Piana 25th Anniversary Party

Pick up something sweet at Candy Manor, then stroll back into Kate Gould Park to enjoy your treat in the shade. A Piana family tradition with the kids.

One of our favorite haunts for a mid-afternoon break from shopping. Head to the Bar (not the Dining Room) and grab a drink, a bowl of clam chowder, or steamers.

A wonderful eclectic gift shop across the street from the hotel. Always fun things inside.

The clothing brand is synonymous with Martha's Vineyard and Cape Cod. The Piana family has no shortage of Black Dog apparel — now you can add to your collection too.

The iconic and beautiful Chatham Bars Inn is a 14-minute walk from our hotel. They have a beautiful outdoor terrace facing the bay, perfect for a fancy lunch or afternoon cocktails. A special note: Jayne's grandmother Clara once worked in the restaurant there.

Further up the road from the Chatham Bars Inn is the Fish Pier, a great place in the afternoon to watch the fishing boats come in and unload their catch (and likely spot a few opportunistic seals). There's also a Fish Market, offering New England staples for a bite to eat.

New to Chatham, Diana's is a family-owned restaurant with delicious offerings. Located just past the Orpheum theater near the rotary.

Breakfast and lunch at the Chatham Municipal Airport — a fun, only-on-the-Cape kind of spot. Watch small planes come and go while you eat.

One of our favorite spots for bagels and coffee in Orleans. A great reason to head up Route 28 in the morning.

A quaint little diner serving the breakfast classics. The first time we had blueberry muffins warmed on the grill — you won't forget it. Come hungry, come with cash.

A Piana family staple and an amazing menu for seafood lovers. We have a feeling the family will be heading here Tuesday for lunch — you're all welcome to join!

A great stop for a bite or a drink before walking over to Veteran's Field to catch a Chatham Anglers Cape League baseball game. A perfect Cape Cod afternoon.

The Orleans version of the Squire — the bar is covered in license plates and old store signs. Great for lunch, a bowl of steamers, or just a cold drink on a warm afternoon.

A Cape Cod classic. There's a convenient location in Chatham, but our favorite is up in Orleans on Route 6A — worth the drive.

One of our favorites in Harwich Port. Fair warning: even the small is as big as your face.

Another Orleans favorite — a reliable stop when you're up that way.

The Cape is great white shark territory, and this center does fascinating work dispelling myths and educating the public. Fun fact: Jaws (1975) was filmed on nearby Martha's Vineyard.

Home of the world's only authenticated pirate treasure pulled from the ocean floor, right here on Cape Cod.

A family favorite — see the aquariums (including a rare pale blue lobster!), plus birding and hiking trails. Close to our Brewster house, so consider combining this with Monday's clambake.

Explore the history of maritime radio communication on the Cape.

Located just below an active Coast Guard lighthouse, this beach offers a beautiful view of the Atlantic. Not ideal for swimming, but a great place to spot seals at low tide.

A large, gorgeous expanse of beach on the Atlantic Ocean. Bigger waves, colder temps, and occasional seal and shark sightings — a very popular spot we love coming to. We plan on visiting after the Monday clambake, but if you'd like to go sooner, just know parking is $35 before 4:30pm.

North of Chatham on the bay side, Skaket offers beautiful sunsets and shallow waters at low tide that you can walk out a mile from shore. A favorite of young families for the warmer water and shallow depths — we still love wading out and looking for sea life.

The Cape is great white shark territory, and this center does fascinating work dispelling myths and educating the public. Fun fact: Jaws (1975) was filmed on nearby Martha's Vineyard.

A beautiful museum preserving the history and culture of Chatham.

A family favorite — see the aquariums (including a rare pale blue lobster!), plus birding and hiking trails. Close to our Brewster house, so consider combining this with Monday's clambake.

Explore the history of maritime radio communication on the Cape.

For those who want to make a day trip to the very tip of the Outer Cape. Climb the tallest all-granite tower in the U.S. at 252 feet for stunning views of Cape Cod Bay.

Close to our Brewster house — great patio, great drinks, and oysters. If you're driving into Chatham Sunday and want to take the scenic route, this is the stop.

You'll spot their Handline Kölsch on tap at restaurants all over the Cape — but come to the source for the full lineup.

Near the canal in Sandwich — a perfect stop coming or going from the Cape. On weekends they serve delicious pizza and some of the best lobster rolls we've ever had.