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Several local charters, cruises, and sailing vessels have special experiences that put passengers on the water for the fleet’s arrival in Boston Harbor.

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For a front-row seat to Sail Boston 250’s Parade of Sail, you’ll need to think offshore. 

More than 60 tall ships and vessels representing over 20 countries will enter Boston Harbor on July 11 during the Parade of Sail, kicking off Sail Boston 250, a five-day waterfront celebration marking America’s 250th anniversary. 

Led by the USS Constitution, the procession will bring ships sailing from Broad Sound through the Boston Harbor channel, passing waterfront neighborhoods, parks, and piers before reaching its docking locations throughout the city. 

While spectators can catch the spectacle from shore, charter operators and cruise companies are giving visitors a chance to experience the fleet’s arrival from the water. 

Here are some of the cruises, sails, and charters available during the Parade of Sail and throughout Sail Boston 250. 

Hindu Charters

Departure: MacMillan Pier, Provincetown
Price: $318, before fees

Passengers can board the Cutter Bloodhound, an 1874 racing yacht originally built for the Marquis of Ailsa, for a seven-hour Parade of Sail excursion departing at 9 a.m. 

The trip includes a light lunch and snacks, and guests may bring their own beverages while watching the fleet enter Boston Harbor. Groups are limited to 10 or less passengers. 

More experiences 

From July 12 through July 15, guests can take two-hour tall ship sightseeing cruises aboard the Cutter Bloodhound and Schooner Hindu, the former World War II yacht that is celebrating its 80th year of chartering and 101st year of sail. Tickets start at $63.50. 

The company also has fireworks sails scheduled for July 11 and July 15 beginning at 8 p.m., with tickets starting at $296.80.

Tall Ships Boston Cruise

Departure: Cape Ann Whale Watch, 415 Main St., Gloucester
Price: $225

This full-day cruise runs from 6 a.m. to 4 p.m. and features narration by tall ships expert Tina McMahon Foley, maritime-themed entertainment from DJ Tracey Souza and TFS Music, and catered meals throughout the day. 

Guests will spend the day on the water watching the arrival of the international fleet while learning about the history and significance of the vessels participating in Sail Boston 250. 

More experiences 

Seven additional cruise options are available throughout Sail Boston.  

Ahead of the parade, passengers can join a July 10 excursion to see the ships at anchor as they prepare for the next day’s procession.

From July 12 through July 15, the company runs harbor cruises showcasing the docked fleet, with tickets ranging from $90 to $125. 

Tall Ships Boston Cruise will conclude its Sail Boston programming with a dockside fireworks-viewing cruise on July 15, priced at $125, and a departure and farewell cruise on July 16 for $150. 

Sail When and If 

Departure: Charlestown Marina
Price: $295 

Sail When and if is offering Parade of Sail excursions aboard three schooners. Tickets remain available for a voyage aboard the Schooner Harvey Gamage, which departs at 7:30 a.m. and returns at approximately 4 p.m. at Fan Pier. 

The excursion includes lunch, and guests may bring their own beverages. Reservations are available through Sunset Sail Salem. 

More experiences 

The historic schooner When and If has a full slate of trips throughout the festival.

Options include 90-minute day sails starting at $89, two-hour twilight cruises beginning at $109, and fireworks cruises on July 11 and July 15 starting at $285. Day sails and twilight cruises depart multiple times daily from July 12 through July 15. 

City Cruises 

Departure: 1 Long Wharf, Boston
Price: $149

City Cruises’ eight-hour Parade of Sail includes live narration from onboard experts, outdoor viewing decks, and indoor spaces with large windows. Concessions and a full bar will be available for purchase. The cruise departs at 7 a.m., with boarding beginning at 6:30 a.m. 

More experiences 

The company will also operate 90-minute tall ship viewing cruises throughout the festival, with tickets starting at $49. 

Additional options include fireworks-viewing cruises, and dinner cruises, and brunch cruises. 

Charles River Boat Company 

Departure: Rowes Wharf 
Price: $456.75

For an all-day experience, Charles River Boat Company will take guests into Boston Harbor from 7 a.m. to 4 p.m. during the Parade of Sail. 

The vessel will have a dedicated anchorage position, giving passengers a clear view to watch the procession from the water. Breakfast, lunch, and a snack are included. 

More experiences 

90-minute tall ship cruises depart from the Boston Children’s Museum dock multiple times daily from July 12 through July 15, with tickets starting at $50. 

The company also has fireworks cruises scheduled for July 11 and July 15, departing from Rowes Wharf. Tickets begin at $111.30. 

Classic Harbor Line 

Departure: 60 Rowes Wharf
Price: $527.88

For one of the most immersive Parade of Sail experiences available, guests aboard Schooner Adirondack III won’t simply watch the procession — they’ll become a part of it. 

The 80-foot schooner is scheduled to sail as a participating vessel in the parade. Guests depart at 7 a.m., gather with the fleet in the outer harbor before the 9 a.m. start, and return at approximately 4 p.m. Breakfast, lunch, beer, wine, and nonalcoholic beverages are included.

More experiences 

Classic Harbor Line is offering a 90-minute Sail Boston harbor cruise aboard the yacht Northern Lights, a two-deck vessel inspired by 1920s-era design. Cruises depart from Rowes Wharf, with tickets up to $65.72 per person. 

Classic Sail Boston 

Departure: Pier 4 in Seaport
Price: $2,395 

Classic Sail Boston will participate in the Parade of Sail aboard Captiva, offering an all-day private charter for up to six guests beginning at 8 a.m. on July 11 and continuing through the conclusion of the parade. 

More experiences 

Classic Sail Boston will also be offering private charters for the duration of the festival, including an extended sunset charter for the fireworks on July 15. The two-hour charters are $850, and the fireworks cruise is $2,495. 

Make it a multi-day maritime getaway 

For travelers hoping to build an entire vacation around Sail Boston 250, several tour operators are packaging harbor cruises together with Boston history attractions. 

One example is the five-day Boston tall ships tour offered by Crosswell Tours from July 10 through July 14. The package combines a tall ships harbor cruise with guided tours of Boston landmarks, including portions of the Freedom Trail, the Boston Tea Party Ships & Museum, Quincy Market, and the Charlestown Navy Yard. 

Prices start at $1,899 per person based on double occupancy.