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.