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.