Whether you’re planning a family vacation for this winter, or simply brainstorming ideas about the approaching summer, planning the ultimate family faction is never an easy task. You’ve heard about the types of trips your friends and neighbors have gone on —large theme parks, National Parks, popular beach destinations. Those types of family vacations are well and good —but are they really as memorable and endurable of an experience as sailing with your family in the Florida Keys? Of course not —because few activities are. 

All too often, family vacations devolve into a series of logistical frustrations and uncomfortable circumstances that arise from that your vacation takes place amongst, well, hundreds of other vacationers. Now what kind of way is that to spend your hard earned time off? Spending time with loved ones should have to be about battling crowds or standing in line. 

When you plan your vacation with Calypso Sailing, it’s not just another vacation. You and your family members will be creating lifelong memories in ways that few other vacation experiences can provide. At Calypso Sailing, we open up the sparkling waters surround Key West to your own unique adventure —an experience that big box theme parks and crowded resorts can’t hold a candle to. 

5. Provisioned Dining:

Did you know that each chartered catamaran comes with an option for provisioned dining? Calypso sailing options provides your family with pre-departure grocery lists so that your vessel will be complete stocked with all the foods and beverages you want for your journey. So whether you’d like to prepare a family classic while at sea, or want the proper ingredients on board to make a special meal during your trip, all the necessary ingredients will be provided to you. We’ll even make sure your little ones have their favorite snacks and drinks to feel right at home on the water. And for adults partaking in the voyage, our provision service also includes whatever alcoholic spirits you’d like to include on board as well. Each of our vessels offer ample refrigeration, chef-quality stoves and microwaves and dishwashers to ensure each of our parties are capable of preparing the same outstanding cuisine make at home —or even fresh fish you catch during your journey!

4. Your Own Private Ocean:

Tired of carving out precious beachfront territory, or with navigating hot sand to enjoy the ocean? Sick of carrying beach equipment from your car across miles sidewalk just to sit amongst throngs of other cantankerous beachgoers? With Calypso Sailing, you’ll be floating peacefully high above the sands —and far away from the crowds. The onboard swim platforms and customized swim ladders on each of our vessels makes access to the water safe and easy —ideal for children and swimmers of all skill levels. When you set sail with Calypso Charters, you won’t just be sailing across the crystal blue waters of the Florida Keys, you’ll be swimming in them too. 

3. Miles Away from the Crowds:

Long lines. Ticketing. Trams. Crowded restaurants. Filthy bathrooms. Are theme park vacations really about you and your family? Renting a charter boat in Key Largo certainly is. Don’t settle for crowded theme park rides about adventures when you can have the real thing, exploring local bays and small islands, seeing aquatic birdlife in their own habitat, surveying marine life, and enjoying relaxing evenings away from crowded bars and restaurants. A sailboat rental in the Florida Keys offers a unique, individualized experience that’s far more rewarding than jostling through crowds of tourists day after day. 


2. Solitary Starlit Nights:

Weary of spending another week in an unkempt, loud hotel? When you set sail on a Key West catamaran charter with Calypso Sailing, loud hotel hallways, over-chlorinated swimming pools and faulty air conditioners will be a distant memory. Each of our vessels offer fully appointed bedroom cabins with their own custom designed interiors. You can also forget about those starchy hotel sheets — each of our sleeping cabins are adorned with the finest of linens and luxurious towels.

1. Let the Sea be Your Playground:

Key West boat charters are about more than being on the water —they’re also about being in it. That’s why we provide all our guests with an array of equipment to enjoy the warm Key West ocean waters. From paddleboards, snorkel equipment and inflatable vests for swimming to lobster nets and fishing rods —there’s never any shortage of potential activities to partake in when you set sail with Calypso Sailing. 

Looking to unwind after your day in the water? Our vessels come complete with state of the art TV & sound systems and DVD libraries with family-friendly selections. And if you’re using your time at sea to take a break from technology, fret not. We also provide range of board games for you and your family to enjoy. What better way to spend a quiet evening at sea?

Questions about a Key West sailing charter vacation? Contact our friendly team today and we’ll be happy to provide you with all the information you need to know about setting sail with Calypso Charters. Our years of experience in Key West waters and diverse fleet of vessels can help you and your family create lifetime memories in a way that’s far superior to conventional trips.