About

Our Story

The Islander (formerly known as "Captain Dave's Thimble Island Tours"), was first established back in the late 1980's by Dave Kusterer, who ran the business for 36 years! In 2018 as he eyed retirement, he began handing over the reigns of his beloved Islander (26' Oldport Launch) to another local, Captain Matt Pinckney.

Matt has had the good fortune to have been raised as a third generation Islander. He and his family and have spent every summer of their lives in the islands. During the other seasons, Captain Matt is a middle school teacher in Northern Connecticut.

THE TEAM

Our Crew

Captain Matt Pinckney - Owner/ operator

Captain Dave Kusterer - Previous owner and captaining sensai

Emma Pinckney- Daughter and part time first mate (with Captain Matt)

THE BOAT

The Islander - Oldport 26

The "Islander" is an Oldport 26, one of the most stable, comfortable launches in service today. She was originally designed to hold up to 26 passengers, but has been recertified to hold 14. This allows customers to have an even more spacious enjoyable experience.
About a half of the boat is shaded under a canvas, while the other half is open to the sky.

As the boat travels through the islands, there will be plenty to look at on both sides of the tour.
There is a central compartment running the length of the boat. This makes all the seats "water side" seats. This is also especially important for private charters, as it provides a stable table for all drinks, snacks and appetizers.

STAY IN TOUCH

Contact Information

Phone (or text) is the best way to reach the Captain. Please be sure to check "latest Info" tab for daily tour updates and weather cancellations.

PHONE: (203) 433-2233
or (203) 646-7369

EMAIL: thimbleislander@gmail.com

WEBSITE: www.thimbleislander.net