A 3-day loop around the Cape’s elbow and its most storied island: an 1839 sea captain’s inn in Chatham, a passenger ferry across Nantucket Sound to Martha’s Vineyard’s gingerbread cottages, and a final run up Route 6 to Provincetown’s dunes and lighthouse views — with real inns, ferry schedules, and 2026 prices for every stop.
Day 1Sandwich to Chatham — The Cape’s Elbow
Pick up a rental car and follow Route 6A’s Old King’s Highway past saltbox houses and cranberry bogs to Chatham, the elbow where the Cape turns north.
🚗 Self-Drive: Route 6A, Sandwich to Chatham
~45 minutes · rental car from $70/day
The Old King’s Highway is a designated scenic byway lined with 18th-century sea captains’ houses, antique shops, and roadside farm stands — resist the urge to rush it. Fill the tank in Sandwich; gas stations thin out past Orleans.
📸 Cape Cod Canal Boardwalk, Sandwich
Free · allow 45 minutes
A flat, paved path along the world’s widest sea-level canal, with a decent chance of spotting a container ship or a fishing charter easing through the locks. It’s a good stretch-your-legs stop straight off the highway before the drive east.
🛎 Check-In: Captain’s House Inn
1 night · from $329/night
An 1839 sea captain’s Greek Revival estate two blocks from Chatham’s Main Street, with a garden courtyard and a full breakfast included every morning. Ask for a room in the original main house for the widest plank floors and working fireplaces.
Captain’s House Inn · www.captainshouseinn.com
🍽 Dinner: The Chatham Squire
~$45/person · no reservations, expect a wait
A Chatham institution since 1968, split between a raw bar, a dining room, and a tavern that fills with locals by 6pm — the lobster roll and the chowder are both the real thing. Put your name in and walk Main Street’s boutiques while you wait.
The Chatham Squire · www.thesquire.com
Day 2Ferry Day — Oak Bluffs to Edgartown
Leave the car at the harbor and take the ferry across Nantucket Sound to Martha’s Vineyard, trading lighthouses for gingerbread cottages and a night on the island.
⛴ Hy-Line Cruises: Hyannis to Oak Bluffs
~1 hour · ~$97 round-trip adult
Passenger-only high-speed ferries run several times a day from Ocean Street Dock in Hyannis, a 30-minute drive from Chatham — park at the dock’s lot for the day. No car-reservation headaches; this is the easiest way onto the Vineyard for an overnight.
Hy-Line Cruises · www.hylinecruises.com
🎠 Oak Bluffs Gingerbread Cottages & Flying Horses Carousel
Free to walk · $3/carousel ride
More than 300 candy-colored Victorian cottages, some barely bigger than a garden shed, packed onto a few blocks around the Methodist Campground. The Flying Horses Carousel next door has been hand-carved and spinning since 1876 — America’s oldest platform carousel still running.
🛎 Check-In: Harbor View Hotel
1 night · from $459/night
A grand 1891 waterfront hotel facing Edgartown Lighthouse across the harbor, with a wraparound porch built for watching the sunset with a drink in hand. It’s a short trolley or taxi ride from the Oak Bluffs ferry dock.
Harbor View Hotel · www.harborviewhotel.com
🍽 Dinner: The Port Hunter
~$50/person · reservations recommended
A reclaimed-wood dining room a block off Edgartown’s harbor, serving raw bar towers and a lobster roll that swaps mayo for drawn butter. Live music most nights keeps the bar loud and the dining room lively past 9pm.
The Port Hunter · www.theporthunter.com
Day 3Edgartown to Provincetown — Land’s End
A morning ferry back to the mainland, then the full length of Route 6 to Provincetown, the Cape’s northern tip and its most eccentric town.
⛴ Ferry Back: Oak Bluffs to Hyannis
~1 hour · included in round-trip ticket
Catch a mid-morning departure to leave time for the drive north — the Vineyard’s ferries run on the hour during summer, so there’s no need to rush breakfast at the hotel.
🚗 Self-Drive: Hyannis to Provincetown
~1 hour · via Route 6
The highway narrows to two lanes past Wellfleet, with the Cape Cod National Seashore’s dunes and pitch pine forest pressing in on both sides. Stop at the Salt Pond Visitor Center in Eastham for a proper look at the seashore before Provincetown.
🏖 Race Point Beach & Cape Cod National Seashore
$25/day parking
A wide, wild Atlantic beach at the very tip of the Cape, backed by grass-covered dunes and known for regular seal and whale sightings just offshore. It’s the least crowded of the National Seashore beaches and worth the detour even for twenty minutes.
Cape Cod National Seashore · www.nps.gov/caco
📸 Pilgrim Monument & Land’s End
~1 hour · $18 adult monument entry
A 252-foot granite tower climbing over Provincetown’s rooftops, with a 360-degree view stretching from Long Point Light to the dunes of Truro on a clear day. Finish with a walk out toward Land’s End at the harbor’s edge before the drive home.
Pilgrim Monument & Provincetown Museum · www.pilgrim-monument.org
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