A week at a five-star resort is obviously a rare thing to indulge. It’s such a treat to escape on a flight somewhere new, but sometimes I only have a night or two to relax. I’m lucky to live just outside Boston, which is an ideal destination on the east coast for a staycation or quick weekend away.
By now I’ve spent so many fun nights out in the city and brought friends from all over the world to stay overnight so we could really let loose! My spouse and I love a quick night away in Boston too, as do my little ones who squeal when the ‘big city’ comes into view on the highway.
Let’s plan your next Boston mini-trip. Here’s a breakdown of the best neighborhoods, where to stay, what to eat, and how to maximize your time.
South End’s classic style and taste
I consider the South End the OG neighborhood of Boston. The reputation is clean, chic, and quintessential Massachusetts city-style, from its trendy restaurants to its tree-lined streets. When I want to feel indulged and relaxed but still be close to the action, I enjoy a night or two in the South End.
The last time I had a staycation, my cousin and I booked a room at the cute StayPineapple hotel. It’s a small chain mostly present on the West Coast, but the Boston property’s vibe is quirky, urban, and very comfortable. While the lobby is simple, each room’s decor offers fun yellow/pineapple themed amenities, plus plush bathrobes, and tropical toiletries.
StayPineapple is connected to the Trophy Room for classic bar meals and tasty cocktails. It’s nice to have the option just downstairs for some hearty bites, and there’s also plenty of walkable options nearby too.
Here’s a few places worth a bite:
Kaia: I haven’t been here yet personally, but no one I know has had a bad meal there. It’s an elevated Mediterranean affair with a delicate raw bar and refined decor.
Barcelona Wine Bar: I’m obsessed with tapas and Spanish food. This is some of the best I’ve had in Boston and overall outside Spain, even as a chain. At least have a delicious red wine and garlic shrimp while wandering the area.
The Beehive: A classic and the must-go place if it’s your first time in the neighborhood, especially for brunch. It’s part of the Boston Center for the Arts building and often offers live entertainment.
Also, after dinner (or before!) don’t miss the new candy shop called Madeleine’s which is super fun to poke around in for a pick and mix bag of Swedish-style treats.
Seaport brings sophistication to Boston’s newest ‘hood
Recently, I had girlfriends fly into Boston for a weekend on Cape Cod, but we wanted to stay a night in the city at first. Some had already enjoyed visits to the North End and the South End before, so I thought the Seaport would be a fun place to land.
We stayed at the Hampton Inn, which was simple, clean, and bright. We treated ourselves to a delivery from Tatte and all had breakfast in bed!
Next time I’d like to try the Omni Seaport: they have some wonderful perks like packages for free parking, which is clutch in the Seaport if you need a car.
For a fun dinner, Citrus & Salt was a winner. Mexican/Baja fusion food satisfied everyone, alongside fun pink-hued decor and fruity, flirty drinks. To keep the vibe going, we had a nightcap at Lolita. While technically in Fort Point, this is a great spot for harbor views on the outside patio and tasty bites.
There are endless things to do in the Seaport, here are a few more to consider:
- In warmer months, the beer gardens are popular. Harpoon, Lord Hobo, and Cisco Brewery all have outdoor seating in the Seaport.
- A Museum of Ice Cream opened this year! It’s fun and kitschy, and offers great photo ops. There’s a bar at the end for cocktails too. Here’s my honest Instagram review:
- There’s some short cruises and boat tours you can take from the docks. I’ve done the Spirit of Boston dinner cruise twice and it’s always lots of fun, especially for groups.
North End’s classic delights leave satisfied bellies
I dreamed of living in Boston’s North End after I moved back home from Spain. It’s the closest thing you’ll find to wandering Europe’s historic streets while in the U.S.
There are no boutique hotels inside the neighborhood, probably due to space. You could do a holiday rental, but they’re often a pain for short stays. It’s worth checking out Battery Wharf Hotel on the harbor. It’s a stone’s throw from the North End and boasts classic decor. If you’re coming in by train or want direct access to the MBTA (or the “T”), CitizenM is located above North Station and offers a funkier vibe, but is still walkable from the North End.
After you’ve checked into your hotel, have a seafood experience or an authentic Italian meal just down the street. Many of the best restaurants will require a reservation…they are busy for a reason!
Little Sage is intimate and lovely for dates, while Neptune Oyster is the place to go to impress your friends. For something that truly celebrates Italian American faire, Cantina Italiana is one of the best in the North End.
Of course living it up in Boston’s Little Italy is well worth the budget, but there are a few spots that aren’t as elegant and worth checking out. I think luxury can also simply mean the freshest ingredients and the most delicious, traditional dishes. My family and I grab a booth at the original Pizzeria Regina every Christmas season, which has been around the city since 1926.
You can battle potential lines at Mike’s or Modern Pastry for a cannoli, but I have a few alternative options. Personally, I love to sip an espresso martini and have a homemade pastry at Cafe Vittoria. Then I can truly savor a sit-down sweet. Or if you need your dessert to go, head to Bova’s (it’s even open 24 hours a day!) and choose from a variety of cake slices, Italian cookies, and of course, cannoli.
Never a dull moment for a Boston getaway
Outside of these three areas of Boston, there is obviously so much more to experience if you hope to splash out on the town. The theatre district is a classic and lovely area to see a show and to rest your head. A few opulent hotels can be found near Boston Common, and South Boston has a few up and coming hotspots too for visitors and travelers. Even surrounding cities such as Cambridge can be well worth sinking into for a night or two.
If you’re looking for more experiences to have in Boston, don’t miss our article that has top recommendations from professional travelers who love this city!
Read more about Boston and surroundings
The Real Person Badge!
Bougie Boston is such a vibe, and your recommendations for indulgent overnight stays really capture the city’s luxury side perfectly. Definitely bookmarking this for my next trip—can’t wait to try some of these spots!
The Real Person Badge!
Love the idea of a girls’ weekend in Boston! Sounds like a trip full of energy and fun, like a bag of bouncy balls waiting to be unleashed.
The Real Person Badge!
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