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When it comes to catamaran and sailing charters in Key Largo, Calypso Sailing is your place to go. We have a lot of experience in Key Largo, 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 Key Largo sailboat charter adventure. Key Largo is a treasure chest of unique and fun things to do, check out our top nine favorites! 

John Pennekamp Coral Reef State Park 
Established in 1963, John Pennekamp Coral Reef State Park is the only first undersea park that was established to protect the coral reefs that line the state of Florida. The John Pennekamp Coral Reef State Park is connected to the Florida Keys National Marine Sanctuary - which creates 178 nautical square miles filled with wildlife, coral reefs, mangrove swamps, and seagrass beds. Contrary to what you might think, the Coral Reef State Park offers more attractions above the surface as well. With a 30,000 gallon saltwater aquarium and theatre, as well as kayaking options and snorkeling areas - the John Pennekamp Coral Reef State Park is perfect for a family outing or couples day out!  

Crocodile Lake National Wildlife Refuge
Founded in 1980, the Crocodile Lake National Wildlife Refuge was created to protect the native crocodile habitat. This is a unique thing to do, as where crocodiles live is closed off to the public. You can only get to this area through volunteering - but what better thing to do then volunteer for a few hours on your day off and get a great experience?! Those who are not interested in volunteering can visit the crocodile habitat to learn more, as well as how to preserve and protect the environment. In addition to learning more about the crocodile’s habit, you can also visit the Butterfly Garden that houses more than 50 unique and local species of plants. 

Dagny Johnson Key Largo Hammock National State Park 
If you are an outdoor enthusiast the Dagny Johnson Key Largo Hammock National State Park is for you! With over six miles of nature trails to hike and explore, you and your family/friends can enjoy a day out in natural Florida habitat. There are over 80 species of protected animals and plants that reside in this national state park, and you have two options when visiting: a Ranger-led trail hikes or self-led trail hikes. Whatever you enjoy! 

Dolphin Cove
Located on the most northern area of Key Largo, Dolphin Cove is a five-acre lagoon that allows visitors to swim and meet with local dolphins. Guided tours last approximately thirty minutes, where visitors learn about the dolphins and their habitats - as well as what to expect when they come in contact with the dolphins. After the thirty minute tour, visitors have the option to participate in the dolphin swimming experience which gives visitors the chance to meet the dolphins up close and personal. 

Florida Keys Wildbird Rehabilitation Center
If you are a bird lover you should certainly visit the Wildbird Rehabilitation Center located in the Florida Keys! The Wildbird Rehabilitation Center is a safe space for injured birds to be rescued and rehabilitate before being released back into the wild. The Wildbird Rehabilitation Center is a great place for visitors to learn more about the local wildlife, how the center rehabilitates, and learn about the species residing within the center. 

USCGC Bibb
If you aren’t into wildlife, perhaps a visit to the USCGC Bibb is for you. The USCGC Bibb was involved in wartime operations in both World War II and Vietnam, and now sits peacefully at the bottom of the ocean in the gulf. The great thing about the gulf is that visibility is impeccable - making viewing of the USCGC Bibb gorgeous! You even have the option to participate in an underwater dive, where you can expect to see sharks, reef fish, and even barracudas. 

Key Largo Parasailing
Looking for an above water view of the beautiful landscape? Consider taking a parasailing adventure and seeing the beautiful Key Largo from the air. The great thing about parasailing is you an do it with a single, or double - meaning if you want to take a partner you are more than able to! 

Capt. Sterling’s Everglade Tours
Capt. Sterling’s Everglade Tours offers three unique options for you if you are interested in taking an Everglades Tour! Captain Sterling offers tours in the Everglades National Park, Florida Bay, and Mangrove Jungle. Not only will you have the opportunity to tour the Everglades, but you can take a manatee tour to experience life next to these gentle creatures. On these tours you also have an opportunity to tour Hemingway Pass, known as one of the most prettiest areas of the Everglades. 

Charter Rental
Charter rentals can be fun and ultimately put the vacation’s control in your hands. 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 Key Largo. 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.

Have we convinced you of a Key Largo location? With all of the activities to do in Key Largo, and the ability to rental a charter, Key Largo is the place to be! When you set sail with Calypso Sailing Charters, the waters in and around the city of Key Largo are yours to visit as you like. We are looking forward to seeing you this season in Key Largo! 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.
 

