What to Pack for St. Augustine in the Winter: A Local’s Advice

If you’re planning a winter getaway to Florida, you might be wondering what to pack for St. Augustine in the winter. The nation’s oldest city is charming any time of year, but winter really is one of the best seasons to visit.

Florida winters are mild, but they’re also unpredictable. One morning it’ll be 48°F with a coastal breeze, and by afternoon you’re peeling off layers in the sunshine. There’s also the random cold fronts that are FRIGID!

As someone who has grown up in central Florida, here’s everything you actually need to pack for St. Augustine in the winter and what you need to know to be prepared.

St. Augustine Winter Weather: What to Expect

If you’re heading to Florida in the winter, or wanting to spend Christmas in St. Augustine, the weather can be beautiful but unpredictable! Generally speaking, winter here is mild but moody.

There’s the random cold fronts where we reach freezing temperatures and combine that with the humidity, it feels VERY cold.

The Florida winter is really just NOT summer. The leaves continue to fall well into January and our grass stays green (though it’s not as lush as summer).

In general, you can expect:

• Mornings in the 40s–50s
• Afternoons warming up into the 60s–70s
• A coastal breeze that can make it feel cooler
• Occasional rain, fog, windy days, and cold fronts

It’s all about layers. However, unlike up north, you don’t need layers to stay warm. Rather, you need layers you can easily remove as the day warms up. If you pack only warm clothes, you’ll overheat. If you pack only light clothes, mornings and evenings will feel chilly.

Check for Any Cold Fronts

Of course, I do recommend checking the weather before packing. If there’s a random cold front, don’t underestimate it! Freezing temperatures here really shock people.

In part because it’s unexpected and in part because the humidity makes it a wet cold which really cuts through you! When it comes to what to pack for St. Augustine in the winter, being prepared for a random cold front is important!

Clothing Essentials

When it comes to what to pack for St. Augustine in the winter, it’s not very difficult! Traveling to Florida is much easier than a true winter destination, but you do have to prepare for the random rainy or frigid weather.

Of course, preparing doesn’t mean you have to go shopping! When I head north for a winter vacation it usually requires me to buy winter clothes, but coming to Florida you won’t likely need to purchase anything, unless you’re coming from the tropics!

Here’s the essentials you’ll need for your time in the oldest city or even day trips from St. Augustine!

Light Layers (You’ll Wear These Daily)

Florida winter is built on layers that are easily removable, rather than warm layers to keep you cozy. I recommend:

• Long-sleeve tees
• Lightweight sweaters or pullovers
• Breathable tops for warmer afternoons
• A flannel or thin jacket for easy on/off

Layering Tips for Cute Outfits

I’ve always loved the layered look people sport in colder climates. However, in Florida the layering can be tricky. There are times I like my layered look but removing a layer changes up the whole outfit!

In Florida, you want to ensure your base outfit is cute, then add the layers or a jacket that you’ll need for mornings and evenings. Or if my light jacket is a main part of my outfit, I’ll add easy to remove layers under it for the cooler mornings or evenings.

Typical winter days in Florida will warm up, especially if you’re in the sun. So when planning your outfits, keep in each phase of the day in mind.

An Outer Layer

Unless there’s a cold front when you’re here, a medium to light jacket will do. This is especially true if you have long sleeves or flannels you can layer underneath.

However, if we will be reaching freezing temperatures, don’t underestimate it. This is when people get surprised by how cold Florida can randomly get.

Early November we got a cold front where I live that reached as low as 33 degrees, (almost freezing)! The feels like temperature was in the 20s! I usually go for morning walks, but I couldn’t handle it! However, since that random cold front, we’ve had highs in the 70s for most of the last five weeks!

Even if you run warm, bring something cozy for the early mornings and evenings.

• Light to medium jacket
• A packable puffer if you get cold easily or there is a predicted cold front

Bottoms

Bottoms are easy! Anything will work! I even wear dresses or shorts on most days and if it’s cold you can throw on some tights. I’ve never layered bottoms unless I travel to a truly cold climate like the time I spent 4 days in Montreal and Quebec City!

Just ensure you have one or two jeans or pants, especially if there’s a cold front.

Keep it simple and comfortable:

• Jeans
• Midweight pants
• Leggings or walking pants for full days exploring

Shoes

St. Augustine’s historic district has cobblestone streets, uneven sidewalks, and lots of walking. So when it comes to what to pack for St. Augustine in the winter, keep the shoes comfy!

