Linda Laban

The first meet-up with a potential love interest is always exciting. There are already plenty of questions—what to wear, what to say, what to feel—so we’re here to help you answer at least one inquiry: where to go. From relaxed menus to conversation-ready atmospheres, these places take the stress out of the first date and allow all the relationship potential to shine (or not). If you don’t want to commit to more than a short time together just yet, grab a drink at one of the best bars in Boston or these top-notch cocktail bars. RECOMMENDED: Full guide to the best things to do in Boston

From Cuba to the Middle East, smoking tobacco is historically a culturally strong social activity. In western society, cigar lounges and hookah bars are now prolific, with nightclubs garnering inspiration from these respective regions to adopt social smoking customs. From shisha (also spelt sheesha and called hookah) to cigar lounges, here are Boston’s top places to join in the fun—just keep in mind that most of which are exclusively 21+. For other casual nightlife outings, check out Boston's best college bars or Boston's best beer bars. Looking for something more refined? The best cocktail bars in Boston will do the trick. RECOMMENDED: See the full list of the best bars in Boston

With so many brainiacs in the region, it’s no surprise the national brand Stump! Trivia was launched just outside Boston. Several bars around town host Stump!, Geeks Who Drink and other trivia nights so you can work the ol' brain while knocking back a few. Sure, it's fun to catch a show at one of Boston’s best live music venues or laugh it up at one of the best comedy clubs Boston, but check out a trivia night and you’ll be part of the action. You might win a prize or even learn a fun new fact or two. RECOMMENDED: See the full list of the best Boston bars

It’s not surprising that the Boston area has so many museums: it offers so much history simply because it was among the earliest Colonial settlements. From there, due to a wealthy merchant class, it became a hotspot during the Industrial Revolution of the 1800s and, in turn, wealth created work for many craftspeople. Also, because of its learned status as the Athens of America, it also produced great thinkers and artists. So, there is much to preserve for posterity and, thankfully, wonderful niche museums present art and artifacts, mostly with a hyper-local focus. Once you’ve visited the best museums in Boston, check these places out. If viewing art is more your thing, check out the best art galleries and other places to see art in Boston. RECOMMENDED: Full guide to the best things to do in Boston

In addition to the best comedy clubs in Boston, the Hub’s underground and alternative comedy spots have something for everyone who wants to laugh. Check out an open mic night, catch illusionists who don't take themselves too seriously, or see a comedy whodunit that is recognized in the Guinness Book of Records as being the longest running play in the USA, ever. To complete an evening of fun, add in dinner at one of the best restaurants in Boston, late night drinks in the city’s best dive bars, or a visit to the city’s buzziest culinary hub, Time Out Market Boston. RECOMMENDED: Full guide to the best things to do in Boston

Named after a British king, and dubbed the Queen of American Lakes, this narrow, glimmering stretch of water runs 32 miles long from Lake George Village at its southern tip to Ticonderoga on the north shore. In the west, it is overlooked by mighty Prospect Mountain, in the foothills of the beautiful Adirondacks. Glacier-formed Lake George gained popularity as a summer vacation spot in the 1950s, and its landscape makes it a good spot to pair forest bathing with beach bathing. Done something on this list and loved it? Share it with the hashtag #TimeOutDoList and tag @TimeOutEverywhere. Find out more about how Time Out selects the very best things to do all over the world.

Food trucks are often a testing ground for new chefs, leading to brick-and-mortar locations (Clover, now a local empire, started as a mere food truck). Or they’re just a convenient way to offer fast, delicious fare to the people. Either way, Boston has a number of fab food trucks offering everything from tacos to dumplings. Many trucks set up near ideal picnic spots like Copley Square or the Rose Kennedy Greenway. Consult the official City of Boston food truck page for who’s parked where. And, of course, check a food truck’s website or social media accounts for schedule changes. If no trucks are around and you're looking for something inexpensive and tasty, you can always seek out the best pizza in Boston or the best burgers in Boston. RECOMMENDED: Full guide to the best restaurants in Boston

Escape rooms offer a portal out of our everyday lives and into the one of strategy, puzzles and make believe. While some escape rooms might have facilities for youngsters, themes and challenges are usually adult-oriented. An escape room brings the fantasy world of online gaming into three dimensions, while adding old-time puzzle game elements and immersive, interactive theater. Still, if a relaxing drink is more in order head to one of Boston’s best bars, or try some non-participatory drama in one of its best theaters. And if a day-long escape is required, head out on one of these best day trips. RECOMMENDED: Full guide to the best things to do in Boston

