Day 1: Cruising and Coastal Wildlife
Start on the water with the Tiki Boat Enchanted—a custom floating lounge. Pair leisure with education by connecting with the Coastal Research and Education Society of Long Island (CRESLI) for expert-led whale watches and marine discovery cruises. Unwind for the evening at The Ocean Bay House, a restored 1800s colonial boutique bed-and-breakfast on Watchogue Creek in Bay Shore.

Day 2: Pier Fishing and Historic Dining
Head down to Captree State Park at the tip of Jones Beach Island. A true fisherman’s haven, Captree features a busy boat basin packed with charter boats for sightseeing and deep-sea fishing. For dinner, head to Tellers: An American Chophouse, an iconic dining institution housed in a grand, renovated bank building featuring a historic vault wine room.

Camping Option: Pitch a tent or rent a cottage right on the Great South Bay at Heckscher State Park.

Day 3: Inlets and Main Street Charm
Travel east to Shinnecock Inlet at Shinnecock East County Park. This tight ocean channel is celebrated for premier sport fishing, particularly for large bass and bluefish. Retreat to the Southampton Inn, which offers upscale accommodations nestled on five acres within walking distance of Southampton village’s boutiques and restaurants.

Camping Option: Swap the saltwater for fresh water by camping at Sears Bellows County Park in the Long Island Pine Barrens.

Day 4: Legendary Surf Fishing in Montauk
Drive to the furthest tip of the South Fork to explore Montauk Point State Park. The coastal terrain leads right to the historic Montauk Lighthouse and offers world-class surf fishing where you can watch the unique, churning “race” of converging ocean tides. Afterward, head to Duryea’s for a chic, casual seafood experience overlooking Fort Pond Bay.

Camping Option: Secure a campsite right on the oceanfront at Hither Hills State Park.

Day 5: Whaling History on the North Fork
Cross over to the North Fork for a quiet morning at Laurel Lake, a serene, foot-accessible freshwater spot. Next, explore historic Greenport Village. Once a major hub for whaling fleets, the downtown is now perfect for browsing waterfront shops, booking a private sail through East End Charters, or catching the day ferry to Shelter Island.

Camping Option: Book a luxury glamping safari tent at Eastern L.I. Kampgrounds.

Discover Long Island:
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