31 Reasons to Have a Staycation in Boston


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If you’re planning on doing a staycation in good ole’ Bean Town, you should take advantage of the things that you don’t normally do (or the things that you perhaps don’t have time to do.) Branch away from the tourists milling around Newbury Street and Boston Commons, and experience a side of the city you’ve never seen.



1. If you’re free on Sunday, devote some time to browsing the SoWa Outdoor Marketplace in the South End. The shopping mecca sets up camp in a parking lot, filling it with some of the coolest items that you simply won’t find in your run-of-the-mill store. Besides being packed with unique sellers, the parameters of the market are lined with food trucks—a big selling point for many who pay a visit!

2. Enjoy the Esplanade. When was the last time you took a stroll or bike ride along this beautiful path? Bring a picnic, your dog, a book and enjoy the Charles River right at your feet. If you’re feeling really energetic, walk across one of the bridges (the Massachusetts Avenue Bridge is always a fun walk!) and take a wander on the Cambridge side, the views of Boson will knock your (red) socks off!

3. Since you’re on the waterfront anyway, why not rent a kayak and row down the Charles River? For a two-person kayak it’ll cost you $20 an hour or $80 for the day if you’re planning on staying out on the water for a while. You’ll get in your exercise, your Vitamin D and see Boston from a whole new perspective!

4. Plan a lovely day on the Boston Harbor Islands that are situated in the beautiful harbor. For only $15, a quick ferry ride will take you to the islands where you can go on walking trails and explore, fish, swim or just relax. Getting out of the city, while still seeing it in the distance may be all you need!

5. Whether you’re a beer drinker or not, go to Harpoon Brewery. The surroundings are great. The people are great. The beer is more than great. If you’re not too savvy with beers, the staff will be more than happy to teach you a thing or two and let you try some different beers until you find one that’s the perfect fit for your palate. Go enjoy a cold brew and many laughs.

6. Do you live in Boston and never go to Fenway Park? If you have that extra time during your staycation, take yourself out to the ball game! The Green Monster will suck you in and spit you out with a whole new Bostonian pride!

7. If you’re looking for something at night to do but don’t want to go to the same bars or clubs that you normally go to—try going to see a band perform at a local venue like Paradise Rock Club or Brighton Music Hall. Feast on some food first in Allston and do as the college kids do and grab a pitcher of beer at one of the Boston University-based pubs.

8. If you want to explore the other side of the river, head into Cambridge and Somerville! In the mood for a biking adventure, hit the Minuteman Bike Path. The 11-mile ride will be a perfect activity and you definitely will not feel like you’re still in your city.

9. Explore the Cambridge Antique Market. The multiple level indoor market will occupy you for hours! Each floor is densely packed with vintage and secondhand furniture, jewelry, clothes, home decor, prints and bikes—you definitely will not be leaving empty handed.

10. Don’t leave Cambridge just yet, go into the different neighborhoods such as Davis Square. This quaint town located near the Tufts campus will make you feel like you stepped onto the set of Gilmore Girls. The best kept secret of this area is the Somerville movie theater. All movies are only $6 before 6 PM and you can buy beer or wine in the lobby for $5 (plus there’s ice cream!) This spot is truly a gem.

11. Stop by Dave’s Fresh Pasta after the movie to pick up some fresh Italian ingredients to bring home and cook dinner. Fresh pasta, meats, cheeses, veggies, breads, sauces and wine. Perfect culinary treat!

12. Take a Willy Wonka-esque tour. You can go on the Taza Chocolate Factory tour where you’ll fill up on amazing chocolate samples. If you take a more mature route, trek over to the Bully Boy Distillers for a tour where you can sip on rum, whiskey and vodka. Pick your poison!

13. Go to the Arnold Arboretum of Harvard University and connect with nature. Have some quiet time without the crowds that you’d come across if you were at the Public Gardens or the Commons.

14. Stop by the museums or the New England Aquarium! Sure, you’ve probably been to a lot of these, but they’re always so crowded on the weekends. If you’re having a staycation on a weekday, make sure you hit up a museum and enjoy the exhibits without herds of people surrounding each painting or stopping to take selfies with statues.

15. If you’re craving a history lesson, skip the Freedom Trail and head on over to Bunker Hill. Make it a whole thing! Take the water taxi ($3 for a ride), explore Charlestown and visit the USS Constitution. You won’t regret it, it may feel like you’re on a class field trip!

Photo: www.nytimes.com

Photo: www.nytimes.com

16. Boston’s Restaurant Week is August 17-22 and 24-29. Hundreds of restaurants participate, so now is your chance to try out one of those expensive spots! It’s easy to stick to your favorites, but take the opportunity to try something new.

17. September seems like it’s far away, but it’ll come faster than we expect! Mark your calendar with the Boston Local Food Festival on September 14th. You’ll meet local farmers and try their produce, eat food from local restaurants and try countless samples of the tastiest treats like earl grey caramels and garlicky pickle spears!

