PRIVATE KEY WEST SAILING ADVENTURES

🌊 Discover Ocean Sailing!

Have you ever watched sailboats drift across the horizon and thought: “That looks amazing… but I don’t know how?”
Now’s your chance to find out just how accessible — and unforgettable — sailing on the open ocean can be!

No Sailing Experience Required — your Captain will handle the heavy lifting. You decide how much you would like to participate.

⚓ Step Aboard a Private Adventure on a Beautiful Beneteau Oceanis 34.1 Sailing Yacht

Modern. Comfortable. Designed for both adventure and relaxation.
Bring up to 6 friends or family to sail on one of the world’s most admired performance cruising yachts — sleek, stable, and surprisingly easy to handle. 

👋 This Could Be You, Today!

Imagine golden light glinting off the water and a light breeze in the sails while you take the wheel! Allow our professional skipper will help you feel the joy of sailing while savoring the zen of it all.

Let us introduce you to something you always wanted to try. Discover the joy of sailing, while enjoying perhaps the most relaxing and beautiful part of your vacation.

This is what our guests experience every day — and it’s waiting for you.

💡 What to Expect

No Sailing Experience Required — your Captain will handle the heavy lifting. YOu decide how much you would like to participate.

Your Fully Private Sailing Adventure — discover where the wind will take you.

Flexible Durations — from sunset sails to overnight adventures.

Friendly, Professional Crew — focused on fun, safety, discovery, and comfort.

🌅 Ready to Try Sailing?

Start today! You don’t need experience - we will teach you everything you need to know to feel the wind in your sails. The ony prerequisites are a sense of curiosity, a love of the sea, and the desire to expand your horizons......see what we did there?

This could be you today. Book now and set sail.

📅 Book Your Sailing Adventure

Sail today, this weekend, or plan a special occasion with up to 6 family or friends.
Availability fills fast — don’t miss out and book now!

👉 Questions? Email us at ahoy@charismasailing.org or call us at 305-396-1331

💬 Sailing Trip Reviews

“We came as total beginners and left completely hooked! Our captain made everything effortless.” — Sarah T.

“The highlight of our trip. The boat was stunning, the crew was amazing, and the sunset… unreal.” — Jason L.

Ready for more?

Try a Learn-to-Sail Vacation

Would you like to try sailing? Enjoy your time on the water and experience the joy of sailing under the care of our US Sailing certified and US Coast Guard licensed instructors and captains.

You will have the opportunity to learn sailing basics such as sailing terms and wind-sensing in a fun way on a safe and stable sailing yacht. Whether close to shore or on extended trips, our instructors ensure everyone’s comfort and will make your sail an enjoyable and memorable experience.

Monohull and Catamaran Cruising Trips with Advanced Sailing Instruction

A sailing vacation is the perfect opportunity for couples or families who consider bareboat charters or boat ownership in the future to spend extended time together on the boat of your choice. Learn how to sail, work on new skills, or complete your bareboat certification. At the same time, you become familiar with how to operate all onboard systems.

We are happy to teach on your suitable sailboat, power yacht, or catamaran in South Florida. Please contact us with your goals to get started.

With a multitude of options, we can create the perfect adventure for your group! How about trying a day sail and see if a multi-day vacation is right for you?

Our friendly crew is always here for help. There’s no commitment, pressure, or obligation when contacting us. What is your dream sailing adventure?