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With 125-miles of island chains, the Florida Keys are a fantastic destination for anyone looking for a truly unique vacation experience. From the culture and nightlife of Key West to the beautiful parks and waters of Islamorada and Key Largo, there is something for everyone to enjoy. At Calypso Sailing, we take great pride in the Florida Keys and want to give you the best sailing experience we can offer. Because of this, we have listed some fantastic activities you and your family can enjoy while vacationing in the Keys.

Scuba Diving and Snorkeling
From Key Largo to Key West, the scuba diving and snorkeling in the Florida Keys cannot be beat! With some of the best underwater sites to discover, divers of all levels can find something to enjoy. A great option to consider is exploring one of the Keys beautiful coral reef ecosystems. Interact with grouper, angelfish, hogfish, and much more at Alligator Reef in Islamorada or Sombrero Reef in Marathon. Take a scuba tour at the John Pennekamp Coral Reef State Park (the first underwater park in the nation) in Key Largo to enjoy more coral reefs, marine life, seagrass beds, and mangrove swamps.

Looking for something even more exciting? Consider shipwreck diving. The Florida Keys are home to the sunken remains of the USS Spiegel Grove, the USCG Duane, the Vandenberg, and more! Divers can explore the wreckage and learn more about the history of the Florida Keys. If you are not ready to dive, but still want to enjoy an underwater adventure- consider snorkeling! The generally warm, clear waters in Key West are perfect for gaining experience. Due to the water’s dense salt content, these areas are particularly buoyant which makes it even easier for all ages, shapes, and sizes to float along the surface.

Sightseeing
The sightseeing available in the Florida Keys rivals its amazing water adventures. With so many islands and attractions to discover, it is hard to know where to begin. For nature lovers, be sure to visit one of the many parks on the islands. From Bahia Honda State Park to the Dry Tortugas National Park, there are seemingly endless trails to hike, exotic birds to watch, and even beautiful park beaches to frolic at with family. For history lovers, consider touring one of the many historical sites in the Florida Keys like the Ernest Hemmingway Home and Museum or Fort Jefferson. For those who absolutely love diving, there is even a History of Diving Museum in Islamorada.
For those looking for a little scare, consider one of the many ghost tours available in Key West. There are also beautiful lighthouses, sandy beaches, and wildlife sanctuaries on many of the islands. For nightlife and shopping be sure to make a stop at Key West’s legendary Duval Street. With bars and attractions for all ages, Duval Street is a fantastic place to enjoy a cocktail or beer with friends! Hoping to find a breathtaking resort? Consider visiting one of the many beautiful resort options on Key Largo. There is something to enjoy on just about every island in the Florida Keys.

Fishing
If you love fishing, you will love the Florida Keys. Home to fantastic spots for deep-sea, fly, and shallow-water fishing. The Marquesas Keys are great for catching large and small fish alike. Begin in the shallows around the mangrove islands to find spectacular Snapper and Grouper. Anglers looking for larger fish can head to the rocky areas just north of the Marquesas to find Barracuda, Yellowtail Snapper, King Mackerel, and even Sharks.
For an even more intimate fishing experience, try exploring the Sugarloaf Keys, just east of the Marquesas. An area abundant with fish, these mangrove flats and creeks are perfect for a long, quiet day of fishing. If you want a local experience, consider fishing under the beautiful Bahia Honda Bridge. If deep-sea adventures are what you crave, visit the West Hump just outside of the island of Marathon. An underwater mountain, these seas have depths of over 500 feet. Test your strength against the massive Marlin and Tuna in this area, for a unique deep-sea fishing experience!

Sailing
Sailing the Florida Keys is a must for anyone visiting. Enjoy true freedom exploring the islands and taking in the crystal-clear waters. Whether it be for a day or weeks, chartering a catamaran or other vessel from Calypso sailing gives you total control over your experience. Spend hours or days at your favorite island snorkeling, swimming, or fishing. Dock one of the amazing Florida Key islands to enjoy the sights you and your family wish to see. With a sailboat charter from Calypso, you have the freedom to go where you want when you want. Why bother with traditional vacations when sailing is an option!

