Luxury Packages for Long Island Trips: The Ultimate 2026 Guide

Table of Contents

• Introduction
• Why Long Island Works for Luxury Travel
• Top Cities & Places in Long Island
• Signature Luxury Activities
• Curated Luxury Itineraries (3–7 Days)
• Tourist Circuits & Themed Routes
• Festivals & Seasonal Highlights
• Practical Travel Information
• Local Luxury Experiences: Food, Shopping & Culture
• Traveler-Specific Tips
• FAQs
• Conclusion

Introduction

From sun-drenched Hamptons beaches and Montauk cliffs to North Fork vineyards and Gold Coast mansions, Long Island is New York’s most glamorous coastal escape. Just beyond the city, you’ll find designer boutiques, chef-driven dining, serene spas, and yacht-dotted harbors—perfectly packaged into effortless luxury trips for couples, families, and friends.

This guide maps the best places, activities, and sample itineraries, then adds practical details—how to get there, where to stay, and estimated costs—so you can tailor a refined Long Island getaway with confidence.

Why Long Island Works for Luxury Travel

• Proximity to NYC with helicopter/seaplane hops and VIP car services.
• Diverse scenes: Hamptons beach clubs, Montauk wellness, North Fork wine country, and historic Gold Coast estates.
• Seasonal buzz: summer beach days, autumn harvest and festivals, cozy winter spa retreats.
• High-touch hospitality: boutique inns, private villas, somm-led tastings, yacht charters, and concierge experiences.

Top Cities & Places in Long Island

The Hamptons (Southampton, East Hampton, Sag Harbor)

• Highlights: designer shopping, art galleries, ocean beaches, chic restaurants.
• Don’t miss: Wölffer Estate Vineyard, Parrish Art Museum (Water Mill), LongHouse Reserve (East Hampton), Sag Harbor’s marina and whaling history.

Montauk

• Highlights: surf culture, dramatic coastline, upscale resorts, fishing charters.
• Don’t miss: Montauk Point Lighthouse, Shadmoor State Park trails, Gurney’s Seawater Spa.

North Fork (Greenport, Southold, Cutchogue)

• Highlights: vineyards, farm stands, waterfront inns, relaxed luxury.
• Don’t miss: Sparkling Pointe, Bedell Cellars, Macari Vineyards, Kontokosta Winery (clifftop views), Greenport’s harbor.

Shelter Island

• Highlights: quiet coves, boutique resorts, nature preserves.
• Don’t miss: Mashomack Preserve hikes, sunset cruises, The Pridwin’s waterfront scene.

Gold Coast (North Shore Mansions)

• Highlights: Gilded Age estates and gardens.
• Don’t miss: Oheka Castle (hotel and tours), Old Westbury Gardens, Planting Fields Arboretum.

Fire Island & Great South Bay

• Highlights: car-free beach towns, dune walks, private boating.
• Don’t miss: Sunken Forest, ocean-to-bay sunsets, curated beach picnics by private chef/caterer.

Signature Luxury Activities

On the Water

• Private yacht or sailboat charter (Sag Harbor, Montauk, Greenport): day cruises, sandbar picnics, sunset sails. Typical day rates: $2,500–$6,000+ depending on vessel/season.
• Sportfishing charters (Montauk): seasonal species with licensed captains.
• Kayak/SUP in calm bays with guide and gourmet beach setup.

Wine & Culinary

• Sommelier-led vineyard tastings and barrel-room tours; reserve or library flights at top estates.
• Farm-to-table chef dinners; in-villa private chef experiences; oyster shucking demos.
• North Fork tasting trails with chauffeured car or classic car add-on.

Wellness & Spa

• Thermal seawater circuits and ocean-view treatments in Montauk; meditation and sound baths at boutique retreats.
• Beach yoga at sunrise; personalized fitness and nutrition sessions.

Arts, Design & Culture

• Curated gallery walks in East Hampton and Sag Harbor; private museum docents.
• Artist home-studios such as the Pollock-Krasner House (by appointment) and seasonal art fairs.

Outdoors & Golf

• Guided biking between vineyards; nature preserves with birding guides.
• Golf at renowned public courses (e.g., Montauk Downs, Bethpage—advance booking required). Caddie/club concierge add-ons available.

Helicopter & Seaplane Experiences

• Fast transfers from NYC to East Hampton, Southampton, Shelter Island, or Montauk via helicopter or seaplane (shared seat or private charter, subject to availability).
• Scenic aerial tours of coastline and lighthouses.

Curated Luxury Itineraries (3–7 Days)

3-Day Hamptons Wellness Escape

Day 1: Arrival & Artful Afternoon

• Helicopter or chauffeured SUV from NYC to East Hampton.
• Check-in at a boutique inn; garden lunch and spa treatment.
• Private gallery tour; sunset beach walk; chef’s tasting menu.

