9 Fun Winter Things To Do In Key West In January

9 Fun Winter Things To Do In Key West In January

Key West Boat Trips

When you decide to visit outside of high season, you’re presented with countless things to do in Key West in January. Since the winters are never too cold, you get to enjoy an average high temperature in the 70s.

There are a few key events that take place during this month, so you’ll want to know what they are so you can have the best possible time exploring Key West and creating memories.

1) Explore The Dry Tortugas National Park And The Sandbars Around Key West

There are a few ways to get over to the Dry Tortugas National Park, including by ferry and by boat. This allows you to see more of the Keys while also taking advantage of the great weather. Since you’re out of the shoulder season, you won’t have to worry about hurricanes, tropical storms, or the rainy season. It’s just smooth sailing.

Here are a few reasons to check out the Dry Tortugas while you’re in Key West in January:

  • It’s made up of 7 islands
  • There are several secluded beaches
  • You can explore Fort Jefferson
  • It’s the best place in the Florida Keys for bird watching
  • Clear waters lead to snorkeling and the ability to see the vibrant sea life

Tip: It can be a bit cold for snorkeling in January in Key West, so a wetsuit will be a great idea.

You can also take a private boat tour, allowing you to indulge in a picnic along a sandbar, cocktails as you ride the waves, and so much more. It’s a great way to see Key West in January and experience the amazing weather.

Dry Tortugas

2) Attend The Key West Food & Wine Festival

One of the key events of January is the Key West Food & Wine Festival. If you’re going to visit Key West, you might as well indulge in all that the island has to offer, including amazing food and wines.

There’s a new theme every year, and 2024’s theme is Spain.

The event runs Tuesday through Sunday, and there are various ticketed events that you can attend. This will allow you to indulge in some of the amazing Key West food, much of which is prepared by local chefs. Many of the dishes are also paired with wine.

If you’ve ever wondered what wine pairs best with Key Lime Pie or conch fritters, you won’t want to miss this festival.

Attend The Key West Food & Wine Festival - Key West, January

3) Run The Key West Half Marathon

If you want to get some amazing views of Key West, one of the best things to do is run the Key West Half Marathon. If running 13.1 miles sounds like too much, there’s also a 5K that you can sign up for.

This marathon has been voted as one of the 10 best across the nation by USA Today.

Along the way, you’ll see some of what makes Key West famous, including Mallory Square, Mile Marker Zero, and Bayview Park.

Key West Half Marathon During The Peak Tourist Season

4) Eat Your Way Through The Seafood Festival

The Florida Keys Seafood Festival is a chance to indulge in some of the finest fresh seafood that the state has to offer. It’s held at Bayview Park, Key West. When you are in Key West in January, this is a must-attend event.

You’ll get to walk around and taste food from an array of different vendors. Try a few different preparations of Key West pink shrimp, taste gumbos, chowders, and conch fritters.

There will also be live music, frozen rumaritas, and more so that you can make a day of it.

It is a family-friendly event, and there will be an Eco Discovery Zone loaded with activities for the kids.

Delicious Grilled Seafood Platter

5) Walk Through The Many Homes With House Tours

Looking for what to do in Key West in January? If you’re not interested in eating your way through your weight in fresh seafood and don’t want to run 13 miles, there’s always one of the key events – house tours.

The tours are presented by the Old Island Restoration Foundation. When you visit Key West because you want to learn about the history and architecture, you won’t want to miss out on this fun.

The tour involves walking through five of the houses and gardens found in the old town of Key West. You’ll get to learn about the ways they’ve been restored and renovated. Plus, the unique interiors may inspire you to decorate your own home after what you’ve seen in Key West.

Key West Woman's Club - Decorated Houses In Holiday Season

6) Embrace Literature With The Key West Literary Seminar

The Key West Literary Seminar is a great way to meet up with readers and authors for a four-day event. The theme for 2023 was “Singing America: A Celebration of Black Literature,” while the 2024 theme is “Florida: The State We’re In.” The Singing America theme was quite a hit, and scholarships were offered for people to attend.

At the event, there will be a seminar as well as workshops. Writers of all levels are invited to attend, and a Young Writers Studio even invites local high school students to enjoy the writing instruction in Key West.

Singing America: A Celebration Of Black Literature

7) Watch The Quantum Key West Race

If you love boating but want to see it from the scenic waterfront, you won’t want to miss the Quantum Key West Race. Every year, over 100 racing boats head to Key West to compete for the title.

The event got its start in 1975 and has become one of the top distance races in all of North America. Boaters start in Fort Lauderdale and race to Key West. Fun fact is that it used to be St. Petersburg to Fort Lauderdale, but the boaters used to stop in Key West for a drink or two. Over the years, the locations changed so that Key West was the finish line.

It’s a free event to watch, and the website offers live tracking so you can see which boats are in the lead. When you’re visiting Key West, it’s worth stopping by to see some of the boats. Plus, there are plenty of bars and pubs where you can enjoy a drink while you take in all the sights. Since it’s out of shoulder season, they won’t be too crowded.

Sailboat Race

8) Embrace The Warm Weather Along Duval Street

January is the coldest month in Key West, which is not actually cold by tourist standards since it typically only gets into the low 60s. It marks the end of the winter season, so it’s a great time to visit Key West and explore Duval Street without all the crowds.

While you wander through the smaller winter crowds of Key West, don’t forget to check out a few top places:

  • Grab a drink at Sloppy Joe’s
  • Enjoy a meal at Hogs Breath Saloon
  • Pet a shark at the aquarium
  • Explore the many bars at Rick’s Bar (there are 8 of them)
  • Take the Old Town Trolley so you can explore more of Old Town Key West

Key West in January allows you to avoid hurricane season, the hottest months of the year, as well as some of the bigger crowds. Don’t expect it to be so cold that you can’t visit Key West properly. The pleasant weather allows you to embrace all the key events and attractions.

The historic and popular Sloppy Joe's Bar on Duval Street in downtown Key West

9) Explore Key West In January With Us!

At Key West Boat Trips, we show you what to do in Key West in January from the best view possible – the water. This is one of the ultimate ways to explore the Florida Keys because you can travel beyond Key West.

We can take you to play around the sandbars and with our private charters, you can sail on your terms. Our captain will ensure you see all the sights while you relax.

When you’re ready to make the most of Key West in January, book your private tour with us!

Key West Boat Trips

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