Worried about what food and drink to bring? Calypso sailing has you covered. With provision dining options, we will take the guess work out of finding a grocery store and worrying what to buy. By utilizing our provision packages, you can board a beautiful sailboat full of your favorite foods, snacks for the whole family, and all the ingredients you need for mealtimes. You can even opt for packages that include your favorite beverages! Because what could be better than enjoying your favorite cocktail while watching the sun sink below the sea? Have your vessel stocked with you and your friends’ favorite wine or beer. Celebrating an anniversary, retirement, or other special occasion?  We can help you design the perfect menu to ring-in these joyous events!

With Calypso sailing, there is never any shortage of fun activities you and your family and friends can indulge in! Contact our team today and we will be happy to provide you with all the important information you need to know in order to explore the Florida Keys. Our years of experience and diverse fleet of vessels can help you create memories that will last a lifetime. Book your dream sailing vacation with Calypso today!

When you set sail with Calypso Sailing, the islands are yours to explore. One of our favorite islands is Key West. A popular destination, the southernmost city in the continental United States is an excellent place to discover during your Calypso Sailing vacation! Whether staying for a day or a week, there are plenty of sites to see and adventures to have. If you are looking to add some fun to your sailing charter, consider exploring this vibrant island for fantastic dining, parks, and nightlife!

Dining, Shopping, and Nightlife
After a day at sea on your Catamaran charter, you may be craving delights one can only find on dry land. Explore what Key West has to offer, starting at Mallory Square. Whether searching for the perfect Key West souvenir or a unique gift, take a moment to tour the eclectic shops at Mallory Square. From hand rolled Cuban Leaf cigars to home décor and commemorative gifts, there is something for everyone. If a day at sea has you famished, consider dining at one of the area’s many restaurants. Between delicious Cuban cuisine, authentic Italian pizza and gelato, mouthwatering burgers, and (of course) fresh-caught seafood, you can find a place to dine that even your pickiest crewmember will approve of. If you find yourself only visiting this charming city for the evening, attending the world-famous Mallory Square Sunset Celebration is a must. Watch the glimmering sun sink into the Gulf of Mexico with your friends and family for a beautiful end to a memorable day.

If imbibing on a local libation is what you are craving, consider a trip to Duval Street. One of the most popular destinations on the island, Duval Street stretches just over a mile through the heart of downtown Key West. Although many bars are temporarily closed due to Covid-19 restrictions, there are still plenty of fantastic places to have a drink. For a cocktail on the water, consider visiting Sunset Pier to enjoy laid-back dining and drinks. For a great outdoor patio and daily drink specials, visit Willie T’s. Once bars have reopened, consider visiting the famous Sloppy Joe’s Bar, established in 1933 and a favorite hangout of writer Ernest Hemmingway. Although great for a drink, Duval Street is also host to a plethora of delightful shops, restaurants, cafes, and museums.  

Enjoy a Bit of History
The city of Key West has many historical attractions you can visit for a break from a day at sea. For a quick trip, consider visiting the southernmost point in the continental US. Located at the corner of South Street and Whitehead Street, this Instagram-able landmark is a great spot to stretch your sea legs. For history and literature lovers, consider the Ernest Hemingway Home and Museum. A great spot to spend the afternoon, this Spanish Colonial style home was built in 1851 and restored by the Hemingway’s in the early 1930s. Boasting beautiful grounds, the first in-ground pool in Key West, unique European antiques, and quite a few six-toed cats, the Hemingway Home and Museum is a great way to learn more about the prolific writer and his time spent in Key West.

If the Hemingway House is not your speed, there are plenty of other historical attractions in Key West! Looking for something to entertain your junior crewmembers? Consider visiting the Key West Shipwreck Museum. Utilizing a combination of actors, film, and artifacts from an actual shipwreck, this museum is a great interactive learning experience for the whole family. With fall months fast approaching, you may be looking for something a little spooky. Consider visiting the Key West Cemetery! This 19-acre cemetery is home to quite a few quirky and unusual gravestones. Use this self-guided tour and map as a great reference during your visit. If you are looking for a gorgeous view, consider visiting the Key West Lighthouse. Built in 1825, the lighthouse features stunning views of Key West and the ocean. Although the view is amazing, it does take quite a climb to reach it. If you are not feeling up to the 88-step ascent, consider touring the grounds and be sure to visit the restored Keeper’s Quarters.

