Isle of View Charters

Like Us On: Like Us On Facebook

Call Us Today! (305) 783-8433


Book Today!

Airbnb and Sailboat Charters in Key West, FL

Experience the breathtaking view of the Florida Keys with Isle of View Charters. Our sailboat charters in Key West, FL, allow your party to experience the sights and sounds of the ocean. Whether staying aboard one of our boats through Airbnb or taking advantage of the many options available through our sailing charters, you cannot go wrong. Call us today to learn more about our various sailing tours and Airbnb options.

With our decades of experience and personalized approach to service, experiencing the perfect getaway is a simple and stress-free experience. We would be happy to discuss availability, pricing, trip customization, and much more. From overnight boat tours to multiple day trips, we’ll help you build the perfect sea adventure package.

Looking over deck

Our Boats

Accommodating Sailboat Airbnb in Key West, FL

Our Accommodations

Contact Us for Sailing Tours in Key West, FL

Contact Us

Create the Ideal Excursion: Personalized Sailing Options Available

The Florida Keys is home to a vibrant community, diverse wildlife, and life-changing ocean views. From the lights and sounds of the nearby towns to the salty air and brisk breeze of the sea, there are many things to see and do in this picturesque region. Join our crew and discover what The Keys have in store for you and your party.

We offer a variety of boat charters, each highly customizable to accommodate parties of different sizes. You’ll sail with the Captain and his crew: we’re thoroughly trained and experienced, and ensure each of our guests has a safe and memorable journey.

Our boat charters can span several nights, and your itinerary may also include visits to many island groups in the Keys, including the Marquesas and the historic Dry Tortugas. Complement your journey with a variety of activities, such as fishing, kayaking, scuba diving, and more.

Whether your plans include a party at sea or a romantic getaway, the Keys and its many treasures are waiting for you. Book a sailboat charter with us today and get ready for the thrill of a lifetime.

About Us

Our owner and captain, Jeffrey Sawyer, is originally a native of Northern Pennsylvania but made the transition to the Florida Keys as a life choice. Jeff is not new to the Keys as he grew up visiting since childhood, enjoying many adventures in this picturesque environment, such as kayaking, scuba diving, and more.

Having been an experienced sailor since high school, Jeff took to the high seas over two years ago with the purchase of the sweetheart, "Isle of View," a 1969 38' Charley Morgan Classic. However, after many exciting adventures in South Florida and the Keys, Hurricane Irma ultimately claimed her at Dinner Key Marina.

Fortunately, that wasn't the end of the story, as "Isle of View II," a beautifully maintained 1985 45' Morgan Nelson Marek (later to become "Catalina Yachts"), carries her namesake. Now a USCG Master Captain, Jeff is once again embarking on sailing tours on the seas around Key West and the rest of the Florida Keys. Take part in the next adventure with Jeff and the rest of our team. We cannot wait to meet you for our sailboat Airbnb services.

Here are some comments from our guests…

"WOW!!!! Not only was the boat beyond our expectations, Jeff as a host was outstanding. We had 2 couples in the "Isle of view 2" and had plenty of room. The hotel amenities are a added bonus. Happy hour that is second to none at the Salty Oyster. Easy access to all the fun things. even a free shuttle to Key West. Just wish we had more time to take a cruise with Jeff."

—James, November 2018

"Jeff is a great host. The boat is very clean and everything was exactly as described in the listing. Hotel amenities are top notch and Marina showers are clean and just a short walk away. Free shuttle runs to Old Town on the hour. Highly recommended."

—Scott, October 2018

Check Out Customer Testimonials for Isle of View II On Airbnb


Contact us to learn more about our boat charters. We are based in Key West, FL.


6000 Peninsular Ave
Key West, FL 33040


Facebook Icon


(305) 783-8433

Service Area

Key West, FL, and the Florida Keys