Boston Holidays
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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.
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
USA
City Break
5 days / 4 nights
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.
Best of New England
USA
Fly Drive Holiday
16 days / 15 nights
16 days / 15 nights
New England is a magical region of towering mountains, quaint historical villages and romantic rugged coastlines.
Unique & Boutique Massachusetts
USA
Fly Drive Holiday
12 days / 11 nights
12 days / 11 nights
From the rolling hills and villages of The Berkshires to the sand dunes and lighthouses of Cape Cod, explore this magical state whilst staying in the region’s most atmospheric hotels and unique inns.
Best of Eastern USA by Rail
USA
Rail
15 days / 14 nights
15 days / 14 nights
Ride Amtrak’s Acela Express between the iconic cities of Washington, Philadelphia, New York and Boston.
New England's Fall Foliage - Insight
USA
Guided Group Journey
8 days / 7 nights
8 days / 7 nights
Discover the best of New England during this remarkable time of year.
Lobsters & Lighthouses of Massachusetts & Maine
USA
Fly Drive Holiday
15 days / 14 nights
15 days / 14 nights
Coastal New England offers an alluring mix of rugged shorelines and beautiful beaches, succulent seafood and picturesque lighthouses, rolling sand dunes and the incredible Acadia National Park.
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.
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
Boston's downtown neighbourhood is a hub of both commerce and history.
Beacon Hill
One of Boston’s most historic and picturesque neighbourhoods, Beacon Hill is Boston's most desirable address.
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.
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 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
Just over the Charles River is eclectic Cambridge, home to prestigious universities including Harvard; its charming campus is well worth a visit.
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.
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
Boston
This prestigious property opened in 1912 and boasts an enviable location on Copley Square.
The Whitney Hotel
Boston
This delightful property blends elegance and sophistication with modern amenities and chic design.
Boston Marriott Copley Place
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.
The Boxer
Boston
Housed in a distinctive flatiron building that dates back to 1904, this appealing hotel offers a sophisticated yet inviting ambience and personalised service.
Aloft Boston Seaport District
Boston
This contemporary hotel features a colourful, hip lobby and offers a refreshing stay in the rejuvenated waterfront district.
Hyatt Regency Boston
Boston
Combining smart accommodation with good value, this modern hotel makes for a convenient base to explore Boston.
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.
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
Attraction Ticket
- Experience historic Boston on the famous Trolleys
- Hop-on-hop-off at any of the numerous stops
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Boston Tea Party Ships & Museum
1 hour
- Relive the infamous Boston Tea Party
- Learn about the Sons and Daughters of Liberty
- A family friendly and immersive experience
Tales from the Trail
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