The Perfect Day in Boston

A one-day trip to Boston is just enough time to start digging deep into history with a walk along the cobblestone streets of the Freedom Trail, and a visit to the always-enchanting Isabella Steward Gardener Museum. Don’t worry: we’ll send you off for some great food and drinks too.

25 Evans Way, Boston, MA 02115, USA
Rembrandt, Vermeer, and Degas, where art thou? That’s a question the staff has been asking at the Isabella Stewart Gardner Museum since 1990, when thieves made off with 13 of the museum’s most valuable pieces, worth an estimated half a billion dollars. Rather than sulk, however, museum officials left empty frames on display both to educate visitors and to serve as hopeful placeholders awaiting the artworks’ eventual return. Meanwhile, you can visit the museum’s lovely courtyard and vast collection of historic and contemporary art at Fenway Court, built to resemble a Venetian palazzo and packed with paintings, sculpture, furniture, and textiles gathered by Gardner, an avid art collector and philanthropist, during her lifetime. Pro tip: Wear a Red Sox hat or shirt to get a $2 discount on admission—as stipulated by Gardner after her beloved Sox won the 1912 World Series (also, you get in free if your name is Isabella).
1704 Washington St, Boston, MA 02118, USA
Toro, located in Boston‘s South End district, is a little slice of Barcelona in the Northeast. The menu is based on small plates (tapas), and while the ingredients are regionally sourced, the wine list is all Spanish, giving Toro a nice mixture of local atmosphere and international appeal. Also, though the standard menu has a traditionally Spanish emphasis on meats and fresh seafood, there are also vegetarian, vegan, dairy-free, gluten-free, and nut-free options.
4 S Market St, Boston, MA 02109, USA
Sure, Faneuil Hall and Quincy Market make up the most touristy part of Boston, complete with street performers, a light show, and the obligatory Yankee Candle store and Cheers restaurant; we nonetheless defy you to stay away. This part of the Boston waterfront has thrived on commerce since colonial times: Faneuil Hall was crowded with merchant’s shops as early as 1743, and the larger Quincy Market was added in 1824 to provide more space (it also was the site of speeches by Samuel Adams and other early patriot leaders). If you’re looking for a Red Sox hat or a “Boston Strong” T-shirt, you’ll find it here.
10 Milk St, Boston, MA 02108, USA
I usually think of tea when it comes to Japan, but one visit to Ogawa changed my mind. Aside from the gorgeous latte art they are known for, this artisan coffee house from Kyoto is committed to the perfection of the beverage through sourcing, roasting and preparation. As soon as you walk in the door, the aroma is enough to give you your afternoon fix. I loved their stadium seating for a unique change of pace and they also offer interesting sandwiches and Japanese snacks in addition to beans. Try the Single Origin Trio, three small cups of single origin coffee served side by side for a bit of caffeine heaven.
44 School St #250, Boston, MA 02111, USA
The Freedom Trail is the artery connecting most of Boston’s key Revolutionary War sites, from Boston Common to the USS Constitution—16 stops in all. Besides providing you with some history, following the red stripe around town also delivers an easy self-guided tour of the heart of Boston, including the lively North End and Charlestown. The Common, Old North Church, the Paul Revere House, and the site of the Boston Massacre are obvious and obligatory stops, but the trail also leads to three legendary cemeteries, the 1718 Old Corner Bookstore (now a Chipotle restaurant, of all things), the 1713 Old State House, and the unmissable Bunker Hill Monument, whose cornerstone was laid by Lafayette to mark the 50th anniversary of the bloody battle between British troops and patriot militias in June 1775.
139 Tremont St, Boston, MA 02111, USA
The Common becomes extraordinary on winter evenings when the Christmas tree is up and soft lights seem to hold back the twilight chill, but the truth is there’s no bad time to visit the nation’s oldest public park. The former cow pasture has been a focal point for Boston’s history and culture since its inception in 1636—a site for riots and rallies from the Revolutionary War to the Vietnam War era as well as weddings, hangings, and burials. Summer splashing and winter skating at the Frog Pond are local traditions, and you can spend hours wandering from landmark to landmark (like Augustus Saint-Gaudens’s famous bas-relief Memorial to Robert Gould Shaw and the Massachusetts Fifty-Fourth Regiment, or the Soldiers and Sailors monument atop Flag Staff Hill). Or you can just laze in the sun on the park’s west-side lawn.

310 Washington St, Boston, MA 02108, USA
This building, a National Historic Landmark, has been described as the birthplace of the American Revolution, as citizens of the colony gathered here to discuss the Boston Massacre, the Boston Tea Party and other events of the day. Built as a Puritan meeting house in 1729, this is where Benjamin Franklin was baptized and the plans for the Boston Tea Party were conceived. See rare treasures that include a vial of tea and a tea-crate label from the Boston Tea Party; a 3-D historic model of colonial Boston built more than 100 years ago; and John Hancock’s portable writing desk.
370 Hanover St, Boston, MA 02113, USA
Walking through the narrow streets of Boston‘s North End might have you thinking about a delicious Italian meal. Take the time, however to explore the area on Hanover Street where the surrounding brick buildings suddenly give way to a park where Paul Revere stands guard. Commemorating his ride to warn the colonists of the impending British Invasion, the statue stands in front of a small park leading to the famous Old North Church. The setting is a perfect spot to relive the beginning of the American Revolution, and after exploring, leaves you in a location filled to the brim with restaurants and cafes to recharge before moving on.
193 Salem Street
Like Sean Bean in National Treasure, you won’t find the booty of the Knights Templar in the basement of the Old North Church, but there is a crypt here with thousands of bodies dating back to the 18th century. This prominent stop on the Freedom Trail is rich in colonial and Revolutionary War history, most notably because the 191-foot steeple was where patriots hung two lanterns on the night of April 18, 1775, warning that British troops were setting out by sea to their fateful encounter with local militias at Lexington and Concord. A walk around the church, constructed in 1723 (making it Boston’s oldest house of worship), is a revelation in irony: While the building played a role in the start of the Revolutionary War, most of its Episcopal congregants remained loyal to King George. Chimes from the steeple still announce Sunday services, thanks to the Bellringers Guild, which is comprised of MIT students.
2 Pleasant St, Charlestown, MA 02129, USA
Like to have a meal with historic spirits? Visit the oldest tavern in MA. and one of the most historic watering holes in America. First erected in 1780 in Charlestown, George Washington dropped in for refreshments and Paul Revere counted it among his favorites. Featuring traditional tavern fare for lunch and dinner, it’s a great pit stop after burning up calories climbing the Bunker Hill Monument just up the street.
100 Hanover Street
The recently opened Boston Public Market is the only year round indoor market in the country to feature exclusively New England vendors. The bounty of 35 businesses representing farms, makers and food producers offers a cross section of all things local to eat from around Boston. Farm fresh produce, meat, poultry, fish, dairy and flowers along with an assortment of speciality and prepared foods. There are even a few beautiful craft artisans in the mix. A great place for families and foodies alike, there is even a selection of locally produced wines, beers and alcohol. Catch the warm glow from the hive at Boston Honey. Interactive classes will take place for all ages in the Market’s demonstration Kitchen. Connect with the people who feed New England in this great community space.
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