Boston Park
Boston Park
Freedom Trail, Boston Gardens and Falmouth
Freedom Trail, Boston Gardens and Falmouth
Minuteman, Lexington and USS Constitution in Boston
Minuteman, Lexington and USS Constitution in Boston
Boston's Museum of Fine Arts and Salem, Massachusetts
Boston's Museum of Fine Arts and Salem, Massachusetts
Stockbridge, Salem and Provincetown in Massachusetts
Stockbridge, Salem and Provincetown in Massachusetts

Experience Massachusetts - History & Culture

11 nights from €1,669 per person Including Flights


We have created this tailormade itinerary with a focus on the history, art and culture of Boston and Massachusetts, packing a great array of experiences into 12 days. You will have the opportunity to visit North Bridge where the “shot heard around the world” was fired, the start of the War of Independence. You'll enjoy a wide variety of art, sculpture and music with a few days in the Berkshires.  You can learn all about JFK, his childhood, life and legacy – at the Presidential Library, at his childhood home and at the museum near the family compound in Hyannis. And through your travels, you can enjoy the delicious food and beautiful sights of this captivating region. Tailormade


  • Explore Boston, walking the Freedom Trail to unlock its history and visiting a wonderful array of museums and monuments.
  • Immerse yourself in the Witch Trials of Salem, experiencing this unique town
  • Enjoy a few days in the cultural hub of the Berkshires, appreciating both the art and the picturesque setting.
  • Visit Provincetown where the Mayflower first landed and Plymouth where the Pilgrims first settled

Itinerary Overview

Fly to Boston 3 nights – Salem 2 nights Stockbridge The Berkshires 2 nights – Hyannis 3 nights – Plymouth 1 night – Fly home

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
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Day 1

Fly to Boston

Arrive in Boston and transfer independently to your hotel. We’ve chosen the Boston Park Plaza as your base in the city, however you could upgrade to the iconic Liberty Hotel or perhaps stay at the historic Omni Parker House.

Overnight: Boston Park Plaza

Day 2 & 3


On this suggested itinerary we’ve allowed two full days to explore Boston, but there is so much history and culture in and around the city that you might choose to extend your stay. If you’ve never visited the city before, then we recommend starting by walking the Freedom Trail. This is marked by a two and a half mile red brick path through the city, taking you to 16 historic sites. Download the map and self-guided tour, starting in Boston Common and ending at the USS Constitution – the world’s oldest commissioned warship afloat – where you must take the free guided tour. This will either take you a couple of hours or all day, if you want to spend some time at some of the sites and stop for a coffee or lunch.

Perhaps on your second day, visit Harvard University, America’s oldest university, founded in 1636, where you can take a free guided historical tour of the campus and its landmarks. Whilst here you could also visit the Peabody Museum of Archaeology and Ethnology, the Harvard Museum of Natural History and the Harvard Art Museum featuring art from the Middle Ages. If contemporary art is more your scene, then visit the Institute of Contemporary Art – a striking building on the waterfront overlooking the harbour. No visit to Boston would be complete without some reference to JFK. You can visit the JFK National Historic Site – his birthplace and childhood home, and the JFK Presidential Library is a fascinating collection of exhibits and videos house in a striking building.

“Boston is such a pristine city, so a glorious place to explore on foot. If you do fancy a jaunt to Harvard, the subway network (America’s oldest) is a simple-to-navigate system, taking you from central Boston to just outside the University in 15 minutes”.
Justin, Social Media & Creative Content Manager

Overnight: Boston Park Plaza

Day 4

Boston – Lincoln – Salem (48 miles)

This morning pick up your hire car and head out of the city to the Minute Man National Historic Park, where North Bridge marks the spot where the first shot of the American War of Independence was fired, the “shot heard around the world”. Here you will be able to stroll through history in this lovely and fascinating park. After a spot of lunch in the gorgeous town of Lincoln, visit the DeCordova Sculpture Park where you will be able to meander around the modern sculptures and installations. Then drive on to Salem to check into your hotel for the next two nights. This evening you might want to take a spooky walking tour, learning about the witches of Salem and visiting the most haunted spots of this enthralling town.

