Planning to spend the day checking out the Tall Ships? Whether you’re strolling along the waterfront, hopping aboard a harbor cruise, or just soaking up the maritime vibes, you’ll probably work up an appetite. Luckily, Boston is packed with great spots for a bite to eat or a celebratory cocktail. Here are some places to add to your Sail Boston itinerary:

Sullivan’s Castle Island

Since Castle Island is THE spot to watch the Parade of Sail, Sully’s is THE Place to grab some casual and fast lunch or dinner! Featuring hot dogs, lobster rolls, burgers, fries, and ice cream, you can check out the full menu here. 

ReelHouse East Boston

Grab a seat on the waterfront patio and enjoy seafood, cocktails, and some of the best skyline views in Boston.  Learn more here. 

The Tall Ship

Part floating bar, part summer destination. Enjoy drinks, food vendors, lawn games, and front-row views of the harbor aboard a historic vessel.  Get all the details here. 

Piers Park

Perfect for a walk, picnic, or firework watching. This waterfront park offers beautiful gardens, open green space, and unbeatable views of the city skyline.

Cunard Tavern

Located just steps from the waterfront, this neighborhood favorite serves elevated comfort food, craft cocktails, and a welcoming atmosphere.  Check out the menu here. 

Angela’s Cafe

A short walk from the Harborwalk, Angela’s is known for authentic Puebla-style Mexican cuisine and is worth adding to your Eastie itinerary.

Row 34

A Fort Point staple known for oysters, lobster rolls, and fresh seafood.

Woods Hill Pier 4

Waterfront dining with stunning harbor views and locally sourced dishes.

Cisco Brewers Seaport

A must-visit for beer, cocktails, food trucks, and outdoor summer vibes.  Learn more about Cisco Brewers Seaport here. 

Nautilus Pier 4

Seafood, steaks, and cocktails in a lively destination featuring patio seating and a weekend raw bar.

Barking Crab

A Boston classic for seafood and waterfront dining with front-row harbor views.

Whether you’re grabbing a quick bite between ship tours or settling in for sunset cocktails, these Southie and Seaport spots offer plenty of ways to make a day at Sail Boston even better.