For a quainter experience, take in harbor views at Stirling House Bed & Breakfast in Greenport. Ask either hotel to suggest a car or limo service (safety first).
Just down the road in Peconic, taste Raphael’s cabernet franc, then fall for gewürztraminer and sparkling cuvée made by long-haired wine whiz Eric Fry at The Lenz Winery.
Backtrack to Southold’s loungy Croteaux Vineyards for pink bubbly or lobster roll on to Mattituck for a buttery pick-me-up at Love Lane Kitchen. House-roasted coffee to go leaves you with a different buzz.
In Cutchogue, we suggest a trifecta of tastings: Start unpretentious at McCall Wines (the operation is wind powered, as well as home to a herd of Charolais cows).
Get a dose of art and red Musée blend in the modern tasting room at Bedell Cellars. To end the day, take out pent-up frustration at your inability to identify strong floral notes at Vineyard 48’s DJ-led dance party (reservations required).
Hungover? Wake up late, grab a pecan-raisin scone from By Aldo, and take the scenic route south through Shelter Island to Sagaponack’s equally picturesque Wölffer Estate. Don’t leave without a bottle of winemaker Roman Roth’s dry rosé or amarone-style cabernet sauvignon (we’re told there are only a few bottles left).
Continue your recovery with artisanal pizza and breaded calamari salad from World Pie, a stroll to kitchenwares shop Loaves & Fishes, and a scoop of vanilla at the retro Bridgehampton Candy Kitchen (2391 Montauk Highway, 631-537-9885).
Quick tip: Thursday through Saturday, St. Ann’s Thrift Shop is pure gold for Hermès scarves and Gucci bags.
Get back to the bottle at Channing Daughters for a flight of interesting whites. Expect varietals like Tocai Friulano, muscat ottonel, and malvasia.
Dinner and killer dessert at the eastern outpost of NYC’s Almond drain the remainder of the day.
Quick tip two: Return to Bridgehampton in August for Harvest East End, where the wineries all come to you.
Onward to Jamesport for relaxed bird- and vine-watching and live music on Clovis Point’s patio. If you prefer people to nature, head inside the refurbished ’20s potato barn for a spot at the pouring bar.
In Aquebogue, book a grounds tour with Paumanok Vineyards’s Charles and Ursula Massoud. Their chenin blancs and Bordeaux-style blends are good to the last drop.
On the way back, stuff pieholes accordingly with Briermere Farms’s raspberry-peach and strawberry-rhubarb versions. The Riverhead spot always has a line, so make it worthwhile with a souvenir jar of raspberry jam.
Cap off the trip with a detour to Wading River for dinner at Amarelle.