Boston, a city full of history, culture, and culinary delights, offers a diverse array of dining experiences. But when it comes to elevating your dining experience—literally—there’s nothing quite like enjoying a meal or a drink at one of the city’s rooftop bars and restaurants. With stunning views of the skyline, waterfront, and historic landmarks, these elevated venues provide the perfect setting for savoring delicious food and drinks while soaking in the vibrant atmosphere.
1. Legal Harborside Rooftop: Situated in the Seaport District, Legal Harborside Rooftop offers panoramic views of Boston Harbor and the city skyline. Whether you’re indulging in fresh seafood or enjoying handcrafted cocktails, this rooftop oasis provides a sophisticated yet relaxed atmosphere. With both indoor and outdoor seating options, it’s the ideal spot for a romantic dinner or a casual gathering with friends.
2. Lookout Rooftop and Bar: Perched atop the Envoy Hotel in the Seaport District, Lookout Rooftop and Bar boasts breathtaking views of Boston’s skyline and waterfront. Featuring a stylish design and a diverse menu of small plates and craft cocktails, this rooftop destination exudes modern elegance. Whether you’re lounging by the fire pits or mingling with fellow patrons, you’ll find yourself captivated by the beauty of the city below.
3. The Envoy’s Outlook Kitchen and Bar: Another gem located within the Envoy Hotel, Outlook Kitchen and Bar offers a unique dining experience with its open-air terrace overlooking the Boston skyline. Combining locally sourced ingredients with innovative culinary techniques, the menu features an array of seasonal dishes that celebrate New England’s rich culinary heritage. Whether you’re dining al fresco or enjoying the cozy ambiance indoors, this rooftop restaurant promises a memorable culinary journey.
4. Rooftop@Revere: Nestled in the heart of Boston’s historic Back Bay neighborhood, Rooftop@Revere offers sweeping views of the city skyline and the Charles River. With its vibrant atmosphere and eclectic menu featuring small plates and creative cocktails, this rooftop hotspot is the perfect destination for both daytime relaxation and evening revelry. Whether you’re soaking up the sun on the expansive terrace or taking in the city lights from the cozy lounge area, Rooftop@Revere offers an unforgettable rooftop experience.
5. Pier 6: Located on the historic Charlestown Navy Yard waterfront, Pier 6 offers stunning views of the Boston skyline and the harbor. With its spacious outdoor patio and nautical-inspired decor, this waterfront restaurant provides a picturesque setting for enjoying fresh seafood and handcrafted cocktails. Whether you’re dining on the outdoor deck or lounging in one of the cozy seating areas, Pier 6 offers a relaxed yet refined dining experience with unparalleled views of the city’s skyline.
From chic rooftop lounges to waterfront restaurants, Boston’s outdoor rooftop bars and restaurants offer a diverse range of dining experiences against the backdrop of the city’s iconic skyline. Whether you’re seeking a romantic dinner for two or a lively gathering with friends, these elevated venues provide the perfect setting for savoring delicious food and drinks while taking in breathtaking views. So, the next time you’re looking to elevate your dining experience in Boston, be sure to head to one of these rooftop destinations for an unforgettable culinary journey above the city streets.
Rooftop Dining Tips for Travelers
If you’re staying in Boston temporarily—whether for business, relocation, or medical treatment—here are a few tips to enhance your rooftop dining experience:
- Make reservations early, especially on weekends.
- Bring a light jacket; Boston rooftop venues can get breezy after sundown.
- Plan transportation around peak hours or walk from your Compass apartment for a scenic stroll.
- Check seasonal menus, as many rooftop spots rotate offerings in spring and summer.
All of these rooftop destinations are located near Compass Furnished Apartments properties in Back Bay, Seaport, and Charlestown. Browse locations
More Things To Do in Boston Near Your Stay
Make the most of your visit by pairing rooftop dining with these local experiences—all walkable from Compass’s Boston apartments:
- Catch a show at the Boston Opera House or a game at Fenway Park
- Explore Boston Common or stroll the Rose Kennedy Greenway
- Visit museums like the ICA or Museum of Fine Arts
- Shop and snack along Newbury Street
Looking for an apartment near top attractions? Check out our Boston furnished housing options.
FAQs: Dining and Staying in Boston
What are the best months for rooftop dining in Boston?
Late May through early October is ideal for outdoor dining, with June and September offering the best balance of weather and availability.
Are rooftop bars family-friendly?
Many are, especially during the day. Legal Harborside and Pier 6 both welcome families with casual menus and relaxed atmospheres.
Can I walk to rooftop bars from Compass apartments?
Yes! Compass’s Seaport and Back Bay apartments are within 10–15 minutes walking distance from several rooftop venues, making it easy to explore the city on foot.
Real Guest Perspective
“After long shifts at Boston Medical, winding down with a cocktail on the Lookout Rooftop was just what I needed. Having my Compass apartment so close by made it feel like I had my own piece of the city.”
— Jessica L., traveling nurse and Compass guest
Why Choose Compass When Exploring Boston
Whether you’re here for a quick visit or a longer stay, Compass Furnished Apartments makes city living seamless. Unlike hotels or short-term rentals, Compass offers:
- Fully furnished units with kitchens, Wi-Fi, laundry, and 24/7 support
- Flexible leasing options from weeks to months
- Prime locations near Boston’s top rooftop bars, hospitals, and transit
- Compassionate service built for travelers in transition
Ready to experience Boston from above—and feel at home below? Explore Compass Boston apartments.
About The Author
Brianna Correia
Hey, guys! It’s Brianna, the Senior Marketing Specialist at Compass. Find me here on LinkedIn and we’ll connect!