Boston Holidays

Boston Holidays 2026/2027: The Complete Guide to America's Most Historic City

Boston is the capital and largest city of Massachusetts, and one of the oldest cities in the United States. Known for its Ivy League-adjacent universities, colonial architecture, and pivotal role in the American Revolution — including the Battle of Bunker Hill — Boston combines deep history with a modern, walkable city experience. It's a top choice for travellers who want culture, coastal scenery, and easy day-tripping in one destination.

What are the best things to do in Boston?

Boston Harbour Islands
The Boston Harbor Islands National Park spans more than 1,600 acres across dozens of islands and peninsulas, and is a protected nesting habitat for coastal birds. Visitors can explore independently or join a guided tour.

• Georges Island is home to Fort Warren, a National Historic Landmark that operated as a Civil War training camp. The Webster Regiment is credited with composing the lyrics to "John Brown's Body" while stationed here.
• Grape Island suits outdoor lovers, with picnic areas, woodland trails, and guided nature walks.
• Little Brewster Island holds the oldest lighthouse station in America; Long Island Light and Graves Light are two of the harbour's most photographed historic lighthouses.

A ferry ride around the harbour is one of the best ways to see the islands before choosing which to visit in person.

Boston Children's Museum
Ranked among the best children's museums in the country, it features a hands-on art studio, a construction-themed play zone (complete with a Bobcat vehicle replica), and a three-storey climbing structure. A gift shop and nearby restaurants make it easy to turn into a half-day outing.

Boston Symphony Hall
Behind-the-scenes tours trace the history of the Boston Symphony Orchestra, starting from the Massachusetts Avenue lobby and moving through the Hall's public spaces and traditions.

Boston Opera House
Dating back to 1827 and renovated in 2002, the Opera House blends French and Italian architectural styles, with grand staircases, chandeliers, and silk wall panels. It hosts a year-round programme of performances and events.

Where is the best shopping in Boston?

• Copley Place (Back Bay): a two-level shopping complex with Emporio Armani, Christian Dior, Burberry, Tiffany & Co., and a wide choice of restaurants.
• Newbury Street (Back Bay): eight blocks of independent boutiques and eateries spanning budget to luxury, with a lively street-vendor atmosphere and wide pavements.
• Prudential Center: shops, restaurants, and the Skywalk Observatory, offering panoramic views over Greater Boston. It's also a starting point for the red Beantown Trolley tour, a two-hour hop-off-anywhere city loop.

How do you get around Boston?

The Boston Duck Tour is a sightseeing cruise aboard a restored WWII amphibious landing vehicle, covering landmarks from the golden-domed State House to the Big Dig and Government Center.

The Emerald Necklace is Boston's 1,100-acre chain of nine connected parks and waterways, listed on the National Register of Historic Places and designed by Frederick Law Olmsted in the late 19th century. Walking its full length, from Boston Common to Franklin Park, covers roughly 7 miles.

Franklin Park Zoo, set within the Emerald Necklace, covers 72 acres and houses over 220 animal species, including the African-themed Kalahari Kingdom, the Outback Trail (kangaroos and emus), and a dedicated three-acre Children's Zoo with rare leopards and farmyard animals.

Planning a Boston holiday? Combine it with New York

Boston pairs naturally with New York City for travellers who want two iconic East Coast destinations in one trip. Charter Travel's New York and Boston twin-centre holiday itineraries are built specifically for this route, combining the history and charm of Boston with the energy of Manhattan in a single, seamlessly organised trip.

Book your Boston holiday with Charter Travel

Charter Travel specialises in tailor-made holidays to Boston and the wider USA, with the local knowledge to build a personal itinerary around your interests — whether that's history, family activities, or shopping. Call 01635 551011 to speak with the team and start planning your 2026/2027 Boston holiday.