Growing up on Cape Cod, I’ve spent countless summers exploring the best local businesses and walking barefoot along the most beautiful beaches. The timeless, charming New England towns are often overrun by tourists who follow the trends but usually miss some of the best spots to visit. So, from my local perspective, I’ve crafted the perfect weekend itinerary and compiled some essential tips to ensure you have the best time on the Cape!
Friday
Afternoon:
It is important to know that Cape Cod is technically an island connected to the rest of Massachusetts by two bridges, so entering the Cape can be difficult. The best times to leave from Boston are before 2:00 p.m. or after 7:00 p.m. to avoid heavy traffic. Still, be prepared for travel times to change at any minute, so allow plenty of buffer time in case of emergencies.
Evening:
After a long travel day, you’ll probably be hungry. However, you would be remiss not to rush to the beach and soak in the beautiful coast. I recommend grabbing pizza from a local favorite, like Crisp in Osterville or Pizza Barbone in Hyannis, and digging in on the beach. Enjoy the sunset, but when you are ready to head to your hotel or hostel, swing by Four Seas Ice Cream in Centerville for their award-winning scoops.
Saturday
Morning:
Once you wake up to the sounds of seagulls and other coastal birds, it is time to get dressed in a beach-appropriate outfit, grab some sunscreen and head out the door. Your first stop should be breakfast at a locally owned diner or cafe: I recommend the Fig Tree Cafe in Marstons Mills or Bagel Heaven in Mashpee. Next, hit the beach! For a family-friendly vibe, go to West Dennis Beach. For a quieter, scenic atmosphere, visit the Coast Guard Beach in Eastham, or Marconi Beach for a more outdoorsy and sporty ocean experience.
Afternoon:
No trip to the Cape is complete without a lobster roll for lunch. The best one is heavily debated, but some crowd favorites can be found at the Skipper Chowder House in South Yarmouth, The Lobster Pot in Provincetown and Sesuit Harbor Cafe in Dennis. After lunch, spend some time in town! Cape Cod is full of local artists, museums and cultural centers that are often under-appreciated but worth visiting. Try asking your waiter for their favorite hidden gems to explore the local hot spots. When you’re ready to return to the water, go see the Nauset Lighthouse and learn about the Cape’s historic significance in the whaling industry.
Evening:
On your last evening, live it up and go to a fancier restaurant. Local favorites include the Ocean House in Dennis, The Red Inn in Provincetown and Five Bays Bistro in Osterville. If you crave a night out, you might be out of luck. The best evening activities on the Cape are beach bonfires and live music. Be on the lookout for flyers around town or check out some local bands’ Instagrams to see what’s happening.
Sunday
Morning:
Once you check out of your hotel, swing by a local coffee shop like Snowy Owl in Sandwich, Nirvana in Barnstable or Lighthouse Keeper’s Pantry in Yarmouth Port. I recommend visiting a few more highlights and hitting the road early because Sunday traffic can ruin the weekend’s mood. Before you leave, however, check out a local market or antique show. The Wellfleet Flea Market and the Chatham Farmers Market are excellent options. On your way out, grab a bag of Cape Cod chips and some penny candy from the Country Store to reminisce about the weekend.
Lastly, here are some general tips to make your weekend as successful as possible. First, bring plenty of layers. The weather turns on a dime, and as the sun sets, temperatures drop rapidly. Second, the tides can really impact your experience at the beach. Look up the tide schedule, and be cognizant of the low tide smell or the rising tide sweeping your belongings away. Third, skip chain restaurants. The Cape is packed with local businesses that need all the support they can get. Finally, respect the wildlife. The dunes and coastline are home to hundreds of species, some endangered, that deserve to feel safe in their environment.
Cape Cod is more than just a summer destination; it’s a place full of history, hidden gems and coastal charm that locals like me hold close to our hearts. By exploring beyond the typical tourist stops and supporting small businesses, you can experience the real magic of the Cape. Whether you’re watching the tide roll in with a slice of pizza in hand or strolling through a sleepy seaside town, a weekend here is a chance to slow down, soak it all in and make memories that will bring you back year after year. So pack your layers, bring your curiosity and enjoy the Cape like a true local.