outsized sense of history, and just enough New…

Boston is a compact, walkable city with an outsized sense of history, and just enough New England charm to make you want to stay a little longer. Check into your hotel, then wander to the Public Garden, where swan boats drift across the lake. Round off the evening with dinner at a neighbourhood spot within easy walking distance.

Your trip includes the Boston Explorer Pass, giving you a pick of 47 activities to fill your time in Boston. We’ve handpicked three that we think make for the perfect Boston introduction.

Top tip: Want to see even more of the city? Upgrade your pass to include four or five attractions, giving you extra flexibility to add on more of Boston’s top sights and experiences.

Boston Public Garden

Day 1

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Welcome to Boston

Boston is a compact, walkable city with an outsized sense of history, and just enough New England charm to make you want to stay a little longer. Check into your hotel, then wander to the Public Garden, where swan boats drift across the lake. Round off the evening with dinner at a neighbourhood spot within easy walking distance.

Your trip includes the Boston Explorer Pass, giving you a pick of 47 activities to fill your time in Boston. We’ve handpicked three that we think make for the perfect Boston introduction.

Top tip: Want to see even more of the city? Upgrade your pass to include four or five attractions, giving you extra flexibility to add on more of Boston’s top sights and experiences.

Boston Public Garden

Day 2 – Walk Where History Was Made

Few cities let you trace the birth of a nation quite like Boston. Follow the iconic…

Few cities let you trace the birth of a nation quite like Boston. Follow the iconic red-brick Freedom Trail and unfold the story of the American Revolution made up of a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship and historic markers. Stroll past the Massachusetts State House, the Park Street Church and the Paul Revere House, the oldest surviving home in downtown Boston.

From there, step into Faneuil Hall, the historic meeting hall once dubbed the “Cradle of Liberty,” before wandering next door into Quincy Market, where a lively food hall and street performers make for the perfect lunch stop. It’s the ideal place to try a classic New England lobster roll or a warming bowl of clam chowder, a real Boston rite of passage.

Cross into Charlestown to climb Bunker Hill Monument, marking the site of one of the Revolution’s defining battles, then continue to the USS Constitution, affectionately known as ‘Old Ironsides,’ the world’s oldest commissioned warship still afloat, free to explore as part of Boston National Historical Park.

In the afternoon, trade cobblestones for open water on a historic sightseeing cruise as part of your Boston Explorer Pass, watching Boston’s skyline unfold from the harbour.

Top tip: If you’d rather save your legs than pound the pavement, pick up a pass for Boston’s underground, “the T”, one of the easiest and cheapest ways to hop between neighbourhoods without the walk.

Day 2

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Walk Where History Was Made

Few cities let you trace the birth of a nation quite like Boston. Follow the iconic red-brick Freedom Trail and unfold the story of the American Revolution made up of a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship and historic markers. Stroll past the Massachusetts State House, the Park Street Church and the Paul Revere House, the oldest surviving home in downtown Boston.

From there, step into Faneuil Hall, the historic meeting hall once dubbed the “Cradle of Liberty,” before wandering next door into Quincy Market, where a lively food hall and street performers make for the perfect lunch stop. It’s the ideal place to try a classic New England lobster roll or a warming bowl of clam chowder, a real Boston rite of passage.

Cross into Charlestown to climb Bunker Hill Monument, marking the site of one of the Revolution’s defining battles, then continue to the USS Constitution, affectionately known as ‘Old Ironsides,’ the world’s oldest commissioned warship still afloat, free to explore as part of Boston National Historical Park.

In the afternoon, trade cobblestones for open water on a historic sightseeing cruise as part of your Boston Explorer Pass, watching Boston’s skyline unfold from the harbour.

Top tip: If you’d rather save your legs than pound the pavement, pick up a pass for Boston’s underground, “the T”, one of the easiest and cheapest ways to hop between neighbourhoods without the walk.

View Boston Sign next to window

Day 3 – Skylines, Streets and the City Beyond

Rise early for uninterrupted views from the View Boston Observation Deck, where on a clear day…

Rise early for uninterrupted views from the View Boston Observation Deck, where on a clear day the vista stretches all the way to New Hampshire.

Spend the rest of your day exploring further afield aboard a hop-on hop-off trolley, or, for the more adventurous, hire a bike and glide along the Charles River Esplanade, both included in your Boston Explorer Pass. Either way, let Back Bay’s brownstones, Newbury Street’s boutiques and the leafy charm of Boston’s wider neighbourhoods reveal themselves at your own pace, with the option to hop off at TD Garden, home to the Celtics and Bruins, and step inside The Sports Museum to relive some of the city’s greatest sporting moments.

Top tip: Why not step aboard a Boston Tea Party Ships & Museum replica ship? Become part of the very event that changed the course of American history.

Day 3

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Skylines, Streets and the City Beyond

Rise early for uninterrupted views from the View Boston Observation Deck, where on a clear day the vista stretches all the way to New Hampshire.

Spend the rest of your day exploring further afield aboard a hop-on hop-off trolley, or, for the more adventurous, hire a bike and glide along the Charles River Esplanade, both included in your Boston Explorer Pass. Either way, let Back Bay’s brownstones, Newbury Street’s boutiques and the leafy charm of Boston’s wider neighbourhoods reveal themselves at your own pace, with the option to hop off at TD Garden, home to the Celtics and Bruins, and step inside The Sports Museum to relive some of the city’s greatest sporting moments.

Top tip: Why not step aboard a Boston Tea Party Ships & Museum replica ship? Become part of the very event that changed the course of American history.

Day 4 – Boston Before your Departure

If time permits, cross the river to Cambridge for an exclusive, insider look at Harvard University,…

If time permits, cross the river to Cambridge for an exclusive, insider look at Harvard University, told through the eyes of the students themselves. ‘The Hahvahd Tour’ is a student-led walk through Harvard Yard and Harvard Square, guides entertaining you with stories, history and lore along the way. Upgrade your Explorer Pass to four attractions to include this experience.

Before heading to the airport, wander back through Beacon Hill, calling in at Cheers Bar Beacon Hill, the very bar that inspired the beloved sitcom, for one last, relaxed drink before your journey home.

Day 4

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Boston Before your Departure

If time permits, cross the river to Cambridge for an exclusive, insider look at Harvard University, told through the eyes of the students themselves. ‘The Hahvahd Tour’ is a student-led walk through Harvard Yard and Harvard Square, guides entertaining you with stories, history and lore along the way. Upgrade your Explorer Pass to four attractions to include this experience.

Before heading to the airport, wander back through Beacon Hill, calling in at Cheers Bar Beacon Hill, the very bar that inspired the beloved sitcom, for one last, relaxed drink before your journey home.

Meals & Inclusions

3 nights hotel accommodation
3 day Explorer Pass

Flights & More Options

With FREEDOM, you can book your Boston City Break city break and flights together, as an ATOL protected package. Our Travel Experts can find the best priced Economy, Premium or Business Class flights for you.

You can also personalise your holiday. Why not add:

  • Extend your Explorer Pass to 4 or 5 attractions
  • Upgrade your hotel or room type for an added bit of luxury

Next Step

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

Boston City Break

4 day City Break – from £359

With flights from £809

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