14 days in Cape Cod Itinerary

14 days in Cape Cod Itinerary

Created using Inspirock Cape Cod trip planner

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Make it your trip
Fly
1
Provincetown
— 6 nights
Drive
2
Falmouth
— 7 nights
Fly

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Provincetown

— 6 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Change things up with these side-trips from Provincetown: Eastham (Coast Guard Beach, Nauset Light Beach, &more) and Orleans (Church of the Transfiguration & Nauset Beach). There's much more to do: appreciate the history behind Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Marconi Beach, stroll through Long Point, and don't miss a visit to Commercial Street.

To find where to stay, more things to do, photos, and more tourist information, go to the Provincetown road trip tool.

Chicago to Provincetown is an approximately 5.5-hour flight. You can also drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Traveling from Chicago in September, expect nights in Provincetown to be about the same, around 57°F, while days are little chillier, around 71°F. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Falmouth.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

Falmouth

— 7 nights
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Change things up with these side-trips from Falmouth: Sandwich (Sandwich Fish Hatchery, Hoxie House, &more), Cape Cod Canal (in Buzzards Bay) and Barnstable (Hyannis Whale Watcher Cruises & Samuell Day Gallery). Next up on the itinerary: tour the pleasant surroundings at Shining Sea Bikeway, engage your brain at Chatham Marconi Maritime Center, browse the exhibits of Edward Gorey House, and examine the collection at John F Kennedy Hyannis Museum.

To find reviews, other places to visit, where to stay, and more tourist information, you can read our Falmouth online tour planner.

Traveling by car from Provincetown to Falmouth takes 2 hours. Alternatively, you can take a bus. In September, daily temperatures in Falmouth can reach 73°F, while at night they dip to 55°F. Wrap up your sightseeing on the 14th (Mon) to allow time to fly back home.

Things to do in Falmouth

Outdoors · Museums · Parks · Tours

Side Trips

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.