Boston Holidays

Getting out onto the Charles changes the view completely. From the water, Boston and Cambridge feel much closer, and the city skyline opens up around you. Hire a kayak or canoe around Allston, Brighton or Cambridge and take it at your own pace.

Once the boat leaves Long Wharf, Boston disappears behind you surprisingly quickly. Cruises head out towards Atlantic feeding grounds where humpback, fin and minke whales are often spotted. Dolphins sometimes appear too, although with wildlife, nothing is ever guaranteed.

A ferry ride out to the Boston Harbor Islands is an easy way to get some space from the city. Some islands are closed to visitors, but the accessible ones offer walking trails, open shoreline and excellent views back towards Boston.

The Charles River Esplanade is made for an easy bike ride rather than a hard workout. The route stays close to the water, with plenty of greenery and skyline views along the way. Pass the Hatch Shell, then stop wherever the river view looks good.

It is unapologetically touristy, but that is part of the fun. A Boston Duck Tour drives past major city landmarks before the amphibious vehicle heads straight into the Charles River. It is a cheerful way to see a lot without spending the whole day walking.

Castle Island works well when you want fresh air without leaving Boston. Walk beside Fort Independence, watch planes coming and going from Logan Airport, then head towards Pleasure Bay if the weather is warm. Sullivan’s is the classic stop for something quick afterwards.

Follow the red-brick Freedom Trail for 2.5 miles through central Boston. Along the way, you will pass 16 historic sites linked to the American Revolution, including Boston Common, Old North Church and Paul Revere House, before the route finishes in Charlestown.

The Black Heritage Trail focuses on Beacon Hill’s free Black community and the people who fought slavery in nineteenth-century Boston. Several stops form part of Boston African American National Historic Site. One of the most important is the African Meeting House, built in 1806.

Built around 1680, the Paul Revere House is one of the oldest buildings in downtown Boston. It later became home to the famous silversmith and revolutionary messenger, and much of the early structure still survives inside.

Charlestown Navy Yard served American naval operations for 174 years before becoming part of Boston National Historical Park. The main attraction is USS Constitution. Launched in 1797 and nicknamed “Old Ironsides”, she remains the world’s oldest commissioned naval warship still afloat.

The Boston Tea Party Ships & Museum brings the events of 1773 to life with costumed guides, interactive exhibits and replica ships. Visitors can even take part by throwing tea overboard into Boston Harbor.

Granary Burying Ground is one of Boston’s oldest cemeteries. Samuel Adams, John Hancock and several other major figures from the Revolutionary era are buried here, so even a short walk through the grounds reveals an impressive amount of early American history.

The Bunker Hill Monument marks one of the first major battles of the American Revolution. The granite obelisk rises 221 feet above Charlestown. There are 294 steps to the top, where the climb is rewarded with broad views over Boston, Cambridge and the surrounding area.

South Boston is the centre of the action every March, with packed pavements, marching bands, flags in windows and pubs filling up well before the parade arrives.

Marathon Monday falls on the third Monday in April and takes over the city in a way few other events do. Boylston Street is the famous finish, but the crowds and noise stretch far beyond it.

Boston Pride for the People is usually held in June. The parade draws big crowds into the city centre, while Boston Common becomes one of the main places for music, community groups and daytime events.

Early July brings Harborfest to the waterfront, mixing Boston’s Revolutionary history with harbour activities, performances and family events over several days before Independence Day.

On 4 July, the Charles River Esplanade becomes the place everyone heads for. The Boston Pops perform in the evening, then fireworks close the night over the river.

Music carries across the park, food stalls stay busy and the parade is one of the highlights. Boston’s Puerto Rican Festival is usually held in July and is one of the city’s biggest cultural weekends.

Summer weekends in the North End can feel completely different during feast season in July and August. Religious processions pass through decorated streets, music plays from temporary stages and food stalls appear everywhere. Saint Anthony’s Feast is the one most visitors hear about.

Walk through the main entrance at Copley Square and head for Bates Hall, with its long tables, green lamps and huge arched ceiling. John Singer Sargent murals are elsewhere in the building, and the courtyard is another lovely surprise. Entry is free.

