Flying into Boston in mid-June? Make sure you look down.

A fabled fleet of tall ships with billowing spinnakers and streaming pennants, some that logged thousands of miles from across the seven seas, converge for Sail Boston in a glorious gam.

Part of the international Rendez-Vous 2017 Tall Ships Regatta, the six-day festival from June 17th through 22nd is the closest you can get to nautical nirvana without weighing anchor and embarking for distant ports.

“It’s the greatest show on surf,” says organizer Dusty Rhodes, and she should know.

Rhodes, Executive Director of Sail Boston 2017, is a prime architect of Boston’s vibrant, maritime spectacles. With an irresistible siren call, she began attracting processions of tall ships into Boston Harbor in 1992.

Dusty Rhodes, President of Conventures, Inc., joined by Boston Mayor Martin J. Walsh and Capt. John O'Connor.

Dusty Rhodes, President of Conventures, Inc., joined by Boston Mayor Martin J. Walsh and Capt. John O'Connor.

Back then, the harbor, with its famed “dirty water,” was the city’s neglected and undervalued backyard. Today it’s more coveted than the Back Bay. High-wattage events like Sail Boston, and a heavy dose of real estate investments, have turned the harbor into the Boston’s shimmering front yard—a new nexus of vitality.

At the helm of Sail Boston, Rhodes has prodded and wooed the most regal ships to sail into Boston Harbor this summer. As President of Boston event planning and communications company Conventures, her command of the harbor provides juice to her juggling act.

“There are only a handful of ports in the world that can handle these ships,” says Rhodes of the stately armada of two-masted schooners, square riggers, barques, ketches, and cutters—50-plus ships in all—dropping anchor here.

“They come from multiple countries. Some are floating embassies,” she says.

Hence, it’s no simple feat to coordinate their convergence.

Rendez-Vous Tall Ships Regatta by Boston Sail

The Chilean ship took perseverance and persuasion. Nevertheless, she persisted.

“We had to lobby to get them to change their sailing schedule to come on a special time and date. It takes years of lobbying and political influence,” says the confident Rhodes.

It sounds a bit like staging the Olympics, but with a difference: “The Olympics is easier,” says Rhodes. “They have an organizing committee.”

Similar to a Macy’s Thanksgiving Day Parade, these magnificent ships from another age inspire a child-like awe when they emerge from the deep, sailing into town under nothing but wind power.

So when one of the most influential women in Boston suggests the best way to experience the biggest draw this summer, take her advice. (This is on your bucket list; you just don’t know it yet).

Rendez-Vous Tall Ships Regatta by Boston Sail

“You want exclusivity?” she asks. Sign up for a deck reception to land that skittish client.

“It’s like the Kentucky Derby on steroids,” says Rhodes. Hats optional.

Imagine boarding a historic schooner, as the ship’s whistle heralds your arrival. Relax on the deck and entertain like an admiral.

Instead of sipping a mint julep at Churchill Downs, you could be enjoying a dark and stormy on a tall ship in Boston Harbor.

“It's a once in a lifetime experience; you don’t find that on the 19th hole of a golf course," says Rhodes.


Most of the events are free, but you can buy tickets to the Parade of Sail grandstand on June 17th for $125 each at To book a deck party, email


*All photos courtesy of Sail Boston