Description

Boston Tall Ships - July 13th through July 15th, 2026

Celebrate America’s 250th anniversary with a once-in-a-generation coastal cruise aboard the WEJACK.

Depart from Gloucester and spend 6 unforgettable hours cruising the North Shore coastline toward Boston, taking in sweeping ocean views, rocky Cape Ann shoreline, beaches, islands, coastal homes, lighthouses, and the dramatic approach into Boston Harbor. Once there, guests will have the rare opportunity to see the Tall Ships from the water, a spectacular way to experience this historic celebration.

Tickets are $250 per person. A minimum of 10 passengers is required for this trip to run. Route and timing may vary based on weather, sea conditions, and harbor traffic. Book online at www.capeanncruises.com/calendar

Prefer a private charter? Contact us at www.capeanncruises.com/contact or call us at 978-515-0484

See below for a list of trip highlights!

Islands & Sights En Route

Along the way, guests may see Cape Ann, Ten Pound Island, Salem Sound, Bakers Island, the Misery Islands, Graves Light, Marblehead’s offshore islands, Nahant, and the Boston Harbor Islands, including the Brewsters, Lovells Island, Georges Island, Long Island, Deer Island, and the Boston skyline as we approach the Tall Ships viewing area.

North Shore Coastline, Massachusetts

Departing from Gloucester, this trip cruises south along the scenic North Shore coastline. Guests may enjoy views of Cape Ann, rocky shoreline, beaches, islands, coastal homes, lighthouses, and the open-water approach toward Boston Harbor.

Boston Harbor Tall Ships, Boston, Massachusetts

Experience the excitement of Sail Boston and the Tall Ships from aboard the WeJack. Guests can expect views of towering masts, classic rigging, historic sailing vessels, international ships, naval vessels, crew activity, harbor traffic, and the Boston skyline in the background. Seeing the Tall Ships from the water offers a dramatic front-row perspective that cannot be matched from shore.

Boston Harbor & Skyline

As we approach Boston, guests can take in views of the harbor islands, working waterfront, historic harbor, and city skyline. It is a one-of-a-kind way to experience Boston’s maritime history during the United States' 250th anniversary.

Gloucester Fishermen's Wives Memorial, Gloucester, Massachusetts

This statute depicts a woman and child looking out to sea, waiting for their family member to return from fishing.

Fishermen's Memorial Monument, Gloucester, Massachusetts

An Iconic statue with a fisherman and a ship's wheel looking out to sea, and is also the Gorton's Fish Logo.  The names of those lost at sea fishing from Gloucester are carved into the memorial stones surrounding this statue and include the crew members from the Andrea Gail from the Perfect Storm, depicted by George Clooney in the Hollywood Blockbuster movie "The Perfect Storm."

Stage Fort Park and Beach, Gloucester, Massachusetts

We pass the Rocky outcroppings of Stage Fort Park where a Cannon is mounted.  This location was once in defense of Gloucester Harbor and Half Moon Beach looks cozy and where one would imagine pirate treasure being hidden.

Niles Beach, Gloucester, Massachusetts

We pass by Niles Beach as part of our tour.  You can actually see Boston from Niles Beach on the distant Horizon.

Ten Pound Lighthouse, Gloucester, Massachusetts

Ten Pound Island and Lighthouse is a former US Coast Guard Seaplane base for chasing down Rumrunners during prohibition.  The island marks the boundary between Gloucester Inner and Gloucester Outer Harbor. The tour passes by it on more than one occasion.

Eastern Point Lighthouse, Gloucester, Massachusetts

Eastern Point Lighthouse is marking the entrance to Gloucester Harbor.  We typically visit the lighthouse just inside the protection of the breakwater, which makes for a stunning photo opportunity.

Hammond Castle Museum, Gloucester, Massachusetts

A stunning view of Hammond Castle from the Harbor during this boat tour.  Its towers rise above the rocky shoreline and inspire the imagination.  This is just a scenic view of the castle and we do not unload. You'll want your camera ready for this view!

What to Bring

Comfortable Shoes, Sunglasses. Sunscreen, Hat. We recommend bringing an extra layer of clothing and a wind block layer.  The temperature tends to be cooler on the water, especially around sunset.

What’s Onboard

We have beverages and snacks for purchase and a toilet (aka head) on board.