Boston City Guide: My Favorite Spots

Boston is by far one of my favorite cities. I don’t know what it is about it, but as much time as I spend here, I am constantly discovering something new!

Here are some of my favorite things to do in the Boston area (and some outside the city, too).

Where to eat and drink

• Beignets at Buttermilk and Bourbon, a New Orleans-inspired restaurant
• Cider donuts (seasonal, available in the fall) in Boston Public Market, where you can also get some really pretty flowers, fresh vegetables, and local goodies
• Cocktails at Legal Harborside on the top floor
• Dessert at Mike’s Pastry (or Modern Pastry across the street. People in this city have a loyalty to one or the other, but I think they’re both great!)
• Drink in the South End is still one of my favorites. (They don’t have a menu, so you just tell them what you like or what you want, and they handcraft a cocktail for you.)
• Grab lunch from one of the many food trucks and sit along the Greenway
• People-watch while dining at Stephanie’s on Newbury Street
• Afternoon tea at the Taj Hotel
• Coffee at Tatte Bakery (several locations around the city)
• Cocktails at Four Seasons Boston

Where to stay

• Hyatt Regency Boston Harbor (for incredible views of the city skyline – this is where we had our wedding reception!) – sit on the outdoor patio if the weather is nice!
• Fairmont Copley (gorgeous inside!)
• Hyatt Regency Boston (near any show you would want to see)
• Any hotel in Copley (so close to everything!)
• Four Seasons Boston (on the Public Garden)

What to do

• Head of the Charles Regatta (held in mid-October)
• Sunset cruise in Boston Harbor
• Check out Salem around Halloween (just be prepared for crowds!)
• Shopping in Beacon Hill, where you will find the cutest little stores among the prettiest backdrop
• Take a short ride out to the suburbs for apple picking and pumpkin picking in the fall months (I’m biased and think that Central MA has the best spots, but you can find orchards closer to Boston, too. Just know that closer to the city you will find much larger crowds, and farther out you will find a more authentic apple picking experience! Head toward Lancaster, MA.)
• Rent a bike from one of the New Balance-sponsored bike stops and do the entire Freedom Trail
• Take a tour of Fenway Park or catch a Red Sox game (did you know it’s a historic ballpark?)
• Visit Cambridge, just on the outskirts of the city, to see Harvard Yard (Here’s my favorite place to stay in Harvard Square!)
• If you need to find a great spot to work, pop into any of the Capital One Cafes in the area

Day trips (and more) from Boston

• If you have more time than just a day or two, take a ride up to Parker’s Maple Barn in NH to see how maple syrup is made (and leave with way too much maple sugar candy)

Or check out one of these locations:

• Portsmouth, NH (about an hour from Boston by car)
• Cape Cod (depending on where you go, 1.5-3 hours from Boston): Where to go on Cape Cod | Chatham, Cape Cod |  Cape Cod packing list | Cape Cod sailboat charter | Cape Cod with Kids (Chatham)
• Nantucket (2 hour drive from Boston plus an hour ferry ride OR you can fly easily from Logan Airport)
• Providence, RI (about an hour’s drive south)
• York, Maine (a little over an hour’s drive)
• New York City, NY (about a 4 hour drive)