4 Nights in Cape Cod with Kids in Tow: A House of Bennetts Travel Itinerary
Cape Cod has a way of slowing you down in all the right places. For our four-night summer escape with two kids and three adults, we found the perfect balance of slow mornings, salty breezes, and seafood that still has us daydreaming. If you're planning a family-friendly coastal getaway that doesn’t sacrifice charm or good food, here’s how we did it.
Where We Stayed
We booked a peaceful 3-bedroom Airbnb tucked near Hyannis Port. The neighborhood was quiet and walkable, and a small, rocky private beach just down the road became our go-to for evening wind-downs. Think tide pools, boat/house watching, and just enough space for the kids to search for treasures while the adults sipped something chilled.
Day 1: Welcome to the Cape
Morning: Arrival and coffee at Lighthouse Keeper’s Pantry—a small, soulful spot that does breakfast right. The breakfast sandwiches are top-tier, and the donuts are a non-negotiable if you’re traveling with little ones (or just a sweet tooth).
Afternoon: We explored the neighborhood, settled into the Airbnb, and let the kids run free at the private beach nearby. During A’s nap, us gals wandered over to The Paper Store—huge and full of classic Cape Cod souvenirs, gifts, and little treasures for the kids to tuck into their travel bags.
Evening: We drove to Craigville Beach, which has a more rugged, rocky feel and felt like a true New England welcome. It’s perfect for beachcombing and catching your breath after a travel day.
Day 2: Beach Bliss & Chatham Charm
Morning to Afternoon: We spent nearly the whole day at Mayflower Beach—and honestly, we didn’t want to leave. It’s the kind of stunning that makes time stand still: powdery sand, gentle surf, and the warm shallows that are perfect for kids to play safely. Pack a full beach day setup—coolers, towels, and all.
Lunch: Grabbed a bite at ACK Gioia, a stylishly casual spot with elevated sandwiches and a relaxed vibe that hits just right after a long beach stretch.
Evening: Headed to Chatham for a sunset moment at Chatham Lighthouse Beach—one of the most scenic spots in the area.
Dinner: We dined at The Impudent Oyster, and every bite was exactly what you hope for in a Cape Cod seafood experience. Think buttery lobster, rich chowder, and fresh oysters in a cozy, nautical setting. Bonus was that it was not TOO stuffy for the kiddos.
Day 3: Seals, Souvenirs & Small-Town Magic
Morning: Back to Chatham Pier Fish Market—this time for lunch. The lobster rolls? Peak perfection. Fish and chips? Crispy and golden. Bonus: watching the fishing boats come in and spotting seals right off the dock was a full-family highlight.
Afternoon: We wandered through downtown Chatham, popping into boutiques and gift shops. We also popped over to Harwich Port for our favorite ice cream: Sweet Izzy. The ENTIRE place is dairy free, and they now have one in Denver too. OBSESSED. Harwich Port also had some great small boutiques, and I scored a $40 dress that I wore to Nantucket the next day!
Evening: Another low-key sunset at the beach near the house and an early night in. (Pro tip: a takeout dinner and a glass of wine on the deck hits differently when the ocean is whispering nearby.)
Day 4: Nantucket Day Trip
We hopped on the ferry for a picture-perfect day trip to Nantucket (we highly recommend renting a Jeep for the full Cape experience—and for easy parking by the ferry terminal).
Breakfast: First stop: Handlebar Café—hands down the best coffee of the trip. Not even close. We also grabbed a light bite at Lemon Press, which offers healthy, beautifully plated dishes and a chic atmosphere.
Shopping: Nantucket is a shopping haven. Some of our favorites included:
SALT for elevated seaside style
Hill House for dreamy dresses and classics
Eye of the Needle for statement finds
For Now for curated, on-trend pieces
Book Lovers Stop: Nantucket Bookworks was a cozy stop for all ages—well-stocked and welcoming.
Midday Adventure: We strolled the docks by The White Elephant Hotel, which is worth a wander even if you’re not staying overnight. The views and the boats are storybook-worthy.
Dinner: We wrapped up the day at Sandbar at Jetties Beach. It’s casual, beachfront, and incredibly kid-friendly (there’s a freaking park you can walk them over to while you wait for food)—plus it’s just close enough to the ferry to make your way back without stress.
Final Morning: Packing Up & Planning Our Return
Before heading out, we took one last quiet walk to the beach, collected a few final seashells, and had a classic diner breakfast/brunch at Grumpy’s and got coffee for the drive to the airport at Nirvana Coffee Company in Barnstable Village. CUTE CUTE CUTE!
Final Notes from the Cape
Cape Cod gave us exactly what we needed—room to breathe, time to connect, and just enough saltwater to keep the kids sandy and smiling. Whether you’re in it for the beach days, seafood feasts, or small-town exploring, it’s the kind of place you can make your own.