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Travel destinations, beaches and attractions and things to do in Florida. Documented by RESIDENTS of Florida.

Escape! Key West Weekend Getaway in Paradise

Escape to paradise with a Key West weekend getaway! Whether you’re tired of the daily grind or simply in need of a break, Key West offers the perfect destination to relax, unwind, and soak up the sun. 

With its vibrant culture, stunning beaches, and endless activities, a Key West weekend getaway promises to be an unforgettable experience. Join us as we dive into the best things to do, must-visit attractions, and hidden gems that will make your Key West escape a truly memorable one. 

Get ready to immerse yourself in the laid-back atmosphere, savor delicious seafood, and create lasting memories in this tropical paradise. So pack your bags, grab your sunglasses, and let’s embark on an unforgettable Key West adventure together!

weekend getaway Key West - sunset
A weekend getaway Key West style will put you in this picture!

Why Choose Key West for a Weekend Getaway?

Key West is a popular destination for a weekend getaway. With its vibrant culture, beautiful beaches, and lively nightlife, it offers a diverse range of activities for visitors. Whether you’re looking for relaxation or adventure, Key West has something for everyone.

Key West weekend getaway - southernmost buoy
This is the most photographed spot in Key West and a must-see on your Key West weekend getaway.

In recent years, Key West has gained significant relevance as a top choice for weekend getaways. Its proximity to the mainland and accessibility through various transportation options make it an attractive destination for travelers. The island’s unique charm and laid-back atmosphere provide a refreshing escape from the hustle and bustle of everyday life.

One of the main highlights of a Key West weekend getaway is its stunning beaches. From the famous Smathers Beach to the secluded Fort Zachary Taylor State Park Beach (our favorite!), visitors can soak up the sun, swim in crystal-clear waters, or simply unwind with a book in hand. Water activities such as snorkeling, kayaking, and paddleboarding are also popular among tourists.

Aside from its natural beauty, Key West offers a vibrant nightlife scene. Duval Street, the main thoroughfare, is lined with bars, restaurants, and live music venues. Visitors can enjoy delicious seafood, sip on tropical cocktails, and dance the night away to live bands or DJs. The lively atmosphere and friendly locals create an unforgettable experience.

For history enthusiasts, Key West has a rich cultural heritage to explore. The Ernest Hemingway Home and Museum, the Key West Lighthouse, and the Harry S. Truman Little White House are just a few of the historical landmarks that offer insight into the island’s past. Walking tours and guided excursions provide an educational and entertaining experience for visitors.

In terms of accommodations, Key West offers a wide range of options to suit every budget and preference. From luxury resorts and boutique hotels to cozy bed and breakfasts, there is something for everyone. Many accommodations are conveniently located near popular attractions, making it easy to explore the island.

weekend in Key West - cruise ship
Cruise ships dock near Mallory Square in Key West sending thousands of curious people roaming the streets looking for the charm of the island. Cruise ships have made Key West into an international destination.

Rich History and Culture 

Key West has a rich history that dates back to its establishment in the early 19th century. The city played a significant role in the development of Florida and the United States. Its strategic location made it a key port for trade and military operations.

One of the must-visit historical landmarks in Key West is the Ernest Hemingway Home and Museum. This iconic house was once the residence of the famous American writer, Ernest Hemingway. Visitors can explore the house and learn about Hemingway’s life and literary works.

Another historical site worth visiting is the Harry S. Truman Little White House. This historic building served as the winter White House for President Harry S. Truman during his presidency. Today, it is a museum that offers insights into Truman’s presidency and the history of Key West.

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For those interested in maritime history, the Key West Shipwreck Treasure Museum is a must-see. The museum showcases artifacts and stories from the era of shipwrecks and salvage operations, highlighting the importance of maritime trade in Key West’s history.

Apart from these specific attractions, Key West’s Old Town area is filled with charming Victorian-style houses and buildings that reflect the city’s historical architecture. Taking a leisurely stroll through the streets of Old Town allows visitors to immerse themselves in the rich history and unique atmosphere of Key West.

things to do in Key West - manatee
If you get lucky, you may see one of these gentle giants in Key West. The manatee roams warm waters.

Things to See and Do in Key West

Key West offers a variety of attractions and activities for visitors. Whether you’re planning a weekend getaway or a longer stay, here are some things to see and do in Key West:

Experience the vibrant atmosphere of Mallory Square, especially during the sunset celebration where street performers, local artists, and food vendors gather.

Known as the heart of Key West, Duval Street is lined with shops, restaurants, and bars. Take a leisurely stroll and immerse yourself in the lively ambiance. A must do on a Key West weekend getaway.

Discover the former residence of the renowned writer, Ernest Hemingway. Explore the beautiful gardens and learn about his life and works.

Hop on the Conch Tour Train for a narrated journey through Key West’s historic landmarks, including the Truman Little White House and the Key West Aquarium.

Don’t miss the opportunity to take a photo at the Southernmost Point Buoy, marking the southernmost tip of the continental United States.

Enjoy the beach, go snorkeling, or take a guided tour of the historic fort, which played a significant role in the Civil War.

Immerse yourself in the enchanting world of butterflies as you wander through the conservatory’s tropical gardens.

Engage in thrilling water activities such as snorkeling, kayaking, jet skiing, or paddleboarding in the crystal-clear waters surrounding Key West.

Take a day trip to this remote national park, accessible by ferry or seaplane from Key West. This takes at least a half-day on a seaplane and about 8 hours by ferry.

