Your guide to the historic city of Boston
 ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

October 19, 2022 | View OnlineSign Up

Dripping with history, unequivocally passionate, and forever at the forefront of US history, this is a special city.

Few places conjure the past like Boston, which proudly clings to its role in the American Revolution, but don’t be mistaken — it’s very much facing forwards. Innovation thrives along its cobblestone streets, modern art adorns its historic galleries, and the world is changed in the labs and classrooms of its two most famous universities.

But aside from its importance, Boston is a joy to experience. Its European layout allows the city’s personality to flow from bar to street to bay, letting you feel, with no doubts, that you’re in The City on a Hill.

Welcome to Boston.


First for everything

As one of the country’s oldest cities, Boston has the honor of many firsts.

The city is home to the US’ first public beach, the first subway system, the first public park, the first chocolate factory, the first Dunkin’ Donuts, the first lighthouse, the first Thanksgiving, the first newspaper, the first public school, the first pub, the first state constitution, the first microwave, the first computer, and the first electric telegraph. And breathe.

Oh yeah, almost forgot a little invention named Facebook, too.


Create emails quickly with structures

Bring your walking shoes

Truly walkable cities are few and far between in the US. Boston is possibly the best of the lot. It’s a compact city as it is, but add in its European roots, excellent public transport, and well-paved streets, and it’s a walker’s dream urban landscape. It’s even nicknamed “The Walking City” among other monikers.

With that in mind, it’s best to leave the car at home if you can and to not even bother with a rental. Parking will be an expensive nightmare with no major benefit. The historic center is only around two square miles anyway.

Not so happy-hours

Despite its well established appreciation for beer, Boston actually had Happy Hour specials banned in the eighties after a drunk driver tragically killed a woman in the city. Since then, bars and restaurants are not allowed to lower the price of their booze for specific periods.

Instead, you might find food specials, like two-for-one tacos, dollar oysters, or even unlimited sushi for a set price.

Pack Smart

Boston can be a tough place to pack for, thanks to its milder climate. Although summer weather can get hot and humid, evening temps can drop pretty quickly, and you’ll be wishing you had more than a t-shirt. At least bring a long-sleeve shirt to compensate and a rain jacket for the occasional storm.

Winter can be brutally cold, with average highs of no more than 42 degrees and frequent snow, so make sure you’re wrapped up if you venture to the city. For the months in between, come equipped for warm and cold. It could switch quickly, so be prepared.


Find the right therapist for you on BetterHelp

Taking care of your mental health matters, and BetterHelp is here to help you find a licensed therapist to meet your needs.

Get help with anxiety, depression, grief, relationships, trauma and more without leaving home. The online platform makes it easy to schedule your first live video, phone or chat session.

Join today and take 25 percent off your first month.


Create emails quickly with structures

Walk through Boston's history

Boston has more than enough going for it to keep you occupied at the best of times, but if you’re not checking out some of the historical aspects of the city, you’re missing out.

The city found itself at the center of some of the most important events in American history, and there are plenty of opportunities to learn more about them and see the places firsthand. The best place to start is the Freedom Trail, a 2.5-mile-long route through the historic heart of Boston. It’s a great way to get your bearings in the city and check out the seventeen historical sites on the way.

Starting in Boston Commons, where British soldiers once set up camp, going through the Old State House, Paul Revere House, and the USS Constitution, all the way to Bunker Hill, you’ll have the opportunity to learn about the events preceding the War for Independence, like the Boston Tea Party, and the Boston Massacre.

You can walk the trail yourself, but for the most in-depth experience, grab one of the many tours available. There is an array of different options depending on your interest level, so do some research. Once you’re done there, go for a wander around the beautiful Beacon Hill, you won’t regret it.

Create emails quickly with structures

Catch a game…or four

Few cities have a sporting tradition like Boston’s. Even if you can’t tell your touchdowns from your free throws, there’s almost no way you haven’t heard the names of Boston’s storied teams.

