7 Best Ways To Spend A Memorable Weekend In Key West

Weekend In Key West

Streamline your weekend visit to Key West by skipping the long road trip and flying straight to the Key West International Airport. You may drive on the iconic Seven Mile Bridge to your historic seaport destination, but the flight into Key West will definitely get you to your perfect weekend getaway much faster!

Not only does this leave more time to explore places like Old Town or Duval Street during your weekend trip to the Florida Keys, but the view on your short drive to the most beautiful tropical destination in the Continental United States is one you will want to capture for your photo album!

From can’t-miss points of interest brimming with rich Key West history to fun attractions in places like Mallory Square in Old Town, there are endless ways to fill your Key West weekend!


1) Start Your Memorable Weekend In Key West On A Sandbar Hopping Tour

The crystal clear waters around Key West are one of the many features that make the Florida Keys a remarkable place to visit, but did you know you can take unforgettable pictures and spend time on a sandbar out in the sea? The captain and crew here at Key West Boat Trips are happy to provide a few different private charter experiences and sandbar hopping tours that will make you feel like you’re walking on water!

We know all the best places to catch some rays on the sandbars of Key West, and will even spoil you with a delectable seafood lunch right on the beach! If you’re searching for an experience you’ll never forget during your Key West weekend trip, then reach out to our team to book your sandbar experience today!

Memorable Weekend In Key West On A Sandbar Hopping Tour

2) See All The Best Sites In Old Town Key West

Old Town Key West is brimming with possibility! Not only is this part of town filled with exciting activities for visitors of all ages, but the Conch Tour Train is a convenient way to see it all in one day! You can stay on the train for the 75-minute tour filled with facts and stories about the Key West historic district, or you can hop on and off at one of three different stops along the route.

One of the locations you can visit on this tour of Old Town is Duval Street, which is a wonderful spot for dining, catching live music, dancing with friends, or grabbing a few drinks at one of the lively local bars.

If you’re looking for a more family-friendly spot on the tour of Old Town Key West, then consider stepping off the train at Mallory Square toward the end of the day to catch the unforgettable sunset celebration!

Mallory Square is the only spot hosting a nightly Key West Sunset Celebration full of fun and excitement for the entire family. Not only will you see the best sunset in Key West Florida, but there are vendors and street performers available to make sure the entertainment never stops!

More attractions you can catch in Old Town include:

  • Key West Lighthouse

  • Southernmost Point Buoy

  • Key West Aquarium

  • Key West Butterfly and Nature Conservatory

Pro tip: The Southernmost Point Buoy is an iconic spot to capture a group photo to commemorate your Key West weekend getaway, so make sure to stop by this colorful landmark to snap a picture.

Duval Street- An Old Town Key West

3) Enjoy A One-Of-A-Kind Meal You’ll Never Forget

Though Key West is known for Key Lime Pie, there are many other delectable dishes you can find around the island. The only way to make your culinary experience truly memorable, however, is to grab an outdoor seat at Blue Heaven and experience the atmosphere of this whimsical eatery.

Not only does Blue Heaven serve up some of the best island cuisine available in Key West Florida, including key lime pie, but their decor is something you’ll never forget! From the colorful coconuts that adorn the restaurant to the roaming cats and chickens, there’s something exciting to experience at every turn. There’s a rooster graveyard, a mysterious leopard-printed mannequin, and a large sail strung between the tropical foliage to keep diners out of the sun.

As if the atmosphere and mouthwatering food weren’t good enough, you’ll also find live music and entertainment here frequently! Stop by for an unforgettable experience with good food, fun people, and even better artwork!

In addition to Blue Heaven, don’t miss these other renowned restaurants while you’re in Key West:

  • Harpoon Harry’s – American restaurant

  • Bistro 245 – American restaurant
  • B.O.’s Fish Wagon – Seafood restaurant

  • Kim’s Kuban – Cuban restaurant

  • Thirsty Mermaid – Seafood restaurant

Pro tip: Make your way to Bistro 245, a waterfront restaurant located at Opal Key Resort & Marina. Here, you can enjoy the mouthwatering dishes from breakfast to dinner, all while enjoying the breathtaking views of the Gulf of Mexico. Whether you’re a family with kids or a couple on a romantic getaway, Bistro 245 is the perfect choice for a memorable dining experience.

Key Lime Pie You'll Never Forget

4) Take A Trip To The Key West Tropical Forest & Botanical Garden

If you’re looking for unique ways to explore Key West, then the Tropical Forest & Botanical Garden is a wonderful place to add to your Key West itinerary. This stunning botanical garden is regarded as the “Keeper of the Trees” and has been operating since the 1930s to preserve the rare and beautiful flora and fauna of Key West Florida.

