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Your Guide to a Socially-Distanced Staycation in Boston

Boston Back Bay Reflection
Wikimedia Commons

If you’re like us, you can’t wait to start traveling again in 2021. And while the restrictions on your ideal destination haven’t been lifted quite yet, there’s a whole lot to see right outside your door (and plenty of people stuck in other towns are desperate to plan a vacation right where you live). Now is the perfect time to get back to your roots with a little staycation while you wait for the end of the world to end. So dial up the sitter and dust off that new outfit you bought last year, because we’re going out (while mostly staying in).

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Luckily, Boston is the perfect town to enjoy from a safe social distance. A big little city brimming with colonial charm and packed with history, and we’re willing to bet you don’t know it as well as you think you do. There’s plenty left to discover on these cobblestoned streets, and now is the perfect time to have once-packed places to yourself. We’ve opted for out-of-the-way museums instead of the usual Duck Boat tours, and found some killer restaurants that snuck open during the pandemic. And since every town looks cooler when you don’t have to make the bed, we rounded up some fresh digs with COVID-friendly amenities that’ll keep you feeling cozy and safe while still providing that much-needed change of scenery.

Where to Stay

StayPineapple Hotel

Stay Pineapple Hotel

Living in the South End is the stuff Bostonians dream of, with its brownstone-lined boulevards, vibrant art scene, and incredible food, and a night or two at StayPineapple will have you feeling like a local without having to fork over the rent. This adorable little hotel is nestled amongst the brick homes and chic boutiques of this very European neighborhood, and it’s a perfect and picturesque place to get lost for an afternoon. You’ll be right down the street from some of the city’s best restaurants if you feel like going out, and the accommodations are decked out with some seriously well-appointed digs (think marble bathrooms and king-sized beds) if you’d prefer a luxurious night in. Downstairs, there’s a spacious lobby lounge where you can relax, grab a drink, and plan your day at a safe distance from your fellow guests. In the morning, skip the Keurig in the room and head around the corner to the Berkeley Perk for a quick breakfast and freshly roasted coffee.

Price: From $109/night

Book at AirBnB

Read more: Best Boston Hotels


If you’ve had enough of cobblestones and tri-corner hats, Yotel is a high-tech hotel in the city’s bustling Seaport, where every other block boasts a shiny new skyscraper. This harborside haunt used to be a series of empty shipping lots, but over the past decade has developed into Boston’s cutting edge, where some of the world’s leading science and tech companies rub elbows with modern art and fine dining. And speaking of cutting-edge: the hotel employs a hospital-grade robotic cleaning system for each room, and guests can check-in and out using digital self-service terminals, keeping both you and the hotel staff safe and comfortable during your stay.

Price: From $97/night

Book at Yotel

The Eliot Suite Hotel

For a taste of classic (and classy) Boston, look no further than The Eliot. The snazzy sushi restaurant downstairs boasts two James Beard Award-winning chefs, and they’ve reserved a few suites in the hotel itself for private dining experiences during the pandemic. The hotel is perched between two iconic Boston neighborhoods, the Back Bay and the Fenway. Stroll down Newbury street for the city’s finest shopping, or skip the crowds and opt for a promenade along the expansive Commonwealth Ave mall to smell the flowers on the Common. In the other direction is Fenway, where the ballpark is opening in March at a limited capacity, if you fancy a game. And if you’re feeling smart, the prestigious (and gorgeous) universities of Cambridge are a quick,  pretty walk across the bridge.

Price: From $195/night

Book at The Eliot

What to Eat

Like most cities, Boston’s dining and drinking establishments took a huge hit during the pandemic, with many beloved institutions hibernating or permanently closed (rest in peace, Eastern Standard). But this city is nothing if not resilient, and plenty of world-class bars and restaurants managed to thrive with innovative safety measures, heated outdoor dining, and to-go options, and there were even a few exciting post-quarantine openings.

Cafe Beatrice Sandwich

Start your day off with a breakfast sandwich and a pastry from Café Beatrice, Chef Will Gilson’s new cafe and bakery in Cambridge Crossing. The Pastry Chef, Brian Mercury, is known for creative and savory takes on sweets, and whether you’re ordering in or having it delivered, don’t sleep on the Earl Grey cookie. If you’re on the hunt for brunch, Harvest in Harvard Square offers a full spread on their heated outdoor patio (complete with a fireplace), and hot cocktails too.

Keep lunch quick and easy with a vegetarian bite from Clover Food Lab. Clover is what you’d get if you took McDonald’s efficiency and added it to high-end vegetarian cuisine–all their ingredients are meticulously sourced, and everything is made from scratch daily, but the average wait time for an order is 3.5 minutes. The local chain began as a food truck, and now has locations all across Boston and Cambridge, so you’ll be able to snag an Impossible Meatball sandwich wherever your adventure takes you. If you absolutely can’t lunch without animal protein, head to Troquet in the Leather District and snag their Boston Speed Dog, a footlong chili dog from a classic French restaurant with a recipe dating back to 1975.

There’s no better cuisine for ordering in than Chinese. Blossom Bar in Brookline offers dine-in, takeout, and delivery for their high-end Sichuan cuisine (those chili peppers on the menu mean SPICY!), and they also happen to have one of the best cocktail lists in the city, which you can also order straight to your hotel room. For more drinks on the go, check out BackBar, a nerdy Somerville speakeasy that’s been doing takeaway cocktails only with a different theme every week, from Harry Potter to Star Wars.

Bow Market

For the ultimate in COVID-friendly dining, head to Union Square’s Bow Market, where you can browse local artist and maker studios, then grab a fire pit outside and order from any of the bars and restaurants in the complex — including a natural wine bar, fresh oyster farm, a pizza joint, and two craft cocktail bars — and have dinner delivered right to your toasty table.

What to Do

Middlesex Fells Reservation

Boston’s status as a small walking city is a boon for tourism in the time of COVID. It’s an easy place to avoid crowded public transportation, and even easier if you get into the trees. Hiking usually isn’t an option 20 minutes from downtown, but the Middlesex Fells Reservation is a 2,200-acre forested reserve with well-groomed trails winding around gorgeous lakes (sorry, no swimming allowed) that’s just a short Uber from your hotel. It’s a beautiful place for a picnic or a trail run, if that’s your thing, and if you’ve got a furry friend in tow there’s an enormous off-leash dog park where you can let them run wild.

For a little bit of culture away from the crowds, take a quiet tour of the Isabella Stewart Gardner Museum. The former private collection of the eponymous owner is housed in Mrs. Gardner’s mansion, a fabulous Victorian castle right in the heart of the Fenway with creaking floors, winding passages, real suits of armor, and an incredible four-story atrium with seasonally changing garden installations. The museum is running at limited capacity during the pandemic, so as long as you book your tickets in advance you’ll have the rare opportunity to get this heavenly spot practically to yourself.

Live music might feel like a thing of the past, but The Beehive is a subterranean jazz club that pays homage to its Prohibition theme by finding a way to thrive during the ’20s. Book a spaced-out table, order a cocktail, and let the nightly live performance carry you back to a time way before COVID when jostling with strangers in a noisy bar was just another Saturday night.

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