Enjoy Nature
Key West is also home to a number of parks, beaches, and conservatories. Consider taking a break from sailing to visit Dry Tortugas National Park. Accessible only by boat or seaplane, the 100-square mile park encompasses seven small islands. At Dry Tortugas you can explore Fort Jefferson, one of the nation’s largest 19th century forts, located on Garden Key. This national park features crystal clear blue waters and is a perfect spot for swimming and snorkeling.

For an experience more inland, consider visiting the Key West Butterfly and Nature Conservatory. Located on Duval Street, this beautiful indoor exhibit allows you to stroll through a “magical world of butterflies.” Take a stroll through this tropical paradise to experience nearly 60 butterfly species and hundreds of these beautiful, fluttering creatures. The enclosed habitat also features more than 20 exotic bird species, beautiful flowering plants, and cascading trees. Be sure to visit the learning center to discover more about the life cycle of the butterfly and view a variety of live caterpillars. If neither of those is what you are looking for, consider hiking nature trails at the parks on Atlantic Boulevard, visiting Smathers Beach, or touring Fort Zachary Taylor State Park!

With so many sites to explore, we cannot wait to see you in Key West! If you have not booked your sailboat vacation, 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 is not 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.
 

You’ve booked your sailboat rental, but perhaps you are looking for some additional fun things you can do while in Key West, Florida. From water sports, to relaxation, Key West truly has something for everyone! Take a look at the many options the region has to offer, and join us this fall! 

Snorkeling
Key West is known for its beautiful and crystal blue waters, what better way to experience them then to enjoy some snorkeling in the warm waters. Snorkeling can give you some valuable time to experience and immerse yourself in the local habitat and wildlife - maybe you’ll be able to see more than just a few of the gorgeous local fish.

Rum
This one is certainly an adults-only activity - but it is a unique one! Have you ever wondered how rum is made? Visit Papa’s Pilar Rum distillery to get a behind the scenes look at how rum is made. Papa’s Pilar Rum is the island’s largest distillery and gives visitors the option to participate in a tasting as well! For only $10, it sure does seem worth it.

Ghosts
Do you like a good scare? Or even ghost story? Key West has long been rumored to be an extremely haunted city - making it the perfect location for a late night ghost tour. Sloan’s Key West Ghost Hunt is the perfect night tour to put your ghost-hunting skills to the test.

Sightseeing
Besides experiencing the beauty of all the natural landscape, you have quite a few places that are worth visiting. Let’s start with visiting the southernmost point of the continental United States in Ballast Key, Florida. Or perhaps you’d like to tour Hemingway’s home - nestled in a beautiful, historic neighborhood. Want a view from above? Several local companies offer helicopter tours from above - making sightseeing not only easy, but unique and something you will never forget! Perhaps something more adventurous such as parasailing is better for your sightseeing adventures? Sailing in the clouds is a popular tourist attraction, and something that only gets better when you are flying high above the clouds.

Water Sports
Perhaps water sports are more of your thing. Besides snorkeling, there are a number of different water sports you can enjoy while spending you time at Key West. Let’s start with scuba diving. Just 140 feet beneath the surface is the USNS Vandenberg - a ten-story tall scuba diving haven. The only thing to remember is that this might be best for those who are experienced scuba divers, as if you are inexperienced it could be dangerous. Don’t worry though - there are plenty of beautiful sites you can see while scuba diving around Key West. 

If staying above water is more your thing, try researching some local kayaking companies. There are plenty of locally-owned kayaking companies that allow you to enjoy a rental for a few hours. What better location to kayak and enjoy the great outdoors than Key West? You don’t just have to get a kayak, you can get a canoe rental as well. While they aren’t as easy to guide, they do give a slightly higher sense of safety and security. 

