I've had a wonderful six week run of staying in the tri-state area until last week's trip to Canada. It's given me the chance to explore Long Island, upstate New York, and Connecticut on the weekends and visit old favorites while discovering new places. The Thimble Islands are totally under-the-radar but make for a great afternoon, with three different boats doing 45 min-1 hr narrated tours of the 23 islands within a three-mile radius. You don't get off on the islands, because they're privately owned. I kept imagining a really wonderful, luxurious B&B on one of them!
Many of the islands have just one Victorian-style home on them, and it feels like you're taken back 150 years. Our guide was full of fun tidbits, like Tom Thumb came to one of the islands to court another little person and circus performer, Miss Emily. And President William Howard Taft made the Thimble Islands his summer White House for a short time.
All three of the boats leave from Branford, CT and if you just show up, one is likely to leave within 15-20 minutes of your getting there. We went on Captain Bob's Thimble Island Cruise.
My aunt lives in Fairfield, CT so on the way to Branford, we stopped in nearby Guilford for a Connecticut-style lobster roll (butter and no mayo) at Guilford Lobster Pound. Perfect summer day!