Overnight: Salem Waterfront Hotel & Suites

Day 5


Today it’s all about witches. You can visit the Salem Witch Trials Memorial, the Witch Museum. the Old Burying Point Cemetery and the Witch House – the oldest house in town and the only structure still standing from the time of the Witch Trails.

Overnight: Salem Waterfront Hotel & Suites

Day 6

Salem – The Berkshires – Stockbridge (194 miles)

A complete contrast - today you’ll journey to the beautiful rural region of the Berkshires – known for its natural scenic beauty, picturesque towns and farm to fork cuisine, but also as a cultural mecca due to its thriving art institutions. The Berkshires are really a particularly beautiful and civilised part of the world. Tanglewood is the summer home of the Boston Symphony, but also hosts various other music events. You have a two night stay in Stockbridge, so depending on what time you arrive, you could visit the Norman Rockwell Museum, which houses near a thousand original paintings and drawings. The Museum is located on a landscapted 36 acre site, so it's a great place to visit after your drive today, as you can stretch your legs with a stroll through the lovely gardens filled with sculptures created by Normam Rockwells son.

Overnight: The Red Lion Inn Stockbridge

Day 7

The Berkshires

A day to explore, and we recommend visiting The Mount in Lenox, which is Edith Whartons country estate – fascinating for an insight into the life of this Pulitzer Prize Winning author, but also as a glimpse into high society at the turn of the century. If the weather is good, then you can enjoy a walk through the gardens and woods to admire the outdoor sculptures. We also recommend taking the 50 minute drive to Williamstown to tour the Clark Art Institute, known for its French Impressionist paintings. Here you will also find a three-tiered reflecting pool set in the beautiful 14- acre campus with walking trails and expansive views of Williamsown, the Green Mountains and Taconic Range.

Overnight: The Red Lion Inn Stockbridge

Day 8

Stockbridge - New Bedford – Hyannis (202 miles)

Leave rural Massachusetts behind and head to the coast, pausing en route in New Bedford to visit the Whaling Museum – fascinating in its own right but particularly in the context of being Herman Melville’s inspiration for Moby Dick. Continue to the lovely seaside resort of Hyannis. This will be your base for the final three days of your holiday, and we’ve suggested various outings for you to enjoy from here, but if you’d rather, you can simply relax in this gorgeous coastal setting.

Overnight: Heritage House Hotel, Hyannis

Day 9


A day to explore the area, perhaps a visit to the JFK Musuem in Hyannis, or taking a break from the historical theme, you could take a boat trip to Martha’s Vineyard.

“No stay in Cape Cod would be complete without an afternoon whale watching. From Barnstable, you can take a 3 hour trip along the bay and witness humpbacks and pods of dolphin for an experience you’ll never forget”.
Justin, Social Media & Creative Content Manager

Overnight: Heritage House Hotel, Hyannis

Day 10

Hyannis – Provincetown – Hyannis (94 miles round trip)

Today perhaps take the scenic drive up the Cape Cod peninsula to Provincetown. Take your time and enjoy pausing at the picturesque villages and beaches along the way, perhaps enjoying a lobster lunch. In Provincetown you will find the Pilgrim Monument and Museum for interesting insights into the history of the Cape. Provincetown is also a very artistic place, with lovely galleries and artists studios.

Overnight: Heritage House Hotel, Hyannis

Day 11

Hyannis – Plymouth (33 miles)

The final stop of this itinerary is Plymouth, founded in 1620 and the site of the first Pilgrim settlement. Plymouth Rock marks the place where the first settlers landed in the Mayflower. Visit Plimoth Plantation, the living history museum where actors bring the original settlement to life, from the perspective of both the Pilgrims and the Native Wampanoag People.

Overnight: John Carver Inn & Spa, Plymouth

Day 12

Plymouth – Boston Airport (40 miles)

It’s time to drive to the airport to drop off your hire car and catch your flight home.

  • Return transatlantic flights
  • Hotel accommodation as shown or similar
  • Full inclusive Car hire
  • Electronic roadbook

What's not included

  • Attractions and activities
  • Car parking charges

Rachel McAnaspie
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