And of course...sailing!
Sailing is not only fun, but it gives you a sense of freedom that other activities may not. First, let’s look at the fun aspect. 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. You could even take your sailboat to the location you are wanting to snorkel to most, or just enjoy a swim in the warm waters of the ocean. 

Sailing provides you with nearly unlimited freedom. 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. That includes visiting port cities, experience nature preserves, go swimming, and snorkeling your way through the ocean, and island hop whenever you want. You are truly in control when it comes to renting a sailboat charter. 

Not to toot our own horn, but renting a sailboat charter from Calypso Charters also makes dining while on your sailboat rental easy! 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.

We can’t wait to see you in Key West! If you have not booked your sailboat vacation, 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.
 

You might not be considering booking a winter vacation right now, but there really has never been a better time. Being stuck indoors might be getting to you, but booking a vacation will not only give you something to look forward to, but you will have the opportunity to save a lot of money! With travel prices at an all time low, it’s time to book your dream vacation and nowhere is better than the Florida Keys. With a rich history, culture is abundant in this warm tropical paradise.

Rumors have it that not long after Christopher Columbus founded the “new world,” he set sail south to Florida looking for the historic and mystical Fountain of Youth. While he certainly didn’t make this discovery, that we know of, he did discover the Florida Keys in early 1513. While it was discovered this earlier, and written about in his writings, it wasn’t until 1822 that Pirates were chased out of the area and the United States Navy pirate fleet set down roots. 

From then on, settlers began to colonize the area, and it really took off. With its natural beauty and abundant wildlife, the area was a prime location for settlers to put down roots. With groves of key limes, the area began to thrive, paving way for a shark factory. If the term shark factory is new to you, you aren’t alone. Many decades ago shark factories were used to catch, and skin sharks. The shark skin was salted down and sent to New Jersey to be made into leather. While the factory thrived at the time, these factories no longer exist. 

The great location allowed the Florida Keys to thrive as a port cities. Trading quickly became a way of life, and ultimately the city became one of the hot destinations in Florida, until the Great Depression hit. Like many United States cities, the Great Depression hit the Florida Keys hard, and the city went bankrupt. Around this same time, hurricane season was not friendly to the Keys, and the city was in tatters. Federal aid helps the area begin to get on its feet, until World War II hit.  While most of the cities inhabitants were sent to war, the US Navy made the area its submarine base which helped the area thrive once again. 

In 1949, the Florida Keys began harvesting shrimp for the first-time...and this truly put the area on the map. Not only was the shrimp outstanding and highly sought after, it brought viable job prospects for the first time in years. Fast forward to modern day, the Florida Keys sees nearly three million visitors each year.

Lucky for you - the rich history of the Florida Keys and surrounding areas provides a fantastic opportunity for fun and sightseeing. Let’s start with visiting the southernmost point of the continental United States in Ballast Key, Florida. Or perhaps you’d like to tour Hemingway’s home - nestled in a beautiful, historic neighborhood. Want a view from above? Several local companies offer helicopter tours from above - making sightseeing not only easy, but unique and something you will never forget! Perhaps something more adventurous such as parasailing is better for your sightseeing adventures? Sailing in the clouds is a popular tourist attraction, and something that only gets better when you are flying high above the clouds.

Another great spot to visit is Old Town Key West - an up-and-coming neighborhood in the area, and it has a rich and full history that will have you dying to move there. This bicycle tour is the perfect option for those looking for a leisurely ride - a local guide will take you to some of the most beautiful and well-known areas of Old Town Key West, including Ernest Hemingway’s house! Join Key Lime Bike Tours on your next visit to Key West - it’s perfect for a great land excursion. 

Last but not least, renting a Sailing Charter will give you the ultimate freedom in seeing all that the Florida Keys has to offer. Sailing is not only fun, but it gives you a sense of freedom that other activities may not. First, let’s look at the fun aspect. 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. You could even take your sailboat to the location you are wanting to snorkel to most, or just enjoy a swim in the warm waters of the ocean. 

Sailing provides you with nearly unlimited freedom. 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. That includes visiting port cities, experience nature preserves, go swimming, and snorkeling your way through the ocean, and island hop whenever you want. You are truly in control when it comes to renting a sailboat charter. 

