Whidbey Island’s long maritime history will be celebrated during the first-ever Whidbey SailFest May 16-23.

One of Washington state’s famous replica tall ships, the Hawaiian Chieftain, joins two of Coupeville’s resident wooden sailing vessels, Suva and Cutty Sark, for week-long activities, including dockside tours, maritime music and kids’ activities.

“We wanted to try and build something more exciting for the community than, ‘oh, there’s a boat here,” said Caitlin Stanton, development officer with Grays Harbor Historical Seaport.

Hawaiian Chieftain, owned by Washington-based nonprofit Grays Harbor Historical Seaport, sails the waters of the Pacific each year along with its companion vessel, Lady Washington, offering educational programs, deck tours and sailing trips. Stanton works remotely from Greenbank and wants to create a greater awareness of Penn Cove’s maritime historical significance.

The first Whidbey SailFest is a week-long celebration of the cove and Whidbey Island’s nautical history and the maritime significance of Coupeville and its wharf, built in 1905.

Numerous groups joined together to bring a celebration of ships, sea captains and nautical history to Whidbey Island, said Stanton. The Coupeville Chamber of Commerce is covering the moorage charge at the wharf for the week and the organizations that own the vessels are each covering their own expenses, she said.

Vern Olsen, director of the nautically-themed singing group Shifty Sailors, was involved in planning the event. He and the other members decided to help cover the costs for the crews and operation of the boats by holding a benefit concert as part of the festival.

“There’s a lot of expenses they had, so we thought, ‘Hey, let’s just make this work,’” Olsen said.

The Shifty Sailors, joined by shanty duo Pint & Dale, will perform maritime music 7 to 9 p.m. Saturday May 19 at the Coupeville Rec Hall; tickets are $15. The evening will also include raffles for a package for a night in local lodging, a meal at a local restaurant and sailing on one of the vessels. Raffle tickets are $1. All proceeds will go to benefit the organizations that operate the vessels.

Since Whidbey Island played a significant role during the first European voyages of Pacific Northwest waters, it’s fitting the island launch its own maritime cultural event, Stanton said.

In 1792, Britain’s Captain George Vancouver sailed the HMS Discovery and its tender Chatham into a spectacular bay that became known as Admiralty Inlet. Discovery’s master, Joseph Whidbey, became the first to circumnavigate the island that would later bear his name.

Local historians Lynn Hyde and Capt. John Stone will lead two ticketed tours aboard the Hawaiian Chieftain 6 to 8 p.m. Friday, May 18 and 6 to 8 p.m. Wednesday, May 23. They’ll share tales of Penn Cove, Whidbey Island and the Salish Sea. Hyde is with Historic Whidbey and Stone is captain of Cutty Sark.

Cutty Sark, a 50-foot classic ketch, and Schooner Suva, built in 1925, both call Coupeville home port each summer. Suva is owned by the Coupeville Maritime Heritage Foundation and handled with an all-volunteer trained crew.

Ticketed group sails on the Chieftain, Suva and Cutty Sark are scheduled 2 to 4 p.m. both Saturday and Sunday. Stanton said anyone with a sailboat is invited to join their ships on the water over the weekend.

“We’re trying to put as many white sails in Penn Cove as we can,” she said.

Free dockside vessel tours of all three tall ships will be offered 10 a.m. to 1 p.m. both Saturday and Sunday. On Saturday, booths on Coupeville Wharf will offer family activities, such as knot tying and pennant making.

The Hawaiian Chieftain and Suva can also be chartered for private events. Suva also offers regular weekend sails.

“I think a lot of people live their lives without ever spending any significant time on the water,” said Stanton, a mariner herself. “There’s this whole new world you can explore on the water, and all you have to do is get on a boat … And I think something every person should have access to is their local waterway.”

Ticket for Whidbey SailFest tours and maritime concert are at www.whidbeysailfest.com

Hawaiian Chieftain will be in Coupeville May 16-23.