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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. 
 

At Calypso sailing, those who embark on a sailing tour of the Key West on one of our catamaran or sailing charters do so with a broad adventure in sight. That doesn’t just mean enjoying their time relaxing on their vessel, but also exploring all the islands they encounter on their trip. From exploring sea turtles and endangered dolphins at one of the islands veterinary relief outfits, to viewing spectacular bird species at one of their wildlife refuges, Key West is a premier travel destination for nature lovers.  

While Key West is known the world over for its vibrant arts culture, incredible cuisine and scenic beaches, the real star of any Key West vacation is it's abundance of wildlife —both above and below the crystal clear waters. That’s why the activity that makes a Key West sailboat charter truly phenomenal is the ability to incorporate snorkeling into each day activities. 

Even if you're new to snorkeling, or have only snorkeled a few times —the waters of Key West are the ideal place to learn and gain practice. That's because waters are particularly buoyant. After all, Key West is where the waters of the Atlantic Ocean and the Gulf of Mexico meet, making the water highly dense with salt – meaning that people of all ages, shapes and sizes can float above the surface with ease.

Whether you choose one charter one of Calypso Sailing’s small catamaran vessels or one of our larger vessels, you can make your reservation with the confidence of knowing that your charter will come complete with snorkeling gear for the entire family to enjoy. That includes flippers, masks and snorkels—even sunblock —everything you’ll need to explore the local reefs.  Snorkeling adds yet another educational, dynamic and group-oriented activity for you and your family to enjoy as you sail the pristine waters of the Florida Keys in your Calypso Sailing charter. What separates Key West snorkeling from snorkeling in other regions of the world? 

Snorkel Right off the Decks of Your Sailing Charter!

Your Calypso Sailing charter won’t just transport you to the clear, tranquil seas off 
off the Florida Keys and the Bahamas —many of our vessels provide you and your loved ones with easy access to the water via onboard swim platforms and custom swim ladders. That means no dangerous bails off the side of the boat, but a relaxed immersion into the shallow waters and for your birdseye view of the wildlife below. 

Warm, Clear Water

Unlike other Florida snorkeling destinations, the waters navigated by Calypso Sailing Charters are among the most reliable snorkeling locations in the world. While other snorkeling locales promise great conditions but can’t always deliver when cool waters and rains make their seasonal approach, the waters off Key West offer ideal snorkeling conditions nearly the entire calendar year. 

Avoid the Crowds

Forget the crowded docks and packed beaches that hampered your previous snorkeling experience. You can also cast away the stress of getting tickets on the appropriate day or having your snorkel adventure postponed to another day of the week due to poor conditions. When you charter a vessel in Key West, the ocean is your playground —and you’ll have unfettered access every day during the duration of your voyage. Anchor in the clear, warm water and explore the sights below with only your boat’s party as company —no lines, faulty rental equipment, splashing kids, or unruly crowds. Your Key West sailing charter offers you safe, easy access to the water and an uninterrupted snorkeling experience you’ll cherish for decades to come. 

A Symphony of Ocean Life

The array of marine life you’ll see while snorkeling in Key West is diverse and beautiful. Jellyfish, sponges, crabs, and sea turtles are among the most common sightings. In addition, you’re likely to see active communities of manta rays, small sharks, sea anemones, squirrelfish, trumpetfish, butterfly fish, parrotfish, angelfish, and more. If you’re worried about the dangers of what wildlife you might encounter, keep in mind that snorkeling in Key West waters is traditionally safe. Best practice dictates that as long as you and your group snorkeling in a non-disruptive and non-threatening manner, the wildlife will let you observe without initiating any contact.

A Lifetime of Memories

Whether you choose to sail your Calypso Sailing Charter on your own, or higher one of our experienced skippers, renting a sailboat or catamaran for exploration of the waters and islands of Key West is a truly immersive and diverse vacation experience. Whether you choose to paddleboard, snorkel, swim, or fish—there’s never any shortage of potential activities to partake in when you set sail with Calypso Sailing. Contact  the Calypso Charters team today  today and we’ll be happy to provide you with all the pre-sail information you need to know about exploring Key West’s with Calypso Charters. Our years of experience and diverse fleet of vessels can help you and your family create long lasting memories in a way that’s far more immersive, educational and fun to conventional vacations.
 

When it comes to catamaran and sailing charters in the Florida Keys, Calypso Sailing is your first mate. Given our diverse fleet of vessels and time spent on Key West waters, there’s no better ally when it comes to exploring Southern Florida, whether at sea, or on land.  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. 

