This is a big week for sailing on Martha’s Vineyard.

It begins with the 87th annual Edgartown Yacht Club Regatta, which starts on Thursday and continues through Saturday.

And this weekend the Vineyard Cup, the popular annual regatta sponsored by Sail Martha’s Vineyard, gets under way in Vineyard Haven with racing on Friday, Saturday and Sunday.

Edgartown yacht club manager Bill Roman said he is expecting hundreds of sailors for the club regatta this week. There will be about 80 Optimists and 70 420s, all captained by young sailors, along with adult racing in one-design sailboats, including Herreshoffs, Shields, Rhodes 19s and Wianno Seniors.

One of the great sights in the Edgartown regatta is the Wiannos when they sail into the Edgartown harbor on Thursday afternoon. Wianno Seniors are 25-foot gaff-rigged sailboats that are classical in design and have a spirited following on Cape Cod.

Regatta racing will take place in the Edgartown outer harbor and in Cow Bay. Lighthouse Beach, Bend in the Road Beach and Memorial Wharf are all good spots for viewing the sailboats and sailboat racing.

Meanwhile, in Vineyard Haven the Vineyard Cup is expecting more than 100 sailboats to participate in this weekend’s racing out of Vineyard Haven harbor.

“We’ve got boats coming from afar, from the South Shore, Rhode Island, New York, New Jersey, and Florida,” said Brock Callen, program director for Sail Martha’s Vineyard.

There will be a number of different races over the three days, for a variety of different vessels from 70-foot sailboats to day sailers out of Menemsha Pond under the eagle eye of fleet captain Bill Glazer.

On Friday there will be races between East and West Chops in the afternoon. A good spot for viewing is Eastville Beach. Saturday is the Shoal to Shoal Race, also between the chops. And the Sunday Pursuit Race has perhaps the craziest finish on the waterfront. Using a handicap system, boats cross the starting line at different times based on their ability to handle speed. The intent is for all the boats to come to the finish line at about the same time.

This year the Vineyard Cup will include a gathering of catboats both from here and from Cape Cod. The cats will have their own short race on Saturday morning and their own awards ceremony. “There is a wonderful amount of history in catboats in and around the Island. This regatta wants to celebrate that tradition,” Mr. Callen said.

The Vineyard Cup is a significant fundraiser for Sail Martha’s Vineyard, a 19-year-old organization whose core mission is to provide free sailing instruction to Island children. This past weekend Sail MV held a benefit seafood buffet and auction. Money from boat registrations in the Vineyard Cup also helps support the cause. Cup sponsors include the Black Dog Tavern.