5 Days to Explore Boston

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  • Boston

  • Massachusetts

  • Food & Wine

  • Arts & Culture

  • Outdoors

  • Entertainment

  • Nightlife

Boston city
Fora’s Take

Boston is rich with history, from the Revolution, of course, but also in its distinctly diverse population and neighborhoods. You cannot help but feel a sense of belonging among the cobble-stone streets, beautiful architecture and the greenery in Boston Public Garden, with the beautiful back-drop of the harbor.

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Where to stay in Boston

The Liberty, a Luxury Collection Hotel, Boston

Blending history, sophistication and hometown warmth, this is the ideal place for a quintessentially Boston experience.

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Omni Parker House

Elegant hotel from the 19th-century with high-end rooms and suites.

Canopy by Hilton Boston Downtown

Immerse yourself in the vibrant spirit of downtown Boston at this contemporary hotel, where modern design, local charm and personalized service create a refreshing and authentic urban experience.

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Things to do in Boston

Boston cruising fun

GoCity Pass Boston - This pass was definitely worth the cost. The majority of your tours will be included, even on your day trip to Salem.

Boston Tea Party Ships & Museum - The tour guides/actors put on a surprisingly hilarious show while teaching everyone about the history and even allowing the tossing of the tea into the harbor.

Whale Watching Tour with Boston City Cruises - The marine biologists were so knowledgeable and gave us some really insightful information during the cruise to the whales. They work really hard to make sure the trip is not in vain, and if it is, they will provide a voucher for another cruise. On our cruise, we ended up witnessing a feeding frenzy and saw over 50 whales gathered together, which was extremely uncommon according to our guide.

Cheers Boston - Stop by here to get a souvenir and get a photo with a life-size cut out of Ted Danson. The Bloody Mary's are good and this is a nice area to break before exploring Boston Common and Boston Public Gardens.

Boston Common & Boston Public Gardens - These are some of the most beautiful parks. Find the Good Will Hunting bench for a photo op.

Hop On/Hop Off Trolley Tour - This is a nice and inexpensive way to get around the city and learn about it at the same time.

View Boston at Prudential Center - Much like Top of the Rock in NYC, this three-floor excursion gives panoramic views of all of Boston. It even shows you some of the famous places around the city, like Fenway Park, MIT and Harvard.

Freedom Trail - This trail marks 16 significant sites of the Revolution and covers about 2.5 miles. There is an actual brick trail running through the city that can be followed with a guide or can be done self-guided. Many of the stops are included in the trolley tour, but not all of them.

Day Trips

Day Trip from Boston To Kennebunkport, ME

(Booked through Viator and operated by New England Trips, Inc.) This was such a lovely day trip to see the coast of Maine and Kennebunkport. There's also a stop in Perkins Cove to walk the Marginal Way, which has some of the most breathtaking views of the Atlantic Ocean. Don't miss the blueberry muffins at Fox's at the Nubble Lighthouse or the Lobster Bisque at Alisson's Restaurant in Kennebunkport. Honorable mention to Maine-ly Drizzle. They have olive oil and balsamic vinegar tasting samples in more flavors than imaginable. None of us left this store empty-handed.

Day Trip to Salem from Boston

Travel to Salem via the Salem Ferry. Do the Witch Museum, lunch at The Howling Wolf and site-see before the final return ferry at 4pm.

Places to eat & drink in Boston

Boston cafe

The Black Rose Pub - Delicious Irish pub with excellent sandwiches or the ever-popular fish and chips. They also have the classic clam chowder.

Buttermilk & Bourbon - Hell's Kitchen runner-up and celebrity Chef Jason Santos' take on southern hospitality. The food was delicious but one thing to mention is the idea is to order and share so all of the plates are appetizer-sized.

The Last Hurrah - Very popular whiskey bar located in the Omni Parker Hotel. They do have a small-bites food menu, but are known for the whiskey cocktails. They also serve the original Boston Cream Pies.

Quincy Market - This is the best option for quick, easy and variety. Our hotel was right across the street, so we found ourselves eating here quite often. The hall is lined with food stalls serving everything from Chinese, bakery items, seafood, smoothies, pizza and so much more.

The Paramount - this small restaurant we stumbled upon in Beacon Hill, was a perfect lunch spot. It was hands-down the best chicken club sandwich and sweet potato fried.

Stratus (at View Boston in the Prudential Center) - While we did not try the food here, they do have appetizer plates to enjoy with your drinks. It was the perfect place to sit and sip while looking out over all of Boston.

Riccardo's Ristorante - One should not visit Boston without eating at a North End Italian Restaurant. Riccardo's was delicious and the atmosphere was friendly and fun.

Tatte - Popular Boston cafe with multiple locations across the city. They have amazing lattes and the breakfast sandwiches are good too.

MIJA - This is a cantina connected to Quincy Market. The margaritas are to die for. The dip trio is also delicious with very fresh salsa and guacamole.

Koy - This was a last-minute selection for our last night because it was right next to the hotel. This was the best meal on the trip and possibly ever. Do not sleep on the Pineapple Coconut Shrimp and the Crab Rangoons.

Need to Know

For more travel tips, check out Fora Advisor Tia Santoro’s guide, . This guide is part of our ongoing series on travel to Boston.

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This guide is part of our ongoing series on travel to Boston.