From Key Largo, Islamorada, Marathon to Big Pine and the Bahamas, Calypso Sailing can offer you the experience, vessel, equipment, and luxuries you need to make your Florida Keys sailing vacation a lifelong memory. One of our most popular sailing charter destination is Marathon, Florida, a world-renowned tropical destination that’s bound to become one of the most interesting cities you’ve ever visited. 

The city of Marathon is located in Monroe County, across thirteen islands in the Florida Keys, among them Knight's Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key islands, each located at the center of the Florida Keys island chain. When you set off on your Calypso Sailing catamaran or sailing charter adventure with Marathon in your sights, there’s no telling what kind of family adventures you’ll embark on. Here, you’ll find a list of just a few of greater-Marathon’s incredible sites, nearly each of which is easily accessible by your vessel. Remember, a Florida sailing charter vacation with Calypso Sailing is always about more than being at sea —it’s about uncovering the amazing culture, food, fishing, wildlife and arts the Florida Keys has to offer. 

Eat, Drink & Be Merry

When you dock your Florida sailing charter at Marathon for a day, a night, or even a weekend, you'll find there's no shortage of delicious cuisine. Dozens of seafood restaurants offer delights that are caught fresh in the waters just outside the city limits. From lobster to sushi, tuna to octopus, there's no sea-borne cuisine you won't find amid Marathon's thriving restaurant culture. In fact, the restaurant scene in Marathon is as diverse as the ocean life in the Florida Keys. Those who have had their fill of seafood can also enjoy the city's Cuban, Caribbean and Italian options. No matter which menu you choose, you'll be able to enjoy your meal on any number of outside dining areas and eat while you enjoy a sunset or the lapping sounds of the warm Atlantic waters. Visitors can even take a quiet seaside stroll before returning to the welcoming comfort of their sleeping cabin aboard their Calypso Charters vessel. 

Swim With the Dolphins

Want to you parlay your Florida catamaran rental experience into a date with dolphins? When you visit Marathon, Florida, you can. Founded in 1984, the Marathon Dolphin Research Center is a non-profit marine mammal education and research facility that is also known across the Florida Keys for it's exciting, education, and immersive wildlife programs. The Dolphin Research Center offers a wide variety of programs ranging from dolphin research experiences, paint with dolphins and a family dolphin swim that will provide you and your family with many happy memories while you explore and learn about one of the world's most fascinating animals. 

Take to the Air

If your relaxing sailing vacation through the Florida Keys has you yearning for a better view, Marathon’s array of helicopter tour operators can help you get it. From quick five-minute jaunts to hour-long sessions, a helicopter tour out of Marathon, Florida is an excellent way to enrich your relaxing sailing charter vacation. Soar high above the teal waters of the Florida Keys and get a once-in-a-lifetime view of the verdant vegetation and colorful architecture. You can even book a tour that cruises over the Sombrero Lighthouse and the coral reef that lies just outside of the archipelago where it sits.

Make Friends With a Turtle

Dolphins aren’t the only marine friends you can explore when your Florida catamaran sailing charter docks at one of Marathon’s islands. The Turtle Hospital is another popular destination where visitors can learn about one of the Florida Keys most precious species: sea turtles. Opened in 1986, The Turtle Hospital rehabs injured sea turtles and returns them to their natural habitat while spreading knowledge about this fascinating species through an annual calendar of community and public education programs. Guests to the facility can take a 90-minute guided educational tour of the hospital facilities and the sea turtle rehabilitation area. It's an excellent destination —particularly if you see a sea turtle in your travels throughout the waters of Key West.

Florida’s Sailing Charter Experts

When you set sail with Calypso Sailing Charters, the waters in and around the city of Marathon are yours to visit as you like. That’s why Florida Keys visitors who set sail with us return season after season. Why be encumbered by crowded tours or stuck in line at overpopulated theme parks? Whether you jump into the crisp, warm waters for a swim, go fishing for your favorite sport fish, or take in the underwater sights and ocean life, Calypso Sailing charters gives you and your family a fully-immersive, educational, and environmentally friendly way to explore the planet in ways you never thought possible. Contact our friendly team today to learn about how you can book an unforgettable Florida Keys sailing vacation and create a lifetime worth of memories. 
 

