Ever taken a walk on the beach and just wanted to keep going? A walk all the way around the Island is on my list of things to do; I’ve just never quite gotten around to doing it. But after talking to some people who have, let’s just say I’ve put a question mark next to that goal.

Donna Diaz of West Tisbury and her friends made the trek last year. There were six of them in all: Donna, Debbie Brewer, and Mary Edwards from Edgartown, Terry Pothier and Kathy Spiro from Oak Bluffs, and Carol Mayrand from Aquinnah.

These ladies, all in their fifties, set out from Oak Bluffs in October and did the walk in segments. It took six days – three in a row one week and three in a row the next. Mary and Kathy each missed one of the legs so technically they didn’t walk the entire Island.

The trip covered sixty-three miles and took nearly forty hours. As Debbie explains, “You have to have a plan. You have to know where you’re going to end up each day so someone can pick you up.”

The first day they went from Oak Bluffs to South Beach in Edgartown (they detoured around the Edgartown waterfront). Day two: South Beach to Lucy Vincent Beach in Chilmark. Day three: Lucy Vincent to Menemsha. Day four: Menemsha to Putnam Road (off North Road) in Chilmark. Day five: Putnam Road to Lambert’s Cove in West Tisbury. And – finally – day six: Lambert’s Cove to Oak Bluffs and champagne on Kathy Spiro’s front porch.

Probably the best time to make the trip is the fall when the sun is not as intense, the weather is more predictable, and there’s less chance of interacting with protective property owners. And regardless of the season, you should check the tides, especially before tackling Gay Head.

“The worst day,” Donna remembers, “was the third day when we tried to get around the cliffs at Gay Head. The tide was pretty high and there was a surf advisory. We almost made it around but were unsure what it was like on the other side of the cliffs so rather than get stranded, we backtracked and ended up walking around the cliffs and down to Lobsterville Beach. That was a very long day.”

They finished that segment of their walk in Menemsha and started the next morning on the other side of the channel. Otherwise they would have had to get a boat ride across; the current there is too strong to swim.

Depending upon the season there are several spots where streams or channels can pose a problem. Donna and her friends were lucky; the cuts at both Tisbury and Edgartown great ponds were not open to the ocean so they didn’t have to swim. When they got to the opening at Lake Tashmoo they flagged down a boat to take them across. They also had to make a little detour around the channel at Harthaven. If you’re making the trip, it would be wise to bring a plastic bag for your belongings in case you have to do some swimming.

They were also fortunate that no property owners threw them off the beach. One spot that has been the undoing for many a walker is the Kennedy property in Aquinnah, where there’s generally a caretaker on duty to rebuff trespassers.

Three friends, Simon Hickman and Lanny McDowell of West Tisbury and Robert Macy, who has since moved off-Island, made the trek in the eighties. They negotiated a deal with the Kennedy caretaker: He would let them pass so long as they walked the length of the property in the water. (Others have not been so fortunate.) Those three men would go on to make the trip in an impressive two and a half days – including Chappaquiddick. For the most part they walked through the night and slept some on the beach in the daytime but as Lanny recalls, “It was more like a forced march.”

Most everyone who has made the circuit will tell you it’s physically very demanding, especially on the north side of the Island where you spend a lot of time walking on rocks. Don’t try it barefoot – you’re asking for cuts, swollen feet, or worse. But even with sneakers or in Debbie Brewer’s case, Crocs, it’s still challenging. Carol Mayrand ended up losing a couple of toenails and Donna is still nursing a bad hip. Since the beach slopes down to the ocean, you’re always walking at a little bit of an angle and that can throw your body’s alignment off after a few days. But when I ask Donna if she has any regrets, she says absolutely not – it was one of the greatest experiences of her life.

“I grew up here,” Donna explains, “but now I appreciate the Island more than I ever could imagine. Plus I did a lot of bonding with my friends; it’s something I’ll remember forever.”

Debbie agrees. “I’ve been living here for about twenty years but never really saw the north side of the Island – it’s beautiful. We even found two bottles with messages in them. One was a Corona bottle and the message just said, ‘For forgiveness to love freely.’ We have some wonderful memories.”

Okay, so I’ll put that in the plus column. But good Lord – losing your toenails?