For nice dinners, you can bring whatever works with your outfit, though if you plan to walk, I recommend keeping it comfy. You don’t have to dress fancy for most places in Florida.

• Comfortable walking shoes
• Waterproof sneakers if rain is in the forecast
• Optional: ankle boots for dinners or photos

Accessories

Since true layering isn’t as much of an option in Florida, I’ve really learned to add fun layers through accessories. For practical purposes, a beanie or scarf is important for cold days. And of course, be prepared for sunny days!

I remember being a full grown adult before learning there was such a thing as a summer scarf! As you can imagine, scarves of any many material are really only worn during the winter months in Florida.

So when it comes to what to pack for St. Augustine in the winter, have fun with the accessories!

• A light scarf (great for windy days near the water)
• A beanie or headband during cold snaps
• Sunglasses — it’s usually sunny

Weather-Specific Add-Ons

While winter tends to be pleasant, you’ll still want to prepare for rainy days or cold fronts.

For Windy or Cold Days

• Windbreaker or warm jacket
• Light gloves if you’re sensitive to cold
• Warm scarf
• Beanie

For Rainy Days

Florida’s summer rain is torrential downpours that tend to move fast. However, in the winter the rain tends to be softer, but lingers longer. Umbrellas are pointless in the summer, but could be useful in the winter so check for any rain in the forecast.

• Compact umbrella
• Waterproof jacket
• Quick-dry socks or comfortable sneakers

What to Pack for St. Augustine Activities

Beach Walks

You can definitely walk the beach in winter and it’s still beautiful when the air is crisp. The sand does get more compact closer to the water, but you’ll likely have to walk on soft sand at some point, so choose shoes that won’t let in a lot of sand. Of course, if it’s warm enough barefoot is always an option!

Don’t forget a light to medium jacket! The water does get cold, then the wind off the water will feel extra cold. If you head to the beach, expect windier and cooler conditions.

• Sweater or jacket
• Comfortable shoes that can handle sand
• Refillable water bottle

Exploring Historic Downtown

You’ll be popping in and out of shops, museums, and cafés, but unlike up north you won’t likely have to take off any layers once you go indoors. You’ll want something light even on warmer days in case you feel colder in the shade or the wind picks up.

Sweaters that you can tie around your shoulders or flannels around your waist can really be helpful with the fluctuating temperatures on an average winter day in Florida.

• Crossbody bag or purse
• Layers you can shed easily
• Good walking shoes (truly worth repeating)

Boat Tours + Nights of Lights Cruises

Even if the daytime is warm, the water gets chilly at night. No matter where you are, being on the water is always windier and colder in the winter and Florida is no exception. A sunset boat tour or a Nights of Lights cruise is worth doing, especially if you’re spending 3 days in St. Augustine or more!

• Warm jacket
• Shawl or small blanket

Check out this top rated Sunset Cruise of St. Augustine

If You’re Planning Photography Days

The charming historic district or a sunrise at the beach make great photo opportunities!

• Portable phone charger
• Mini tripod or handheld grip

Toiletries & Personal Items

• Sunscreen or hat
• Chapstick (wind + cool air = dry lips fast)
• Moisturizer or aloe
• Hair products for humidity or wind
• Any medications or supplements

Tech & Travel Gear

• Portable charger (St. Augustine is very walkable—phone batteries drain fast)
• Camera or GoPro
• Car charger if you’re road-tripping
• Lightweight daypack or sling
• Reusable water bottle

Holiday & Nights of Lights Extras

Christmas in St. Augustine is so charming with the Nights of Lights. If you’re visiting between mid-November and mid-January:

• Cute but warm layers for photos
• A small blanket or jacket for trolley tours
• A festive outfit if you’re dining out

Wondering where to stay in St. Augustine for Christmas? I have an article dedicated to helping you find the right area for your trip: Where to Stay in St. Augustine for Christmas: Best Areas & Festive Hotels.

Final Tips Before You Go

• Pack layers.
• Bring comfortable shoes—you’ll walk more than you think.
• Check the forecast the day before you leave to prepare for rain or cold fronts.

What to Pack for St. Augustine in the Winter

St. Augustine is beautiful year-round, but winter has this calm, cozy charm that makes it one of my favorite times to explore. Pack smart and you’ll be ready for everything—from sunrise beach strolls to festive Nights of Lights evenings.

I hope you have the best time visiting St. Augustine for a winter vacation! It’s a great time to be outside in the sunshine state!