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Boston Travel Guide: Where To Stay, What To Eat, and More

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 fully 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 they live). Now is the perfect time to get back to your roots with a little getaway 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)

Luckily, Boston is the perfect town to enjoy from a safe social distance. It’s 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 cobblestone 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 managed to stay 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-precaution-friendly amenities that’ll keep you feeling cozy and safe while still providing that much-needed change of scenery.

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Where to Stay

Best Location: Staypineapple Hotel

Staypineapple Hotel
Staypineapple

Living in the South End, with its brownstone-lined boulevards, vibrant art scene, and incredible food, is the stuff Bostonians dream of, 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 among 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-size 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.

  • Nearest airport: Boston Logan International Airport
  • Time: 11 minutes by car
  • Distance: 4.2 miles

Read more: Best Boston Hotels

Best Modern: Yotel

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 it 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.

  • Nearest airport: Boston Logan International Airport
  • Time: 6 minutes by car
  • Distance: 2.8 miles

Best Luxury: 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 Avenue mall to smell the flowers on the Common. In the other direction is Fenway, where the ballpark opened in April 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.

  • Nearest airport: Boston Logan International Airport
  • Time: 11 minutes by car
  • Distance: 8.2 miles

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.

Café Beatrice

Cafe Beatrice Sandwich
Instagram/@cafebeatricecx

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.

  • Best for Breakfast
  • $$

Browse the Menu at Cafe Beatrice

Harvest

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.

  • Best for Brunch, Lunch, and Dinner
  • $$$

Browse the Menu at Harvest

Clover Food Lab

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.

  • Best for Lunch and Dinner
  • $

Browse the Menu at Clover Food Lab

Troquet

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.

  • Best for Lunch and Dinner
  • $$$$

Browse the Menu at Troquet

Blossom Bar in Brookline

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.

  • Best for Dinner
  • $$

Browse the Menu at Blossom Bar Brookline

BackBar

For more drinks on the go, check out BackBar, a nerdy Somerville speakeasy that’s been doing takeaway cocktails with a different theme every week, from Harry Potter to Star Wars.

  • Best for Dinner
  • $$

Browse the Menu at Backbar

Union Square’s Bow Market

Bow Market
Flickr/Leslee

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, a fresh oyster farm, a pizza joint, and two craft cocktail bars — and have dinner delivered right to your toasty table.

  • Best for Dinner
  • $

Browse the Menu at Bow Market

What to Do

Middlesex Fells Reservation

Middlesex Fells Reservation
Flickr/kernsandcairns

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 ride 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.

Isabella Stewart Gardner Museum

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.

The Beehive

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.

How to Save Money on Your Trip to Boston

Experiences

Known as one of America’s most historic cities, Boston has lots more to offer than you think. Whether you’re in for some history and park adventures or simply trying out impressive dishes, the Boston experience is worth it. However, we all know that it takes careful planning to enjoy a great escapade. To take some off the hassle and help keep you on your budget, Airbnb.com has a variety of options when it comes to rental and hotel accommodations depending on your desired location, all at different price points.

Hotels

While Boston may feel like a small town, it is still a cosmopolitan city and is considered a hotbed for skyscraper stunners. From luxury hotels to rental houses, you will not find yourself in shortage of accommodation offers. If you are still on the lookout for the best place for you to stay in when you visit Boston, Hotel Tonight, Airbnb.com, and Kayak.com are the websites worth checking. They provide you with a wide range of options at a reasonable price.

Vehicle Rentals

Being rich with United States colonial history, Boston offers a lot of places to visit, from contemporary museums to parks to restaurants. So before you visit, make sure to rent a car so you can conveniently explore Beantown. Kayak.com is a great website to look for vehicle rentals in Boston as they have huge options that won’t have you breaking the bank.

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