Weather 
Boston wears its history proudly all year round, but this summer it will be sailing into new territory.
For six days this July, timed to coincide with the America 250 semiquincentennial celebrations, Sail Boston — known to locals as “the Tall Ships”— will transform Boston Harbor into a floating spectacle of towering masts, billowing sails and maritime tradition.
More than 60 vessels from around the world converge on the city in the largest gathering of tall ships since 2017. Best of all? It’s totally free.
It all kicks off with the “Parade of Sail” on Saturday, July 11, when participating vessels will assemble in Broad Sound before making their dramatic morning entry into Boston Harbor.
Once docked along the city’s waterfront, the ships will remain open for public visitation through July 15, with sailing demonstrations, workshops and direct interaction with crews and naval cadets.
This year’s entourage includes naval vessels representing nations including Argentina, Colombia, Germany, India, Italy, Romania and more.
City officials expect the celebration to draw millions of visitors to the waterfront over the course of the week, when any and all spectators are invited to board the ships and interact with the crew. Beyond the spectacle, organizers said the event is designed to foster cultural exchange.
“At the end of the day, these ships are navy ships and private ships, but it’s all about goodwill,” said David Choate, COO of Conventures, the company that produces Sail Boston. “The navy ships in particular are sovereign soil of those countries — they’re essentially floating embassies.”
At a time when gas tops $5 a gallon, international flights are reaching record prices, and buzzy events like the FIFA World Cup draw ire for their steep price tags, a trip to one of America’s most walkable cities to see the Tall Ships might be the most economically sound way to step on Italian soil this summer.
For those planning a trip, Boston’s hotels, restaurants and waterfront venues are leaning into the moment, turning Sail Boston into a citywide celebration. Here’s where and how to experience it.
The best hotels
For a waterfront viewpoint, the best option is the Envoy in the Seaport. Many of the rooms in this all-glass building offer stellar views, as do both the ground-floor restaurant’s patio and the rooftop bar.
While not on Boston Harbor, the Liberty Hotel over in Beacon Hill is offering a “Sail Away Stay” package that includes an overnight stay for two, Champagne toast upon arrival and a voucher for the hotel’s acclaimed Clink bar, redeemable for one dozen Wellfleet oysters paired with a bottle of Decoy Brut.
The best bars
If the sun is shining, you’ll want to be outside for the party. East Boston has the unique advantage of offering views across the water onto the downtown core. A tall ship-turned-oyster bar will be the center of the action.
Over in Seaport, check out ReelHouse for an indoor-outdoor experience. From an authentic townie vibe, head over to Pier 6 in Charlestown’s Navy Yard.
The best restaurants
There are many restaurants near the waterfront in Boston, but the ones with the best Harbor views for a brunch on Parade of Sail Saturday are: 1928 Rowes Wharf for a fun scene; Rowes Wharf Sea Grille for an elegant perch inside the Boston Harbor Hotel; and Mida in East Boston.
Or, over in the Seaport, plate up at Davio’s, the dining room at Woods Hill Pier 4, or Legal Sea Foods Harborside. If leaving the crowds behind is more your speed, then on July 16, drive 20 minutes into nearby Lexington for an elegant dinner at the Inn at Hastings Park, which will offer a French-themed tasting menu with Champagne Billecart-Salmon pairings.
The best cruise
Classic Harbor Line Boston offers a variety of sailing and cruise experiences during Sail Boston, including both sunset and brunch cruises, but the most in-demand ticket will be aboard its Adirondack II and Adirondack III schooners, which will embark in the official Parade of Sail flotilla on July 11.