18. Since you’re on “vacation”, take advantage of Boston’s countless Dollar Oyster Happy Hours. Marliave is a great spot for this, although my personal favorite is Rialto in the Charles Hotel in Harvard Square. It’s only offered on Monday nights starting at 5:30 at the bar, but you won’t regret budgeting some time for this. The champagne mignonette given with these oysters will leave you craving more. (Oh, you will definitely order more!)

19. You may have been to The Butcher Shop in South End for dinner, and you probably loved it. Barbara Lynch’s restaurants are always a hit and this tiny establishment isn’t an exception. Come for lunch and enjoy a light meal of gourmet hot dogs. Swing by The Beehive after for a cocktail at the bar while enjoying some live music before continuing on your way.

20. If you want to treat yourself to a great dinner, go to Grotto and feast upon the fonduta appetizer for starters. What is this exactly? Well its fontina cheese fondue that comes with portobello mushrooms and beef tenderloin tips to dip right on it (oh and don’t forget the sides of aged balsamic and truffle oil for additional flavoring.) As if that isn’t enough to have you out the door and on your way right now, the main course of gnocchi and braised short ribs still has my mouth watering.

21. If you’re in the mood for a great outdoors brunch, but not on the city streets, go to Sam’s at Louis in the Seaport neighborhood. You can sit outside on their deck right over the Harbor. The food is great, but you probably won’t even pay attention to that because of the amazing location. Afterwards you can explore the growing Seaport district and uncover some hidden gems of your own!

22. Make your way out to Coolidge Corner. The quaint area packs a lots of personality and the breakfast/brunch menu is available all day at Zaftigs. Trust me when I say, the cheddar biscuit egg benedict dish is worth the ride on the T’s Green Line.

23. If you’ve lived in Boston for a while, you probably know of most of the restaurants in the city. But when you’re on vacation you shouldn’t be eating in the same places—try something new, perhaps on the other side of the river like Flatbread Company and Sacco’s Bowl Haven (they’re together) in Somerville’s Davis Square. This place is a guaranteed perfect date night or night out with your friends! Amazing pizza, craft beers and candlepin bowling. Flatbread Company is also great because they foster relationships with local farmers, local producers and the community in general.

24. Try out Alden Harlow, a fairly new restaurant in Harvard Square. The food is to die for and the cocktails are as tasty as they come. If a dish titled “House Made Squid Ink Bigoli” (consisting of snails, pork belly, breadcrumbs, green garlic pesto) or the “Chili and Honey Glazed Octopus” with pistachio, spring onion, chick peas and pickled lamb intrigues you- then this is the place for you. The cocktails are just as uniquely crafted—the Terremoto is Mezcal based with celery-thyme shrub, green Chartreuse and lime. Yum.

25. You’ve most likely seen East Coast Grill on a variety of food TV shows, but have never gone because it’s out of the way? Well, stop making excuses and head over! If you go for Saturday lunch or Sunday Brunch, you can have a “make your own” Bloody Mary to go along perfectly will your raw bar binge. Afterwards you can walk up the block to Lord Hobo, a bar with an extensive beer list.

26. The amazingly tasty Union Square Donuts are relatively new, but crazy popular. The maple bacon donut was love at first sight (there are actual pieces of bacon on top of these!) These monster sized donuts are flavored to perfection and are definitely a guilty pleasure of a snack!

27. If you have been thinking that JP Licks is the premiere ice cream in Boston, then you’re terribly mistaken. You MUST go to Toscanini’s in Central Square or venture over to Christina’s in Inman Square (I recommend it after a leisurely dinner at East Coast Grill and drinks at Lord Hobo.) The flavors of these ice creams will blow your mind, and they’re all made on site in their own creamery. Sweet treats like coco pudding and rose tea biscuit are things that one can’t simply forget about after tasting.



28. Wake up bright and early, pack some snacks and water, lace up your sneakers and make your way on over to the Blue Hills. Hike up these mountains and get a phenomenal Boston skyline view from the top. The walk will refresh you, I promise!

29. Go to Plum Island. This tiny beach located in Newburyport will make you feel like you’re on a high-end vacation. The number of cars allowed here is very limited so you have to make sure you get there early. Down the road from the main beach is a smaller area (with even less parking) that you quite possibly will never want to leave. Sand bars, clear water, starfish and a dense forest backdrop—unusual for this part of Massachusetts, but that you’ll happily find here.

30. Head over to Concord and question life. Visit Walden Pond and have a Thoreau moment.

31. Visit Louisa May Alcott’s Orchard house and imagine yourself part of the Little Women with pesky Amy as your sister. Challenge yourself not to use your smartphone or tablet while you’re here (only to take a few pictures) and experience these places as they’re meant to be experienced!

What about you? What are you favorite staycation spots in Boston?


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