8 a.m. Shop in Greenport like it’s 1881
Have a hearty, old-school breakfast at Nookies in the restored 1950s-era Silver Sands Motel, on 45 acres at the end of Silvermere Road in Greenport. After a maple-perfumed, Bunyanesque slab of French toast ($15), enjoy a beach walk or walk back to the Main Road on Silvermere, and a few yards east to Wm. J. Mills & Co. if you’re looking for canvas travel bags or a set of sails. Preston’s Chandlery on Greenport’s Main Street is the place for charts, navigation aids, waterproof boots and jackets. The East End’s marine supply store of choice since 1880, it could be a museum of boating. And for those who prefer books printed on paper, Burton’s Bookstore, which opens at 11 a.m., will take you back to the days of creaky wooden floors and a staff of eager bookhounds behind the register.
11:30 a.m. From a long island to a shorter one
The North Ferry from Greenport to Shelter Island is a sea-sprayed, 15-minute cruise from one island to another. You should take your car, but once you land, park in the ferry lot and walk up the path through Prospect Park into the Shelter Island Heights Historic District, a Victorian-era idyll planned in 1872 as a Methodist retreat. The greensward downhill from The Chequit (once the dining hall for the retreat, and now a hotel) is Rainbow Park, where an Adirondack chair is the spot for a view of Dering Harbor and the mansions of Harbor Lane. From the perennial border at the entrance to Rainbow Park, it’s a few steps to Stars, where you can assemble a portable lunch that could include a mahi wrap ($16) and macarons ($2.50) or scones ($5) baked by owner Lydia Martinez, who grew up in Slovakia with pastry in her blood. From Stars, walk seven minutes north on Grand Avenue back to your car at the North Ferry.
1 p.m. A path you can paddle
From the North Ferry parking lot, it’s a seven-minute drive to the Town Landing at the end of Burns Road for The Coecles Harbor Marine Water Trail. Call ahead to reserve a kayak, paddles and safety vest from Kayak Shelter Island (rates are $35 for single kayaks for two hours, $55 for tandems). For those who like a guide, Adam Mills, the owner, or Chris Stone, a former ferry captain, will accompany a four-person-or-fewer group ($300 for boats and guide) to make sure you don’t miss that osprey flying overhead with a fish in its talons, or get rocked by the wake of a passing motorboat. The water trail runs along a mostly undeveloped shoreline, in and out of pristine creeks with great blue herons above and schools of fish below. Taylor’s Island is a town park with a landing for your kayak, picnic tables and a rustic cabin with a porch for enjoying 360-degree water views of Coecles Harbor.
3 p.m. “To live again in these wild woods…”
Once you turn in your kayak, you are a 10-minute drive from the ancient, shady woods and gardens of Sylvester Manor, a 17th-century provisioning plantation that produced food and lumber for the sugar trade using enslaved Africans and indentured laborers. It is now a center for historical research and an educational farm on 200 acres of fields, woods and trails. Here you can take a walk through Sculpture @ Sylvester Manor. There is no admission fee for the self-guided exhibit “Paradise Lost,” which continues through the summer. Sculptures, installations and photography by 23 artists appear along a one-mile trail on the banks of Gardiner’s Creek. This is the second year for this surprising and whimsical exhibit, which was created by the curator Tom Cugliani and features a new group of East End artists whose works inhabit and reference the land.
4 p.m. A lighthouse that looks like a bug
It is a five-minute drive from Sylvester Manor to the North Ferry (allow 15 minutes in case of a line) for the ride back to Greenport, where you can park near the Greenport terminal. Reserve ahead and don’t be late for the Bug Light Cruises and Tours ($75 for adults, $30 for children), leaving from the East End Seaport Museum at 5 p.m. sharp every Saturday. Long Beach Bar Lighthouse is called Bug Light because of its strong resemblance to an insect when viewed from afar. It’s a two-hour round trip aboard a fishing boat (porgies are often hauled aboard a few hours prior) with sunset views of the Shelter Island and Greenport shorelines and a close-up inspection of Orient’s still-working lighthouse. Built in 1870, the lighthouse was destroyed by fire in 1963, rebuilt and recommissioned in 1990. Proceeds from the boat tours support maintenance and improvements to Bug Light.
7 p.m. Beverages on the boardwalk
Now that you are back on terra firma, walk a few steps from where you disembarked to Port, a restaurant with a waterside bar just off the Greenport boardwalk. Here you may enjoy the entertainments of docking ferries, sand-covered beachgoers, and the train and jitney riders coming and going while sipping glasses of sauvignon blanc ($18) or locally brewed summer ale ($9).
8 p.m. A dinner of land and sea
Fifteen years ago, Chef Noah Schwartz and his partner and sommelier Sunita Schwartz opened Noah’s in Greenport, a restaurant that says “local” with every bite. With 17 small plates and nine not-so-small on offer (local strawberries on arugula with toasted almond slivers and crunchy, bitter cocoa nibs, drizzled in a syrupy balsamic reduction for $20; sweet roasted beets with mint and orange topped with labneh, $18; seafood stew with sea scallops, littleneck clams, mussels, squid and a silky, spicy sauce to slurp, $48), the menu reflects the chef’s enduring relationships with local farms and fishers and is a showcase for the North Fork’s finest foods. The wine list has an excellent selection of the Long Island wines that grow together and go together with the local farm bounty.