From experienced mariners and fisherman to vacationing families, Calypso Sailing’s reputation for offering some of the best catamaran and sailboat charters in Key West is well established. But what you may not know is how many businesses from across Florida and the continental United States utilize our diverse fleet of vessels for both their annual corporate outings and for client celebrations.  

What better way to celebrate the tremendous contributions of your top sales earners or executive team than with a private party boat that cruises off the waters of Key West, Key Largo, Islamorada, Marathon, or Big Pine. If you think the Calypso Sailing vacation charters are an experience to behold, wait until your team of hardworking employees sets sail for an evening on one of our vessels. What sets Calypso Sailing apart from other corporate charters in Key West? 

Customized Themes

Calypso sailing will work with you and your team on any customize sailing or catamaran trip you desire. Whether you would like to fashion your Key West business charter in a theme that aligns with your business, special occasion or holiday, or a theme that’s been pre-determine by your organization, our friendly staff will work closely with you to make that dream a reality. Setting sail for your corporate outing with a customized theme is just one of the ways you can insure your that your business charter will be remembered forever. 

Personalized Itineraries 

Looking to spend an evening at sea or a whole weekend? When your business chooses Calypso Sailing you can decide for yourself. That’s because our fleet of charter vessels can cater to groups from 6 to 42 people. Depending on which vessel you choose, you and your team can set sail for a weekend of snorkeling and deep sea fishing, or simply a catered evening of food and drink. Our skilled business charter team can even arrange to have your charter split up between parties and days, so that each of your associates can appreciate the same experience. 

Team Building Itineraries

Looking to foster camaraderie or trust amongst your team? You can when you book your corporate charter with Calypso Sailing. When you choose our team building regattas option, our expertly-trained crew  will organize your group into teams that help navigate, hoist sails and drop anchor aboard our vessels. What better way to spark an environment of trust and fellowship among your coworkers than to set sail on the beautiful blue waters of Key West, the Bahamas, or the Florida Keys. 


Customized Menu & Dining Options

You name it, we’ll serve it on board. Calypso Sailing has affiliations with myriad local caterers and restaurants, so matter which type of cuisine you’re eager to serve at your corporate event, we can have it available to you and your crew on the day or evening your charter takes to the waters. Whether you have breakfast, lunch, dinner, or a buffet in mind, Calypso Charter can help you plan your menu and recommend beverage options.  

A Full Service Bar, Stocked with Your Preferences

Whether you’re hosting an ornate dinner or simply cold beers and seafood, the Calypso Charter team can help you stock a bar that will give your patrons access to the tropical adult beverage of your choice. We can also discuss catering staff options that can include your own personal bar and cocktail service staff. 

An Unforgettable Experience

At Calypso Sailing, customization is our speciality. Whether you’re celebrating the finale of a huge project, a successful business year, a new merger, retirement, or anniversary for your business, choosing a Key West catamaran or sailboat charter to celebrate your business and your employees is the ideal way to create lasting memories that you and your team will cherish forever. You can even designate a guest as Honorary Captain, complete with hat, captain’s certificate and a personalized bottle of rum or wine.

Schedule Your Key West Corporate Charter with Us!

Questions about a Key West sailing charter for your company or business? 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 for corporate events. Our years of experience in Key West waters and diverse fleet of vessels can help you and your team create lifetime memories in a way that’s far superior to conventional corporate outings and formal dinners.