Wianno Club: Wianno

I grew up in South Dennis — not too far from here — but I belonged to the salt-of-the-earth class of the Cape, not the Vineyard Vines, pink-shorts-wearing, Waspy world just across town. Fast-forward about two and a half decades. A dear friend of mine spends part of every summer here — usually four to ten days, depending on how life’s going. Her family are members & she is as well they summered here for years when she was a kid, and she’s kept the tradition alive. I arrived a day or two after she’d settled in, armed with nothing but a suitcase, too many tattoos, and an open mind. Trusted by preppies, dressed by chaos, I tried to inhale the waspy salt air and blend in. The property itself is stunning — especially in early August. It’s one of those perfectly picturesque places where time seems to stand still, and everyone else seems to have old money and a yacht named Tradition. Most of the guests have been coming here for generations; they’re the sort who would’ve been seated first class on the Titanic — pearls, posture, and probably a lifeboat waiting. One of the first things I learned upon arrival was that, in the dining area or any common room, I needed to cover all visible tattoos. It was August. Everything I packed was short-sleeved. And yes — I am, shall we say, decoratively inclined. So off I went to Mashpee Commons, where I purchased some Vineyard Vines gear and fully committed to cosplaying as the preppiest version of myself imaginable. Once properly disguised, I had an incredible time. The rooms were simple yet elegant — exactly what a beach club should be. The beach itself was lovely, though I’m more of a bayside guy. Still, they raked and cleaned the seaweed daily, which felt wonderfully excessive in the best possible way. The food was consistently fantastic, and the staff — truly world-class. We even had a full moon one night, glowing perfectly over the water. It was unexpectedly romantic, a little spiritual, and entirely unforgettable. For a week, I got to pretend to be a WASP — and honestly, it suited me far better than it should have.

This passed as a beach side club, geared more to tennis and golf. Some beach facilities but not developed to it's full potential. Nor are decors/infrastructures up to par for a beach front club for the 2020's and Internet age. Management should perhaps look to peers/reciprocal clubs for their experience how to modernize a 100-200 years old club. I do like the polite staff and their efforts to help reciprocal members like me, however.

Beautiful venue, but I definitely got the stare down from the staff, which doesn’t feel great as a person of colour.

Very nice country club in Osterville, on the ocean. Classic older main building with dining options and a nice bar. Rooms themselves for staying over night are outdated and could be refreshed. Tennis courts are in good shape and evidently the golf course is very nice. Not really geared to non members and functions, as most clubs like this are...

This place is beautiful. The food was very good and the views were amazing. We really had a good time here and would love to come back.