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#5 Lolita’s (253 Summer Street, Boston)
This is the second Lolitas, as the original one is located in the Back Bay. The new Fort Point location is a home run. The inside of the restaurant is always packed with hip Bostonians, but they recently added an outdoor patio that makes this a great choice for those looking to eat and drink outdoors. The gentle breeze coming off the water paired with a mojito or a cold Corona Light hits the spot. A perfect spot for a date or meet up with friends for drinks. They are known for their Mexican food and tequila, so I suggest you swing by and check it out!
#4 Fiore (250 Hanover Street, North End)
Fiore is located right in the middle of the North End, surrounded by dozens of other Italian restaurants. To stay in business selling Italian food in this neighborhood, you really need to have good food. While many people know about Fiore, not many people are aware it has an awesome roof deck bar and patio area. The bar menu has some great options if you are looking to get some light Italian food while enjoying a pretty cool view.
#3 Reelhouse (6 New Street, East Boston)
The number one reason to go to East Boston these days is to check out ReelHouse. While the neighborhood is starting to change, with more development of luxury condos on the water, it’s still “in progress” and has some rough areas. You will not find a better view of the City’s skyline than from ReelHouse. The outdoor patio is gorgeous, with tons of space and a fun bar scene. It’s even better if you jump on the water taxi to get there so you can soak in the harbor views on your ride over. Added bonus, you can get a complimentary boat ride from Pier 6 across to ReelHouse (same owners) and catch two great bars on the same day.
#2 Coppersmith (40 W. 3rd Street, South Boston)
A little off the beaten path in Southie this place is a real gem. While the indoors is great for watching a Patriot’s game or having dinner, they have really stepped up their patio game. The restaurant offers both a porch where you can play corn hole toss or other games, but also has a cool rooftop deck with a fire pit and bar. Plus it offers some great people watching as it gets a very attractive crowd.
#1 Pier 6 (1 8th Street, Charlestown)
The best of the best. Pier 6 is the perfect place to grab a drink while overlooking the Boston Harbor. Filled with both Charlestown locals and other trendsetters, it always has a fun crowd. The weekend crowd is the best. You can arrive and depart by boat, and sit by the bar or in the lounge area to catch some rays. It is not as packed as some of the other Seaport patio bars, so you know that you can saddle up to the bar and get a drink and some food from the best bartenders in the city. An added bonus, there is a 99% chance I will be at the bar when you arrive!