Starlight Sailing Charters

I have sailed with Captain Toby many times and it’s always a wonderful experience. He is friendly, knowledgeable and always willing to go above and beyond to make sure everyone has a great time. I can’t wait to sail with him and Starlight again!

A-​mazing. You know that trip where the sun is setting, the water is perfect, that boat is incredible, the captain knowledgeable and friendly and you don’t want it to ever end? This was that trip. Loved every minute of it, can’t wait to do it again.

One of the nicest days of my life. Two moms and 4 teenagers sailed with Toby on August 7. The kids had never been on a sailboat.
I should talk about Toby first. Toby made the day so wonderful with his intuitive sense of what different people need. He catered to our interests, understood our fears, and helped each one of us be comfortable in this new experience. To my more daring son, he had a kayak aboard the ship and he loved the experience. He arranged for a colleague of his to take the kids wave riding. He knew the type of restaurant we were looking for and took us to SALT in Shelter Island. We had the pleasure of eating lunch withToby and learned so much about his beautiful sailboat and his history.
And for my other son who is sun sensitive, he had the most beautifully maintained living area and bedrooms, the cleanest toilet, the charming living room and kitchen where my son could retreat when he needed it.
Toby’s entire ship was ours for the entire day. We could use anything and everything. For me, I loved that he has a very shady canopy and comfy cushions and pillows near the wheel. I loved going out to the front of the boat and sitting there as well.
I adored Toby by the end of the trip, and realized that if we had just spent the day with someone who was not as personable and kind and patient, that we would not have had the same experience.
The boat is immaculate. Seeing the islands from the boat, is peaceful and tranquil.
The next day, I was actually depressed because I knew that Toby was going on a three night excursion with a couple, and I realized that I couldn’t text him for another quick trip.
I totally recommend Toby and the Starlight Sailing Charter for anyone. Perfect day!!!

My wife and I went on an overnight sailing excursion with Toby and Starlight. A fantastic experience. The boat is beautiful, and beautifully equipped, while Toby combines impressive seamanship with 100% likability. That’s quite a rare combo!
Thoroughly recommend.