Discover the Hamptons - Chic Coastal Escapes on Long Island

• Day 1: Coastal Elegance & East Hampton Charm

  • Morning (11:00 AM - 1:00 PM) Arrival and Check-in: Arrive in East Hampton and check into your chosen upscale boutique inn (e.g., The Hedges Inn, The Maidstone Hotel, or a similar charming property in the heart of East Hampton). Take some time to settle into your luxurious surroundings. This itinerary assumes a two-night stay at an average of $450/night, totaling approximately $900 for accommodation for two. Parking is usually included at inns; if not, municipal parking lots are available.
  • Afternoon (1:00 PM - 6:00 PM) Gourmet Lunch & Boutique Browsing: Head to Nick & Toni’s (136 N Main St, East Hampton, 0.5 miles from Main Street) for a sophisticated Mediterranean-inspired lunch in a beautiful setting. Expect to spend $80-120 for two. Post-lunch, stroll along Main Street and Newtown Lane (within 0.1-0.3 miles). Indulge in high-end boutique shopping at stores like LoveShackFancy, Ralph Lauren, and various local art galleries. Allow 2-3 hours for browsing. Beach Relaxation: Drive to Main Beach (1.5 miles from town center, ~5 min drive). Spend a couple of hours relaxing on the pristine sands, listening to the waves. Parking at Main Beach can be challenging in peak season; aim for late afternoon when crowds thin, or use a ride-share service ($10-15 each way).
  • Evening Sunset Cocktails & Fine Dining: Return to your accommodation to refresh. Enjoy pre-dinner cocktails at The Palm East Hampton (94 Main St, East Hampton) known for its classic atmosphere and superb drinks ($40-60 for two). For dinner, experience the renowned seasonal American cuisine at The 1770 House Restaurant (143 Main St, East Hampton, 0.2 miles from The Palm). A truly luxurious meal with wine will be $250-350 for two.

• Day 2: Vineyard Views & Sag Harbor’s Allure

  • Morning (9:30 AM - 1:00 PM) Leisurely Breakfast & Scenic Drive: Enjoy a gourmet breakfast at your inn (often included, or a separate cost of $30-50). Afterward, embark on a scenic drive to Sag Harbor (approximately 15-20 minutes, 8 miles from East Hampton). Explore the charming historic village, walk along the waterfront, and admire the yachts at the Sag Harbor Yacht Club. Visit the Sag Harbor Whaling & Historical Museum ($10 per person entry) to delve into the village’s rich past. Allow 2-3 hours for exploration.
  • Afternoon (1:00 PM - 5:00 PM) Waterfront Lunch: Have a delightful lunch overlooking the harbor at The Beacon (8 West Water St, Sag Harbor). Expect $80-120 for two for fresh seafood and exquisite views. Winery Experience: Drive to Wölffer Estate Vineyard (139 Sagg Rd, Sagaponack, 10-15 min drive from Sag Harbor). Indulge in a sophisticated wine tasting experience in their beautiful tasting room or on the idyllic patio ($30-50 per person for a flight/glass). Allow 1.5-2 hours to savor the wines and atmosphere.
  • Evening Sunset Dinner: Return towards East Hampton (10-15 min drive). Enjoy a spectacular sunset dinner at Moby’s (341 Pantigo Rd, East Hampton, 2 miles from town center) for fresh seafood and a vibrant, chic atmosphere. Dinner for two with drinks will be $180-280. Optional: If you prefer a quieter, more intimate setting, consider The American Hotel (45 Main St, Sag Harbor, 15 min drive from East Hampton) for a classic Hamptons dining experience.

• Day 3: Serenity, Art & Farewell

  • Morning (9:00 AM - 12:00 PM) Morning Wellness & Farm Fresh Breakfast: Start your day with a tranquil walk or a morning yoga session (many inns offer partnerships or local studios like Kula Yoga in Bridgehampton, 15 min drive). Enjoy a final exquisite breakfast at your inn, or venture out to Jack’s Stir Brew Coffee (146 Montauk Hwy, Amagansett, 10 min drive) for organic coffee and freshly baked pastries ($20-30). Art & Culture: Visit the Parrish Art Museum (279 Montauk Hwy, Water Mill, 15 min drive from East Hampton, $20 per person entry). Explore its impressive collection of American art with a strong focus on Long Island artists and their landscape. Allow 1.5-2 hours.
  • Afternoon (12:00 PM - 3:00 PM) Chic Farewell Lunch: Return towards East Hampton for a final memorable lunch. Consider Cittanuova (29 Main St, East Hampton) for delicious Italian fare in a bustling, stylish setting, or Fresno (8 Fresno Pl, East Hampton) for upscale American cuisine. Budget $70-120 for two. Last-Minute Souvenirs & Departure: Take a final stroll through East Hampton for any last-minute souvenir shopping or to capture a final photograph. Check out from your accommodation and begin your journey home, refreshed and rejuvenated from your luxury Hamptons escape.