Are you dying to visit the Florida Keys now? We are excited to have you! With all of the activities to do in and around the Florida Keys, and the ability to rental a charter, it is the place to be! When you set sail with Calypso Sailing Charters, the waters in and around the area are yours to visit as you like. We are looking forward to seeing you this season! 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.
 

So you’ve booked your catamaran charter - but now what? If you aren’t staying on your charter, and need some place to stay you might be frantically looking for a hotel that will give you a fantastic experience. Your catamaran charter rental with Calypso Sailing will make your vacation dreams come true, your vacation rental should not fall short! The beautiful beaches, amazing sunsets, and fun in the sun should extend past your catamaran charter rental and in to the night.

While you have many options available for locations to stay in Key West, here are our top four neighborhoods you should consider staying in: 

Mallory Square
You can’t get a much better location than Mallory Square! If you love to be in the center of the “party,” and enjoy easy access to shops and restaurants you should highly consider a stay at Mallory Square. This area is known for its many restaurants, shops, museums, and even theatres - perfect for a single traveler, young couple, or even family. With so many options your family will never feel bored! What is most amazing about staying in Mallory Square are the views you will take in. The dock directly outside of the area has a beautiful view of the ocean that only intensifies at night with the sunset. Home to the Key West Aquarium, and the Shipwreck Museum, this really has some of the best tourist spots in the area. Also, there are two hotels in the area that are perfect for a stay:
Margaritaville Key West Resort and Spa: Not only does this hotel features some amazing amenities (think state of the art fitness center), it has a beautiful oceanfront view and is right next door to the Key West Aquarium. This hotel is perfect for all ages and all vacation-types. 
Pier House Resort & Spa: Wow. If you are looking for a luxury stay, whether your alone or with your family, Pier House Resort & Spa is the place to go. With a private beach, spa, lavish guest rooms, and a fantastic restaurant on site - this is perfect if you are looking for a relaxing getaway.

Duval Street
Duval Street can easily be considered the main street in Key West. It might be small, but it is certainly mighty! Featuring plenty of bars, restaurants, and even shops, this area is perfect for those looking to experience local eats and unique cocktails. Duval Street is truly one of the perfect spots for families, singles, and even couples looking to get a taste of local Key West flavor. Ripley’s Believe It or Not, the Ernest Hemingway Home and Museum are two other attractions in this area that are perfect for tourism. Now let’s talk about where you can stay:
Douglas House: Douglas House is not great for families, in fact it’s adult only! But if you have fur-babies...bring them along! Douglas House has great amenities and is even a short walk away from local attractions. It’s well worth a visit, as long as you aren’t trying to bring the kiddos. 
Avalon Bed and Breakfast: This charming bed and breakfast is the perfect spot to stay if you are looking for a little beach getaway. Just a ten minute walk from the shoreline, Avalon Bed and Breakfast boasts comfortability, beautiful hardwood floors, and being the perfect place to stay for nearly all travelers. 

Historic District
One of our personal favorites, the Historic District, is filled with beautiful homes, landmarks, and landscaping. The Historic District, named a district by the United States, Nancy Forrester’s Secret Garden and the famous Mile Marker 0. As one of the oldest neighborhoods in the city, Historic District is the perfect location to surround yourself with the beauty of old Key West. Our two favorite hotels are perfect for your vacation stay: 
Old Town Suites: The perfect family-friendly place, Old Town Suites provides guests with an amazing tourism experience. Old Town Suites is the perfect location for those looking to enjoy the pristine Key West beaches and visit the Butterfly and Nature Conservatory. 
Old Town Manor: Looking for another adult only option? Old Town Manor is not only adult only, but this once again is a pet-friendly option for fur babies. The Old Town Manor is the perfect place for travelers to unwind, relax, and soak up the gorgeous scenery that the historic district of Key West has to offer.

Always remember that you are welcome to adjust your sailboat vacation rental and turn it into an overnight option. Staying on your catamaran rental is a unique way to stay connected with the local nature and landscaping, as well as have a truly unforgettable experience!

We can’t wait to see you in Key West! If you have not booked your sailboat vacation, 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.