easy
2–3 hours
Suitable for all fitness levels, including beginners and families with children.
Discover family-friendly sailing adventures with Chatham Sailboat Rentals in Great Barrington, Massachusetts. Experience expert guidance, pristine waters, and the perfect escape on Hobie Cats and Hobie Waves.
Wear sunscreen, sunglasses, and a hat to protect against strong sun exposure while on the water.
Show up ahead of your booking time to get a thorough briefing and familiarize yourself with the boats safely.
Choose footwear that can get wet and supports footing on the boat and when accessing sandbars.
Review local wind and weather forecasts before heading out to ensure safe and enjoyable sailing conditions.
Sailing in this region dates back decades, with local businesses like Chatham Sailboat Rentals preserving traditional sailing culture alongside modern recreation.
The company emphasizes responsible boating practices to protect marine habitats and keeps the waters clean for wildlife and future visitors.
Mandatory for safety while on the water, provided by the company but always good to bring your own fit.
Protect your skin from prolonged sun exposure during sailing trips.
summer specific
Keeps you comfortable if you get splashed or spend time on the beach.
summer specific
Helps with traction on wet surfaces and walking on sandbars safely.
summer specific