When it comes to catamaran and sailing charters in the Florida Keys, Calypso Sailing is your place to go. We have a lot of experience in Key West, and have a diverse fleet of vessels ready for all of your needs. The team here at Calypso Charters prides itself on decades of experience in expertly guiding families, commercial parties, and couples through their Florida Keys sailboat charter adventure. 

As you are looking to book your ultimate vacation to the Florida Keys, we’ve put together some of the most important reasons you should consider pursuing a charter with Calypso Sailing and what you need to be aware of moving forward. 

Why a charter?
Fun: First and foremost, pursuing a sailboat charter is fun. You can spend as much time as you’d like on the water enjoying the beautiful weather of the Florida Keys and enjoying the company of your friends and family. From snorkeling to swimming, you have options! 
Freedom: We just talked about the fun you can have, but what about the freedom that a charter can bring you? With traditional vacations you might have to book all of your travel and you are restricted to certain times and destinations. With a sailboat charter, you’re free to go where you want when you want. Sail the seas with your closest family and travel up and down the coast of the beautiful Florida Keys. Visit port cities, experience nature preserves, go swimming, snorkel your way through the ocean, and island hop whenever you want. You are truly in control when it comes to renting a sailboat charter. The best part? You will be able to avoid the tourists.
Dining: One of the best things about a sailboat charter is that you can easily sail around Key West to some of the best dining spots on the coast. If dining out isn’t your thing, not a problem. Our chartered catamaran comes with an option for provisioned dining, meaning you can choose to have a pre-stocked grocery list before you even leave the bay. Your catamaran will come stocked with your favorite foods, the best ingredients for your recipes, and your children’s favorite snacks.
The Scenery: You’ve traveled to Key West for the scenery - what’s better than experiencing the ocean from your private charter? Travel the gorgeous waters with friends and family during the day. Experience the beautiful starry night from your ship’s deck and get a spectacular view of the stars away from the city lights.

Can I afford it?
Sailboat charters are more affordable than you’d expect - particularly when splitting the cost with family or friends. However there are a few things you can do to lower the price even further. The earlier you book a charter, the more you save. Not only this, but you will have plenty of available dates and times to choose from. By booking early, you will also avoid paying surging prices for rentals and you’ll pay the lowest price possible. 

Also, take advantage of current promotions sailboat companies are having and check Groupon for any lower prices. When looking at Calypso Sailing Charters, always feel free to contact us to learn more about our rental prices and how we can take your vacation to the next level. 

What does Calypso Sailing Charters Offer? 
We have a number of different options to meet your sailing needs, including: 
Catamaran Charters: Our Catamarans are the top of the line and offer you the luxury experience you deserve. 
Bareboat Charters: Bareboat Charters give you the chance to create your own yachting experience - you’re in charge! 
Provisional Service: We’ve already mentioned this, but we want to let you know again! We can get your trip off on the right foot with all the food and drink you need to make an impact. 

Boating Safety
Boating safety is top priority when renting with Calypso Sailing Charters. When preparing for your voyage, keep an eye out on the weather and be prepared. It’s good to check weather every few days leading up to your trip and stay in contact with your charter company to be fully prepared. Prepare for all possible situations and have an emergency preparedness plan ready. For example, if a man goes overboard what will you do? If your steering fails how will you regain control? Somethings you won’t have to worry about if you have a manned charter. 

No matter what, have emergency names and numbers ready for the company and know where the medical supplies are and how to administer them. Make sure you, as well as all those on board, are familiar with safety equipment and proper procedures. 

Your Next Steps
Now that we’ve convinced you, you might be wondering about your next steps, take a look: 

• Complete our booking request form 
• We will be in contact with you afterwards
• Once you’ve been approved - submit to us your sailing itinerary and dates
• Review and sign our contract agreement
• Decision Time - Would you like to captain the vessel yourself, or would you like to hire a crew
• Confirm your snorkel size, and those of everyone else on the trip
• Review the Leopard Manual 

Our Bareboat Charter does require some additional steps after booking - including a vessel orientation and introduction by a licensed captain. Bareboat charters do require previous sailing experience in a similar sized boat, and those interested in booking will need to undergo an captain assessment. A float plan will also need to be drafted to ensure full safety and accountability while on your trip. 

Have we convinced you? When you set sail with Calypso Sailing Charters, the waters in and around the city of Marathon are yours to visit as you like. Those who visit the Florida Keys return season after season and have the luxury of avoiding overcrowded beaches, congested theme parks and experience the crisp, warm waters of the Florida Keys. We are looking forward to seeing you this season in Key West! Contact us at Calypso Sailing Charters where we can answer all of our questions, address your concerns, and help you book the vacation of your dreams.