1. The Freedom Trail
This 2.5-mile stretch of bricks laid in the sidewalk will take you past some of the most historic landmarks around the city. And I’ll remind you we’ve got a lot of them, including the Old North Church, the site of the Boston Tea Party, the Paul Revere House and Boston Common. Walk the trail solo or with a guide donning Revolutionary-era dress, and soak up the historic vibes that are ingrained in the personality of the city.
Tours start at 139 Tremont St., Boston, MA 02108. +1 617-357-8300; thefreedomtrail.org
2. The Red Sox
One of our favorite hometown sports teams is the Red Sox, who play at Fenway Park, the country’s oldest. Even if you’re not a big fan of baseball, you can’t help but get excited when you’re sitting in the bleachers out in right field surrounded by die-hard Sox fans. And, of course, we all belt out the lyrics to "Sweet Caroline" during the seventh-inning stretch, all out of tune but loving it anyway.
4 Yawkey Way, Boston, MA 02215. +1 877-733-7699; boston.redsox.mlb.com
3. The Lobstah Roll
One of Boston's best dishes and one I look forward to at the start of each summer is the lobster roll. Boston Harbor is teeming with lobsters, so you know you’re eating the freshest here. Get yours warm with butter (our specialty), and to feel like a local, call it a lobstah roll. My favorites are at Barking Crab and James Hook.
Barking Crab, 88 Sleeper St., Boston, MA 02210. +1 617-426-2722; barkingcrab.com
James Hook & Co., 15 Northern Ave., Boston, MA 02210. +1 617-423-5501; jameshooklobster.com
Every globe-trotter and traveler will enjoy this, and in fact it’s one of my absolute favorite spots in the city — and one that somehow manages to fly below most people's radar. The Mapparium is a three-story stained-glass globe that you can walk through to experience a light and sound show with countries of the world based on a 1930s Rand McNally map.
200 Mass Ave., Boston, MA 02115. +1 617-450-7000; marybakereddylibrary.org
5. Isabella Stewart Gardner
This Boston lady was a visionary, making it her life’s work to amass a collection of the finest art from around the world to share with the public. Her distinctive style was brought to life and preserved in the Isabella Stewart Gardner Museum, which houses everything she collected over her lifetime; it was curated quite precisely by the late Ms. Gardner herself.
25 Evans Way, Boston, MA 02115. +1 617-566-1401; gardnermuseum.org
6. Swan Boats
Enter the Boston Public Garden and you’ll be surrounded by trees from around the world. In this, the first public botanical garden in the States, you can enjoy the greenery from aboard a pedal-powered swan boat. These whimsical crafts were inspired by Wagner's Lohengrin, and 139 years after their debut they continue to offer a peaceful ride around the pond.
4 Charles St., Boston, MA 02114. +1 617-522-1966; swanboats.com
7. Harvard Museum of Natural History
When you head to Harvard to tour its famous campus, be sure to include a stop at the Harvard Museum of Natural History. There you’ll find a display of glass flowers that you’ll swear are real, wildlife from around the globe, and thousands of rare, sparkling gemstones.
26 Oxford St., Cambridge, MA 02138. +1 617-495-3045; hmnh.harvard.edu
8. Sam Adams
Founding Father, statesman and political philosopher Sam Adams is a famous figure in American history. Perhaps more importantly, Sam Adams is also our most popular beer. Brewery tours are free and come with the chance to taste various beers. Afterward, just because you can, go to the Beantown Pub for a cold Sam Adams while looking at a cold Sam Adams (the bar is, ahem, across the street from his grave).
Boston Brewery, 30 Germania St., Boston, MA 02130. +1 617-368-5080; samueladams.com
Beantown Pub, 100 Tremont St., Boston, MA 02108. +1 617-426-0111; beantownpub.com
9. Boston Public Library
Consistently ranked one of the most beautiful libraries in the world, and regularly booked out for weddings, the Boston Public Library is an architectural delight that houses an immense collection of texts. I recommend going for the architecture tour and the summer series of courtyard concerts.
700 Boylston St., Boston, MA 02116. +1 617-536-5400; bpl.org
10. Faneuil Hall
Faneuil Hall is the third-most-visited public space in the United States, after Times Square and the Las Vegas Strip, of course. Actually, Faneuil Hall is in a way like the Boston equivalent of Times Square. Just as Boston is the smaller, friendlier, less-crowded cousin of NYC, so too is its central meeting point. Faneuil Hall is not filled with skyscrapers and giant billboards, but instead is the historic site of Boston’s original docks and markets, now filled with contemporary stores, restaurants and street performers.
Faneuil Hall Marketplace, 4 South Market Bldg., 5th flr., Boston, MA 02109. faneuilhallmarketplace.com