Upon Arrival: Boston

Indagare’s Annie Fitzsimmons shares her latest intel on the newly reopened Four Seasons Boston—plus an insider’s favorites: what to see, where to eat, shop, stroll and more.

At the Four Seasons Hotel Boston, which reopened this year after an extensive design update by AD100 designer Ken Fulk, there is a full-time Director of Creative dreaming up magical moments for guests and fostering a spirit of generosity that I rarely see at hotels—it is now one of my favorite urban retreats in the U.S.

The property is opulent but soulful, with Boston Public Garden views; sophisticated but playful, with “vaults” on every floor stocked with free snacks like M&M’s, Swedish Fish, bags of nuts, plus drinks. Upon arrival in the lobby, a hand-painted mural depicts the public garden with willow and oak trees—one special swan holds a key. My four-year-old daughter was then handed a key to the mystery closet behind the front desk where she could (gleefully) choose from a veritable treasure chest of toys and books. There is a state-of-the-art gym and a long eighth-floor indoor swimming pool that overlooks the garden; Coterie is an excellent brasserie serving New England classics like crab cakes and clam chowder. But Sottovento just might be my favorite place, a gourmet coffee shop equal to the city’s best (though this is Boston and Dunkin’ Donuts reigns supreme). Start each morning with complimentary barista-made drinks like delicious cappuccinos and iced coffees—or order it from the Four Seasons app for delivery.

I immediately trusted guest experience manager Jeanne Lynch, who grew up in Boston and directed me to spots she knew I would love. Below, some of her favorites close to the hotel.

Contact Indagare or your Trip Designer for assistance planning a trip to Boston. Our team can match you with the hotels that are right for you, as well as advise on all our favorite activities and must-see sites.


I like The Thinking Cup on Newbury Street, a little cafe with great pastries.

Breakfast and Brunch

The Friendly Toast serves breakfast until 4:00 p.m. and is really fun but also perfect for people with dietary restrictions—they have gluten-free pancakes and French toast. Tatte has great shakshouka and breakfast bowls, with nice outdoor seating.”

Perfect Lunch

“On Newbury Street, there are beautiful little patios for people-watching. My favorite is Saltie Girl for hot or cold lobster rolls. You can reserve.”


“Head to Charles Street for the best boutiques. Upstairs Downstairs has antiques where every piece tells a story; Beacon Hill Bookshop features a lot of local authors with a coffee shop and restaurant downstairs.”


“The other Four Seasons in Boston [at One Dalton Street] has an incredible spa. Near us, CorePower Yoga is one block away; SoulCycle a few blocks. Or a beautiful walk across the street in Boston Common.”

Culture Moment

“Boston’s culture is so diverse. The North End is a fantastic blend and feels European—sometimes you feel like you’re in Italy. There’s a mix of authentic food and historical buildings, like The Paul Revere House amid the restaurants and shops. People line up every day for hours for The Daily Catch and Giacomo’s, but my favorite is Trattoria Il Panino.”

The Best Tour

“As a context refresher, I recommend the Freedom Trail tour with one of our favorite guides. You can start at the hotel and weave through the Common, over to the historical points and end in Charlestown at the U.S.S. Constitution.”


The Franklin in the South End is a hidden gem where you won’t find many tourists. It’s where a lot of bartenders go. They have Negronis on draft and a full menu until 1:00 a.m. Anchovies is a total Italian dive bar—think chicken parm and a Miller High Life.”

Date Night

“I love Grill 23 & Bar, a seven- or eight-minute walk from here, for their frosted martinis and classic steak house vibes.”

Outside Central Boston

“Harvard Square has its charms; Kendall Square, where MIT is, has an interesting mix of architectural styles with the classic brick of Cambridge alongside buildings that have an engineering influence—they kind of look like robots.

More Inspiration

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