Make the Most of Southold
One of the North Fork’s most iconic landmarks sits right in Southold, perched above the Long Island Sound at the end of a quiet road through farmland. The bluff at Horton Point offers sweeping views of the Connecticut shoreline across the water, and the lighthouse grounds are open for exploration on weekends throughout the season. It is the kind of place that earns its reputation. Arrive for the view and stay longer than you planned.
Southold is bordered by both Peconic Bay to the south and the Long Island Sound to the north, which means the water is never more than a few minutes away in any direction. Town Beach and Founders Landing offer easy bay access for swimming, kayaking, and paddleboarding, while the Sound side draws anglers and those who simply want a quieter stretch of shore. After a day on the water, your Luxury Beach Getaway home is the right place to rinse off and watch the light change over the bay.
Southold sits squarely in the center of the North Fork wine trail, with acclaimed vineyards in every direction. Shinn Estate, Corey Creek, and Bedell Cellars are just minutes away, and the broader trail stretches from Mattituck to Greenport with dozens of tasting rooms in between. Spend a leisurely afternoon working through a few favorites, or find a vineyard lawn worth settling into for the afternoon. Either way, a bottle or two finds its way back to your Luxury Beach Getaway home for the evening.
Greenport is just a short drive east and delivers everything a harbor town should, with waterfront dining, independent shops, a carousel, and ferry access to Shelter Island. Cutchogue is equally worth a visit for its historic village green and concentration of excellent wine tasting rooms. Both make for easy and rewarding day trips, with your Luxury Beach Getaway home in Southold always a comfortable place to return to at the end of the day.