A game at Fenway Park should be at the top of the list. Arguably the most famous baseball stadium in the world, the Boston Red Sox have called it home since 1912, cultivating one of the most passionate fanbases in the sport, so expect an electric atmosphere at any time of the year. At best, you’ll catch a home run ball; at worst, it’s a brilliant day out.

The Patriots can’t be ignored when talking about Boston sports. The most successful NFL team of all time, albeit without Tom Brady, is always worth watching. 

Elsewhere, the Boston Celtics provides an atmospheric night out for basketball fans, and the Bruins dish out the adrenaline-pumping excitement of the NHL. With so many options, you'd be wise to take in at least one game while you’re there.

Create emails quickly with structures

Live the island life

Okay, so it might not be the Caribbean, but Boston Harbor is home to thirty-four islands ripe for exploration. Only eight of them are currently accessible to the public, but there’s more than enough to keep you occupied. Just hop on one of the water taxis.

Georges Island is by far the most popular island. The 55-acre lump of land hosts Fort Warren, a prison during the Civil War, which can be explored via a ranger-led tour. It’s also supposed to be haunted by “The Lady in Black,” a woman supposedly executed there for trying to free her husband during the war.

For a more outdoorsy getaway, Spectacle Island should be your choice. Double the size of Georges Island, visitors can enjoy over five miles of trails, stunning views of Boston itself, and even a beach to enjoy the vistas from.

Little Brewster Island is the furthest from Boston of all the islands. It’s only accessible by organized island tours but is well worth the trip. The main attraction here is the lighthouse, the first in the United States, named Boston Light. It’s still functioning and manned today — a rarity.


Create emails quickly with structures

A hotel revolution

Travelers are spoilt for choice when visiting Boston. Its rich history lends to a selection of outstanding historical stays; from Victorian manor homes to renovated jails, you’ll have no issues embracing the past.

If you want to keep Boston’s history firmly in the museums, worry not. All the big names are here, offering tried and true comfort and out-of-this-world luxury.

Create emails quickly with structures

Our Top Pick: The Kendall Hotel

Boston, Massachusettes
$$ | See inside

A wonderful piece of history at a wonderful price. The Kendall Hotel is located inside a Victorian firehouse built in 1895 on the edge of the picturesque Beacon Hill neighborhood. Its rooms are cozy and strive to replicate an intimate B&B, as opposed to a mega-chain establishment. Its downstairs lobby is just as cozy, perfect for curling up with a cocktail in the evenings.

The real gem is the Black Sheep restaurant attached to the hotel, where guests can enjoy breakfast, lunch, and dinner. Its vegan menu is wildly popular too.

At under $200 a night, it’s a steal.

Book Your Stay

Other Top Picks


Create emails quickly with structures

Bean there, done that

You’d be letting the side down if you didn’t tuck into some of Boston’s excellent seafood. Lobster steals the show, whether by itself, in a roll, or even in Mac and Cheese. But don’t sleep on the clam chowder and oysters.

The most famous of Boston's culinary produce, however, is the baked bean. Typically sweetened with molasses and then flavored with pork or beef, it’s a local staple going all the way back to the Native Americans that called the region home. Grab a plate on the Freedom Trail.

Our Top Pick: Wood Hill Pier 4

Boston, Massachusettes
$$$$ Menu

An utter delight. One glance at Woods Hill’s menu is enough to know it’s going to be spectacular. Everything is locally sourced, from the vegetables to the divine selection of seafood on offer.

The only thing possibly matching the food is the location, steps from the waterside in the Boston Harbor. If you’re splashing on one meal, make it this one.

Reserve a table

The Best of the Rest


Advertising Policy | Terms of Use | Privacy Policy

Want to break our hearts? unsubscribe

© 2022 Dollar Flight Club, All Rights Reserved.
113 Cherry St (PMB 79116), Seattle, Washington 98104-2205 US

Email Marketing by ActiveCampaign