In every season, Boston charms us. We love strolling across Boston Common on a glorious fall day. We love seeing sailors and scullers on the Charles River in summer. And we especially love visiting on St. Patrick’s Day, when the whole city celebrates the impending arrival of spring by putting on its flip-flops (40-degree weather be darned) and hitting the pubs. 

Boston can be an expensive place to visit, but cheap eats abound and the train system (the T) makes it easy to get around without a car. The CityPASS can also save you money: for $56 per adult, you get admission to four popular Boston attractions. Ready for your Boston adventure?

Five fun things to do in Boston

1. Walk the Freedom Trail. If you’re a history nerd (like we are!), spend a bright morning strolling along the Freedom Trail, a 2.5-mile route downtown that leads to 16 different historic sites. You can opt for a tour led by a guide in Colonial garb, or explore on your own — just look for the red line. The trail winds from Boston Common to Bunker Hill and the USS Constitution. Our favorite stop is the King’s Chapel Burying Ground, a cemetery with ornately carved headstones.
2. Visit Fenway Park. You don’t have to be a die-hard Red Sox fan to appreciate the history of Fenway Park, which was home to Babe Ruth, Ted Williams and Manny Ramírez. The best way to experience Fenway is by attending a game, of course (just don’t sit in Outfield Grandstand Sections 5-8, which face away from home plate).¹ A tour will take you inside the dugout, the press box and the locker room (depending on the season) and even let you sit on the Green Monster.²
3. Explore the Boston Harbor Islands. From May to October, ferries take visitors to the Harbor Islands — beautiful, uninhabited places where you can hike, camp, sunbathe and explore old ruins. There are 34 islands in all, but just eight are accessible via ferry. Favorite spots include Little Brewster Island, home to a lighthouse that has been shining for more than 300 years, and Georges Island, site of a haunted Civil War-era fort.
4. Take a North End food tour. Boston’s North End is home to its Little Italy, a historic neighborhood full of Italian restaurants, bakeries, and shops. A tour is a great way to taste all that the North End has to offer. Chef Michele Topor’s market tour teaches participants about Italian food culture; the Off the Eaten Path tour will stuff you with cannoli, arancini, bread, and gelato. If you’re lucky, your visit will coincide with one of the North End’s summertime feasts, religious observances marked by processions and festivals.³
5. Immerse yourself in one art collector’s obsession. Isabella Stewart Gardner was a wealthy Bostonian who sank into despair after losing her 2-year-old son. To cheer her, Gardner’s husband took her on a world tour, sparking a lifelong passion for art that led to her amassing more than 15,000 treasures.⁴ The Gardner Museum displays work from masters like Degas, Titian, and Whistler, as well as the empty frames remaining from an audacious, unsolved $500 million art heist in 1990.

Four outstanding boutique hotels in Boston

Sure, Boston has big luxury hotels aplenty. But for a truly memorable Boston getaway, stay at a smaller boutique hotel. For location, it’s hard to beat the Revere Hotel on Boston Common. Recently remodeled, this hotel boasts modern art, a pool and a chic rooftop lounge overlooking Back Bay. The Boxer Boston Hotel, which occupies the distinctive, triangular Flatiron Building, offers modern, pet-friendly and accessible guestrooms.

If you’re doing Beantown on a budget, it’s not too hard to find affordable boutique hotels in Boston. One is Verb, a rock-n-roll-themed hotel near Fenway Park with free breakfast, a vinyl record library, and surprisingly low rates. In Back Bay, the Charlesmark Hotel is perfect for simplicity seekers. This Euro-style boutique hotel has small but modern rooms, plus a complimentary breakfast.

Three of the best places to eat in Boston

Choosing just three great restaurants is an almost impossible task. But if you’re spending a long weekend in Boston, we’d recommend experiencing the city’s classic cuisines: Italian, Irish and seafood.

The best Italian restaurants in Boston can be found in the North End. We suggest Mamma Maria for a special night out with white tablecloths, intimate dining rooms, and expertly rendered Italian classics like beef carpaccio, osso buco, and Frutti di mare pasta.

The Atlantic Fish Company in Back Bay is a favorite for super-fresh New England specialties like clam chowder, raw oysters, and Maine lobster. The buttery bread is a crowd favorite as well.

Before you leave Boston, you have to raise a glass in at least one Irish pub. The oldest family-run spot in the city is J.J. Foley’s in the South End, which dates to 1909. Fancy it’s not, but authentic it is, with talkative bartenders, filling bar food and Guinness and Magners Cider on tap.

Heading to Boston for a few days? Travel insurance is invaluable even for short domestic trips, protecting you in case of covered delays, cancellations or interruptions, even lost or damaged luggage. Find the plan that’s right for you!

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