Ah the hoodie, your go-to sweatshirt. We're beach bums for a reason. We're there day and night. If you've been searing yourself to a golden brown all day and the the sun drops, that refreshing ocean breeze becomes a severe windchill. Whether you're staying on the beach to relax around a fire or rolling out to some joint for an early dinner, having an extra layer handy is never a bad idea. The Cape's a casual place, sweatshirts are practically uniform.
Lesser known beaches/hot spots
One of my favorite beach spots is located right out of Osterville or Cotuit and easily reached by boat or kayak. Here you'll find rows of boats anchored to shore and locals drinking and playing horseshoes (most likely me). So stick your chair on the sand, your feet in the water, and grab a cold one.
(Don't confuse it for Sampson Island in Orleans which is part of the National Seashore.)
Head down Rte 28 towards Falmouth and when you've hit the end you'll find yourself in Woods Hole. It's definitely the very edge of Cape Cod. If you have a boat you can spend the days shooting around the islands and stopping to have the beaches all to yourself. Or zip over to Martha's Vineyard for a day.
"Woods Hole Houseboats"
If you look out onto Great Harbor you can see all the moorings and houseboats. When I say "houseboat" I mean floating house with no motor. I'm told that those that exist have mostly been family owned for years and no more can be built. If you happen to make friends with a local who owns one, have a great time reveling all night, jumping from the roof to the water, and watching the sun come up.
""The Spit" in Popponesset Bay"
If you're in the South Mashpee, New Seabury, or Popponesset area you can head down to this cozy little strip of land by walking or by boat. It's a little more crowded where it connects to Popponesset Beach as I'm sure people are too tired to carry on walking and instead just plop themselves down. It's amazing how quickly the time passes and you may just find that the sun is going down and you've been here for 8 hours. Pack a cooler and if possible bring a grill.