The Museum of Fine Arts is far too big for a quick wander. Egyptian artefacts, Japanese art, American paintings and major Impressionist works all sit inside, including pieces by Monet and Renoir. Pick a few galleries and leave the rest for another visit.

This is not a white-walled gallery where everything sits neatly in rows. Isabella Stewart Gardner created something closer to a Venetian home, filling the rooms with paintings, furniture, sculpture and books around a plant-filled courtyard. Raphael and Titian are among the names inside.

Symphony Hall has hosted the Boston Symphony Orchestra since 1900. If there is a performance during your stay, have a look at the programme; the orchestra is one of the orchestras traditionally known as America’s “Big Five” and regularly performs with leading guest musicians and soloists.

August in the North End can mean bunting overhead, food cooking on the street and religious processions passing between the neighbourhood’s restaurants and old buildings. Different weekends honour different Catholic saints. Saint Anthony’s Feast is usually the biggest and busiest of them.

Acorn Street gets the photographs, but wandering the surrounding Beacon Hill lanes is more interesting than making a single stop there. Brick pavements, old townhouses and gas lamps appear around almost every corner, particularly along and around Charles Street.

Across the river in Cambridge, Massachusetts, take the Red Line to Harvard and walk through the gates into Harvard Yard, the historic centre of Harvard University. Afterwards, browse the Harvard Coop or one of the independent bookshops around the square. Street performers often gather near the T station too.

Listen for the missing “r” in words such as “car”, but do not expect everyone in Boston to sound the same. The accent changes between neighbourhoods and generations, and plenty of locals speak without the strong version usually heard in films and television.

Fenway Park feels historic before the game even starts. It has been home to the Boston Red Sox for more than a century, and the famous Green Monster dominates left field. Even without a ticket, a stadium tour is worth doing.

A Celtics or Bruins game at TD Garden gets loud fast. The crowd stays involved from the opening minutes, and the atmosphere carries even up into the higher seats. For live sport in Boston, this is one of the big nights out.

Broadway shows, ballet, touring productions and live performances all land in Boston’s Theatre District. The Boston Opera House is the best-known venue, but there are several theatres packed into the surrounding streets, making this an easy area to plan an evening around.

Candlepin bowling looks familiar until you actually try it. The balls are smaller, the pins are tall and narrow, and you get three rolls in each frame. It is a proper New England pastime and much harder than it first appears.

Boston changes completely on Marathon day. Crowds gather along the route, neighbourhoods turn into cheering sections and the finish area becomes packed with runners and supporters. The race is held every April and is one of the city’s biggest annual events.

Boston evenings tend to start early and finish earlier than in cities such as New York. That still leaves plenty of time for Irish pubs, historic taverns, comedy clubs, live music and sports bars. Just do not leave your plans until midnight.

Start at Boston Common, which dates back to 1634, then cross into the Public Garden next door. The mood changes straight away. There are flower beds, a lagoon and the famous Swan Boats, which return during the warmer months.

Come here hungry. Quincy Market is packed with food stalls, while the surrounding marketplace has shops and street performers. Faneuil Hall brings the history, with a past tied closely to public meetings, speeches and political life in Boston.

You do not need to walk more than 40 miles of the Harborwalk to enjoy it. The sections around Seaport and Fan Pier are easy to fit into a day and give you open water, harbour activity and some excellent views back towards the skyline.

The giant ocean tank is the part everyone remembers, with sea turtles, sharks and marine life swimming through several levels of the building. The New England Aquarium sits right on the waterfront, so it also fits neatly into a day around Boston Harbor.

This is a good rainy-day option, especially with children. The Museum of Science has hands-on exhibits, live demonstrations, lightning shows and planetarium programmes, and there is enough inside to keep you busy for a few hours without forcing the pace.

Newbury Street is easy to wander without a plan. Designer shops sit beside independent boutiques, cafés and restaurants, all set against Back Bay’s brownstones. Carry on towards Copley Square and you can easily combine it with the Boston Public Library.