Day 2: Ocean Wellness & Wine

• Sunrise beach yoga; seawater therapy session.
• Sommelier-led reserve tasting at a Hamptons vineyard; farm dinner.

Day 3: Sail & Savor

• Half-day sail from Sag Harbor with catered brunch.
• Return transfer; optional short aerial tour en route.

Indicative budget for two: $3,500–$8,000+ (season, transfers, and lodging class drive variance).

5-Day North Fork Wine & Sail

Day 1–2: Greenport & Vines

• Private driver from NYC or seaplane to Shelter Island/Greenport.
• Two days of VIP tastings (sparkling and reserve programs), oyster farm visit, and sunset cruise.

Day 3: Chef’s North Fork

• Farm tour with chef; hands-on cooking class; multi-course wine pairing dinner.

Day 4: Lighthouse Loop by Yacht

• Full-day yacht charter—swim stops, clifftop winery visit, bayside lunch.

Day 5: Leisure & Departure

• Spa morning or cycling to farm stands; chauffeured return.

Indicative budget for two: $5,000–$12,000+.

7-Day Ultimate Long Island Circuit

Days 1–2: Gold Coast Glamour

• Stay in a historic mansion hotel; private garden tour; classic car drive.

Days 3–4: The Hamptons

• Designer shopping, art museums, beach cabana setup, and fine dining.
• Optional horseback beach ride (where permitted) or guided surf lesson.

Day 5: Shelter Island Slowdown

• Kayak the creeks, picnic on a quiet bay, sunset ferry ride.

Days 6–7: Montauk Edge

• Seawater spa, lighthouse hike, and sportfishing or sunrise sail.

Indicative budget for two: $12,000–$25,000+ depending on air/heli charters, yacht class, and suite category.

Tourist Circuits & Themed Routes

• Beach & Wellness Loop: Southampton → East Hampton → Montauk (spas, yoga, oceanfront dining).
• Wine & Lighthouses Trail: Greenport → Orient → Montauk (vineyards, seaside villages, lighthouse climbs).
• Mansions & Museums Route: Oheka Castle → Old Westbury Gardens → Parrish Art Museum.
• Island-Hop by Ferry: North Fork ↔ Shelter Island ↔ South Fork (curated with driver and timed ferries).

Festivals & Seasonal Highlights

• May: Montauk Music Festival; spring wine releases.
• Late Aug–Early Sep: Hampton Classic Horse Show (book lodging far in advance).
• September–October: North Fork harvest season; Oyster Bay Oyster Festival; Hamptons International Film Festival (October).
• Summer (June–August): Polo events, outdoor art shows, bayside concerts.
• Winter–Early Spring: Cozy spa stays, tasting-room firesides, off-peak privacy.

Practical Travel Information

How to Reach Long Island

• By Car: From NYC via I-495 (LIE); 2–3.5 hours to East Hampton off-peak; 3–5+ on summer weekends. Tolls apply; EV charging available in many villages.
• Train: Long Island Rail Road (LIRR) to towns including Montauk, Southampton, East Hampton, Greenport (some seasonal connections). Reserve peak-season trains early.
• Coach: Hampton Jitney/Hampton Ambassador luxury coaches from Manhattan to multiple Hamptons/North Fork stops.
• Air: Fly into JFK/LGA; regional Long Island MacArthur (ISP) for closer access. Private flights to East Hampton (HTO) or Montauk (MTP) subject to regulations and availability.
• Helicopter/Seaplane: Seasonal services between Manhattan and Hamptons/North Fork (shared seats or full charters). Weight limits and weather contingencies apply.
• Ferries: Shelter Island ferries (North and South), Cross Sound Ferry (New London–Orient Point) for New England connections.

Accommodation Options

Hamptons

• Topping Rose House, The Roundtree Amagansett, Baker House 1650, The Reform Club.
• Indicative rates: $600–$1,800+ per night in peak season; 2–7 night minimums may apply.

Montauk

• Gurney’s Montauk Resort & Seawater Spa, Marram, Hero Beach Club.
• Indicative rates: $450–$1,200+ per night peak; spa/sunbed fees may apply.

North Fork

• The Menhaden (Greenport), Sound View Greenport, Jedediah Hawkins Inn.
• Indicative rates: $250–$900+ per night depending on season and room type.

Shelter Island

• The Pridwin Hotel & Cottages, Shelter Island House.
• Indicative rates: $300–$900+ per night peak; ferry access required.

