Sloane's Last Dance
Sloane's trading her handicap for a honeymoon—let's send her off in style.
Luxury Cedar-Shingled Estate
A 6-8 bedroom estate with heated pool, hot tub, chef's kitchen, and manicured grounds is the HQ for a Sloane-caliber weekend. East Hampton's proximity to Wölffer Estate Vineyard and Nick & Toni's makes this the perfect base for a golfer-foodie who appreciates both the course and the table. Pricing is estimated based on luxury Hamptons market rates for August peak season.
$15,000 total per night ($1,875 per person split 8 ways)/nightThe crew lands at Long Island MacArthur (ISP) and meets at the house by 11:30 AM. Settle in, claim rooms, pool float check. This is HQ for the next 72 hours.
Assign someone to stock the fridge with sparkling water, electrolytes, and a bottle of Sloane's favorite rosé before arrival.
Light lunch spread—local cheeses, fresh bread, oysters if you can swing it. Sloane's a foodie; start the weekend with quality ingredients and no rush.
Order from a local Hamptons caterer the day before; this is not a DIY moment.
Float, read, nap, catch up. This is the breathing room—no schedule, no pressure. Sloane's a golfer who appreciates pacing; let the weekend settle.
30-minute drive to Montauk. Group surf lesson with instructors who specialize in making beginners look comfortable on a board. Sloane gets her beach moment, everyone laughs, the ocean resets the vibe.
Bring a dry bag for phones and keys; the instructors provide boards and wetsuits.
Shower, change into linen and sundresses. Pre-game playlist on the deck. Champagne and snacks. The night is building.
Private tasting at Wölffer Estate's Sagaponack vineyard. Rosé flights, estate Chardonnay, a view of the vines that belongs on a magazine cover. Sloane's in her element—food, wine, refinement.
Book the private tasting 2 weeks ahead; August is peak season. Designate a non-drinker as the driver or book a car service.
The Hamptons institution since 1988. Wood-fired Tuscan cooking, seasonal produce, a regulars list that includes everyone who matters. Sloane's foodie dream. Reservation for 8 under her name.
Book this 3+ weeks ahead. Request a table on the patio if weather permits. Order the wood-fired branzino and the burrata.
Bohemian Montauk motor lodge turned summer cocktail destination. Campfire pit, string lights, effortlessly cool crowd. One drink, low-key vibe. Sloane's had a full day; keep it chill.
It's a 30-minute drive from Bridgehampton. Leave by 11:45 PM to avoid the late-night crowd.
Bagels from Goldberg's Famous Bagels (Southampton), fresh fruit, coffee. No rush. Sloane's a foodie who appreciates the ritual of a proper breakfast.
Order bagels the night before for pickup at 10:30 AM.
Japanese-inspired wellness sanctuary in Water Mill. Individual spa suites, outdoor baths, silence policy. 3-hour reset before the big night. Sloane gets restored, the crew gets quiet time to recharge.
Book massages and facials 2 weeks ahead. Arrive 15 minutes early to settle into the spa energy.
Pool float, rosé, light snacks. Get ready slowly. This is the calm before the storm—no schedule, no pressure. Sloane's had a spa morning; let her soak it in.
Styled picnic setup between Shinnecock Bay and ocean. Vintage rugs, floral arrangements, chilled champagne, local catering spread. This is the foodie moment—charcuterie, local cheeses, fresh seafood. Sloane's in her element.
Book this 2 weeks ahead. Bring a light wrap for the breeze; the sun drops fast over the water.
Shower, sequins, perfume. This is the big night. Playlist on full volume. Champagne flowing. The crew is locked in.
Have everyone pick one outfit option the night before to avoid last-minute chaos.
Private chef arrives with a passed appetizer spread—crudités, cheese, charcuterie, champagne cocktails. This is the house party nightlife moment. Sloane's surrounded by her crew, no pressure to go anywhere yet.
Hire a private chef to arrive at 8:45 PM with a 90-minute spread. Cost: ~$800 total for the group.
The Hamptons' closest thing to a proper nightclub. Bottle service, a real dance floor, Saturday night energy that runs past midnight. Sloane's the main character; she owns this floor.
Book the party bus pickup from the house at 10:15 PM. Reserve a VIP table at 1 OAK 2 weeks ahead. Minimum spend: $2,000 for bottle service (vodka, champagne, mixers). Dress code: dressy—sequins, heels, statement jewelry.
Nautical-modern dining room with a raw bar and excellent oysters. Late-night energy that keeps the night alive. Sloane gets her second-wind food moment.
Call ahead to confirm they're open late; summer hours vary. Order oysters and a charcuterie board.
