There are a ton of great beaches all over the Cape. If you're looking to stay close to Osterville, we recommend Craigville, Kalmus, or Dowses beach (requires a beach sticker but can walk from town). Don't forget to bring a beach towel, and if you find yourself at Craigville, stop by the Barnacle for fish and chips to take to the beach. If you're venturing farther, we are big fans of the Beachcomber, Skaket, and Nauset beach.
For biking, Cape Cod Rail Trail with entry points throughout the Cape; for hiking, Great Island Trail in Wellfleet or Eagle Pond in Osterville (closer to home and Fin's favorite); for yoga, Evoke in Hyannis; for mini golf, Steve & Sue's Par-Tee Freeze & Lightning Falls Mini Golf... and when in doubt run to the water.
Breakfast: Spanky's, Aimee (pastries); Sea Street Cafe; Fig Tree. Lunch: Fancy's (market); Crisp (Joe's favorite); Four Seas lobster rolls; the Barnacle. Dinner: Tug Boats; Black Cat; Sesuit Harbor (BYOB); Dennis Oyster Company; the Pheasant.
Four seas is a must ... for both ice cream and lobster rolls on white bread; Steve & Sues for a a soft serve twist; Kandy Korner; Craigville Pie Shop (Oprah's favorite); and Fancy's for a slice of chocolate cake (Steph's favorite).
We love Osterville! There is a Farmer's Market at the historical society every Friday morning; Island Outfitters and Details And Goods for clothing; Melange & Mercantile for home goods; Hardware store for beach games and everything else you may have forgotten. Fancy's is a staple.
To many good ones to list ... you'll never go wrong with a day trip to P-Town, Chatham, or Welfleet.