Five-Day Cape Cod Itinerary for Family Fun

Here’s to the perfect family vacation, the one you don’t have to plan.

Day One: Classic Cape
Today, step back in time to old-fashioned summer. Dig into breakfast at the Pancake Man in South Yarmouth, where the buttermilk stacks have been locally famous since 1961, and the radio jingle has been stuck in our heads for almost as long. There’s old-fashioned, and there’s timeless: Catch the late-morning tour on Hyannis Whale Watcher to see the magnificent humpbacks of Stellwagen Bank National Marine Sanctuary. (If it rains, indulge your seafaring heart at the Cape Cod Maritime Museum, featuring a replica boat shop, ship models and scrimshaw gallery.) Either way, you’ll have a sailor’s appetite by late afternoon. Go for old-school fried clams at the Kream ’n Kone in West Dennis or the namesake chowder, boat drinks and view of Nantucket Sound at The Skipper Restaurant & Chowder House. When dusk hits, it’s worth the trip out to the 1957 Wellfleet Drive-In. Bring pajamas for the kids and settle in for the double-feature.

Day Two: Crowd-Pleasers
The best day of vacation is the one where everyone’s happy. Begin with a Brewster bun from Eat Cake 4 Breakfast Bakery in Brewster (pastry chef Danielle Nettleton trained at Le Cordon Bleu in Paris) and linger over coffee before heading out to the Cape Cod National Seashore. Forty miles of shoreline means that you may have trouble choosing among the six spectacular beaches; if it comes down to flipping a coin, Coast Guard Beach in Eastham repeatedly tops the country’s best-beaches lists, and Marconi Beach in Wellfleet is a favorite for its vast stretch of sand beneath dramatic dune cliffs. Anywhere on the Outer Cape, a proper beach outing starts with the Box Lunch (one in each town from Eastham to Provincetown), so stock up on “rollwiches” to-go for an afternoon picnic on the shore. After napping on the sand, you’re ready for action. Stop by Liam’s at Nauset Beach for fresh fried scallops and a milkshake (extra thick) before cheering on the Cape Cod Baseball League. Your home team for the night is whatever town you’re in.

Day Three: Fun & Games
You’ll need energy for this. Fuel up on early morning Eggs Benedict at the Fairway Restaurant in North Eastham. (If you’ve trekked cross-Cape for this breakfast, you won’t be the only one). Rain or shine, next up is the Cape Codder Water Park in Hyannis, where a spouting humpback and looming pirate ship are at home among water slides, rapids, waterfalls, a wave pool and kiddie play pool; day passes to the water park are available for purchase by non-hotel guests. In the afternoon, hit the giant wet and dry rides at Cape Cod Inflatable Park in West Yarmouth for wacky adventure (ride a bull, climb a sinking ship, or rock’em-sock’em on a balance beam). At least once every summer, dessert must come before dinner: gourmet cones at the Cape Cod Creamery in South Yarmouth and Hyannis. But leave room, because dinner is all-you-can-eat at the Brazilian Grill in Hyannis, with rotisserie barbeque cooked over natural wood, or the seafood platter at Cooke’s Seafood in Hyannis, batter-fried with the Haidas brothers’ treasured family recipe. Take your time; your last stop—Wackenhammer’s Clockwork Arcade—is open late. End the night with classic arcade games and a dazzling turn on the antique carousel, all on Main Street in Hyannis.

Day Four: Larger Than Life
Take it up a notch. The Original Marshland has been a Sandwich landmark for 50-something years. Grab a diner stool at the counter and debate between the hearty breakfast entrees or a just-baked cinnamon bun. From there, head to the nearby Adventure Park at Heritage Museums & Gardens to navigate zip lines and bridges through five aerial, treetop-canopy trails for a fresh perspective on Cape Cod scenic beauty. High-octane adventurers will be equally charged with Heritage's 2018 Indy 500 exhibit, featuring race cars from the world’s most iconic motorsport event. And for those who prefer to keep feet firmly planted, the two-acre Hidden Hollow on the museum grounds features a new “splash” area with a dramatic waterfall, streams, fun water learning stations, and dam-building for eager beavers. Never fear the rain; bowl in style at the new Ten Pin Eatery (opening in late April at Cape Cod Mall), or try out the two-story laser tag arena at the dining & entertainment complex. Tonight, dinner is no ordinary pizza—the artisan pies at Wicked range from shrimp alfredo to scallop BLT, with a salted caramel banana pizza for dessert. You’ve built up to a grand finale: Watch the sunset at Old Silver Beach, followed by the late show—and a toast—at the Falmouth Cinema Pub.

Day Five: Lazy Bones
Breakfast is served all day at the Hearth ’n Kettle (in Hyannis and South Yarmouth), which means you can sleep late before tucking in to the “hungry pilgrim” pancakes with a side of baked beans. Then, while away the day on any of the Mid-Cape’s bay beaches, where warm waters are suited for young swimmers and you’re never far from the day’s next meal or waffle cone. On rainy days, little ones will stay happily occupied at the Cape Cod Children’s Museum in Mashpee until the sun comes out again (it always does). Wave to the ferries over an early dinner at Spanky’s Clam Shack on Hyannis Harbor before putting your skills to the test at Pirate’s Cove Adventure Golf in South Yarmouth. The swashbuckling pirate-themed course is the stuff of kid dreams, but the cascading waterfalls, dark caves and lurking pirates serve as a warning to adults. You’ll be just as easily hooked.

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