When you set sail with Calypso Sailing Charters, the waters of Key West are yours to explore. Whether you jump into the crisp, warm waters for a swim, go fishing for your favorite sport fish, or take in the underwater sights and ocean life on a series of scuba dives, there’s no shortage of fun to be had when you rent a catamaran or sailboat in the Florida Keys. And when you sail with Calypso Charters, you can do so with the added joy of knowing that all the supplies you need to have fun on the water will be awaiting you before you get on board. But the joys of the ocean are just the start of your island sailing adventure when you choose to book a charter with Calypso Sailing. After all, what makes your Florida Keys sailing charter an adventure of a lifetime isn’t simply the adventures and relaxation you’ll find on the water, but the thousands of activities, people and locations you can see throughout your island travels. That’s because our fleet allows you access to a variety of locations across the region —and the pleasures that can be had on land.

The island of Islamorada, located in the the Upper Keys, is easily accessible by your Calypso Sailing charter and offers a variety of fun activities for both families and couples. Long regarded as one of the world’s premier fishing destinations, Islamorada is also home to a rapidly developing range of tourist and cultural attractions and a variety of newly established outdoor recreational opportunities. The island also has the distinction as being the Keys region’s unofficial headquarters for Florida Keys history, and is home to a burgeoning arts scene that’s fast becoming a must-see for all visitors to the Upper Keys and surrounding islands.  And for couples looking for a romantic retreat from their time at sea, Islamorada also lays claim to some of the Upper Keys most well-regarded restaurants and iconic tiki bars where you can enjoy a meal of fresh seafood and a quiet cocktail while your catamaran or sailing charter anxiously awaits your return.

Morada Way Arts and Cultural District

Setting sail on Calypso Charters with a passion for arts and culture? Islamorada’s Morada Way Arts and Cultural District is the epicenter of the Upper Keys’ Arts & Cultural District, an area of the island comprised of a  6-block corridor marked by the cornerstones of the iconic Green Turtle Inn and the Hurricane Monument. The primary arts thoroughfare in the Florida Keys is Morada Way —a lively neighborhood that offers a potpourri of things to do on a daily basis. From live music, to galleries displaying the works of local painters, sculptors and fashion designers, to a variety of shops, cafes and restaurants, Morada Way is an exciting, educational and even delicious way to spend the day away from sailing in your Calypso Charter.

Indian Key

If your a part of a family looking to make your Calypso Charter adventure as educational as it is fun, than Indian Key Historic State Park is for you. It’s perfect for families who enjoy spending time in nature, or for kids who are curious about wildlife. Located near Islamorada and accessible only by boat, visitors come here to swim, picnic and to hike on various nature trails. What better way to expand your Florida Keys charter rental adventure than to get an up close and personal look at regional flowers and birdlife. Kayak rentals are available from several local charter companies, which allow you to enjoy the waters up close and personal while you’re taking a break from your catamaran or sailing charter adventures. Kayaks and canoes can float across most of the islands flats and offer you and your kids a wide variety of opportunities to see some of the best wildlife the Florida Keys can offer, from dolphins and manatees to sharks and rays.


Florida Keys History & Discovery Center

From from shipwrecks, hurricanes, pirates, and sunken treasure to vacationing movie stars, you can experience the entire colorful history of the Florida Keys when you visit Islamorada’s Florida Keys History & Discovery Center. Not your run-of-the-mill, stuff museum, the Florida Keys History & Discovery Center offers you an experience as exciting and vibrant as your Florida Keys sailing charter. Constructed in 2014, the Discovery Center is a a two-story 7,500 square foot oceanfront museum with a state-of-the-art theater featuring a wide variety of exhibits and illustratively outline the cultural history of the Florida Keys, from their time as a secluded natural wonder to the present day. From an on going lecture series that presents island historians and artists, to exhibits displaying hand-carved reproductions of Native American tools, the Florida Keys History and Discovery Center is a great way for you and your family to appreciate the vast history of the Florida Keys region while you sail through it in your chartered vessel. 

One Charter, a Lifetime of Memories

When you set sail with Calypso Charters, you’re embarking on an adventure that you and your family will never forget. Interested in learning more about a Florida Keys sailing adventure, or a Florida Keys catamaran rental, contact Calypso Sailing today.  Contact our knowledgeable team of Florida Keys sailing experts today to plan your next adventure. Remember, sailing in the Florida Keys isn't just about the wonderful experiences that you have on the water, but the memories that you make on the islands you visit as well!
 

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.