Rooftop Hopping in Boston.

There's nothing like a good view and a drink in your hand, and summertime is the perfect time to patio hop for outdoor drinks. While some are lucky enough to have their own patio to drink a bottle of wine on, the rest of us have to pay to do it. Luckily there are a lot of great spots to sip a drink outdoors in Boston. Here are some of my favorites by area:

Seaport:

Envoy Rooftop - My personal favorite, and they expanded the rooftop, meaning more room and less of a wait to get up!

Legal Harborside - Pro tip: Go here when there's a concert at the Blue Banks Pavillion and you can enjoy music and an outdoor drink are the same time.

Waterfront/North End:

Tia's - Watering hole for 20 somethings and finance bros at night, great spot for drinks and a view by day.

The Landing - This entirely outdoor bar is a great spot to grab a drink after work or before dinner in the summer.

Ristorante Fiore - Italian food and a roof deck - what more could you want?

Back Bay/South End (this section is the longest as it's my go to area after work):

Precinct - Slightly hidden in the lower level, this spot is a prime location for after work drinks in the Copley area.

Earl's - I find myself here far too often, mostly for the rotating $5 drink of the month.

Banyan Bar + Refuge - Located in the heart of the South End, the string lights make this a prime nighttime patio spot (they have an amazing fried chicken sandwich too).

Buttermilk & Bourbon - Patio furniture perfect for lounging on, and another great spot for food and fried chicken (can you tell I have an obsession?)

Barcelona South End - Great tapas and a large patio, they also have a great patio in Brookline as well.

Charles River Bistro - Enjoy a drink with a view of the Charles River on Wednesdays and Sundays during the summer.

Cambridge & Somerville:

ArtBar - With an amazing view of the Boston skyline and a smores dessert you won't be able to stop eating, this spot pairs well with a glass of wine.

Bow Market - This new marketspace comes equipped with food vendors, and Remnant Brewing, which has a great patio to enjoy some bites and beers in the sun.

Daedalus - A slightly shaded roof in Harvard, this spot is perfect for an afternoon cocktail.

Felipe's Taqueria - This less expensive and more authentic version of Chipotle also has a rooftop perfect for sipping margs and Corona's on all night long.

These are just a small handful of ones I have been to, but new one's seem to pop up every day! Luckily Boston Magazine has compiled a list of 52 here, summer beer gardens here, new patios here, outdoor dining here.

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Boston Winter Date Guide.

One of the questions I get asked a lot is, where should I go for a date that’s not drinks? Whether you’re single, dating or in a serious relationship, I think a lot of us get stuck in the rut of usual spots and struggle to explore more. Especially during the winter, planning a ‘fun’ date can feel too tedious to do knowing that you’ll have to brace the cold to get to the date. While this is a date guide, it can be perfect for anyone looking for things to do in the winter in Boston. Here are a few date ideas ideal for winter in Boston.

For the foodie:

• Test out your partner’s chef skills. The city is filled with cooking classes covering everything from basics to fermenting your own food. Check out Mei Mei dumplings, Milk Street Cooking School, Cambridge Education Center, and Eataly for upcoming classes.

• Eat you way through Eataly - you could have a three course menu without ever sitting down at one of the restaurants. They also frequently have events themed around certain foods and regions of Italy.

• If you prefer something sweet, Taza Chocolate has a great tour, but if you like your chocolate with a twist, check out Cocktails & Cannolis.

• Bow Market in Somerville is a great spot with a brewery, plenty of food options, and lots of shops to stroll around.

For the adventurer:

• If you want to do something more active than eat on your date, test your support abilities by rock climbing at Brooklyn Boulders or Central Rock.

• If you really want to test the sanity of your date, try axe throwing.

• If you prefer the blades on your feet, try ice skating on the Frog Pond.

• Test your dates knowledge at an Escape Room, Boda Borg, or one of the many trivia nights in the city through Geeks Who Drink or Sporcle.

• Old school video game fans can check out A4cade in Cambridge or Versus downtown.

• With new spots like Spin, PKL, and Puttshack there are plenty of places to release your inner child.

• Catch a Celtics or Bruins game at the Garden. Better yet, get wicked cheap tickets last minute on StubHub or AceTicket.

For those who don’t want to nix drinks completely:

• Dating is hard, wine helps. While you could go to a trendy bar for a drink, there are plenty of other ways to imbibe in the city. There are a slew of breweries I featured on my rainy day post, but tours and tastings for the other boozes can be found at City Winery and Bully Boy Distillery.

• Check with your local wine store as well for tastings - I have Urban Grape right across the street from me and they host more than I can manage to attend.

• If you want a trendy drink you can only get in the winter, head to the rooftop at the Envoy and drink in an igloo while looking over the city.

For the people who want to see a show:

• I think it’s easy to forget after living in Boston for so long how many great theaters and performers there are in the city. For comedy there is the Improv Asylum, Improv Boston, a show called Dirty Disney at Laugh Boston, and the long running Shear Madness.

• Don’t forget we also have a theater district with plays, ballets and more running on a daily basis.

• Finally between the Garden, House of Blues, and many more, there’s always a concert to see in Boston.

If you still want more ideas, check out my rainy day guide for bowling locations, karaoke tips, museums and more.

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