Boston Favorites

Chelsea Papa

Boston is forever my favorite Northeastern city for its sense of history, endless charm, and small town feel. I lived here for four years as a student and visit as often as I can when I'm back in New England. My insider’s guide includes practical advice and curated lists of the restaurants, hotels, and things to do I've grown to love over the years, plus a few I’m excited to try next time! If you find this helpful, a tip is always appreciated! This mini guide is similar to what you can expect from my custom lists.

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When to Go

May - November is the best time to visit Boston given how long and harsh winter can be. Fall is picturesque, but more crowded with students and visitors. Summer is more calm but humid. Avoid sports playoffs and graduation weeks!

Transportation

Getting There

✈️ Logan is Boston’s main airport. It’s easy to access and not far from most parts of the city. From there, you can Uber/Lyft or take the T (silver line) for free. You can also take a water taxi!

Boston Water Taxi | City Cruises

www.cityexperiences.com

🚂 If you’re coming from elsewhere in New England, you can take Amtrak or a bus into South Station and take Uber/Lyft or the T from there.

Boston Logan International Airport

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South Station

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Boston’s main train station. From here you can take the T to the airport or into the city.

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Getting Around

🚶🏻‍♀️ Boston is relatively walkable as a small city.

🚇 Take the subway (T) to travel longer distances. Fill up a reusable Charlie Card at one of the kiosks in the underground stations and use an app to help you navigate the system. It’s pretty straightforward. The lines are differentiated according to color: green, red, orange, blue, and silver.

🚗 A car is not necessary for most people, but if you’re renting a car or driving in, download the ParkBoston app.

Neighborhoods

My favorite neighborhoods for aimless exploring and picture taking will always be the quaint ones with beautiful architecture and historic charm.

Stays

Charming boutique hotel options in Boston are limited and pricey. Book well in advance and avoid traveling during sports playoffs or graduation / move in week.

Food + Drink

Local Specialties

🦞 Lobster Rolls

🦪 Oysters

🥣 Clam Chowder

🥧 Boston Creme Pie

🥫 Baked Beans (the reason Boston is called Bean Town, but most people don’t seek this out)

Coffee Shops + Bakeries

Restaurants

Seafood

Bars

These all serve food and could work for dinner too. Happy hours also don’t exist here.