Castles, Crustaceans, and Coastline

Make a pit stop on your journey and savor a breakfast at My Three Sons Bagel Cafe. This welcoming family-owned café offers a variety of mouthwatering bagels with an array of tasty fillings.

Book the one-hour tour of historic Oheka Castle days ahead, and arrive with plenty of time to start the tour of this Gatsby-era mansion, listed on the National Trust for Historic Preservation.
The opulent estate was also used in Taylor Swift's popular video for her hit song "Blank Space," though it's worth a closer look on the tour, which lasts about an hour.

You're finally heading into prime seafood territory. About half an hour outside of Montauk, New York, Harbor Market & Kitchen in Sag Harbor, New York, creates splendid farm-to-table fare and a helluva lobster roll (warm buttered lobster, toasted split-top bun, swipe of mayo.) Also get fruit salad and muffins to go to store in the mini fridge in the kitchenette in your guest room for breakfast in the morning.

About half hour from Harbor Market you'll find your resort for the night, Driftwood on the Ocean. Nestled on a quiet stretch of sand in Amagansett, New York, the mid-range property with beach-house vibes sits on a quiet stretch of Amagansett Beach with outdoor lounge chairs. All units have kitchenettes or kitchens, and some have patios or decks that overlook the ocean. There's even an outdoor pool with lounge chairs, grills, and picnic tables, and yoga and Pilates on the beach in addition to a communal lounge and Free Wi-Fi.
Check in, drop your bags, fill the minifridge in your room with your goodies from Harbor Market, then grab your suit and drive to nearby Ditch Plains Beach.
Please note: There is resident-only parking near Ditch Plains Beach, so you have a couple of options: either park in a remote parking lot and enjoy a scenic 30-minute walk through the state park, or take a cab directly to the beach.

Park at this parking lot near the Shadmoor State Preserve and venture forth on foot to Ditch Plains Beach, a beautiful walk along the ocean.

Blend with the surfers and sunbathers on Ditch Plains Beach, where you can relax and unwind after your road trip.
This delightful beach beckons both seasoned wave riders and those just starting out, thanks to its remarkably long break and ideal surfing conditions. However, don't think that Ditch Plains Beach is only for surfers! It's also a fantastic destination for families and beach lovers seeking relaxation and the chance to bask in the sun.

Head back to the car and drive to nearby Harvest on Fort Pond for a lovely sit-down dinner on the patio.

Enjoy a beautiful sunset over Fort Pond as you indulge in a menu of fresh seafood and locally-grown produce. The restaurant has family-style service, a stream of loyal customers, and a friendly atmosphere.

When you've had your fill at the restaurant, return to Driftwood Resort and turn in for the night.