3 great days in Cape Cod
Sandcastles and sunny skies, whale watching and piled-high ice-cream scoops… Your perfect beachy weekend awaits
Your weekender guide to the best things to see and do in Cape Cod, Massachusetts. Find more travel inspiration for your next Vrbo vacation here.
An idyllic string of seaside towns, Cape Cod‘s rugged beauty has long attracted artists, writers, and anyone seeking an East Coast respite. Though each town has unique characteristics, the overall vibe is one of radiant ocean views, windswept sand dunes, and harbors festooned with colorful buoys and lobster traps.
You can watch the fishermen haul in the daily catch—plucked from the sea just hours or even minutes ago. The lobster rolls are to swoon over, and you can get your seafood from a quaint fry shack or with the razzle-dazzle of fine dining, depending on your mood.
Drive the Old King’s Highway (Route 6A) and you’ll find salty beaches peppered with firepits, lush marshlands, and the Cape’s beloved hydrangea flowers in cotton-candy pink and blue.
Fill your days with seaside strolls, small-batch ice cream, and boating—including the area’s renowned whale watch tours—but leave time for local vineyards, retro drive-in movies, and leisurely evenings of stargazing.
Cape Cod summers bring fabulous outdoor events like the Cape Cod Jazz & Arts Festival, which runs throughout July and August. Wellfleet, iconic in its own right, hosts the Wellfleet Oyster Fest each October; meanwhile, vibrant Provincetown is known for its vibrant LGBTQ+ and art community. Wherever you roam, you’ll be immersed in postcard-perfect cottages, bungalows and other vacation homes—scroll to the bottom of the page for just a few of our favorites.
Your ultimate weekend itinerary
Friday
9am: Grab a Continental-meets-Cape breakfast
Cape Cod looks like an elf boot, and today celebrates the twirly toe end—Provincetown, Truro, and Wellfleet. Start the day at South Wellfleet’s PB Boulangerie Bistro with a ham and cheese croissant.
10am: Explore Provincetown’s historic dune shacks
Follow the likes of Jackson Pollock and Jack Kerouac when you head to the dune shacks of the Peaked Hill Bars Historic District. These primitive shacks (which still lack electricity and running water) have been granted as residences for artists from the 1920s to the present day. Provincetown-based Art’s Dune Tours offers SUV experiences to explore them.
12pm: Refuel with local-legend lobster
A beloved local institution, The Lobster Pot offers waterfront dining, award-winning clam chowder, and sunny cocktails like the watermelon martini. If you buy just one bit of vacay merch, consider a T-shirt from here: The retro-chic neon lobster sign channels big-time Cape vibes.
2pm: Sip and savor at Truro Vineyards
About seven miles south of Provincetown, Truro Vineyards await year-round. There you can hunker down in an Adirondack chair and sample the rotating weekly tasting flight—five tasters for $15.
6pm: Dinner and a drive-in movie
Round out your first day with dinner at the family-run Wellfleet Bookstore & Restaurant, followed by the nostalgic goodness of the Wellfleet Drive-In Theatre. Just like the good ol’ days, guests access the movie’s sound by setting the car radio to a designated station.
Saturday
8am: Choose from beaching or bogging
Harwich, Chatham, and Orleans make up today’s Cape adventure. Start with breakfast at the locally-loved Ruggies Breakfast & Lunch in Harwich (try the signature Ruggie giant bap). Afterwards, spend the morning at Red River Beach or take a $20 Cranberry Bog Tour.
Noon: Indulge in shopping and ice cream
Close to the water, Main Street in Harwich offers an idyllic shopping experience—from antiques to quirky gifts. Stop by Dr. Gravity’s Kite Shop and make the most of the ocean breeze. Nearby, locals love Sundae School Ice Cream, while the whimsical Cape Cod Lavender Farm sells everything from fresh lavender lemonade to lavender lemon marmalade.
2pm: Make friends on a seal watch tour
Make your way to Chatham Bars Inn to indulge in James Beard-celebrated chef Andrew Chadwick’s seaside menus, which include produce from the inn’s farm. Next, make new friends—Cape Cod-style—on a Harbor Seal Boat Tour, get fudge at Chatham Candy Manor, and visit Chatham Lighthouse.
6pm: Seek a seafood dinner
Drive up the scenic coast a few miles to The Chatham Pier Fish Market to pick out some fresh-catch dinner ingredients to cook up back at your vacation rental. On Tuesdays, pick up fresh fruit and veggies at the Chatham Farmers’ Market, or head to Orleans Whole Food Store, about 15 minutes away. As you head back, snag pies and sides at the beloved Marion’s Pie Shop.
8pm: Kick back at the bar
Head to Hog Island Beer Co. in Orleans for local brew. Sip a Moon Snail Pale Ale and lap up the live music in the garden, where local and international acts perform all summer long.
Sunday
9am: Grab on-the-go gourmet
It’s the Cape; of course, you have to go on a whale watch. But first, caffeinate with some robust coffee at Barnstable’s Nirvana Coffee Company. Pair it with breakfast sandwiches, including gluten-free options.
10am: Set sail on a whale watch
Just down the road, get amped for the ultimate Cape Cod experience—the chance to see dolphins and a half-dozen species of whales, including humpbacks and orcas. Check the schedule for Hyannis Whale Watcher Cruises, which sets sail at varied times on Sunday mornings.
2pm: Refresh with a bayside low-tide stroll
After four hours on the water, it’s time for lunch at Captain Frosty’s on 6A in Dennis. Once you’ve had your fill of lobster rolls and fried platters, get your land legs back with a laid-back low-tide beach stroll from Mayflower Beach down to Corporation Beach.
7pm: Enjoy the starry, starry night
As your Cape Cod getaway winds down, stop for a waterfront dinner on Saquatucket Harbor at Harwich Port’s Brax Landing Restaurant, and then take advantage of the Cape’s night-sky magic. This area, near Red River Beach, comes highly recommended for stargazing by members of the Cape Cod Astronomical Society.
Cape Cod Vrbos for you and your people
Wonderful Vrbos for water babies
Melanie Carden is a Boston-based travel writer and former chef focusing on food, culture, and immersive adventure. Her work has appeared in Thrillist, Business Insider, Paste Magazine, The Gay & Lesbian Review, and Film Fest Magazine.
