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The Boston skyline lights up the evening sky reflecting across the water of the Harbour in Massachusetts, USA

Boston Holidays


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Boston holidays offer a friendly, attractive city which blends history and culture with chic bars, a lively sports scene and fantastic shopping.

Some of the best things to do in Boston include walking the historic Freedom Trail to learn about America’s revolutionary past, touring the campus of famous Harvard University and discovering some of the superb bars and restaurants the city has to offer. Boston is famed for its excellent seafood such as clam chowder and lobster rolls.

Boston is a compact and walkable city and enjoys distinct neighbourhoods. Explore downtown Boston which is home to Faneuil Hall and historic Quincy Market, affluent Back Bay home to great Newbury Street shopping, charming Beacon Hill and the Waterfront.

Trailfinders offers a range of Boston holidays and our expert travel consultants are a mine of information about what to do, often with first-hand travel experience. Whether you want to explore Boston as part of a fly drive holiday, a sociable guided group tour or create amazing memories on a family holiday – they are the perfect people to ask.
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OUR HOLIDAYS IN BOSTON

Nobody offers more ways to explore Boston than Trailfinders.

Here's a snapshot of some of our most popular Boston holidays. If you don’t see what you’re looking for, click on the link below them to see our complete range of holidays and tours in the destination.
Boston City Break
Boston City Break
City Break
5 days / 4 nights

As one of the oldest cities in the USA, handsome Boston has plenty of historic character and combined with its waterfront setting and plethora of attractions, it makes for a fantastic city break.

Guide Price: €509 £425 pp

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Best of New England
Best of New England
Fly Drive Holiday
18 days / 17 nights

New England is a magical region of towering mountains, quaint historic villages and romantic rugged coastlines.

Guide Price: €3,529 £3,099 pp

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Classic New England & The Adirondacks - Motorhome Holiday
Classic New England & The Adirondacks - Motorhome Holiday
Motorhome
16 days / 15 nights

Experience Maine’s rugged shorelines, the mountains of New Hampshire, the beautiful wilderness of the Adirondacks and the charming villages of Cape Cod.

Guide Price: €2,379 £2,099 pp

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Best of Eastern USA by Rail
Best of Eastern USA by Rail
Rail
16 days / 15 nights

Ride Amtrak’s Acela train between the iconic cities of Washington, Philadelphia, New York and Boston.

Guide Price: €2,149 £1,899 pp

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New England's Fall Foliage - Insight
New England's Fall Foliage - Insight
Luxury Guided Group Journey
8 days / 7 nights

Discover the best of New England during this remarkable time of year.

Guide Price: €5,149 £4,325 pp

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New York, New England and Eastern Canada
New York, New England and Eastern Canada
Cruise Holiday
15 days / 14 nights

Whether you travel in spring, summer or for the autumn fall foliage, this fantastic holiday offers a great mix of history, culture and natural beauty.

Guide Price: €4,299 £3,399 pp

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View all holidays in Eastern USA

WHERE TO GO IN BOSTON

Each area of Boston boasts its own attractions and appeal. It would be just as easy to spend all your time exploring the historic sights of the Freedom Trail, as it would to be to hit the shops and restaurants of Back Bay or the Waterfront.

Take a look at the destination guide below the Boston map for more details on each area. Alternatively, if you are looking for some inspiration for your Boston holiday, give us a call and speak to one of our expert travel consultants.
Downtown
Downtown
Boston's downtown neighbourhood is a hub of both commerce and history. Here you’ll find a large portion of the Freedom Trail including Faneuil Hall and Quincy Market, two of the city’s most popular landmarks.
Beacon Hill
Beacon Hill
One of Boston’s most historic and picturesque neighbourhoods, Beacon Hill is Boston's most desirable address. Loved for its cluster of cobbled streets, grand brownstone houses and quaint gas lamps, it makes for a charming place to wander and browse the antique shops.
Back Bay
Back Bay
The Back Bay neighbourhood is renowned for its sensational shopping, be it at the gleaming mall, designer stores or the hip independents of Newbury Street. It’s also a hub of bars and restaurants as well as being home to charming Copley Square.
Waterfront & Seaport District
Waterfront & Seaport District
Once an industrial part of the city, Boston's waterfront and seaport have been redeveloped and revitalized over recent years and is now a hub of contemporary hotels and a great selection of restaurants.
The Freedom Trail
The Freedom Trail
The Freedom Trail is a 2 ½ mile long route that takes in much of Downtown Boston, incorporating 16 historic sites that tell the story of the American Revolution and the country’s founding fathers.
Cambridge
Cambridge
Just over the Charles River is eclectic Cambridge, home to prestigious universities including Harvard; its charming campus is well worth a visit. Explore Cambridge’s many museums and discover its hip bars and student hangouts.

OUR RECOMMENDED HOTELS IN BOSTON

We feature a great range of accommodation in Boston, with something to suit all budgets and tastes – from luxurious and stylish to modern and good value.

What you won’t find here are thousands of Boston hotels to wade through. We have done the hard work for you and selected the best places to stay and our travel consultants are on hand to help you plan your Boston holiday, often with first-hand experience.
Fairmont Copley Plaza
Fairmont Copley Plaza
5 star

Boston

This prestigious property opened in 1912 and boasts an enviable location on Copley Square.
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The Whitney Hotel
The Whitney Hotel
4 plus star

Boston

This delightful property blends elegance and sophistication with modern amenities and chic design.
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Boston Marriott Copley Place
Boston Marriott Copley Place
4 star

Boston

This modern property sits in the heart of Boston’s Back Bay neighbourhood, close to a plethora of restaurants and shops as well as the Back Bay’s famous brownstone buildings.
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Aloft Boston Seaport District
Aloft Boston Seaport District
3 plus star

Boston

This contemporary hotel features a colourful, hip lobby and offers a refreshing stay with bright and modern rooms.
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Hyatt Regency Boston
Hyatt Regency Boston
4 star

Boston

Combining smart accommodation with good value, this modern hotel makes for a convenient base to explore Boston.
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WHAT TO DO IN BOSTON

As well as some great sightseeing opportunities, Boston is home to some unforgettable experiences which provide a unique way to get to know the area.

One day you might be exploring Boston on the famous Old Town Trolley, the next looking out for humpback, minke and fin whales on the Stellwagen Bank Marine Sanctuary. Whether you’re learning the history of the Freedom Trail or exploring the streets of Beacon Hill, our collection of unmissable experiences will really help bring your Boston holiday to life.
Boston Old Town Trolley Tour
Boston Old Town Trolley Tour
Attraction Ticket
Departs: Boston

A great way to familiarise yourself with this city of firsts is to explore the sights of Boston on ...

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Boston History & Highlights
Boston History & Highlights
2 hours
Departs: Boston

Explore the Boston of old and new as you travel beyond the Freedom Trail and take a walk through ...

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Boston Tea Party Ships & Museum
Boston Tea Party Ships & Museum
1 hour
Departs: Boston

Jump back in time to the famous event that led to the American Revolution. While onboard learn ...

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