Maidstone Harbor Yacht Charter
Maidstone Harbor Yacht Charter – Captain’s Log August 26, 2025
Route: Sterling Harbor, Greenport, NY → Maidstone Harbor, East Hampton, NY → Shelter Island and Maidstone Harbor Yacht Cruise
Departure Time: 11:30 AM ET
Fuel at Departure: 100%
Crew Onboard: Captain Tim, First Mate Michaeline, First Pup Ivey 🐶
Weather: 70°F, bright sunshine, crisp fall-like feel
Wind: NW at 9 mph
Seas: Flat, calm, glass-like conditions
Distance: ~20 nautical miles, including loop around Shelter Island
Notes from Port:
We departed Sterling Harbor Marina in Greenport to begin our Maidstone Harbor yacht charter. Our stay in Greenport was warm and welcoming. The town continues to charm with its small-harbor vibe and excellent marina hospitality. Special thanks go to Christian, who made sure we had the most comfortable stay. Overall, Sterling Harbor is a standout in the Safe Harbor family and a top choice for any Greenport yacht charter.
Course:
From Greenport, we cruised smoothly into the Peconic Bay. The waters around Shelter Island were calm, offering stunning views of the shoreline. With flat seas and bright sunshine, it was the perfect setting for a leisurely yacht cruise. After circling Shelter Island, we continued south toward Maidstone Harbor in East Hampton.
Crew Notes:
The glassy conditions made for a relaxed ride. First Mate Michaeline enjoyed the smooth passage, while Ivey stretched out in the sun on deck. Spirits were high as MagicTime made her way to our next destination.
Remarks:
This leg of our journey blended the charm of Greenport, the beauty of Shelter Island, and the tranquility of Maidstone Harbor. Greeport highlights include Aldo’s artisan roasted coffee, unquestionably, the best coffee of the summer and a ferry ride to Leon1909 on Shelter Island for the best dinner of the summer! Additionally, the calm approach into East Hampton’s Maidstone Harbor — certainly a quintessential late-summer Maidstone Harbor yacht cruise.