Winter Getaway to Key West

Somewhere, a snow shovel is waiting. Fortunately, it does not have to be waiting for you.

When winter brings gray skies, freezing temperatures and one too many layers, Key West offers a warmer alternative. Think palm trees instead of bare branches, swimsuits instead of snow boots and evenings spent outdoors instead of racing from one heated building to another.

Here is how to escape the cold and plan the ultimate winter getaway to Key West.

Start With a Resort That Feels Like Summer

The quickest way to forget winter exists is to check into Blue Flamingo Resort, change into a swimsuit and head for the pool.

With two outdoor pools, shaded cabanas and The Backyard Pool & Social Club, Blue Flamingo makes it easy to spend an entire winter afternoon outside. Order breakfast at Toasted Coconut, grab a frozen drink at Rum Row and let the rest of the day happen at its own pace.

WINTER-ESCAPE TIP

Reserve a cabana before arrival, particularly during popular holiday and winter travel weekends.

Spend Your Days Outside

Winter is one of the best times to explore Key West without the intense heat of summer. Build your itinerary around the outdoors.

Relax at Fort Zachary Taylor

601 Howard England Way

Spend the afternoon swimming, snorkeling or relaxing beneath the trees at Fort Zachary Taylor Historic State Park. Explore the historic fort before settling along the shoreline for sunset.

Explore Old Town by Bicycle

Key West is compact, colorful and mostly flat—three excellent reasons to explore on two wheels. Ride past historic homes, waterfront streets and hidden gardens, stopping whenever something catches your eye.

Blue Flamingo’s Bike Around Key West package includes two bicycle rentals per day, making spontaneous exploration even easier.

Get Out on the Water

Book a snorkeling trip, dolphin watch, kayak tour or sandbar excursion. Winter weather can vary, so choose a flexible operator and check marine conditions before departure.

Eat and Drink in the Open Air

One of the greatest luxuries of a Key West winter is eating outdoors without a patio heater.

Enjoy seafood beside the harbor, brunch under tropical trees or cocktails along Duval Street. For a relaxed resort day, stay poolside at Blue Flamingo, where island-inspired food and drinks are always close.

Winter is also stone crab season in Florida, generally running from October into May. Look for current local catches and seasonal specials when dining around the island.

Watch the Sunset Without Shivering

A winter sunset is considerably more enjoyable when gloves are not required.

Join the nightly celebration at Mallory Square, find a quiet place at Fort Zachary Taylor or book a sunset cruise for open-water views. Bring a light layer for the breeze, then stay outside as the sky moves from gold to pink.

Enjoy Key West’s Winter Events

Winter brings some of Key West’s most anticipated cultural and culinary events, including holiday festivities, literary programming and the Key West Food & Wine Festival.

Schedules change annually, so check current calendars before booking. Popular event weekends can increase demand for accommodations, dining and excursions.

Pack for Warm Days and Breezy Nights

Bring:

• Lightweight clothing and swimwear
• Sunscreen, sunglasses and a hat
• Comfortable walking shoes
• A light sweater or jacket for evenings
• A compact rain layer
• Something slightly dressier for dinner

Leave the heavy coat at home. It has done enough.

Book your winter escape at Blue Flamingo.

Frequently Asked Questions

Is winter a good time to visit Key West?

Yes. Winter is popular for its generally warm weather, outdoor activities and seasonal events. It is also peak travel season, so early reservations are recommended.

Can you swim in Key West during winter?

Many visitors enjoy resort pools, beaches and water excursions throughout winter, although air and water temperatures vary.

What should I wear in Key West during winter?

Pack summer clothing, swimwear and sun protection, plus a light layer for cooler or breezy evenings.

How many days do you need for a winter trip to Key West?

Three or four days provides time for the pool, Old Town, a water excursion, sunset and several memorable meals without rushing.