Where to Eat, Drink, and More During Sail Boston: Southie + Seaport Edition

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.
Mr. H
Headed to Sail Boston? Stop by Mr. H for bento boxes and to-go cocktails one day only, July 11th, 12pm-4pm!
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! Seapoint is located at 367 East 8th.
Committee
Committee’s Sail Boston Harbor Lounge: Make Committee’s waterfront patio your home base for Sail Boston from July 11th through July 16th, featuring front-row harbor views, Mediterranean-inspired bites, and specialty summer cocktails. On Saturday, July 11th, Executive Chef Sebastian Zuluaga will host a special outdoor seafood experience from 3 p.m. to 8 p.m., serving freshly shucked oysters, crudo, and shrimp cocktail during the Parade of Sail.
The Broadway
Perfect for brunch, lunch, dinner, or a round of drinks with friends. Check out the menu here.
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. Get the detail here.
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. Learn more here.
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. Check out the menu here.
ReelHouse Oyster Bar
From front-row harbor views to cold drinks, great food, and all-day waterfront fun, Reel House Oyster Bar Seaport is the place to be along the Parade of Sail route.🥂
Barking Crab
A Boston classic for seafood and waterfront dining with front-row harbor views.
Seaport Boston Sail Boston Pop-Ups
The Tall Ships are in town, and there is so much to discover in Seaport while they are here. Stop by Seaport Common on Saturday, July 11 for exclusive moments where businesses are popping up.
9am-12:30pm
Ballers – Bringing the energy of the court to the waterfront with games, gear, and fun.
Blu Dot – Showcasing modern design and stylish surprises for every space.
Bond Vets – Bringing treats, toys, totes, and tail-wagging perks to keep Boston’s four-legged sailors happy.
Equinox – Inspiring guests to elevate their wellness journey, one day pass at a time.
Helly Hansen – Outfitting waterfront adventures with performance gear inspired by life on the water.
Maple + Ash – Delivering bold flavors, elevated hospitality, and a preview of what’s inside.
Mai – Serving vibrant flavors, refreshing sips, and a taste of celebration by the harbor.
MiniLuxe – Delivering a little self-care and a lot of polished perfection. Pop by for some press on nails, cuticle treatments, and more with feel-good essentials.
12pm-4pm
Bond Vet – Bringing treats, toys, totes, and tail-wagging perks to keep Boston’s four-legged sailors happy. Putting guests in the driver’s seat with high-speed fun and winning perks.
FI Arcade – Putting guests in the driver’s seat with high-speed fun and winning perks.
Kings – Bringing playful energy to the parade with fun giveaways and entertainment vibes.
LL Bean – Bringing outdoor adventure, classic New England spirit, and a little friendly competition.
Mini Luxe – Delivering a little self-care and a lot of polished perfection. Pop by for some press-on nails, cuticle treatments, and more with feel-good essentials.
Rhone – Bringing performance-driven style and premium swag for life on the move.
Sev Lader – Helping guests glow beyond the parade with scrunchies and eye masks for clients that sign up for an appointment.
Tuscan Kitchen – Sharing a taste of Italian hospitality with delicious appetizer samples and menu offers.
Get all the details here.
ICA Tall Ships Experience
All aboard! Experience the Tall Ships Parade of Sail from the ICA, one of the most sought-after viewing locations on Boston Harbor! Check out the ICA’s lineup of special events on July 11:
🖼️ Admission to the galleries will be FREE all day! Visit the John Hancock Founders Gallery for an unbeatable view of the Boston Harbor and the Parade of Sail.
🥂 The ICA Wine + Coffee Bar will transform into a waterfront lounge just steps from the ships from 9 AM–4 PM. Enjoy a day of coastal-inspired cuisine complemented by an all-day premium open bar!
🎆 Watch fireworks sparkle over the Tall Ships during an elegant evening reception from 7–10 PM. Sip from a premium open bar and enjoy the magic of the harbor, surrounded by unforgettable views and festivities.
Reserve your spot here.
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.

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.


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