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Exploring Shelter Island from the bay allows you to notice aspects of its natural beauty you would miss at a faster pace. (Credit: Tara Smith)

A warm sun graced Coecles Harbor last Thursday and calm waters provided a relaxed kayaking trip with Adam Mills, the owner of Kayak Shelter Island. Experiencing the Island from a kayak can be compared to how you would see it while strolling or biking instead of driving by in a vehicle. At a slow pace, you notice aspects of its natural beauty you would miss at a faster pace.

Just ask Mills, who spent 25 years working in the city before relocating to Shelter Island and buying the business from previous owner Jay Damuck. He worked for Damuck during the summer of 2020, and after Labor Day that year, he purchased the business. The former operator is frequently on site, offering advice to boost the success of the business, Mills said.

Shelter Island wasn’t new to him. He summered on the Island as a youth and was a lifeguard at Crescent Beach in the 1990s, staying with his grandparents, who had emigrated from Estonia to the United States. He lives in their house now.

He once envisioned a career teaching music, but early on decided it wasn’t for him and ended up in New York City working for a beer distributor where, for 25 years, he dealt with customers, filling their orders and often convincing them to try different brands they hadn’t considered and making sure the right stock was on delivery trucks.

When his company merged with another and he was ultimately offered overnight work in a warehouse in the South Bronx at half his salary, he decided on a life on the waters of Shelter Island.  

Last Thursday, two kayakers new to the sport, joined him at the Burns Road ramp. He had them don life jackets and instructed them in how to use a paddle. Instructions finished, he and a staffer — Shelter Island Buck right fielder Billy Sullivan — helped the newbies into their boats at the edge of the ramp where Billy eased them into the water.

Meeting the two kayakers on the water later, they seemed to be totally enjoying the experience and were debating whether they had time to visit Town-owned Taylor’s Island. Those familiar with the area know they can paddle out to Taylor’s Island and, if they choose, even bring a picnic lunch and go ashore. They can also observe the beauty of the Mashomack Preserve, which belongs to The Nature Conservancy. Those going out on their own are told that, except for Taylor’s Island, they shouldn’t land around Coecles Harbor where private houses dot the landscape. But, of course, in an emergency, a kayaker should pull onto any property if possible and Mills or a staff member will respond to assist.

Most of those who rent kayaks choose the self-guided tours as opposed to joining a group, Mills said. 

A day like Thursday was perfect. Other boat traffic was non-existent, winds were calm and being on the water is arguably the most peaceful way to experience the best of Shelter Island. Islanders are accustomed to seeing man-made platforms with osprey nests. But from the water, you can observe bird-created osprey nests in trees surrounding the water. As the kayakers paddled near enough to observe one nest more closely, a territorial osprey looked down,  signaling not to come any closer.

Mills said there are frequent turtle sightings, though none were spotted last week. He’s already seen some small jelly fish, predicting they would increase in numbers and size as the water heats up after what has been a cool, cloudy and sometimes rainy spring. On this day, the air was comfortably warm and the water didn’t feel cold.

Choosing a seasonal business wasn’t going to be extremely lucrative, he knew. But gave Mills enough income, while obviously filling his soul.

You can book a self-guided or group session at Kayak Shelter Island by calling Mills at 631-749-1990. To learn more about special tours, visit the website at