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. One of our favorite spots to sail is Key West - long known for its gorgeous pristine beaches and its famous sunset celebration. Our world-class boats give you the opportunity and the freedom to truly explore Key West, and experience all that the area has to offer. Here are a few reasons why sailing around Key West should be your top trip destination.

The History
The history of Key West is long, and rich with culture and tradition. Key West was first discovered in 1521 by Ponce de Leon when he was on the search for the Fountain of Youth. Upon discovery, he originally named the island Cayo Hueso, which means Bone Island in Spanish. In 1763, the British took control of the Island, but later the Spanish regained control in 1815. It wasn’t until 1822 that Key West became part of the United States and quickly became one of the richest cities in the country. With easiest access to the ocean, Key West quickly became haven for industries such as turtling, salvaging, and wrecking. Ever since, Key West has been used as a haven for naval bases and has grown in popularity - it is not a top travel destination and a dream location for many retirees. 

The Culture
Key West has some of the best culture in the Caribbean. Including festivals year around that should be on your bucket list.
Fantasy Fest - A week-long celebration at the end of October where parades line the streets and people dress up in costumes 
Sunset Celebration - Every night street performers, and food vendors line the street to celebrate the sunset - this is a must see while you are in the area!
Outside of the festivals, Key West is known for its friendly feel and ease of travel. The easiest way to travel while on the island is by bike, or take your boat around a few times! If you are willing to explore Key West, island locals are certainly ready to show you the ropes.
 
Things to Do
While you are sailing through Key West on your sailboat and catamaran charter rental - take a break to enjoy some of the best things Key West has to offer. Once you dock your rental check out some of the amazing food restaurants in the area. Duval Street is famous for its bars, restaurants, and overall culture. Duval Street (named after the first territory governor) is a street filled with unique bars - making it the perfect place to unwind. Key West has some of the best fresh seafood around, and with ocean side restaurants and bars you can’t get enough of the local cuisine. 

Experiencing the local food and drink isn’t the only thing that you can enjoy after docking your rental. One of the most popular things to do is hop on the Key West Conch Tour Train - a train that will show you the area’s gorgeous historic buildings and tropical landscape while hearing all about the history of Key West. In addition, why not take some time to go on a local snorkeling tour or see the water from the air with parasailing? Key West ha some of the best things to do to experience the outdoors. Looking for a fast, short adventure experience? Rent a jetski and take them around the area - Key West is spectacular from the water. 

Key West also has the most beautiful butterfly and nature observatory - home to over 50 species of butterflies and over 3,500 plants. The glass 5,000 square foot aviary is also called home by over 20 species of birds. The serene and calming environment has been one of the top ranked things to do in Key West.

If you are looking to experience more of what Key West has to offer, take a visit to Hemingway’s home to learn more about his life and his love of cats. All 60 cats that are currently inhabiting the property are descendents from Hemingway’s initial cat, Snowball. It’s thought that while Hemingway was in Key West he worked on some of his most famous works, including “For Whom the Bell Tolls,” and “Death in the Afternoon.”

If you love music and art, visit the Green Parrot on the weekends and catch a local performance that is likely to spill into the streets. The Green Parrot even has a jukebox that is island-famous! While we talk about music and art, The Green Parrot isn’t all to consider. Key West has theatre troupes that perform across the island at famous theatres and there are dozens of art galleries spread across the island. Each gallery has a unique identity and art even spills into the street during some of their busiest times of year. 

Key West - The Unique Facts
Key West has some of the most amazing history, sights and activities. But it also has some pretty amazing and unique facts! 
Chickens are free to roam the island - you might come across some! 
Key West is connected to mainland Florida by 42 bridges
The third largest barrier reef in the world is in Florida 
With a small population, Key West is home to just under 25,000 people
Rumors have it that Key West is haunted - might be worth checking out after the sun has set before you turn in for bed in your cozy rental

When you are ready to book your sailboat vacation to Key West, 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 Key West sailing adventure and provide you with the information you need to book your next event. Remember, sailing in Key West 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.
 

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.

 

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.
 

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.