A First-timer’s Guide to Boston, MA

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Advisor - Tracy Delossantos
Curated By

Tracy Delossantos

  • Arts & Culture

  • City Travel

  • Couples Travel

  • Family Travel

  • Boston

  • History

  • Architecture

  • Local Culture

A view of the city from over the water with a cloudy sky overhead.
Curator’s statement

As my home away from home for multiple years, Boston holds a special place in my heart. It’s a charming city packed with rich history, culture and beauty that lures foodies, history lovers and sports enthusiasts alike. Walkable with access to public transit, you can explore Boston’s diverse neighborhoods without ever needing to rent a car and enjoy this city in any season of the year.

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Where to stay in Boston

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Things to do in Boston

A baseball park full of people watching a game.
  • Get some fresh air at the Charles River Esplanade. Use one of the many pedestrian bridges to walk along the esplanade and catch a beautiful sunset.

  • Cruise the Boston Harbor. Opt for a sunset cruise to get beautiful views of the harbor.

  • Visit the scene of the largest art heist in history. With art from around the world, the Isabella Stewart Gardner Museum is where 13 works of art were stolen and never recovered. Their frames still hang empty on the walls.

  • Visit the beautiful Boston Public Library. This library has mesmerizing architecture that you can enjoy at your own pace or opt for a guided tour.

  • Explore the Seaport District. Get unobstructed views of the Boston Harbor from Fan Pier Park. If it happens to be a Thursday, be sure to visit the Institute of Contemporary Art for free. Taste some local beer and grab a pint at Harpoon Brewery or Trillium Fort Point.

  • Tour the oldest baseball park in MLB. Fenway Park is the home of the Red Sox and the famous Green Monster. Whether you’re a fan of baseball or not, this tour is something everyone visiting Boston should put on their list. If it’s not a game day, swing by the Bleacher Bar to get a unique view of centerfield.

  • Make a picnic at Boston Public Market and enjoy it at Rose Kennedy Greenway. This year-round indoor market hosts local vendors from New England that offer fresh food, crafts and specialty goods. My favorites: Mo’rockin Fusion, The Popover Lady and Red Apple Lady. Cross the street and enjoy your picnic on the Rose Kennedy Greenway with unique views of downtown Boston.

  • Relax in the Boston Public Garden. As the first public botanical garden in America, Boston Public Garden is right in the heart of the city. You can ride the famous Swan boats or enjoy the peacefulness of this beautiful park from one of the many paths.

Day trips

  • Provincetown. Take the ferry ride across the Cape for a fun day trip to Provincetown. You can explore the charming shops along Commercial Street or rent a bike to visit one of the many beaches

  • Salem. Just a quick train ride away, you can explore the home of the Salem Witch Trials and most of the filming locations for the movie Hocus Pocus.

Places to eat & drink in Boston

A lobster roll on a hotdog-style bun with fries on checkered paper.

Breakfast:

  • Mike & Patty’s Bay Village. Open since 2008, this tiny sandwich shop sells sandwiches all day where you can order and pick up on your way to start your day of sightseeing. My favorites: The Fancy and the Breakfast Grilled Crack.

  • The Friendly Toast. This quirky restaurant serves breakfast and brunch all day. The portions are as large as the menu, so I recommend sharing a dish — or two. This place tends to fill up, so you can join the waitlist before you show up. My favorites: The Chicken Cordon Bleu Benny and the Cookie Monster Pancakes.

  • Flour Bakery + Cafe. This is a local staple led by the famous Joanne Chang, who is a James Beard award-winning pastry chef. There are multiple locations throughout Boston and Cambridge. My favorites: The breakfast egg sandwich, brown butter cinnamon roll and parmesan chive scone.

  • Theo’s Cozy Corner. Cozy spot in the North End serving up huge portions of everything on their American, Italian and Brazilian menu. My favorites: Corned Beef & Hash and the porto wine french toast.

Lunch & dinner:

  • Yankee Lobster is a no-frills multigenerational, counter service restaurant that serves up hearty seafood. My favorites: The traditional lobster roll and the lobster mac & cheese.

  • Parish Cafe & Bar is an awesome restaurant that features unique sandwiches curated by some of Boston’s famous chefs, this place has a high-quality menu that changes from time to time. My personal favorites are Le Mistral and The Zuni Roll.

  • MIDA. Most first-timers make the trek to the North End for Italian food, but beat the hassle of trying to fight the crowds and go to the South End neighborhood for a delicious Italian dinner. Chef Couglass Williams has created a true gem with a unique menu. My favorites: Gnocchi cacio e pepe and the short rib lasagna.

  • Atlantic Fish Company serves up a fancy seafood menu where you can chow down on clam chowder.

  • Monica’s Mercato. This specialty grocery store and deli makes sandwiches that will set a new standard for Italian subs. My favorite: the Tuukka Special.

Dessert:

  • Bova’s Bakery. A family-owned bakery with a variety of sweets to choose from at any time of day. They’re open 24/7. My favorites: The florentine shell ricotta cannoli and pistachio macaroons. Tip: This is a cash only spot.

  • Little Miss Cupcape. This decadent spot has fun cupcakes, yummy cookies and the best cinnamon rolls.

Drinks:

  • Harpoon Brewery is a great way to end a day exploring the Seaport District. The beer is very good and you have plenty to choose from all year round. If you have room, order one of the salted pretzels to dip into their housemade IPA cheese.

  • Night Shift Brewing - Lovejoy Wharf. Located near the Zakim Bridge and TD Garden, this brewpub offers small batch and experimental brews.

Need to know

The most popular times to visit are summer and fall. No matter the season, bring your best walking shoes as you'll be walking quite a bit.

Advisor - Tracy Delossantos

Travel Advisor

Tracy Delossantos

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This guide is part of our ongoing series on travel to Boston. Looking for more travel inspiration? Check out Tracy Delossantos' guide, Banff & Beyond: A Family-Friendly Canadian Rockies Adventure.