Start from 44 curated places around Sag Harbor, NY, then choose the recommendations that fit your guests.
Restaurants & cafés
The American Hotel
An 1846 landmark on Main Street that has been a serious restaurant since the 1970s, known for a wine cellar that gets Wine Spectator's top award and a menu that leans French-American without apology. The bar room is the village's preferred spot for a drink among people who live here year-round. Reservations are necessary; walk-ins at the bar are sometimes possible.
Tutto il Giorno
A Bay Street Italian that manages to feel like the real thing without the usual Hamptons markup anxiety. The pasta is made in-house and the approach is coastal Italian — light, seafood-forward, vegetable-leaning. The outdoor terrace facing the water is where you want to be on a clear evening.
Trails & outdoors
Elizabeth A. Morton National Wildlife Refuge Trail
The main loop at Jessup's Neck combines a woodland nature trail with a long beach walk along Noyack Bay. The terrain is flat and easy, and the habitat transitions from forest to salt marsh to sandy beach make every section feel different. The fall and spring migrations bring raptors, waterfowl, and shorebirds that make this one of the top birding walks on Long Island.
Mashomack Preserve
A 2,350-acre Nature Conservancy preserve covering a third of Shelter Island, accessible by ferry from Long Wharf. The trail network is color-coded and ranges from a short 1.5-mile loop to the 8-mile Red Trail that circles the southern peninsula through tidal creeks, bluffs, and open meadows. The ferry ride is part of the experience.
Things to do
Bay Street Theater
A 299-seat professional theater on the Long Wharf that has been doing serious work since 1991 — new plays, established works, and a summer comedy program that draws touring talent. The size means no bad seats, and the pay-what-you-can policy for certain performances makes it accessible in a zip code that isn't. Year-round programming.
Sag Harbor Cinema
The renovated three-screen art-house cinema at 90 Main Street, rebuilt after a 2016 fire and reopened as a nonprofit community cinema with a bar, café, and roof terraces. The programming leans toward independent and foreign film with regular retrospectives and Q&As with filmmakers. One of the better small cinemas on the East Coast.
Landmarks & sights
Sag Harbor Whaling Museum
Built in 1845 as the home of a whale oil merchant, this Greek Revival mansion at 200 Main Street now holds one of the more honest accounts of the whaling industry you will find anywhere. The collection covers harpoons, logbooks, scrimshaw, and the full arc of how a small village became one of the busiest ports on the eastern seaboard. Give yourself at least an hour.
Old Whalers' Church
An 1844 Egyptian Revival church on Union Street with a facade that looks more like a pharaoh's temple than a New England chapel, which is the whole point — it was built to project prosperity and novelty. The interior is plain white by contrast. The steeple was lost to a hurricane in 1938 and never replaced, so what you see is the truncated original.