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, South Boston and the Seaport are 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. 

Local 149

A neighborhood favorite for burgers, tacos, cocktails, and beer on P Street.  Local 149 is just a short walk from Castle Island.

Seapoint

This family owned and operated restaurant is located overlooking Carson Beach and features steak tips, pizza, burger, cocktails beer and more!

The Broadway

Perfect for brunch, lunch, dinner, or a round of drinks with friends.

Roza Lyons

This neighborhood favorite features a shared plates menu and craft beer program.

Park City

Southie’s favorite outdoor venue serving up food, drinks and live music

Castle Island Brewing

This 9,000-square-foot space features 20+ draft lines, a spacious outdoor patio, and an in-house kitchen partnered with Bardo’s Bar Pizza.

Shy Bird

This fun and casual spot is open for brunch, lunch, and dinner, and features a menu with sandwiches and salads, plus rotisserie chicken, smash burgers, fun cocktails, and more.

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.