Lookout Rooftop and Bar
If you want to experience a panoramic skyline and beautiful views of the Boston Harbor, Lookout Rooftop and Bar is a must. The restaurant is located at the Envoy Hotel, so although it offers a relaxed atmosphere for brunch and lunch, it also serves as a premier nightlife destination. With glowing fire pits and intimate seating arrangements that include igloos in the winter, this sleek rooftop bar offers a unique dining experience.
The Union Oyster House
Dating back to 1826, the Union Oyster House, located on the Freedom Trail, prides itself on being the oldest restaurant in America. A Boston fixture and National Historic Landmark, the building in which it is housed was built before the American Revolution, and the stalls and oyster bar are still in their original positions. With only three owners during its existence, the Union Oyster House carries on its rich traditions in dining and service, having won multiple awards over the years.
Citrus and Salt
Citrus and Salt is a coastal Mexican-inspired restaurant and tequila bar with a vibrant atmosphere. It's known and beloved for its modern decor and Instagrammable food and drink presentations. With a trendy setting and funky Day of the Dead theme, it shouldn't be missed. Food choices range from the popular fried chicken and waffle tacos to pulled pork carnitas crunchy tacos, and there's a variety of tequila options.
The trendy name hints at the unusual ambiance when you enter CLINK. This contemporary restaurant is inside the Liberty Hotel at the former Charles Street Jail site. You'll have a unique dining experience surrounded by prison bars and jail decor. The menu is an artful fusion of American traditions, global influences, and modern innovation, and you'll find only the freshest North Atlantic seafood and seasonal New England fare.
For casual pub fare combined with a remarkable history, check out Warren Tavern. Built in 1780 as one of the first buildings erected after the famous 1775 Battle of Bunker Hill, it's the oldest tavern in Massachusetts and one of the oldest in America. Frequented by some of the founding fathers, including George Washington and Paul Revere, a distinct colonial charm makes it a favorite with locals and visitors alike.
If you're looking for a French-Italian hybrid menu in a luxurious, upscale setting, Menton delivers. Ingredients are carefully sourced for a seasonal menu of inspired classics. You'll also find craft cocktails and a stellar wine list with rare vintages from lesser-known vineyards. The modern space has been curated to create an elegant yet whimsical ambiance.
The restaurant has received multiple accolades since opening in 2010 and is Boston's only Relais & Châteaux, with Chef Barbara Lynch being the country's only female to hold the title of Grand Chef Relais & Châteaux.
When you're in the mood for Polynesian-inspired food, Tiki Rock is one of Boston's favorite tiki bars. While menu options include rice bowls, poke bowls, and a raw bar, this establishment is known for its many cocktail options and vibrant atmosphere. It's upbeat and high energy, with loud music and bright strip lights contributing to a defining modern twist on the traditional 1930s tiki bar vibe. Tiki Rock boasts a large bar area, lounge seating, regular indoor dining, and patio seating.
Lolita Cocina and Tequila Bar
Another upscale Mexican restaurant that shouldn't be missed is Lolita Cocina and Tequila Bar. The inside is dimly lit and has dramatic gothic-style decor, and the ambiance offers an elevated dining experience that expertly balances restaurant, bar, and nightlife. The mouthwatering dishes and cocktails on the menu provide a modern, unexpected, and sophisticated take on Mexican favorites while giving a subtle nod to Boston's local cuisine. Lolita's is also known for its unique private dining spaces that allow you to host private events and receptions of all sizes.
Paying homage to the illicit establishments that served alcohol during the prohibition era, modern speakeasies are designed with the hidden bar in mind. Located in the Leather District, Offsuit Speakeasy is considered one of Boston's best-hidden speakeasies and is tucked in an alley behind a door. You can't just walk in, though. You'll have to call the number on the door for admission! However, there's no password, no dress code, and no boring drinks served here. You know it's a great vibe with drinks called Put a Ring On It, Hired Gun, Conspiracy Theory, and Burden of Proof.
Burro Bar, located in South End, brings Boston residents and visitors a bottomless brunch where you can eat as many of its delectable entrees as you want for an hour and a half. From French toast to huevos rancheros, the dishes are fun and familiar, bringing creativity to the forefront and showcasing ingredients and local produce. With over 100 tequila bottles, the Burro-tested and approved drink menu offers many options. Bottomless brunch is excellent for a weekend date, girls' day out, or any other occasion.
When you're in the mood for good food and world-class music, The Beehive delivers. Located in The Boston Center for the Arts complex, The Beehive features a variety of music genres, including blues, country, cabaret, burlesque, and electronica. Still, it has been named one of the Top 100 Jazz Clubs in the world. According to popular publications, including The New York Times, Zagat, and Travel & Leisure, it's a must-see venue.
This classy venue has funky and eclectic decor and upscale yet rustic comfort food. The menu draws influences from the Middle East, America, and Eastern Europe, with exotic cocktails, diverse wines, and tasty beers. Perfect for a special date night or a casual meal with friends, The Beehive can also accommodate private parties and large group gatherings.
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*Header photo courtesy of Lookout Rooftop - The Envoy, Boston