Perfect 3-Day Itinerary for Boston and Cape Cod

So, you’ve got three days and you’re torn between a city adventure and a beach escape. Here’s the good news—you don’t have to pick. Boston and Cape Cod are close enough that you can enjoy both without feeling rushed. Think of it as the best of both worlds: history, cobblestone streets, and lobster rolls in Boston, followed by sandy beaches, lighthouses, and clam shacks in Cape Cod.

Here’s a relaxed but fun 3-day itinerary that balances city energy with coastal chill.

Day 1: Explore the Best of Boston

Morning: Freedom Trail & Downtown
Start your trip by diving straight into Boston’s history. The Freedom Trail is an easy way to see a bunch of the city’s historic spots in one go. It’s a 2.5-mile red-brick path that winds through downtown and hits landmarks like the Old State House, Faneuil Hall, and Paul Revere’s House. Even if you’re not a big history buff, walking through these spots gives you that “old America” vibe.

Lunch: Quincy Market
Right along the trail, you’ll find Quincy Market. Yes, it’s touristy, but it’s also fun. You’ll see food stalls selling everything from lobster rolls to clam chowder in bread bowls. Grab something to go and eat outside while people-watching.

Afternoon: Boston Common & Back Bay
Head over to Boston Common, the oldest public park in the U.S. It’s a nice place to stretch your legs. From there, wander to the Public Garden, where you’ll spot the swan boats in warmer months. Then make your way toward Newbury Street in Back Bay. The brownstone buildings here are gorgeous, and the street is lined with shops and cafes.

Dinner: North End (Little Italy)
Boston’s North End is famous for Italian food. Think cozy trattorias, pasta, and of course, cannoli from Mike’s Pastry or Modern Pastry. End your night with a stroll through the neighborhood—it’s lively, charming, and feels like you’ve been dropped into Europe.

Day 2: Drive to Cape Cod & Relax by the Water

Morning: Road Trip to Cape Cod
It takes about 1.5–2 hours to drive from Boston to Cape Cod, depending on traffic. So grab some coffee and hit the road early. Once you cross the Sagamore or Bourne Bridge, you’ll feel like you’ve entered a whole different world—slower pace, sea breezes, and those classic shingled houses.

Late Morning: Sandwich or Hyannis
If you want a low-key start, stop in the town of Sandwich. It’s one of the oldest towns in Cape Cod and has that picture-perfect New England feel. Stroll the boardwalk, peek into little shops, and just enjoy the coastal vibe. Another option is Hyannis, which has a bustling harbor and the John F. Kennedy Hyannis Museum if you’re into history.

Lunch: Lobster Rolls by the Water
No Cape Cod trip is complete without a lobster roll. You’ll find plenty of seafood shacks along the way—some serve them hot with butter, others cold with mayo. Try one of each and decide which team you’re on.

Afternoon: Beach Time
Cape Cod has endless beaches, so take your pick depending on where you land. Craigville Beach (near Hyannis) is family-friendly, while Nauset Beach (in Orleans) offers bigger waves if you’re into boogie boarding. Wherever you go, set up your towel, dig your toes in the sand, and just soak it all in.

Dinner: Classic Clam Shack
For dinner, go casual. Find a clam shack and order fried clams, chowder, or scallops. Eating seafood by the water just tastes better. Afterward, grab some ice cream—Cape Cod is loaded with little ice cream shops that locals swear by.

Day 3: Cape Cod Adventures & Back to Boston

Morning: Lighthouse Hopping
Cape Cod is known for its lighthouses, and they’re scattered all over the cape. Nauset Light (the one on the Cape Cod Potato Chips bag) is a must-see. Chatham Lighthouse is another beauty and still in operation. They’re all postcard-worthy, and kids usually love climbing around and exploring the grounds.

Optional Detour: Provincetown
If you’re up for a bit of a drive, head all the way to Provincetown at the tip of the cape. It’s artsy, colorful, and full of character. The Pilgrim Monument gives you amazing views if you don’t mind a climb. Plus, the dunes around Provincetown look almost otherworldly.

Lunch: Cape Cod Fare
Before heading back to Boston, grab one last seafood meal—maybe clam chowder and oysters this time.

Afternoon: Head Back to Boston
Depending on your flight or travel plans, you can either make your way back to Boston in the afternoon or stick around Cape Cod a little longer for one last beach walk.

If you do get back to Boston early, take a quick walk along the Seaport District. It’s got a modern, trendy vibe with waterfront views—a fun way to close out the trip.

Final Thoughts

Three days in Boston and Cape Cod goes by fast, but you’ll cover so much. You’ll get your dose of history and city energy in Boston, then balance it out with sandy beaches and seafood feasts in Cape Cod. It’s the kind of trip that feels both busy and relaxing at the same time.

So, pack comfy shoes for city walking, a beach bag for the Cape, and maybe leave some room in your suitcase for a box of cannoli or a bag of Cape Cod chips. Trust me—you’ll thank yourself later.