If you haven’t explored the North Fork of Long Island, NY yet, you MUST add it to the very top of your list! From amazing wineries to sunflower fields to beautiful coastline, the North Fork really has it all! A few weeks ago I had the chance to drive out to Greenport, NY (a small town on the North Fork) with my mom and Emma and we had the BEST time. If you’re looking for a truly unforgettable summer experience, you’ll definitely want to take a trip out to Greenport, NY and make sure you book a sailing charter with East End Charters! Keep reading for all the details about sailing off the North Fork with East End Charters!

About East End Charters + The Crew

East End Charters is the most established charter company out on the North Fork and it certainly shows in their professionalism, attention to detail, and overall enthusiasm! The yacht, “Surprise” is a spacious, custom-built wooden ketch. Unlike most other yachts this size, Surprise can access secluded beaches and harbors thanks to her shallow draft. Surprise easily hosts up to 6 passengers with plenty of room on deck and below! In addition to day charters, you can also book Surprise for an overnight charter for 4 people.

Co-Owners and life partners, Captain Erick and Mate Hannah are the truest definition of a “dream team”! They are eager to create the perfect excursion for you and your friends/family! Learn about their charter options here, or create your own custom charter with the East End Charters team! We were also lucky to be joined by another crew member and Long Island native, Helena, during our sail. A HUGE thank you to Erick, Hannah, and Helena for making our afternoon out on the North Fork one of the highlights of our summer!

Learn more about Erick and Hannah here!

What Makes East End Charters Special

Captain Erick and Hannah were so genuinely friendly and easy to get along with! Have you ever gone to book a sailing charter and hesitated, wondering if the crew will be fun & easy going or if it will be an awkward few hours on the water? Even as someone who has been on many charters and has always had pleasant experiences, there was certainly a difference between my previous charters and East End Charters! Pulling up to East End Charter’s private dock (which also offers private parking, a huge plus!), felt like we were coming to visit friends versus people we’d never met before. Now that is one of the things that made this afternoon so special.

I also LOVED how knowledgable Erick and Hannah were about the area. They offered us dinner recommendations, the best places to find fresh oysters (more on this in a little bit), and stories from their experiences on the North Fork.

East End Charters’ Service

East End Charters’ commitment to service was obvious from the moment we booked our sailing charter. Hannah, who we corresponded with via email leading up to the charter, replied back to our messages quickly and with enthusiasm! Emma even said she was so excited to meet Hannah because she could just tell how awesome she was from her email exchanges! (True story!)

From the moment you step out of your car you’ll be greeted by the East End Charters crew eager to assist with your bags and guide you onto the yacht. If you choose to bring your own food & beverage, the crew will handle plating up your spread and bringing out plates, napkins, utensils, etc! The East End Charters crew arranged for us to have local oysters from Little Creek Oysters on our sail. Guys, these oysters were honestly the best I’ve had. Hands down. We brought our own bottles of Lot 170 Muscadet from my favorite, 90+ Cellars. This Muscadet is known to pair perfectly with oysters and we were not disappointed. I 100% recommend recreating this exact combination on your sail!

What To Bring

Unless you’ve arranged meals with Hannah, you’ll want to plan on bringing your own food & beverages. I also brought my favorite acrylic wine glasses that seem to travel with me wherever I go, ha! They were especially ideal for being on a sail boat! A few other things you’ll probably want to pack…

-Swimsuit
-Sunscreen
-Additional Clothing/Layers (just in case it get windy!!)
-Non-Marking Shoes (or just ditch the shoes on the dock, which is what we did!)
-Cash Tip for the Crew (customarily 20%)

More info on what to bring is linked here!

Where We Sailed…

Captain Erick navigated us around Shelter Island during our sailing excursion. I think my mom, Emma, and I all enjoyed sailing past the beautiful homes on Shelter Island and doing a little sight seeing. We even sailed past a sailing race, which was exciting!

The Perfect Charters For Any Occasion!

The next morning on our drive home from Greenport, we all agreed that East End Charters is really the perfect charter for any occasion! Surprise is spacious enough to accommodate a family, and yet feels perfectly intimate for a romantic evening for 2. As for our Girls Trip to Greenport… I think it’s going to have to be a yearly tradition!! If you’re coming from Fairfield County/Westchester County, you can certainly do an afternoon sailing charter and drive home the same day, but we really enjoyed turning our sailing charter into an overnight trip out on the North Fork!

Make sure you head on over to my IG Reels to check out a quick tour of Surprise!

Have any questions?

Feel free to drop a comment below, or reach out to East End Charters at info@eastendcharters.com !!