When we flew up to Boston for our summer vacation, I knew I wanted to explore the nearby small towns like Cape Cod and Nantucket. Martha’s Vineyard didn’t make the cut due to time, but it sure can be another day trip adventure if you’re looking for one. We rented a car in Boston, and took the 1.5 hour drive to Cape Cod. After exploring there for a few hours we took the Hyannis-Nantucket High Speed ferry (1 hour) to Nantucket. There is not a shortage of things to do and both these small towns can easily be more than just a day adventure! I actually wish we would have stayed a night on Nantucket (specifically at the Nantucket Hotel), because it rained half the day while we were there. We didn’t let that take away from the magic, and the place was just as dreamy as ever!

Cape Cod is pretty big for just a day trip. It’s made up of 4 parts: Upper Cape, Mid-Cape, Lower Cape, and Outer Cape. Each part has it’s own cute small coastal towns that are waiting you to explore. We went to Cape Cod specially to get to Nantucket, so didn’t spend time anywhere except Hyannis. Hyannis is lively, with lots to do, so we didn’t feel short changed.

Cape Cod National Seashore
Takes up a major part of the “Outer Cape” and maintained by the National Park Service. 40,000 acres of beaches, hiking and cycling trails, and salt marshes. You’ll drive through this area if you’re trying to reach Provincetown.

The tip of Outer Cape and site of the Mayflower’s landing in 1620! Visit Race Point Beach and Race Point Lighthouse after or before a day of shopping and eating on Commercial Street

The most southern part of Cape Cod with ferries going to Martha’s Vineyard. Tons of outdoor food places overlooking the water. Have some fresh seafood and cocktails at The Boathouse on Pier 37

Main Street Chatham
Downtown Chatham is the perfect family shopping outing and we aren’t really “shoppers” when it comes to family outings with 4 young kids. There are so many children’s boutiques, candy stores, and even a few ice cream shops for both kids and adults. Ducks in the Window is super cute and usually a favorite with the littles.

Hyannis Kennedy Legacy Trail is a self guided walking tour with 10 different sites in Hyannis. There is also a small John F. Kennedy Hyannis Museum available to visit for an extra charge.

Cape Cod Potato Chip Factory, Hyannis
(Currently CLOSED as of June 2021)

The Nantucket Hotel
If you’re looking to stay the night on the island, this hotel is picture perfect.

Young’s Bicycle Shop

For bike rentals to get around the island

Brant Point Light house

Take a little tour of the island by bike and head to the Brant Point Light House. The houses and their gardens on the way to the light house are dreamy during the summer months!

The view at sunset, leaving Nantucket on the ferry back to Hyannis

Children’s Beach
Small, calm beach with a lawn area full of play equipment and small café nearby. Boat watching galore, since it’s right in the harbor.

Jetties Beach
Popular family friendly beach with nearby Sandbar Restaurant.

Straight Wharf Restaurant
Serving up fresh, local, and/or in-season eats!

Whaling Museum

Go for the huge whale skeleton hanging above you, leave with interesting information about the island of Nantucket!

The Juice Bar
For Nantucket’s best homemade ice cream! Right by the Whaling Museum

Cisco Brewers
Cute rustic brewery serving up local brews, wine, and live music.