Latest News & Blog

Why The Bahamas should be your sailing destination

July 10, 2019

As one of the most well-known, professional and reliable sailboat and catamaran charter companies in Key West, Calypso Sailing is here to make your vacation dreams come true. When renting your sailboat or catamaran, you will have the opportunity to explore waters off the islands of Key Largo, The Bahamas or the Florida Keys! Our world-class boats give you the opportunity and the freedom to truly customize and design your own vacation. While you have many destinations, there are a few reasons why sailing to The Bahamas should be your top trip  destination.

With over 100,000 miles of pristine waters and beautiful beaches, The Bahamas is the premiere sailing destination for 2019. The Bahamas is only separated from Florida by 700 islands, making it a short sailing destination from Key West. Once you arrive at the beautiful islands of The Bahamas, you can experience some of the most unique and amazing wildlife on the planet. Enjoy sailing by beaches with coconut palms and mangroves while hermit crabs, birds, and curly tail lizards bask in the sunlight. The amazing wildlife does just refer to what is on the pristine beaches, but also extends to the water. On a clear day, when you look over the edge of the boat you can see sharks, exotic fish, rays, and even reefs scattered along the bottom.

The Bahamas is not only beautiful in landscape and wildlife, but in culture as well. The Bahamas has a truly unique culture rich with different backgrounds from around the world. In a few words, the culture of The Bahamas is welcoming, friendly, lively, and easy-going. The official language of The Bahamas is English, and they are deeply religious. Despite their religious ties, they are adamant about freedom of religious expression and the constitution even guarantees freedom of expression on the islands. 

There are many islands for you to visit, but when determining which island to visit there are a few things to consider. While wifi is pretty abundant throughout, it is almost elusive in the Exumas. While you can find and utilize wifi, it can be expensive and might not always be worth the cost. Another island you might consider visiting is Nassau - the palm gardens on the eastern end of the island are truly spectacular and you can visit them for minimal cost. In addition, Nassau is home to one of the best well kept secrets in The Bahamas, the Rose Island. Another great area to visit? The Abacos are one of the most amazing places to visit and is less affected by tourism than other locations in The Bahamas. 

Another great thing about The Bahamas? The amazing weather. This is almost not one bad time to visit The Bahamas, but if you had to choose a time we recommend from mid-December to mid-April. These months are the peak season for tourism, although temperatures rarely drop below 60 degrees. Something to keep in mind is Hurricane season, which is between June and November of each year. While this doesn’t have to deter your vacations, it is something to keep in mind if you are hoping to avoid hurricanes! 

We haven’t touched on the local cuisine, but we promise it is worth the visit. Food in The Bahamas is a unique combination of Caribbean and south American styles. It’s comfort food meets spice, and it is completely worth the trip. Local restaurants and cafes line the shorelines of the islands, where you can get a taste of local flavors and maybe even sample the national dish of the islands. The Conch, the islands most notable shellfish, is something that you can happily sample before departing from your vacation.

There are a number of activities that can be suited for any interest as well. If you are interested in fishing, one of the biggest activities in The Bahamas is sport fishing - there are several tournaments a year. Despite this, there is always the option to participate in sport fishing just off shore of the islands. If you are interested in experiencing some of the underwater wildlife, you have the option to go snorkeling and scuba diving at some of the amazing reefs in the world. In addition, many of the inhabited islands have plenty of options for food, dining, and even local shows that you can catch.

As you prepare for a vacation to The Bahamas, here are some fun facts to keep in mind when deciding to visit The Bahamas - we promise it’s worth the visit: 
The Bahamas is home to the third-largest barrier reef in the world
Out of the 700 islands, only 30 are inhabited 
The Bahamas is home to the clearest waters in the world - with visibility on a good day reaching 100+ feet underwater 
One of the most amazing things about The Bahamas is the underwater cave system available to those who enjoy scuba diving
The Bahamas sits on the edge of the infamous Bermuda Triangle 
Despite the notoriety of the Great Blue Hole in Belize, The Bahamas is actually home to the deepest hole in the world 
The origin of the name The Bahamas comes from the Spanish phrase “Baja Mar,” meaning shallow sea

When you are ready to book your sailboat vacation to The Bahamas, contact us here at Calypso Charters. Our team will help you put together a vacation you will never forget complete with sun, sand, and activities. If you are unsure or have questions, contact us. We are here to help you learn more about a Bahamas sailing adventure and provide you with the information you need to book your next event. Remember, sailing in The Bahamas isn't just about the wonderful experiences that you have on the water, but the memories that you’ll take with you for the rest of your life.


