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Freedom Trail, Lobster Rolls and Cannolis in Boston, Massachusetts with Kali Roberge

Best things to do in Boston Massachusetts Kali Roberge garden

I’m really excited to interview Kali Roberge of Beyond Your Hammock about Boston, Massachusetts. Kali moved to Boston from Georgia and has fully embraced the New England lifestyle. Kali’s tips for the best things to do in Boston include walking the Freedom Trail, where to find the best lobster rolls, and eating pizza at Regina’s in the North End.

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Best things to do in Boston Massachusetts Kali Roberge Charles River

View of Boston skyline from across the Charles River

Boston, Massachusetts

Boston is a vibrant city that is very popular with tourists. It is the capital and most populous city in Massachusetts. The city is well known for the long-running TV show “Cheers,” its famous baked beans, and its successful sports teams. The Boston Red Sox play baseball in Fenway Park, which is MLB’s oldest baseball park (1912) and home of the Green Monster. The city has incredible history and many key battle sites and landmarks from the Revolutionary War are dotted throughout the city. You can explore many of these cherished landmarks by walking the Freedom Trail.

We share a lot of resources and local suggestions in today’s podcast, but you should also check out Boston U.S.A., the local convention and visitor’s bureau. They are a wealth of information and can help you plan an itinerary based on your time, budget, and interests.

When you visit, use the Boston CityPASS to save 46% on the four of the most popular attraction in Boston. The CityPASS includes admission to the New England Aquarium, Museum of Science, Skywalk Observatory, and a Boston Harbor Cruise or the Harvard Museum of Natural History.

If you’d like to learn how to travel for free using airline miles and hotel points, check out my free 7-day email course.

Best things to do in Boston Massachusetts Kali Roberge North End

Boston’s North End

Getting around Boston

The local airport is Boston Logan International Airport (BOS), which is about 5 miles by car or 15 minutes by train to downtown.

Kali says that there’s no need to rent a car when you visit. Boston has really great public transportation using its subway system. The city is a very walkable city and the more you walk around, the more historical buildings and sites you can see.

Uber and Lyft are excellent ways to get around. If you need to rent a car, click here for the best offers from Avis, Budget, or Hertz.

If you only need a car for a couple of hours, you can rent by the hour with Zipcar. Join now to get $25 loaded into your account.

sicilian-cannoli-3686050_1920 Pixbay Lucas Holiday

Make sure to try a cannoli dessert in the Italian North End. Photo courtesy of Lucas Holiday on Pixabay.

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Kalli Roberge about Boston, Massachusetts. You can zoom into the map and click on each dot to explore the city.

  • Red dots = best places to eat in Boston, Massachusetts
  • Green dots = best things to do in Boston, Massachusetts
  • Yellow dots = best places to stay in Boston, Massachusetts

Who is Kali Roberge?

Kali Roberge is the Chief Operations Officer and Director of Marketing for Beyond Your Hammock. It is a financial planning firm based in Boston, Massachusetts, that specializes in helping people in their 30s and 40s use money as a tool to live a satisfying life right now, while still planning responsibly for tomorrow. Kali is also the co-host of the Beyond Finances podcast.

Best things to do in Boston Massachusetts Kali Roberge at the harbor

Kali at the Boston Harbor

Here are a few articles and podcasts where you can hear more from Kali Roberge:

You can connect with Kali at her personal website or at her company site, Beyond Your Hammock. You can follow Kali on social media on Twitter, Instagram, and LinkedIn.

Big thanks to today’s affiliate partner – AwardWallet

This episode is brought to you, in part, by AwardWallet. Using airline miles and hotel points makes travel affordable, but keeping track of all of those loyalty programs can be a challenge.

That’s why I use AwardWallet to track my miles and points balances, reservations, and special goodies like free hotel night certifications and airline companion passes.

Having everything in one easy to use dashboard helps ensure I don’t let any rewards expire and makes logging into my accounts super easy. Go to to start your free account.

Best things to do in Boston Massachusetts Kali Roberge tallships

Take a tour of the historic tall ships in Boston Harbor

Stay tuned for our next episode

Rossilyn with the Pittsburgh skyline. Photo by

Listen to the next episode when Rossilynne Culgan, the author of “100 Things to Do in Pittsburgh Before You Die,” shares her unique tips for Pittsburgh, Pennsylvania. We talk about the renaissance of this Rust Belt city, where Mr. Rogers lived in Pittsburgh, and riding the city’s famous inclines. We hope you’ll join us when We Travel There.

What’s your favorite part of Boston? Send us a Tweet, let us know in the comment section below, or continue the discussion in our Facebook group!

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Related episodes

For more tips about the New England area, listen to these episodes:


  1. Luke Vader

    Lived in Boston for 8 years after college (more than 20 years ago), absolutely loved my time there. Went back to enjoy the 4th of July fireworks along the Charles River last year. For delicious cannoli in the North End, Mike’s Pastry is probably the most famous “dealer”… their store is often packed, with lines running out the door.

    • Comment by post author


      I’ve been to Mike’s before. Great shop, but the lines can be long. Kali recommended going to Bova’s (just around the corner) if you don’t want to wait. Have you ever been there?