Off Cape Cod’s southwestern edge, Martha’s Vineyard is about 20 miles wide and 10 miles tall. It’s divided into up-island to the west, and down-island, the more densely populated eastern side. The Vineyard is also split into wet and dry towns, and the latter do not allow alcohol sales. Armed with these facts, plan accordingly. Naturally blessed with beautiful beaches and comprising mostly conservation land, the island is famously known as the setting for the 1970s movie ‘Jaws’, and for its wealthy and creative residents. This island of quaint towns and winding country lanes is where wild turkeys – and artists – roam free. Done something on this list and loved it? Share it with the hashtag #TimeOutDoList and tag @TimeOutEverywhere. Find out more about how Time Out selects the very best things to do all over the world.

Over the last decade or two, the Boston area has become flush with farmers markets, each a colorful display of locally grown fruits and vegetables. (You may encounter tempting small-batch dairy and baked goods as well.) Environmentally and nutritionally sound, market shopping is so good you wish it were year round—and some markets are! If you don’t feel like cooking your farmers market haul but want to keep it fresh and light, check out the best restaurants for vegans in Boston, the best restaurants for vegetarians in Boston, or the best seafood restaurants in Boston.  RECOMMENDED: Full guide to the best restaurants in Boston

The Boston area offers many options for moviegoers, including modern multiplexes, black box-type minis, and lavish old theaters. While most people want entertainment and flock to the blockbusters, some seek art and enlightenment at places like the Brattle or the Harvard Film Archive. Some want comfort that luxury cinemas provide, with fancy treats and massive recliner seating that mimics the coziness of home viewing. Of course, regular cinema nights are as important to locals as visiting one of the best live music venues in Boston. Why not start or end the evening’s entertainment in one of the best dive bars in Boston. Or, if dinner and a movie is your go-to, check out one of the most romantic restaurants in Boston. RECOMMENDED: Full guide to the best things to do in Boston

The suburbs aren’t so bad when the hotels are this glamorous. Hotel Indigo gives you a four-star experience at a more manageable price owing to its slightly out-of-the-way location. The boutique hotel includes an award-winning restaurant, top-flight gym and glamorous pool scene (oh, those cabanas). The rooms are modern and bright, with extra-plush bedding, and are also pet-friendly. Most Boston attractions are a 12-mile drive away, but hotel parking is free, and there’s also an MBTA stop a few minute’s walk away if you prefer to go the public transit route—it’s about a 40-minute ride into town. The hotel’s restaurant, BOKX 109 American Prime, overlooks the pool and is open for breakfast, lunch and dinner.

At the courtyard entrance of the Revere Hotel Boston Common’s restaurant and bar, Rebel’s Guild, a large, threatening-looking cannon is aimed squarely at the door. It’s a humorous touch and one that fits the Revolutionary War-themed décor. The restaurant and bar’s name honors the Sons of Liberty’s many members who were craftsmen, and their historic deeds are depicted in fetching wall-to-wall custom murals. The menu includes Boston classics like baked beans and delicious brown bread made with molasses, and Northeast delicacies like bluefish paté. The large bar is adjacent to a seasonal patio overlooking busy Stuart and Charles Sts. Rebel’s Guild is open for breakfast, lunch, dinner, and an all-day bar menu.

Situated on the lower level of the Hotel Indigo Boston - Newton Riverside, BOKX 109 American Prime overlooks a large pool patio flanked by tall trees and a view belying a suburban location right by I-95. This classic American steakhouse-styled restaurant is lined with toffee-colored banquettes and booths. Along with steaks, sauces, and sides to create your own plate, there’s New England clam chowder, crab cakes, and other seafood standards. The bar serves a casual menu and there’s convenient, free self-parking.

Situated in the Theater District, a short stroll from the Public Garden, the hotel’s revolutionary namesake is etched throughout this 356-room boutique property; there’s no missing the almost-life-size steampunk metal sculpture of Paul Revere and his horse in the large, comfy lobby lounge. The spacious, whimsically-furnished guest rooms have sliding doors that open onto a Juliet balcony. Along with a fitness center, there’s a small sixth floor pool adjacent to the extensive Rooftop@Revere lounge, which is a local hotspot during the warmer months. The restaurant, Rebel’s Guild, is open for breakfast, lunch, dinner, and an all-day bar menu.

