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11 things to do on your first visit to Boston

11 things to do on your first visit to Boston

Downtown Boston as viewed from the Skywalk Observatory

One of the enjoyable things about visiting a major city in the US is that most enable you to see the country through a slightly different prism: New York, Las Vegas, Los Angeles, Chicago, Miami… all offer a very different perspective and experience.

Boston, in Massachusetts, may not be one of the country’s biggest cities, but the viewpoint it brings is one of history. Massachusetts is the state where the Pilgrim Fathers landed in the Mayflower in 1620 and it’s where the US War of Independence began in the mid-1770s.

Whereas some US cities can be dated back to the turn of the 20th Century, and the arrival of the local railroad, Boston – which in the late 1600s was the third biggest port in the world after London and Bristol – has a history going back well over 300 years. It’s also the heart of New England, regarded as one of the most beautiful areas of the US.

For visitors from the UK, the city has recently become a little more accessible. Norwegian Airlines launched another of its low-cost routes from Gatwick at Easter. Book enough in advance and flights to Logan Airport cost as low as £149 each way.

I flew on a 787 Dreamliner, one of the most modern and greenest planes in the air.

It features windows with dimmer controls, hours of entertainment via its Android Inflight Entertainment System, plus plug-in points for phone and laptop chargers. If, like me, you fly Premium, you can also access the brand new Number One lounge at Gatwick, to kick start your trip in style.

Once there, here are some suggestions for how to make the most of your trip – whether it’s just an extended weekend or longer.

1. The Freedom Trail

The Freedom Trail is a 2.5km walking route in downtown Boston that includes 16 historical points of interest. It takes in the Old State House, the Granary Burial Ground (which although small, actually contains well over 5,000 bodies!), and the sites of the Boston Massacre and Boston Tea Party.

I joined an organized tour, which was illustrative but a little on the slow side. Alternatively, download a Freedom Trail app to your smartphone and just follow the trail at your own pace.

Boston Common on Memorial Day weekend
Boston Common on Memorial Day weekend

2. Boston Common

If you do the Freedom Trail, you’ll probably start at Boston Common – the US’s oldest surviving city park. You won’t fail to miss the gold-domed State House or Frog Pond, and the park hosts regular events at weekends in the summer. It neighbors the slightly more formal Boston Public Garden, with its famous Swan boats – a popular spot for marriage proposals.

3. Dine at an Italian in the North End

Boston is famed for both its Irish and Italian communities. The latter are dominant in the city’s North End, which offers dozens of Italian restaurants and bakeries. Head for Quattro (264 Hanover Street at Parmenter Street) for hand-stretched pizza or homemade ravioli – I personally recommend the ravioli of spit roasted chicken with wild mushroom ragu.

Cheers in Boston
Cheers in Boston

4. Have your photo taken outside Cheers

OK, it’s cheesy, but can you resist? The exterior shots for the opening sequence of the classic 80s sitcom were filmed outside this Boston bar (right). The basement bar is nothing to do with the TV show, but is decked out in a similar wood-paneled, traditional style. You’ll find it on the edge of Boston Common, at 84 Beacon St, Boston, MA 02108.

5. Shop on Charles Street

One of Boston’s more upmarket areas is Charles Street, which offers a selection of boutiques, antiques, designers stores and independents. There’s also plenty of food options, such as delicious fresh ice cream at Caffe Bella Vita.

Want it fancier still? Nearby Newbury Streets has global brands such as Dolce & Gabbana, Marc Jacobs and Burberry. You’ll also find Shreve, Crump and Low – the oldest jewelers in the US.

6. Step back in time at the Omni Parker House Hotel

Not only is the Omni Parker House the oldest hotel in the US still in operation, but it was also the birthplace of the Boston Cream Pie, considered to be one of the city’s signature dishes. The beautifully preserved Parker restaurant is visually stunning and well worth a visit.

Quincy Market
Quincy Market

7. Eat at Quincy Market

Want to really taste New England? Go straight to Quincy Market – part of the Faneuil Hall Marketplace. The indoor market is packed with food stalls and restaurants. This is the place to head for fresh lobster, crab, brick-oven baked pizza and corn chowder – as well as cuisine from the rest of the world. North Market, South Market and the Boston Public Market (a must for food lovers) are all within the same area.

8. Gaze out from the Skywalk Observatory

The Prudential Center is a shopping mall in the South End of the city. Besides retail and restaurants, you can visit the very top of the Prudential building for the city’s best elevated view – the Skywalk Observatory is 52 floors above street level. It costs $18 for adults, $13 for kids.

Downtown gay bar The Alley
Downtown gay bar The Alley

9. Cruise The Alley

Recently revamped – complete with a mural of the Boston skyline dominating one wall – The Alley is popular with the local bears. The two-story venue is recommended for anyone seeking to mingle with the local men. I checked it out on a Saturday night, when the DJ played seminal 80s tracks on the mezzanine floor and husky hunks sunk balls on the pool table below.

10. Sunday brunch at Club Café

Club Café is a big, brash gay bar and club with a rotating line-up of cabaret. One of it’s most popular sessions is its Sunday brunch, where for $16.50 you can eat all you like from the buffet. At 3pm, cabaret kicks off in portioned off section of the venue. Until late July, catch the drag version of the Golden Girls!

For other food options, the South End also offers The Beehive brasserie and Stella’s. Hip breakfasts spots include the tiny Mike & Patty’s and Flour.

11. Get out of the city and take a day trip to Provincetown

OK, so it’s not something to do in Boston, but if you’re visiting the city for any length of time, consider at least a day trip to Provincetown. The seaside resort and village fishing at the top of Cape Cod is a short flight or 90-minute fast ferry ride away. Bay State Cruise Company run a service several times a day throughout the summer months. The destination is an LGBT hotspot, with dozens of bars, restaurants and other LGBT venues, and a high gay population.

Boston as pictured from the ocean
Boston as viewed from the ocean

For more suggestions, check Visit Boston and Visit Massachusetts.

Getting there

A Norwegian plane takes flight
A Norwegian plane takes flight

Norwegian fly a year-round four times weekly direct service between London Gatwick and Boston Logan International Airport. The flights are operated by a fleet of brand new Boeing 787 Dreamliner aircraft with two cabins – Premium and economy. Fares start from £149 one way at or 0330 8280854 (opt. 1).
Passengers travelling in the Premium cabin can enjoy spacious seating with extra legroom, complimentary drinks, dinner, inclusive luggage, fast track security and access to select airport lounges from £399 one way.


Rooftop cabana at the Revere Hotel Boston Common
Rooftop cabana at the Revere Hotel Boston Common

David Hudson stayed at the Revere Hotel Boston Common. This affordable, business hotel offers 365 modern guestrooms, balconies with views overlooking the city, two separate restaurants, spa, indoor pool, fitness center and rooftop bar, among other amenities. It’s centrally located, just a couple of blocks from Boston Common.

Rooms start at $299/night. Click here for a fuller review.



Images: Boston Common – Tim Grafft/Massachusetts Office of Travel and Tourism (MOTT); Boston from the ocean – Fayfoto (MOTT); Quincy Market via Quincy Market; The Alley – David Hudson