Three summers, three trips to Boston, and no signs of stopping. What started as a spontaneous couples getaway has turned into our official annual tradition: a Red Sox game at Fenway (behind home plate), a home base near Boston Common, and a few days of doing exactly what we love — good food, good shopping, and a whole lot of baseball. If you're looking for a Boston trip that's built entirely around what the adults want to do, this one's for you.
Why We Keep Coming Back
Boston in the summer just works for us. We've been lucky with weather every year — warm, but never the brutal heat you'd expect from a July or August trip — and there's something about the energy of the city in baseball season that makes it feel like a proper celebration every time. It's become the one trip we protect on the calendar no matter what else is going on that year.
Where We Stayed: The Newbury vs. the Four Seasons
We always plant ourselves around Boston Common — it puts us within walking distance of everything on this list, and there's nothing better than a stroll through the park before or after dinner.
This year we stayed at The Newbury, a boutique hotel with a cozy, elevated feel and a location that's tough to beat. It was intimate, stylish, and exactly what we wanted for a few nights.
Last year, we stayed at the Four Seasons on Boylston Street, and we loved it so much we tried to book it again this year — except it was completely sold out thanks to the World Cup. Honestly, can't blame anyone for wanting to be there. Comparing the two: both hotels were fantastic, but the Four Seasons edged it out on room size and amenities. Every single floor had its own free snack room (a small detail that somehow makes a huge difference), our room overlooked Boston Common, and the bar and restaurant downstairs had genuinely great food with five-star service from start to finish.
If you want boutique charm, book The Newbury. If you want more space and a few extra bells and whistles, the Four Seasons is worth planning ahead for — just know it books up fast around big events.
Tradition #1: A Red Sox Game at Fenway
No Boston trip is complete without a game at Fenway Park, and we always spring for seats behind home plate. There's something about watching a game at one of the oldest ballparks in the country, glove-close to the action, that never gets old no matter how many times we do it. This is the non-negotiable of the entire trip — everything else gets planned around it.
Tradition #2: Shopping on Newbury Street
Newbury Street is a full afternoon (or two) every time we visit — there are so many shops and restaurants packed into those few blocks that you could easily make a whole day of it.
A few Newbury Street traditions of our own:
- Last year, my husband surprised me with my very first Chanel bag for our anniversary — still can't walk past that store without smiling.
- This year, I treated myself to a watch I've wanted for ages.
- We always pop into Rails — it's a reliable stop every single year.
- The J.Crew on Newbury got a major glow-up — it's now a brand-new, much larger store and well worth a look.
- I also picked up my first pair of Back 70 sneakers at TREND, which I'm now firmly on team over Sambas or Golden Goose.
Between the boutiques, the flagships, and the little discoveries in between, Newbury Street alone is a reason to come back every year.
Tradition #3: Dinner in Little Italy at Carmelina's
Every trip ends with dinner in the North End (Boston's Little Italy), and we always go to Carmelina's. It's become as much a part of the trip as Fenway at this point — the kind of meal you plan the rest of the evening around.
A Few More Boston Favorites
Beyond our North End tradition, a couple of other restaurants have earned a permanent spot on our list:
- Atlantic Fish Co. — a Back Bay seafood staple and an easy walk from Newbury Street, making it a natural stop before or after a shopping afternoon.
- Cafe Sauvage — a cozy French spot that's become one of our go-tos when we want something a little different from Italian.
- Yvonne's — a stylish downtown supper club that's great for a dressed-up dinner or drinks if you're looking to make a night of it.
- Krasi — a Greek meze and wine bar tucked just off Newbury Street, perfect for small plates and a glass of wine mid-shopping-day.
- Avra — a newer Greek seafood spot right on Newbury Street itself, so it's an easy stop without even leaving the shopping strip.
Boston for Adults: A Few Tips If You're Planning Your Own Trip
- Book behind-home-plate Fenway seats early — they go fast, especially in peak summer months.
- Stay near Boston Common if you want to walk to Newbury Street, the North End, and Fenway without relying on rideshares for everything.
- If a major event is happening in the city (World Cup, a big convention, etc.), book your hotel as far in advance as possible — we learned that lesson trying to re-book the Four Seasons this year.
- Leave room in your suitcase. Between Newbury Street and the North End, you will end up shopping.
FAQ: Planning a Boston Couples Trip
When is the best time to visit Boston for a Red Sox game? We've gone every summer for three years and have consistently had good luck with the weather — warm without being unbearable. Summer is also peak Red Sox home game season at Fenway, so it's an easy pairing.
Where should couples stay in Boston? Anywhere near Boston Common is a great home base. We can personally vouch for both The Newbury (boutique, cozy, incredible location) and the Four Seasons on Boylston Street (more spacious, excellent amenities, a free snack room on every floor).
What are the best shops on Newbury Street? It's hard to go wrong — we always make time for Rails and the newly expanded J.Crew, plus whatever boutiques catch our eye that year.
Where's the best place to eat in Boston's North End? Carmelina's is our go-to every single trip and hasn't let us down yet.
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