Where to Stay
- For sea views from your bedroom, stay at Inn on the Sound, a 1904 shingled “cottage” on a bluff overlooking Provincetown harbour and the National Seashore where you can whale spot from the terrace at breakfast (innonthesound.com)
- Or for a a great downtown location of Provincetown, Stay at Crowne Pointe Inn (crownepointe.com) with historic boutique charm, a spa plus a great restaurant and wine bar.
- The Salt House Inn is a really cool spot in converted salt miners’ cottages a few minutes from Provincetown centre. (salthouseinn.com)
- Fort Hill Bed & Breakfast is a 19th century Greek Revival farmhouse and if I’m not mistaken, it’s the only place on Cape Cod that’s on the dune-backed National Seashore (forthillbedandbreakfast.com).
- Also really lovely is A Little Inn on Pleasant Bay, South Orleans. Think rose-covered trellises, overlooking Pleasant Bay. It was built in 1798 and the floorboards still have the trap door from the house’s days as a stop on the Underground Railroad. You can swim off the inn’s dock. (alittleinnonpleasantbay.com)
- Wellfleet is arguably the Cape’s most picture-perfect town with its saltbox cottages, all clapboard and wooden shutters. They only have one hotel, Endless Coast, but it’s very affordable.
Seeking and Doing
Wellfleet is also home to one of the nation’s last drive-in theaters (with mini golf and a flea market) and lovely spots to eat like Winslow’s Tavern, Moby Dick’s, Mac’s Shack, The Wicked Oyster, Bookstore & Restaurant and Beachcomber.
For a semi-secret hiking spot of shifting dunes and pines, try Great Island in Wellfleet, deserted now, but once home to Wampanoags and 17th-century English settlers. Or explore them with Art’s Dune tours, a family run business founded by Art in 1946, now run by his son Rob. He can even organise dinner on the beach for you.
The neighbouring small towns of Chatham, Brewster, Orleans and Sandwich are all charming, offering up a quaint mixture of antiques shops, bait shops, galleries and restaurants, each with its own general store, which makes you feel like you’ve entered a timewarp. You should definitely stop for ice cream at the general store in Brewster.
Between Wellfleet and Provincetown, Truro is one of the most pristine and undeveloped little towns on the East Coast, boasting the most beautiful of beaches, a historic lighthouse, a great golf course overlooking the ocean, and a good number of delicious restaurants for such a tiny place (try Blackfish). Plus they have a vineyard you can visit for tastings.
Cycle between towns using the rail trail – miles of flat path through pine forests, past salt marshes, glinting ponds and towering sand dunes (there’s also a bike bus that can take you back).
If you love antiques, you must drive Route 6A from Sandwich, where the rows of antique shops begin (take a quick stroll on Sandwich’s marshland boardwalk, to Town Neck Beach, before carrying on), to Orleans.
Don’t miss the chance to see a Cape Cod league baseball game for a heartwarming taste of small town America. From mid-June to mid-August, Cape Cod League teams play almost every day. With teams in 10 different towns across Cape Cod, it’s always easy to find a game nearby!
Go looking for Great White sharks (from a boat). The best time to go whalewatching is morning or sunset, before most of the recreational traffic but late August/early September is a very active time for Humpbacks and Right Whales. Spend an afternoon on the Hindu, or the Bay Lady II – both schooners are a wonderful way to sail around the bay. Or you can rent your own boat (no license necessary) from Flyer’s Boat rentals (behind Joon Bar).
Take a day trip to the island of Nantucket. You can get to Nantucket by ferry from the Hyannis port in Cape Cod and leave behind your car. Once you’ve soaked in the vibe of the wharves with the beautiful yachts and fishing boats, you can take a trip down the cobblestone streets to the famous Whaling Museum. Take a stroll down Main Street. Some historic homes are open for tourists so that you can get an authentic feel of these perfectly preserved houses. Pop into Murray’s Toggery Shop and do some fine dining at Straight Wharf and before getting on the ferry, you can visit the second oldest functioning lighthouse in the USA – Brant Point Light, close to the wharf.
Eating and Drinking
In Provincetown, go to Canteen, grab a hot lobster roll and some fried pickles and head to their garden in the back or post up in the window to people watch.
See a drag show at the Post Office cabaret.
The Old Colony Tap is a great dive bar loved by the locals – rumor has it that it was built from the wreckage of old fishing boats.
The Red Inn is the last restaurant on Cape Cod, and has absolutely gorgeous views. Fanizzi’s for Italian and American seafood in a casual, “very Cape Cod” setting overlooking the sea.