Go Sailing
Everything you need for your first sail, and a private captain when you're ready.
Book Your SailReady to Go Sailing?
Going sailing is one of the simplest ways to slow down and enjoy the water. Once the sails are up, the engine goes quiet and it's just wind, waves and open sky. You don't need your own boat, special gear or any experience to go sailing. All you need is a good day on the water and a captain who knows the way.
This guide covers what to expect, what to bring and when to go, so your first time out feels easy.
What to Expect When You Go Sailing
An easy start
Before leaving the dock, your captain shows you around the boat, where to sit and how to move around safely.
Smooth and quiet
When the sails fill, the boat leans gently and glides along. Most first-timers are surprised how calm it feels.
Hands-on if you like
Take the wheel, help trim a sail, or simply sit back and enjoy the view. On a private sail, it's up to you.
What to Bring When You Go Sailing
- Layers. A light jacket or sweater. It's usually cooler on the water than on land. See our full guide to what to wear sailing.
- Soft-soled shoes. Sneakers or boat shoes with non-marking soles. No heels.
- Sun protection. Sunscreen, sunglasses and a hat that won't blow away.
- Water and a snack. Fresh air and sunshine make you thirsty.
- A camera or phone. You'll want photos of the view.
- Seasickness prone? Ask your pharmacist about options before the trip, and keep your eyes on the horizon once you're out.
When Is the Best Time to Go Sailing?
Wind is what moves a sailboat, so timing matters. In many coastal places, San Diego Bay included, a steady sea breeze usually builds from late morning into the afternoon. That's often the best window for real sailing.
Mornings tend to be calmer, which is great for a relaxed first sail. Sunset sails trade a little wind for beautiful light and cooler air. And in a mild climate, you can go sailing year-round. Curious how the wind actually moves a boat? Read how wind power drives a sailboat.
Go Sailing FAQ
Do I need experience to go sailing?
No. With a captain on board, you can go sailing with no experience at all. Learn as much or as little as you like, or simply relax and enjoy the ride.
Will I get seasick?
Bays and harbors are usually much calmer than the open ocean, so most people feel fine. If you're prone to motion sickness, ask your pharmacist about options before the trip, stay in the fresh air and keep your eyes on the horizon.
What if there's no wind?
Most sailboats also have an engine, so you'll still get out and back on time. Light-wind days are often the calmest, most relaxing sails.
Can kids go sailing?
Yes, kids usually love it. Make sure every child wears a properly fitted life jacket, and ask your captain about age guidelines when you book.
Can I go sailing if I can't swim?
Yes. Many non-swimmers go sailing safely. Wear a life jacket, let your captain know, and stay seated when asked.
How long should my first sail be?
Two to three hours is a great first sail: long enough to settle in and enjoy it, short enough that nobody gets tired or chilly.
Go Sailing With a Private Captain
When you're ready, join a shared sail or book the whole boat on San Diego Bay. An experienced captain handles everything, so all you have to do is enjoy it. Wondering about price? See how much it costs to go sailing.