Winter may mean snow, ice and heavy coats across much of the country. In Key West, it means sunshine, swimsuits, waterfront dining, outdoor adventures and some of the island's most popular events.
December, January and February bring comfortable temperatures and plenty of reasons to spend the day outside. You can explore Old Town, head to the beach, listen to live music, tour historic homes or simply find a waterfront table and remember that somewhere else, someone is shoveling a driveway.
If you're traveling from Southwest Florida, Key West Express makes getting there part of the getaway. Relax on the ride across the Gulf and arrive in Key West near the Historic Seaport, ready to explore.
Winter brings:
Each winter month has its own personality.
December combines tropical weather with a little holiday spirit—and Key West naturally puts its own spin on the season.
Palm trees and holiday lights work surprisingly well together.
Throughout December, holiday celebrations pop up around Key West with decorated boats, waterfront festivities, lights and special events.
December's more comfortable temperatures make this an excellent time to slow down and explore Key West on foot.
Walk beyond Duval Street and you'll find colorful historic homes, tropical gardens, hidden lanes and some of the architecture that gives Old Town its unmistakable character.
If you'd rather have a plan before setting out, use our Key West Walking Tour Guide to build your own route.
The 67th Annual Key West Home Tours begin December 29–30, 2026.
These self-guided tours offer a rare opportunity to step inside privately owned historic homes and discover the architecture, stories and details normally hidden behind Key West's gates and garden walls.
The tours continue on select weekends throughout the winter.
New Year's Eve in Key West isn't known for being ordinary.
Instead of one traditional celebration, the island offers multiple parties and quirky countdowns around Old Town. Whether you want a lively night on Duval Street or something more relaxed near the waterfront, New Year's Eve gives December one final burst of Key West personality.
January is prime Key West season.
Warm afternoons, cooler mornings and a packed event calendar make it an especially popular month to trade mainland winter for island time.
The Key West Half Marathon & Runfest returns January 15–17, 2027.
The weekend includes 5K, 8K, 10K and half-marathon events, giving runners a chance to experience Key West from a completely different perspective.
Even if running isn't part of your vacation vocabulary, the event brings plenty of energy to the island.
From January 26–30, 2027, Key West fills with Red Dirt, Americana and singer-songwriter music during Mile 0 Fest.
The festival isn't confined to a single stage. Performances spread across the island at the Coffee Butler Amphitheater, theaters, resorts, waterfront locations, bars and other venues.
Photo Credit: Mile0Fest
We've already put together a complete Mile 0 Fest Key West 2027 Guide with festival details, venues and planning tips.
January's comfortable weather makes it easy to spend an afternoon moving between Key West's galleries, studios and creative spaces.
You'll find everything from tropical landscapes and contemporary works to folk art, photography and pieces inspired by the island itself.
Explore our Key West Galleries Guide before you go and build your own art crawl through Old Town.
January is also one of those months when simply being outdoors feels like an activity.
Rent a bicycle. Walk the Historic Seaport. Take a sailing trip. Go fishing. Find a patio for lunch.
Or head to Fort Zachary Taylor Historic State Park and combine history, beach time and one of Key West's best sunset spots in a single afternoon.
February keeps the beautiful winter weather going while adding art, history, seafood and a little romance.
The Florida Keys Seafood Festival returns February 13–14, 2027, at Truman Waterfront Park.
This annual celebration highlights the Keys' commercial fishing heritage with fresh local seafood, live music and family-friendly activities.
Come hungry.
The winter Key West Home Tours return February 12–13, offering another opportunity to explore private homes normally closed to the public.
For anyone interested in Key West history, architecture or simply wondering what's behind some of those beautiful Old Town gates, this is a unique way to see another side of the island.
February is a great month to browse galleries, meet local artists and discover the creative community that has long been part of Key West.
Art events traditionally bring artists and craftspeople together during the month, while the island's galleries provide plenty to explore at your own pace.
Our Key West Galleries Guide can help you find stops throughout Old Town.
A sunset, two chairs by the water and nowhere you absolutely have to be.
Key West doesn't make romance very complicated.
Couples can spend the day wandering Old Town, sharing a waterfront meal, relaxing at the beach or watching the sunset together.
For more ideas, explore our 10 Romantic Things to Do in Key West for Couples.
Not everything needs an event date.
Some of the best winter days in Key West happen when you leave room in the schedule.
Winter is still beach season in Key West.
Fort Zachary Taylor, Smathers Beach and Higgs Beach each offer a different experience. Conditions can vary, so choose your beach based on whether you're looking to swim, snorkel, walk or simply sit beneath a palm tree.
Our guide to the best beaches in Key West can help you choose.
Mallory Square may be the famous choice, but it isn't the only one.
Try Fort Zachary Taylor, Sunset Pier or another west-facing waterfront spot and give yourself enough time to watch the whole show.
The Historic Seaport is especially enjoyable during winter's comfortable weather.
Walk the harbor, watch boats come and go, browse the shops and stop for lunch or a drink beside the water.
Best of all, travelers arriving aboard Key West Express begin their Key West adventure just steps away.
Winter may be the best season for simply wandering.
Old Town is compact enough that you can discover historic sites, restaurants, galleries, shops and quiet residential streets without spending your entire visit getting from one attraction to another.
| Month | Typical High | What It's Great For |
|---|---|---|
| December | Upper 70s°F | Holiday events, walking, waterfront dining |
| January | Mid-to-upper 70s°F | Festivals, biking, sightseeing |
| February | Upper 70s°F | Outdoor events, couples getaways, exploring Old Town |
Winter evenings can feel cool, especially on the water, so bringing a light jacket or sweater is a good idea.
There's one important difference between fall and winter in Key West:
More people have the same idea you do.
Winter is one of the island's busiest travel seasons. If your trip revolves around a major festival, holiday weekend or special event, make lodging, attraction and transportation plans ahead of time.
Then leave some empty space in the itinerary.
Key West is very good at filling it for you.
If you're starting in Southwest Florida, there's no need to turn your Key West getaway into a long drive.
Key West Express offers high-speed passenger ferry service between Fort Myers Beach and Key West, allowing you to relax on the Gulf instead of spending hours behind the wheel.
Check current Key West Express fares and travel information and book your trip to Key West when you're ready to trade winter for island time.