For many, Cape Cod is close enough to make repeat trips. For the rest, we must choose. No matter how much time you have (even if it’s one day), though, rich and diverse experiences are easily reached. Yes, you must still pick and choose carefully because who has time to waste on one bad meal, or one less-than-stellar overnight. These suggestions come from having explored the Cape since childhood and during my adult years as a professional travel writer. Enjoy.
As a starting point, check out the “A Perfect Day In …” for each town. See which strikes your fancy and knit them together. Why not start with Chatham (which will lead to all the rest and are all linked).
You’ll need to be efficient. Visit the village of Sandwich, poke around antiques and artisan shops on Route 6A, and drive down scenic bayside roads north of Route 6A, spending two nights mid-Cape. On the third morning, pop down to Main Street and the lighthouse in Chatham, and then head to the Outer Cape and the famed Cape Cod National Seashore beaches, stopping at the Salt Pond Visitor Center in Eastham. Spend two nights on the Outer Cape (or in Orleans): Visit galleries in Wellfleet, walk the Atlantic beaches and short nature trails, and take a day trip to Provincetown.
You’ll end up with a very enjoyable trip. Spend three nights mid-Cape and three on the Outer Cape. Do all of the above, plus linger longer in Sandwich, visiting the Glass Museum and/or Heritage Museums & Gardens. Add a beach walk at Barnstable’s Sandy Neck Beach and/or Nauset Beach in Orleans. Visit the Cape Cod Museum of Natural History in Brewster and/or the Wellfleet Bay Wildlife Sanctuary. Spend a day and a half in Provincetown—watching people, walking Commercial Street, ducking into art museums and the informative Provincetown Museum, taking in a sunset from Race Point or Herring Cove, heading out on a whale-watching excursion.
You’ll be very happy. Allot the entire three additional days (from the above plan) to Martha’s Vineyard. (Trying to see the Vineyard in a day borders on silliness.) Or add a night or two in the diverse Falmouth–Woods Hole area and a day trip to Nantucket. Back on the Cape, get out on the water with a trip to Monomoy Island in Chatham or some other boat tour. Add a couple of whistle-stops at the Cape’s small, sweet, historic museums.
You’re really lucky. Allot three days to one of the islands. Add a quiet canoe or kayak paddle somewhere. Take a leisurely bike ride or an aerial sightseeing flight. Get tickets to summer stock and cheer on the home team at a free baseball game. Slip into a parking space at the Wellfleet Drive-In. Investigate an old cemetery. Take an art class. Visit Mashpee’s South Cape Beach State Park.
Oh, and if you want a deeper dive, my Explorer’s Guide to Cape Cod, Martha’s Vineyard and Nantucket happens to be the best beloved guide to the region.