We know, in a weekend, you could not visit all these. Our Key West recommendations for a first-time visit would be:

  • Take the Conch Train Tour to see all of Key West in an hour or two.
  • Catch Sunset at Mallory Square
  • Hit the Beach at Fort Zachary Taylor
  • Get a picture at the Southernmost Buoy

These four things plus a must-visit to the most famous pub in Key West, Sloppy Joe’s, are the must-dos for first-timers!

Here is a more complete list of things to do in Keys West.

beaches in Key West - Fort Zachary Taylor Beach
We like Fort Zachary Taylor Beach in Key West because of its remoteness and it’s a getaway for locals too!

Delicious Seafood in Key West

Being surrounded by the Atlantic Ocean and the Gulf of Mexico, Key West is known for its fresh and delicious seafood offerings.

Here is a list of the best seafood restaurants in Key West for a Key West weekend getaway:

  • Latitudes: Situated on Sunset Key, an island just across the inlet to the harbor, Latitudes offers breathtaking ocean views and a menu featuring a variety of seafood options. Indulge in their delicious seafood platters while enjoying the island ambiance. One of the top 3 restaurants in the Florida Keys.
  • Half Shell Raw Bar: A local casual favorite, Half Shell Raw Bar is renowned for its raw oysters, clams, and peel-and-eat shrimp. This casual spot is perfect for a laid-back seafood experience.
  • A&B Lobster House: With its waterfront location and elegant setting, A&B Lobster House is a top choice for seafood enthusiasts. Their menu boasts an array of lobster dishes, as well as other seafood delicacies. One of the oldest and best-known waterfront restaurants in Key West
  • Conch Republic Seafood Company: Offering a lively atmosphere and waterfront dining, Conch Republic Seafood Company serves up a variety of seafood options, including their famous conch fritters and fresh fish dishes.
  • Santiago’s Bodega: While not exclusively a seafood restaurant, Santiago’s Bodega is known for its delectable tapas, including a selection of seafood small plates. Enjoy a diverse range of flavors in a cozy setting. One of our family’s favorite restaurants.
  • Louie’s Backyard: Combining stunning ocean views with a creative seafood-focused menu, Louie’s Backyard is a must-visit. Their dishes feature locally sourced ingredients and innovative flavor combinations. Consistently rated as the best restaurant in Key West.
  • The Stoned Crab: Located at the Historic Seaport, The Stoned Crab offers a unique dining experience with its focus on stone crab claws. Indulge in this Key West delicacy and savor the flavors of the sea.
  • Blue Heaven: While not specifically known for seafood, they are the best breakfast and lunch restaurant on the island and a must-visit for their quirkiness! Located in the heart of Key West, Blue Heaven is known for its fresh seafood dishes and vibrant atmosphere. The seafood dishes they prepare are excellent also. We never miss Blue Heaven on our visits to Key West.
Key West Weekend Getaway sailing
You can charter a sailboat to explore the clear waters of Key West.

Walk the Colorful Streets and Charming Architecture of Key West

Key West is renowned for its captivating architecture and charming streets. This tropical paradise offers a delightful experience for visitors seeking a weekend getaway.

The city’s unique architectural style, influenced by Caribbean and Victorian designs, creates a picturesque backdrop for exploration. As you wander through the streets, you’ll encounter vibrant pastel-colored houses with intricate details, quaint cottages, and inviting porches adorned with lush greenery.

The iconic Key West lighthouse stands tall, offering panoramic views of the city and its stunning surroundings. The streets are lined with charming shops, art galleries, and cozy cafes, where you can immerse yourself in the local culture. Key West’s architecture and charming streets truly make it an ideal afternoon tour.

Top Places to Stay on a Key West Weekend Getaway

Our Suggestions of the top places to stay in Key West for a weekend getaway:

  • Casa Marina Key West: A historic landmark, this oceanfront resort boasts elegant rooms, a private beach, and a large swimming pool surrounded by lush gardens. Great place for a semi-private Key West weekend getaway.
  • Ocean Key Resort & Spa: Offering breathtaking views of the Gulf of Mexico, this upscale resort provides luxurious rooms, a full-service spa, and a waterfront restaurant.
  • Sunset Key Cottages: Located on a
    Key west things to do - Shipwreck Museum
    There are many things to see and do in Key West that revolve around history like the Shipwreck Museum near Mallory Square.
    secluded island just off Key West, these charming cottages offer a tranquil escape, private beaches, and access to a spa and fine dining.
  • Hyatt Centric Key West Resort & Spa: Situated in the lively Truman Annex neighborhood, this contemporary resort offers comfortable rooms, a poolside bar, and easy access to popular attractions.
  • Southernmost Beach Resort: Positioned right on the beach, this resort offers a range of accommodations, multiple pools, and a lively beach bar with live music.
  • Opal Sands Key West Resort: Next to Mallory Square, this is one of our favorite places to stay just off Duval Street. Clean, reliable and great waterfront views.

Please note that the availability and amenities of each place may vary. It is recommended to check their websites or contact them directly for the most up-to-date information. Florida Travel Blog highly recommends you book early since Key West gets very busy during the season.

Key West: The Perfect Weekend Escape

Not many destinations can offer you everything you could want for the perfect weekend getaway to Key West. With amazing things to do, fun things to see, easy airline flights to the island, magnificent sunsets and a vibrant nightlife – there is not much more you could ask for in a weekend getaway to the Florida Keys.

Get your planning started now. Get those flip-flops and sunscreen packed and head out for a weekend getaway in Key West.

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