Nantucket is the trip I recommend when someone tells me they want to relax without feeling like they’re missing anything. It’s small enough to see in three days, precious enough to stretch to five, and every part of it — the harbor, the moors, the grey-shingled everything — looks better in person than in photos.
Getting there
The fast ferry from Hyannis is the move unless you’re bringing a car you don’t need. The island is walkable and bikeable, and a car mostly means you’re paying to park it. If you’re coming for a wedding or traveling with a group, I can arrange a private charter instead of the ferry queue.
Where to stay
I typically split recommendations two ways:
- In-town — walk to dinner, walk to the harbor, no car needed. Best for a long weekend focused on the town itself.
- ’Sconset — quieter, rose-covered cottages, a short bike ride from the lighthouse. Best if you want mornings on the beach and evenings on a porch.
Both directions have properties I can get you into with upgrades that aren’t bookable directly.
What to actually do
Skip the checklist-tourism version of the island. The one non-negotiable is a sunset at Madaket — bring a blanket, not a reservation. During the day, rent bikes and ride out to Sankaty Head Lighthouse; the ride matters as much as the destination. If it’s foggy (it will be, at least once), that’s when the town itself is at its best — walk the cobblestones, duck into the whaling museum, and let an afternoon disappear into a bookstore.
Where to eat
Book ahead for anything with a view of the harbor — in-season, tables go fast. My go-to order is simple: something with bay scallops (they’re only truly in season a few weeks a year, and it’s worth timing a trip around it if you can), and whatever the raw bar is running that day. Ask your server what came in that morning rather than what’s printed on the menu; the good places change it daily and don’t always update the paper.
When to go
Late June through Labor Day is the island at full volume — beautiful, but booked out and busy. I usually steer clients toward mid-September: the water’s still warm, the crowds have thinned, and the light gets that particular gold that makes the whole island look staged for a photograph. If you can only come in summer, book your stay the moment you know your dates.
If any of this sounds like your kind of trip, get in touch and I’ll build the itinerary around it.