Party bus returns to the estate. Poker, blackjack, roulette set up on the dining table. Chips, cards, a dealer (hire one or designate someone). Sloane's competitive; this is the final nightlife moment—intimate, high-energy, just the crew.
Buy-in: $200 per person. Hire a professional dealer from a local event company (~$300 for 2 hours). Set a house rule: all winnings go to Sloane's honeymoon fund.
Classic French bistro. Croque madame, brilliant Bloody Mary, sun-drenched patio. Sloane's a foodie; this is the final meal moment. Reservation for 8.
Book 2 weeks ahead. Order the croque madame and a round of Bloody Marys. Sit on the patio if weather permits.
Golden-hour shoot on the dunes or in East Hampton village. Local photographer. Sloane gets professional photos that belong in her wedding album—this is the keepsake moment before everyone leaves.
Book the photographer 3 weeks ahead. Coordinate outfits the night before (linen, sundresses, matching robes if you want). Shoot for 90 minutes.
Pack up, settle the house, head to Long Island MacArthur (ISP) for evening flights. Aim for 5:00 PM+ departures to avoid rush.
Pre-book airport car service the night before. Designate someone to do a final walkthrough of the house.
Waterfront Lounge with Live Music
Iconic Montauk waterfront lodge hosting live music on the dock every summer evening. The single best place to watch the sun drop into Fort Pond Bay. Dress code: linen and sundresses. Reservation recommended.
Bohemian Cocktail Lodge
Bohemian Montauk motor lodge turned summer cocktail destination. Campfire pit, string lights, effortlessly cool crowd. Craft cocktails, no pretense. Perfect for a chill evening.
Italian Wine Bar
Italian-accented wine bar where the aperitivo hour runs long. Negronis perfectly stirred, natural wines, every table looks like a Vogue editorial. Smart casual dress code. Reservation needed.
Intimate Craft Cocktail Bar
Intimate East Hampton cocktail bar with rotating seasonal menu and impressive natural wine list. Rewards leisurely sipping. Not ideal for large groups, but perfect for a quiet nightcap.
Nightclub with Bottle Service
The Hamptons' closest thing to a proper nightclub. Bottle service, a real dance floor, Saturday night energy that runs past midnight. Dressy dress code. VIP table reservation required.
Italian-Mediterranean Tasting Menu • $95–$150 per person (wine pairings extra)
The Hamptons institution since 1988. Wood-fired Tuscan cooking, seasonal produce from their own kitchen garden, a regulars list that includes everyone who matters. Sloane's foodie dream.
New American Farm-to-Table • $120–$180 per person (wine pairings extra)
Tom Colicchio's farm-to-table restaurant inside a Greek Revival mansion. Produce from its own kitchen garden, elevated and deeply seasonal. Perfect for a golfer-foodie who appreciates both the setting and the plate.
French Bistro Brunch • $45–$75 per person
Classic French bistro that locals swear by for weekend brunch. Croque madame, brilliant Bloody Mary, sun-drenched patio. The recovery brunch moment.
New American Raw Bar • $60–$100 per person
Nautical-modern dining room with excellent oysters and a late-night energy. Perfect for the 1:00 AM second-wind food moment after the club.
Seafood Casual • $50–$85 per person
Lobsters pulled from traps in Montauk Harbor and served at weathered picnic tables with sweeping water views. The definitive Hamptons lunch—casual, fresh, iconic.
Transport: Day 1: Rideshare (Uber XL) from Long Island MacArthur (ISP) to the house (~$120 total, $15/person). Day 1 evening: Private car service to Wölffer Estate and Nick & Toni's (~$200 round trip, $25/person). Day 2: Private car service to Shou Sugi Ban House and Dune Road picnic (~$250 round trip, $31/person). Day 2 evening: Party bus pickup from the house at 10:15 PM, drop-off at 1 OAK Montauk, return to house at 3:00 AM (~$600 total, $75/person). Day 3: Rideshare to Long Island MacArthur (ISP) for evening flights (~$120 total, $15/person). Total transport per person: ~$156.
Nightlife Strategy: Night 1 (Day 1): Wine tour + dinner at Nick & Toni's + one cocktail at Ruschmeyer's. Low-key, refined, sets the tone. Night 2 (Day 2): THE big night. Pre-game at the house with a private chef (9:00 PM), party bus to 1 OAK Montauk (10:30 PM) with a VIP table and bottle service ($2,000 minimum for vodka, champagne, mixers), late-night oysters at Moby's (1:00 AM), then casino night at the house (2:30 AM). This is the peak. Cover charges: 1 OAK is VIP-only, no walk-ups. Bottle service minimum: $2,000 for a table of 8. Dress code: dressy—sequins, heels, statement jewelry. Reservations: Book 1 OAK 2 weeks ahead.
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