This is the only frost-free botanical garden in the Continental United States with three of the last freshwater ponds in Key West. There are always fun educational events planned throughout the year, so be sure to check their online calendar ahead of your weekend to make the most of your visit to the garden.

Key West Tropical Forest & Botanical Garden

5) Explore The Key West Shipwreck Museum For A Fun Historical Tour

Whether you’re searching for a fast, affordable activity to get you out of the sun or you love a good pirate story, you won’t want to miss the opportunity to step back through time at the Shipwreck Museum in Key West. It only takes about 20 minutes to stroll through this artifact-filled museum, but you’ll leave with a wealth of knowledge about the rich history of the wrecking age in the Florida Keys.

Climb to the top of the museum’s lookout tower to peer through the scope and get an unforgettable sweeping view of Key West and the crystal clear waters beyond the nearby beach.

The Key West Shipwreck Museum is an excellent option for families with children looking for a fun-filled weekend getaway.

 Key West Shipwreck Museum For A Fun Historical Tour

6) Journey To The Dry Tortugas National Park

While there are plenty of parks to explore in Key West, the Dry Tortugas is the most elusive spot of them all. The only way to reach the distant national park is to hop aboard the Yankee Freedom Ferry or hire a boat or seaplane to get you to your destination.

Once on the island, you’ll be free to explore the historic Fort Jefferson that still stands in the park or roam down trails and beaches to discover sea life and other interesting finds along the way. There are no restaurants or shops at Dry Tortugas National Park, so you’ll want to come prepared for your visit. If you rode in on the ferry you’ll have a sack lunch to enjoy, but otherwise, you’ll have to bring a picnic to enjoy at one of the provided tables.

Explore the beauty of Dry Tortugas National Park, where adventures await:

  • Discover the historic Fort Jefferson

  • Snorkel amidst vibrant coral reefs and tropical fish

  • Take a leisurely stroll along the sandy beaches

  • Discover diverse bird species that call this park home

No matter what you decide to do with your day at Dry Tortugas, it’s destined to be a tropical adventure you’ll never forget!

Journey To The Dry Tortugas National Park

7) Take A Stroll Through The Past At Key West Cemetery

While you can always grab a self-guided tour map of the location at the entrance, there are always Key West Cemetery tours available. The grounds stretch over 19 acres and include more “residents” than all the people in Key West living today.

There are many gravestones with humorous quips or interesting phrases, which makes this location a fun scavenger hunt-like experience for history lovers in Key West.

As you wander through the tombstones and mausoleums, you’ll uncover the stories of the island’s past residents. From famous figures to ordinary citizens, each grave tells a tale of Key West’s rich cultural heritage. Don’t miss the chance to pay homage to the island’s vibrant history and gain a deeper understanding of its people.

Stroll Through The Past At Key West Cemetery

Planning A Weekend Getaway You’ll Never Forget

Now that you have an idea of all the exciting things waiting for you here in Key West, you can get started on planning a weekend you’ll never forget!

Looking for a romantic evening surprise for your significant other? How about a relaxing end to a long day of exploration? A sunset cruise is a wonderful way to wind down or wine and dine with your loved one at the end of a day in Key West.

Let Key West Boat Trips help you create a memory-making experience with one of our sandbar tours! Not only are our captains aware of all the best locations to enjoy a day on the sandbars, but we even offer a delicious seafood and lobster meal on some of our excursions!

Contact us on our website to learn more about how we can help you create a memorable experience here in Key West!

3 to 4 hours
Group Size
Up to 12

Sandbar Tour For Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

3 to 4 hours
Group Size
Up to 6

Hopping Sandbars In Key West

What a perfect day to take a boat ride! You will see not one but several different sandbars on this tour! It will only take 25 minutes to get there on our epic adventure, and we can stop as long as you want at those sandbars that interest you the most. This is something you cannot miss!

Experience the mangrove trails of Mud Keys and hang out with locals at Snipe Point after. You won't want the day to end.

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2 hours
Group Size
Up to 6

Key West Sunset Cruise

Ocean, meet our captain! One of the best things about the backcountry waters is how it’s never too crowded. So jump in and enjoy the peacefulness and remoteness as you stand in the "middle of the ocean" with nothing but water around you. Optionally, bring some champagne to enjoy with the sunset as a backdrop. Then, just sit back and relax as you cruise on out into the middle of nowhere, leaving behind any stress or worries.

2 hours
Group Size
Up to 6

Mud Key Mangrove Safari

It's time for some adventure and excitement with a boat trip through the backcountry. After only a short ride, we'll take you on a leisurely cruise down to Mud Key Sanctuary, where you can enjoy the countryside and take in all the wonders of nature that surround you. Stop by the sandbar for a refreshing dip or just stroll around and soak up the sun. Capture your memories and cherish them forever.