Estimated Total Budget for 2 People:

• Accommodation (2 nights): ~$900
• Dining (3 Breakfasts, 3 Lunches, 2 Dinners + Cocktails): ~$1020
• Activities (Museums, Wine Tasting): ~$130
• Transportation (Gas/Parking/Ride-share estimates): ~$100
• Total Estimated Cost: ~$2150 This leaves a comfortable buffer of ~$350 within your $2,500 budget for any additional shopping, extra drinks, or slightly higher dining preferences.

• Day 1: Southampton Elegance & Coastal Charm

  • Morning (10:00 AM - 1:00 PM) Arrive in the Hamptons and head directly to Southampton. Begin your exploration with a leisurely stroll down Main Street and Jobs Lane, famous for their upscale boutiques, art galleries, and historic architecture. Admire the grand Gilded Age mansions from the street. Consider popping into The Southampton Arts Center (free admission, donations welcome) to see current exhibits.
    • Distance: If driving from NYC, approximately 90 miles (1.5-2.5 hours, depending on traffic). Parking in Southampton can be found in municipal lots or on side streets (metered or 2-hour limits).
    • Practical Tip: Arrive early to find parking more easily, especially on weekends.
  • Afternoon (1:00 PM - 5:00 PM) Enjoy a casual lunch at Sant Ambroeus on Main Street (expect to spend $60-80 for two) or a more relaxed bite at Golden Pear Cafe ($30-40 for two). After lunch, drive to Coopers Beach (approximately 2 miles, 5-minute drive). Recognized as one of America’s top beaches, it offers stunning white sand and ocean views. Spend the afternoon relaxing by the waves.
    • Cost: Beach parking typically $50 for non-residents during peak season; often free or reduced during shoulder seasons (early June/late Sept).
    • Time: Allow 2-3 hours for beach relaxation.
  • Evening Check into your chosen charming boutique hotel or B&B in East Hampton or Sag Harbor (we’ve allocated approximately $350-400/night for 4 nights, totaling $1400-1600 of your budget). Freshen up before heading to Tutto il Giorno in Southampton for an exquisite Italian dinner by the water (expect to spend $120-160 for two, including drinks).
    • Driving: Southampton to East Hampton is about 15 miles (25 minutes). Southampton to Sag Harbor is about 10 miles (20 minutes).

• Day 2: Historic Sag Harbor & Artistic Flair

  • Morning (9:30 AM - 1:00 PM) Begin your day in the charming whaling village of Sag Harbor. Start with a visit to the Sag Harbor Whaling & Historical Museum (approx. $10-15 per person, allow 1-1.5 hours) to delve into the town’s rich maritime past. Afterward, wander along Main Street, exploring unique independent boutiques and art galleries like Grenning Gallery or RJD Gallery (free admission). Take a peaceful stroll along the village’s picturesque waterfront.
    • Distance: From East Hampton, Sag Harbor is about 10 miles (20-minute drive). Parking is available on street or in municipal lots.
  • Afternoon (1:00 PM - 5:00 PM) Enjoy lunch with a view at Baron’s Cove (expect $70-90 for two) or a more casual option like Dock House for fresh seafood by the marina ($50-70 for two). In the afternoon, explore more of Sag Harbor’s side streets or take a short drive to nearby Bridgehampton (7 miles, 15 minutes) to visit the Parrish Art Museum (approx. $20 per person, allow 1.5-2 hours) which showcases American art with a focus on Long Island artists.
    • Practical Tip: The Parrish Art Museum has beautiful grounds worth a walk around.
  • Evening Return to Sag Harbor for dinner at the historic The American Hotel (expect $130-180 for two) for a classic, sophisticated dining experience. Afterward, consider a nightcap at their cozy bar.

