The Best Things to Do in Boston On A First Time Visit

The ultimate first timer’s travel guide to Boston! I’ll tell you where to stay, what to do and what to eat during your first visit to Beantown!

Boston holds a very special place in my heart. Not only is my husband a born and raised Bostonian, but I went to college there (proud Boston University graduate!) and lived there for nine years before home.

Fortunately, with so many of our friends and family still living in Boston, we go back recently which means people are always asking me for my “must see” spots in the city. Needless to say, this travel guide is long overdue but I’m so excited to finally share with you my first-timers travel guide to Boston.

First up, you’re going to want a hotel that is easily accessible to the T (the country’s oldest subway!) and within walking distance from various shops, restaurants and other attractions.

I first learned about The Eliot Hotel when my parents visited me during college but during my recent stay I was blown away by the modern updates and spacious suites throughout the property. All 95 guest rooms have a separate bedroom and living space making this a top choice for families as well.

If you’re visiting Boston for the first time, I highly recommend a visit to the Skywalk Observatory located on the 50th floor of the Prudential Center which is just a short 8-10 minute walk from the hotel. This 360-degree view of the city is a great way to get a lay of the land before you head out to explore the city.

While there, grab a bite to eat at the Top of the Hub located on the 52nd floor and offering one of the best views of Boston in the whole city.

You can’t go wrong with anything on the menu but I highly recommend the lobster roll. Afterall, you can’t visit New England without trying a lobstah roll. Note: I wouldn’t recommend Top of the Hub for small kiddos as it is on the more upscale side.

The next spot I always recommend to people visiting Boston for the first time in Faneuil Hall Marketplace. Featuring over 70 retailers, Faneuil Hall has been around since 1742 and is often referred to as the country’s first public trading space/shopping area. Pro Tip: Boston has no sales tax on clothing, shoes, and purses. You’re welcome.

Craving a sweet treat or a bite to eat? Head to Quincy Market located in the center of Faneuil Hall. This food hall is lined with various quick-serve eateries offering food from all over the world, plus local classics like Boston clam chowder, Italian pastries and more.

Another must see spot in Boston is the Public Garden and Boston Common.

Both are filled with history: the Public Garden was the first public botanical in America established in 1837 and the Boston Common is America’s oldest park.

One of my favorite spots to walk around, have a picnic or people watch, this is a great spot to let kids run around and burn off energy.

From the Boston Common and Public Garden, head to Charles Street where you can stroll the Beacon Hill neighborhood.

This upscale, historic district is lined with beautiful brownstone houses and countless restaurants and boutique shops. It’s about as charming as Boston gets.

For a fun and casual lunch on the water, head to The Barking Crab. This is one of my favorite spots to get local dishes like steamers, chowder, mussels and more.

Of course, you really can’t beat the view either.

Next, you must carve out time to visit Harvard Square. Located in Cambridge just across the bridge (a 10-15 minute drive depending on traffic), Harvard University is a sight to be seen by anyone visiting Boston for the first time.

A great place for shopping, walking around, people watching or grabbing a bite to eat, Harvard Square is a fun, eclectic neighborhood buzzing with energy.

My husband wouldn’t be happy if I didn’t mention his favorite neighborhood: The North End! This historic Italian neighborhood is lined with bakeries, restaurants, shops and more.

Our favorite bakery to get half moons and cannolis is Bova’s Bakery, open 24 hours. For an incredible Italian dinner, we love Antico Forno.

Last but not least, for espresso and coffee, stop into Cafe Vittoria. My husband and I spent many evenings there in our early years of dating.

One of my favorite streets to walk down is Newbury St. lined with countless retailers including independent boutiques, national retailers, luxury shops and endless restaurants and bars.

Pro Tip: The shops closer to Arlington Street are more upscale (think: Burberry, Chanel, Versace, etc.) and progress to more affordable as you head down the street.

Last but not least, take the Green Line of the T out to Brookline for breakfast or lunch at one of my favorite Jewish restaurants: Zaftigs Delicatessen. If you’ve ever craved homemade matzo ball soup, potato latkes (pancakes) or a traditional corned beef sandwich, this is your spot.

Have I convinced you to visit one of my beloved cities of all time, Boston? I sure hope so. If you visit, please let me know what you think!

Your passport is waiting.

Disclosure: Boston USA coordinated my hotel, activities and meals during my stay. I was not compensated to write this post. All thoughts are my own. 

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