The Grand Tasting: Sloane Edition

The bridesmaids arrive at the East Hampton house, settle into rooms, and get oriented. Pool and hot tub are ready. Assign someone to stock the fridge with sparkling water, electrolytes, and the welcome kit essentials.

Tip: Have the maid of honor arrive 30 minutes early to unlock and do a quick walkthrough.

First afternoon is for settling in — float in the pool, soak in the hot tub, change into linen, and let the Hamptons energy sink in. No agenda. This is where the inside jokes start.

Tip: Set up a speaker on the patio with a curated playlist — Sloane's vibe, not chaotic.

Drive to Sagaponack (15 min) for a private rosé and Chardonnay tasting at Wölffer Estate. The vineyard is stunning at this hour, and the sommelier will tailor the flight to Sloane's palate. This is the Foodie's kind of arrival activity — refined, educational, and delicious.

Tip: Designate a non-drinker or light drinker as the driver; the winery provides water and snacks between pours.

Back at the rental by 7 PM. Shower, change into something elegant (linen, sundress, or a nice blouse), and prep for dinner. Light appetizers and rosé on the patio while everyone gets ready.

Tip: Have the maid of honor order charcuterie from a local spot (Balducci's or similar) to have ready when everyone returns.

The Hamptons institution since 1988 — wood-fired Tuscan cooking and a regulars list that includes everyone who matters. Reserve the best table (request when booking). Order the handmade pasta, the wood-fired fish, and the dessert. This is Sloane's kind of first night — elegant, locally celebrated, and delicious.

Tip: Book this 4+ weeks ahead; mention it's a bachelorette party and they may upgrade the table.

Italian-accented wine bar in Southampton (20 min drive) where the aperitivo hour runs long and the negronis are perfectly stirred. Every table looks like a Vogue editorial. Order wine, order a digestif, and let the evening wind down naturally.

Tip: This is a 'dress code: smart casual' spot — everyone should still be in dinner clothes.

Late, leisurely breakfast on the patio — fresh pastries from Goldberg's Famous Bagels (order ahead), smoked salmon, fruit, and strong coffee. No rush. Sloane sets the pace.

Tip: Order bagels the night before; they're best fresh but hold well if wrapped.

Drive to Water Mill (20 min) for individual spa suites, couples massage, facials, and outdoor baths. The silence policy is real — phones away, no talking. This is Sloane's reset before the big night. Everyone emerges glowing and calm.

Tip: Arrive 15 minutes early; the spa provides robes and slippers. Bring a light layer for the outdoor bath.

Back at the rental by 3 PM. Pool float, nap, or lounge on the patio with sparkling water and snacks. This is the breathing room — no agenda, no pressure. Everyone recharges before the evening.

Tip: Have the maid of honor set out a charcuterie board and electrolyte drinks on the kitchen counter.

Styled picnic setup between Shinnecock Bay and ocean with vintage rugs, floral arrangements, chilled champagne, and a local catering spread. This is the Foodie's dream — refined, beautiful, and unhurried. Sloane gets to be celebrated in the most elegant way possible.

Tip: Wear linen and bring a light wrap; the ocean breeze picks up at sunset.

Back at the rental by 6:30 PM. Shower, change into evening clothes (dresses, heels, jewelry — this is the big night). Hair and makeup happen at the house. Open champagne, play music, and build the energy.

Tip: Have a hair/makeup person on speed dial in case anyone wants touch-ups; book 48 hours ahead.

Photographer arrives at the house or meets the group at a nearby scenic spot (East Hampton village or dunes). Golden-hour shoot with Sloane as the centerpiece. Editorial, timeless, not trendy. Everyone gets individual and group shots.

Tip: Coordinate outfits the day before — linen, pastels, or jewel tones photograph best in golden light.

Tom Colicchio's farm-to-table restaurant inside a Greek Revival mansion with produce from its own kitchen garden. This is the splurge dinner — elevated, deeply seasonal, and worth every penny. Request a private or semi-private dining room for the group.

Tip: Book 6+ weeks ahead and mention it's a bachelorette party; they may offer a special menu or wine pairing.

Return to the house by 10:30 PM. Set up blackjack and poker tables on the patio or in the living room. Assign a dealer (or rotate). Buy-in: $50–$100 per person. Champagne, cocktails, and snacks flow. This is the big night — Sloane is the center of attention, the bridesmaids are competitive and laughing, and the energy is high but controlled.

Tip: Have the maid of honor print out simple rules for each game and assign someone to manage the chip bank.

Early-ish morning at Ditch Plains Beach in Montauk (30 min drive). No lesson, no structure — just the ocean, the bridesmaids, and Sloane. A gentle way to move the body and get salt air before the drive home.

Tip: Bring a cooler with water and electrolytes; the beach is beautiful and quiet at this hour.

Back at the rental by 11 AM. Brunch is already prepped — bagels, smoked salmon, fresh fruit, pastries, and strong coffee. Bloody Marys and mimosas for those who want them. Everyone eats, hydrates, and shares favorite moments from the weekend.

Tip: Have the maid of honor play a soft playlist during brunch — nothing loud, just ambient.

Pack up, settle any shared expenses via Venmo, and exchange hugs. Flights should be booked for 3 PM or later; rideshare to the airport is pre-booked the night before.

Tip: Send a group photo to the chat before everyone leaves — this is the last memory of the weekend.