Solo/Couple’s Trip

If I had 48 hours in Boston with my sweetie, here’s what I would do:
(Boston Proper)
Morning walk on the Esplanade
Walk the Freedom Trail from the Boston Common to the North End
- Lunch at anywhere in the North End (not as crowded during the day), followed by cannoli at Modern Pastry (Mike’s Pastry is great but Modern is always fresh).
- Dinner or Brunch at Lolita in Fort Point or in Chinatown. Chinatown is woefully undervisited by tourists but is quite affordable and fascinating.
- Stroll the shops on Newbury Street - my favorites - TriDent Booksellers & cafe, MUJI, and I really just like the Anthropologie on Newbury (I know that’s so basic!!)
- Visit the courtyard/reading room at the Boston Public Library - designed by McKim
- Get rush tickets to see the Boston Symphony - only $10 - not available on Fri/Sat evenings but totally worth it!
- Jamaica Plain - amazing boutiques on Centre St., the Sam Adams brewery, and Ten Tables is one of the best restaurant experiences you can have in Boston.

I’m also an affiliate for CityPass Boston. I have visited each and every one of the venues included in the pass. I would recommend any of them to you:

  • The aquarium is big (penguins!)

  • The Museum of Science is huge (amazing planetarium)

  • The Skywalk Observatory is magnificent. Catch dessert at Top of the Hub while you’re at it.

  • The Museum of Natural History is really gorgeous and everyone loves the Blaschka Glass Flowers

  • But if you do nothing else, I think the Boston Harbor Cruise at sunset is absolutely a must-see, and very romantic.

    Since you’re not saddled by littles, I also recommend the following which are harder to visit with littles in tow:
    Isabella Stewart Gardner - just trust me. Bonkers.
    JFK Library & Museum - give yourself 2 hours, much less busy before noon.
    MFA - your admission actually allows you a return visit within 10 days (applies to full-price Adult, Senior, and Student tickets only).
    ICA - take the watershuttle out to the Watershed!

Breakfast at the Friendly Toast in Kendall Square
Thrift/vintage shopping at Garment District in Kendall Square
Walk around Harvard Square
Visit the Harvard COOP bookstore
Hot chocolate at Burdick’s

Coolidge Corner is where you can visit the JFK Birthplace, eat delicious crepes or nosh at Rami’s or Zaftig’s Deli), and go to the historic Coolidge Corner Theatre.

Families with Young Children

I want to caveat a couple of the tourist magnet eateries, especially for families as I think there are better, more family-friendly ones than Cheers and Quincy Market. For example, the Boston Public Market has a great little area with picnic tables and play elements for families to eat with their littles! Plus, all of the vendors are local and I’ve never had a bad meal there. I also think taking food to go from Flour Bakery or even Whole Foods and going to a park for a picnic on a bench cannot be beat. My kids were a mess as was I so eating in restaurants was always

Ice cream is a huge priority for my kids, so may I suggest J.P. Licks (all over Boston) and Christina’s in Somerville.


The Martin Richard Playground (Children’s Wharf Park) was built for all the children who live in and visit Boston. I hope the weather is nice enough for you to spend some time there. It is very close to the… Boston Children’s Museum which is excellent. It’s Arthur-themed! It’s almost definitely going to be crowded during any day of summer, but it’s big enough and interactive enough that you can still enjoy your visit.

The Boston Public Library at Copley Square has a very large children’s room if you find yourself wanting a free place that is air-conditioned or warm, depending on the season.

Splash around in the Boston Common’s Frog Pond (bring a towel) in warm weather. In winter, it turns into an ice skating rink which is fun and cold, obviously :) Another area to cool off is on the Rose Kennedy Greenway where you’ll find splash parks and cool public art.

The Duck Boats are fun but very spendy. Your littles may actually enjoy the Swan Boats in the Public Garden just as much and for a fraction of the ride price.

I’m also an affiliate for CityPass Boston. I have visited each and every one of the venues included in the pass. I would recommend any of them to you:

  • The aquarium is big (penguins!) and always crazy crowded.

  • The Museum of Science is huge (amazing planetarium) and will take the better part of a day.

  • The Museum of Natural History is really gorgeous and everyone loves the Blaschka Glass Flowers. Harvard University is a lovely place to walk around but can be tricky to navigate with a stroller, just a heads-up!

Families with Tweens/Teens

I absolutely think the JFK Library & Museum is worth a 1.5-hour visit. If you go, be sure to visit the Edward M. Kennedy Institute next door. It’s a Senate simulation and very interactive, so it’s a great experience for students who are learning how the democratic process works. You also receive $2 off admission at either JFK or EMK if you visit the other. There is free parking at the JFK/EMK complex, but you can also take a free shuttle from the Red Line JFK/UMASS station.

The Duck Boats are fun and your kids may get some of the jokes ;)

If you can make a game at Fenway happen, good on ya. Sing “Sweet Caroline” for me! If you can’t score tickets to a game, you can still tour the park, which can be fun, too.


My kids love Lolita in Fort Point, especially because every meal is chased with cotton candy topped with pop rocks.
Eataly has something for everyone, but is decidedly very touristy.