Return To Blog

Where you should stay when sailing in Key West

March 11, 2020

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.