Gold Coast

• Oheka Castle Hotel, The Garden City Hotel.
• Indicative rates: $300–$1,000+ per night; event weekends book early.

Note: Rates vary widely by season and weekend/weekday. Taxes and resort fees are additional. Some beaches require town permits or day passes for parking—plan ahead.

Estimated Costs for Luxury Packages

• 3-day Hamptons wellness (2 guests): $3,500–$8,000+.
• 5-day North Fork wine & sail (2 guests): $5,000–$12,000+.
• 7-day ultimate circuit (2 guests): $12,000–$25,000+.

Typical à la carte pricing (subject to change, seasonality, and vessel/venue):

• Helicopter NYC→Hamptons: $1,000–$1,500+ per seat shared; $3,000–$6,000+ private charter each way.
• Seaplane shared seat: ~$600–$1,200+ per person, route-dependent.
• Yacht day charter (35–60 ft): $2,500–$6,000+ plus fuel/gratuity.
• Reserve wine tasting with guide: $75–$200+ per person.
• Private chef in-villa: $150–$300+ per person (menu-dependent) plus staff/gratuity.
• Spa 60–90 min treatments: $200–$450+ per person.
• Beach club cabana/daybed: $200–$1,000+ per day (limited availability).

Local Luxury Experiences: Food, Shopping & Culture

Food & Dining

• Fine dining: Nick & Toni’s (East Hampton), Le Bilboquet (Sag Harbor), 1770 House (East Hampton), Jean-Georges at Topping Rose (Bridgehampton).
• Seafood standouts: Duryea’s (Montauk), Crow’s Nest (Montauk), Frisky Oyster (Greenport).
• Casual chic: lobster rolls at “Lunch,” farm cafes, and vineyard lunches with reserve pours.
• Tips: Book 2–4 weeks ahead in summer; ask for terrace or waterfront tables at sunset.

Shopping

• East Hampton & Southampton: designer flagships, art/books/home decor.
• Sag Harbor: indie boutiques and nautical chic.
• Americana Manhasset (North Shore): luxury labels in a landscaped open-air setting.

Culture & Hidden Gems

• Parrish Art Museum (Water Mill), Guild Hall (East Hampton), LongHouse Reserve.
• Pollock-Krasner House & Study Center (appointments recommended).
• Lighthouses: Montauk Point, Horton Point (Southold) for photo-worthy vistas.

Traveler-Specific Tips

For Families

• Choose suites or cottages with kitchenettes; look for lifeguarded beaches.
• Kid-pleasers: Long Island Aquarium (Riverhead), easy bay beaches, farm visits.
• Bring sun protection, light layers, sand-friendly strollers; book early dining slots.

For Honeymooners & Couples

• Sunrise beach walks, private sails, couples spa rituals, sunset tastings.
• Consider midweek stays for privacy and premium suite availability.

For Friends & Celebrations

• Villa or multi-room inn buyouts; driver for winery days and nights out.
• Plan a signature moment: yacht day with catered lunch or clambake on the beach (permitted areas only).

General Safety & Planning

• Beach permits and parking rules vary by town; secure passes in advance where possible.
• Summer weekends bring heavy traffic—arrive Thursday or early Friday; depart Monday or early morning.
• Tipping norms: 18–22% for dining and car services; 10–20% for charters and spa, per policy.
• Weather can change quickly on the coast; have flexible plans for boat/air services.

FAQs

Q: When is the best time for a luxury Long Island trip?

A: June–September offers peak beach weather and events. May–early June and September–October deliver milder crowds, great dining, and wine harvest—excellent for luxury value and availability.

Q: Do I need a car in the Hamptons/North Fork?

A: Not strictly, but a car or driver adds convenience. Town centers are walkable, and ride-hailing is limited late nights. Many luxury packages include a chauffeured SUV for transfers and daily outings.

Q: Are Long Island beaches private?

A: Most beaches are public, but parking often requires town permits or day passes for non-residents. Some resorts offer beach access or shuttles; confirm details before arrival.

Q: How far in advance should I book?

A: For peak summer weekends, secure lodging 3–6 months ahead; restaurants and spa 2–4 weeks; yacht/air charters as early as possible, especially for holidays.

Q: Can I get day access to beach clubs?

A: Limited and highly seasonal. A few venues offer daybeds or cabanas for non-guests; availability varies and often sells out. Packages that bundle resort stays may include priority access.

Conclusion

Long Island blends coastal beauty with polished hospitality: beachside spa days, reserve wine tastings, yacht adventures, and artful evenings. With smart routing between the Hamptons, Montauk, North Fork, and the Gold Coast—and advance planning for permits, transfers, and reservations—you can craft a seamless luxury escape that feels worlds away yet sits right next to New York City.