Sample stays · Built by the owners
Three ways
to stay.
A weekend reset, a three-day escape, or a full week on Cape time
How long do you have?
Pick a pace.
We’ll handle the rest.
These aren’t tourist itineraries pulled off a travel blog. They’re the weekends we actually take when friends come up — the beaches we send them to, the restaurants we book, the moment we tell them to stop driving and just sit on the porch. Pick a length. We wrote all three.
Thursday to Sunday
3-Day Weekend
One extra day changes everything. Bay side, ocean side, and one long night in Wellfleet.
Day 1
Thursday — Land on Cape time
Afternoon
Check in, walk to the beach
Sunken Meadow is five minutes on foot from the Barn. Get the lay of the bay before dinner.
Evening
Dinner at Van Rensselaer's
Old-school Eastham, steamers and a martini, low-key. Save the fancier spots for later in the trip.
Day 2
Friday — Outer beaches
Morning
Marconi or Coast Guard Beach
Coast Guard is classic — the dune, the boardwalk, the kettle pond behind. Marconi is wilder and quieter. Pick your mood.
Lunch
Mac's Shack, Wellfleet
Order the tuna tacos and a dozen oysters at the raw bar. Sit upstairs if you can.
Evening
The Beachcomber for sunset + music
Cahoon Hollow — drinks on the deck, feet in the sand, a band by 9. Arrive before 6 or the lot closes.
Bars & Music guide →Day 3
Saturday — Bikes, oysters, sunset
Morning
Rail Trail north to Wellfleet
Rent bikes in Eastham. Ride the trail up to Wellfleet harbour. Oysters at the Pearl or Mac's on the Pier.
Afternoon
Nauset Light or Nauset Marsh kayak
Either laze on the ocean at Nauset Light, or rent a kayak on the Salt Pond and paddle out into the marsh. Look for ospreys.
Evening
Dinner at The Local, First Encounter for stars
Good wine, small plates, then drive to First Encounter after — no lights, no moon if you time it right, the Milky Way sits on the water.
Day 4
Sunday — The long way home
Morning
Breakfast at the Barn
Bring pastries back from Hole in One. Eat them slowly. Pack slowly. You are allowed.
On the way
Provincetown for lunch, or Chatham
Drive to the tip of the Cape for one last meal on Commercial Street, or head south through Chatham and back. Either adds 90 minutes and pays you back in full.
1460 Massasoit Road · Eastham
Pick your dates.
The rest writes itself.
Instant booking on Airbnb · or browse The Barn & The Main House