Why you should consider a sailboat rental on your next Florida Keys vacation

June 12, 2019

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.

Top Reasons to Host Your Wedding on a Key West Charter Boat

May 16, 2019

At Calypso Sailing, we’re proud to be one of the most well-known, professional, and reliable sailboat and catamaran charter companies in Key West. Whether you're eager to explore the waters off the islands of Key Largo, the Bahamas or the Florida Keys our fleet is prepared and ready to offer you a once-in-a-lifetime experience exploring one of the world’s most sought-after travel destinations. And while private Key West catamaran rentals and corporate charters are areas we excel in, we also offer couples from around the globe the ability to host their wedding aboard one of our vessels. That’s right —a wedding charter with Calypso Sailing with offer you, your significant other, and your guests a wedding experience like they have never had before. What sets a Key West sailing charter wedding apart from a traditional event wedding?

Control the Number of Guests
At Calypso Sailing, our vessels can comfortably host between 6 and 42 people. And while that may not seem like much for those planning a stadium-size wedding, it’s important to consider the positives of holding an exclusive wedding event on the calm, soothing blue waters of the Florida Keys. Choosing to host your wedding on one of our vessels in the waters of Key West allows you to keep your list of invitees exclusive to those family and friends who are most important to you. Why waste time and energy thinking about which long lost college friends or far away aunts, uncles, and cousins to attend when you can plan your event knowing that only your closest friends are aboard? With seemingly everyone you know eager to share in the celebration of your wedding day; it can be difficult to limit the guest list without hurting other people’s feelings. However, getting married aboard a boat gives you an ideal out to keep your guest list trim, because everyone understands you can’t break maritime occupancy rules!

Cut Down on Costs

While planning a Key West charter boat wedding may seem like an exorbitant cost —it might actually save you considerably. A pared down guest list means that you’re free to commit more to other event costs that will make your sailing charter wedding all the more memorable for those in attendance. Best of all, the talented, experience team here at Calypso Chaters will work one-on-one with you to make sure your event goes exactly to your specifications —from soup to nuts. From specialty food and drink options to a range of entertainment ideas, hosting your wedding on a Calypso Sailing charter boat allows you to fine-tune your special day down to the very last detail. That not only means that you’ll be giving your loved ones a once-in-a-lifetime experience, but a day that you and your significant other will cherish forever. 

Mobile, Customizable Event Schedule

The wedding charters here at Calypso Sailing are unhindered by the obstacles set forth by time, roads, and brick and mortar establishments. Whether you want to host your entire wedding aboard one of our vessels, or simply utilize one of our catamarans or sail boats as a part of your wedding ceremony, the Calypso Sailing team can adapt to whatever your specific wedding plan needs. Our experiences event specialists will help you choose one of our gorgeous Key West wedding themes, or they can work from your plans to create the custom wedding celebration you’ve been dreaming of for years.

Pick your guests up at a certain local for a sunset cruise where you and your wedding-partner-to-be can exchange your vows in front of breathtaking views. Better yet, you can have your party picked up at the conclusion of your vow ceremony and cruise the calm Key West waters all evening complete with a catered meal you design and to the sound of on-board entertainment you select. 

Looking for incredible wedding pictures? A Key West wedding charter is the perfect solution. Whether you choose to have you and your new spouse photographed aboard one of our sailboats at the conclusion of your ceremony, or if you and your wedding party simply want to take photos aboard one of our vessels, Calypso Charters will be here to cater to all of your event needs. 

When you book your tropical destination wedding here in Key West with Calypso Charters, you’re embarking on an event that you and your loved ones will never forget. Interested in learning more about a Florida Keys sailing adventure, or a Florida Keys catamaran rental, contact Calypso Sailing today. Our knowledgeable team of Florida Keys sailing experts today to plan your next event, whether it’s a wedding, reunion, or corporate party. Remember, sailing in the Florida Keys isn't just about the wonderful experiences that you have on the water, but the memories that you’ll take with you for the rest of your life.

Corporate Party Charter Boat Rentals in Florida

April 17, 2019

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. 

Top Reasons to Incorporate Snorkeling in Your Sailing Charter

March 20, 2019

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.