• Day 3: East Hampton’s Grandeur & Vineyard Delights

  • Morning (9:00 AM - 12:00 PM) Immerse yourselves in the quintessential Hamptons experience in East Hampton Village. Begin with a walk past the iconic Hook Mill and the historic Town Pond. Explore the upscale boutiques and charming shops along Newtown Lane and Main Street. Don’t miss the tranquil beauty of the Nature Trail and Marine Museum (free, donations appreciated).
    • Distance: If staying in East Hampton, all within walking distance.
    • Practical Tip: Grab coffee and a pastry at Citarella for a quick and delicious breakfast on the go ($20-30 for two).
  • Afternoon (12:00 PM - 5:00 PM) Drive to Bridgehampton (7 miles, 15 minutes) for a visit to the renowned Wölffer Estate Vineyard. Enjoy a wine tasting flight on their beautiful terrace, overlooking the vineyards (expect $40-60 per person for a tasting flight, totaling $80-120). Pair your tasting with a light lunch from their menu of cheeses and charcuterie (approx. $70-90 for two including lunch and tasting). Afterward, perhaps explore a nearby farm stand like Green Thumb Organic Farm.
    • Time: Allow 2-3 hours for the vineyard experience.
  • Evening Return to East Hampton for a memorable dinner at Nick & Toni’s (expect $140-180 for two) known for its Mediterranean-inspired dishes and celebrity sightings, or enjoy the cozy ambiance of Rowdy Hall ($100-140 for two).

• Day 4: Montauk’s Rugged Beauty & Lighthouse Views

  • Morning (9:00 AM - 1:00 PM) Embark on a scenic drive to the easternmost point of Long Island – Montauk (approximately 20 miles from East Hampton, 35-45 minutes). Your main destination is the iconic Montauk Point Lighthouse (approx. $15 per person entry, allow 1.5-2 hours), the oldest lighthouse in New York State. Climb to the top for breathtaking panoramic views of the Atlantic Ocean. Explore the museum and gift shop.
    • Practical Tip: Dress in layers as it can be windy at the lighthouse.
  • Afternoon (1:00 PM - 5:00 PM) Enjoy a casual seafood lunch at The Lobster Roll in Amagansett (on the way to Montauk, or a short drive from Montauk Point, expect $60-80 for two) for a classic Hamptons experience, or head to John’s Drive-In in Montauk for burgers and shakes ($30-40 for two). Afterward, explore Camp Hero State Park (free admission), an abandoned Cold War-era military base with fascinating remnants and stunning cliffs, or relax at Ditch Plains Beach, a popular surfing spot.
    • Time: Allow 2-3 hours for exploring the park/beach.
  • Evening For dinner, savor fresh, local ingredients with stunning water views at Harvest on Fort Pond in Montauk (expect $120-160 for two), offering family-style Italian dining. Alternatively, enjoy a more relaxed meal at a local Montauk pub or restaurant.

• Day 5: North Fork Vineyards & Farewell Sips

  • Morning (9:30 AM - 1:00 PM) Check out of your hotel. For a different vineyard experience and to fulfill the “vineyards” theme further, head towards Long Island’s North Fork wine country. You can take the Shelter Island Ferry from North Haven to Shelter Island, then another ferry to Greenport (a scenic route, approximately 1 hour total travel from East Hampton, including ferry wait/ride time; car ferry is about $20). Or drive directly via Riverhead (approx. 1.5 hours). Visit Kontokosta Winery (Greenport) for cliffside views and elegant tastings, or Macari Vineyards (Mattituck) for excellent reds.
    • Cost: Expect $25-40 per person per tasting flight ($50-80 for two at each vineyard).
    • Practical Tip: Pace yourselves; two vineyards are usually a good number before lunch.
  • Afternoon (1:00 PM - 3:30 PM) Enjoy a delightful farm-to-table lunch on the North Fork. The North Fork Table & Inn in Southold offers an upscale experience (expect $80-120 for two, including drinks), or for a more casual bite, grab gourmet sandwiches at Love Lane Kitchen in Mattituck ($40-60 for two). After lunch, perhaps a final tasting at one more vineyard if time permits, or simply browse the charming shops in Greenport Village before beginning your journey home.
    • Driving: From the North Fork back to NYC is approximately 80-90 miles (1.5-2.5 hours).
  • Evening Depart from the Hamptons and the North Fork, reflecting on your diverse exploration of Long Island’s East End.

Estimated Budget Breakdown (for 2 people):

• Accommodation (4 nights): ~$1400 - $1600 (Based on $350-400/night for a charming B&B/boutique hotel)
• Dining: ~$1000 - $1300 (Mix of casual lunches, nice dinners, coffee/snacks)
• Activities & Tastings: ~$350 - $450 (Museums, lighthouse, multiple vineyard tastings, beach parking)
• Transportation (Gas & Ferries): ~$150 - $200
• Buffer/Shopping: ~$450 - $1100
• Total: ~$4000