Boat Charters & Water Activities at Thimble Island Ventures Inc
Difficulty
easy
Duration
1.5–4 hours
Fitness Level
Suitable for most guests, no strenuous activity required
Overview
Set sail on a private boat tour of Connecticut’s Thimble Islands with Thimble Island Ventures Inc. Discover rocky coastlines, historic homes, and enjoy personalized adventures on the water.
Private Charters on the Islander- The Little Boat
For all ages! • 1, 1.5, or 2 Hours • Up to 13 passengers • Memorable evening cruise!
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About This Adventure
Experience the beauty of Connecticut's Thimble Islands with a private boat charter, perfect for friends and family. Choose from narrated or unnarrated trips, and enjoy stunning views of rocky coastlines and historic homes. Customize your adventure with a stop at Outer Island to stretch your legs and capture unforgettable memories.
Book the boat to yourself - perfect for friends and family!
Duration
1, 1.5, or 2 Hours
About
Hire out the whole boat for your small group or party. Narrated (Extra cost) or unnarrated trips through the island. You can even request a stop on Outer Island to stretch your legs! A private boat charter in Thimble Islands offers a unique opportunity to explore the beauty of this archipelago in Connecticut. You can enjoy the stunning views of the rocky coastline, hidden coves, and historic homes while cruising around the islands.
What to bring
- Camera
- Light Sweater
- Water
Adventure Tips
Bring Sun Protection
Wear sunscreen, hats, and sunglasses to stay comfortable during sunny boat trips.
Book in Advance
Private charters are popular; reserve early to secure your preferred date and time.
Wear Appropriate Footwear
Choose non-slip shoes suitable for getting on and off the boat safely.
Bring a Camera
Capture scenic views and wildlife along the route with a good camera or smartphone.
Local Insights
Wildlife
- Harbor seals
- Ospreys
History
The Thimble Islands have been inhabited since the 1800s and were originally used for fishing and quarrying.
Conservation
The area emphasizes sustainable boating practices to protect local wildlife and promote environmental health.
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Adventure Hotspots in Bridgeport
Frequently Asked Questions
Recommended Gear
Sunscreen
Protects your skin during sunny trips on the water.
summer specific
Hat and Sunglasses
Shield your eyes and face from sun exposure.
spring, summer, fall specific
Waterproof Jacket
Keeps you comfortable during cooler, unpredictable weather.
winter specific
Camera or Smartphone
Capture scenic views and wildlife sightings.
spring, summer, fall, winter specific