Montauk Seaside Luxury Experience for 4 for 3 nights

Beyond the Hamptons, lies its saltier sister, Montauk, where luxurious dining and accommodations sit alongside world-class surfing, fishing, and hiking. This 4-person package includes a 3 night stay at the Crow's Nest Inn (2 rooms), an exclusive, 14-room waterfront hotel, known for its magical sunset views, romantic atmosphere, and exceptional Mediterranean-inspired food. You'll experience the best Montauk has to offer with a private fishing charter, followed by dockside drinks, and a cook-what-you-catch dinner. The next day, you'll head out into the waves with a private surf lesson at one of the East Coast's most iconic beaches, Ditch Plains, followed by a sandy beach lunch. All meals are included, and feature Montauk's impressive array of fresh seafood, paired with waterside views. Your hosts, Giving Kitchen supporters Jamie Hyder and Michael Trotter, are excited to share their beloved Montauk with you!

• Available Monday-Friday in the first two weeks of June 2026 only.
• Based on double occupancy (2 rooms)
• Gratuity is NOT included and the winner is responsible.
• Travel not included.
• 21+ Only.

POSSIBLE ITINERARY:

Day 1:
Arrive via Train or Car - 2.5/3 hours from NYC
Check In @ Crow's Nest
Option for:

• Bike Ride
• Beach Time (quick bike ride) - Ditch Plains is the closest beach, and famous for surfing
• Ditch Witch is a famous food truck there
• Paddle Boarding on Lake Montauk
• Montauk Lighthouse Visit
• Sunset Drinks @ Crow's Beach Bar
• Dinner @ Crow's - Their lobster pasta is my FAVE

Day 2:

• Breakfast @ Crow's
• Fishing Charter w/ Capt Pete (I've chartered 3 times with him in the past)
• Lunch on board - couple great local sandwich spots
• Waterside drinks at Montauk Yacht Club - at dock where we meet/end charter
• Cook our Catch Dinner @ Star Island Grill - Casual waterfront spot
• Option: Salty Post-dinner drinks

Day 3:

• Breakfast @ Crow's
• Surf Lesson w/ Corey's Wave
• Waterfront Lunch @ Duryea's
• Afternoon Option for:
• - Bike Ride
• - Beach Time
• - Paddle Boarding
• - Montauk Lighthouse Visit
• Drinks TBD - Crow's or other options
• Dinner TBD - Crow's or other options

Day 4:

• Return to NYC