Enjoy craft cocktails named for United States presidents, such as a John Adams (Ketel One Citrus, Triple Sec, lemon juice, honey, and pink peppercorns), or a James Madison (Pama Pomegranate, Triple Eight Blueberry Vodka, Champagne); local beers and domestic wines; and nouveau American cooking at this Coolidge Corner casual restaurant, whose name honors Founding Father Alexander Hamilton.

The younger, sister venue to Harvard Square’s Hong Kong restaurant, which opened in 1954, is less of a restaurant and more of a bar and club, boasting brightly colored, immensely drinkable Scorpion Bowls to get you in the mood for a big night out.

This dedicated karaoke venue in the Theater District has a main stage with larger public sessions, three nights a week, and private rooms that can fit up to 40 people available every night by prior reservation. As Limelight is available for private events, call ahead to make sure the Mainstage is open. Limelight serves beer, sake, and wine, and has a bar menu.

This casual bar and restaurant, just off Davis Square on Holland Street, has parking in the lot across the street, and offers burger of the week specials, along with sports viewing on the TVs. So, arrive early for dinner, catch up on the game, and then air your lungs out during the weekly Sunday night karaoke sing-along.

This afternoon tea comes with one of the best views anywhere: Rowes Wharf Sea Grille is set on the harbor, overlooking the water. Bid city traffic and concerns adieu, while nibbling tartlets, canapés, and petit sandwiches like goat cheese with beet and micro basil on whole wheat bread, or a mini smoked ham and Swiss croque monsieur. Pastries include scones, cocoa nib teacakes, and fresh fruit tarts, plus mousses, meringues, and macarons. The tea selection is extensive: robust Big Ben English Breakfast, Blue of London Earl Grey, stimulating Sencha Ariake, and delicate Bai Mu Dan. For the connoisseur there are limited edition selections too. Add tea cocktails like the Green Tea Sparkler, which pairs green tea with peach liqueur, peach purée, and prosecco. Or simply add a glass of sparkling rosé.

This pretty outdoor rink—the surrounding trees are strung with fairy lights—is located in Kendall Square’s North Plaza, off Athenaeum Street, and is open December through March, weather permitting. There is a concession with skate rentals; lessons are available, and the rink is available for private events—check ahead before venturing out. Locker rental and skate sharpening are available for a fee. There is a snack bar, but all your favorite Kendall Square eateries are nearby for a post skate warm-up.

This indoor rink—owned by the Department of Conservation and Recreation (DCR)—is a North End staple. It is open seasonally, November through March, and offers water views. There is on-site skate rental and a snack bar serving the usual contenders to keep skaters fuelled. As it is a community hockey arena, check ahead to make sure it isn’t booked for a game or private event. While skating is free, there is a $5 charge for skate rentals.

This community art space is tucked into a tiny storefront on South Street, but the gallery is packed with powerful imagery and artworks from local artists who might not normally be exhibited in larger, downtown spaces. The shape of the place lends itself to casual browsing—the small space is equally accessible to the curious passerby as to the more serious art fan.

Notoriously, Jane Birkin romped naked as a teenager in Michelangelo Antonioni’s film, Blow-Up; married Bond film composer John Barry; cooed erotically with her former lover, the late, undoubtably great French pop provocateur Serge Gainsbourg on “Je t’aime… moi non plus”; and, yes, she inspired the Hermès Birkin bag. There’s more, of course, but these days she’s renewing her musical relationship with Gainsbourg. Joined by the Wordless Music Orchestra and guest Rufus Wainwright, Birkin performs at Carnegie Hall Thursday, February 1. The show is part of a world tour for her recent album, Birkin/Gainsbourg: Le Symphonique, which retunes Gainsbourg’s songs as orchestral pieces, exquisitely arranged by Emmy Award–winning composer Nobuyuki Nakajima, who will also be accompanying on piano at Carnegie Hall. Speaking from her home in Paris, Birkin asserts that Le Symphonique is about Serge. Mais non, we assert, it’s about Birkin et Gainsbourg. Le Symphonique’s arrangements are beautiful. How are the songs different in this format?People hear the words more, because of the way Nobuyuki orchestrated them—he lets me fly above the orchestra. It’s wonderful to rediscover the words Serge wrote. When I first sang them, I don’t remember realizing the beauty of the words. It was so stressful having to interpret words that were about me; they were about him and me. Fifty years later, it is as if I am interpreting songs about [overall] romance and life. It’s not about me anymore. The most famous