Stop Packing Like It’s July: The Winter Travel Guide You Actually Need
- Melissa Lenox
- 3 days ago
- 4 min read
Let’s be real. When you book a trip to Florida or the Caribbean in the winter, you’re picturing one thing: scorching sun, piña coladas, and sweating by the pool.
You are probably packing five swimsuits, three pairs of flip-flops, and zero long sleeves.
That is a rookie mistake. You'll end up in the gift shop spending $80 per sweatshirt for every member of your family!
While your friends back home are shoveling snow, you will have beautiful, warm days. But here is the catch: winter days in the tropics are shorter, and when that sun drops at 5:30 PM, the temperature drops with it.
Don’t be the traveler shivering in a tank top at the buffet. Here is your survival guide to packing for the "warm" winter months.
1. The "Layering" Rule (It’s Not Just a Cliché)
In the winter, tropical weather is bipolar.
11:00 AM: You are roasting in the sun (80°F).
7:00 PM: You are freezing on a windy deck (65°F).
You don't need a parka, but you do need to be prepared. Pack a denim jacket or a high-quality "shacket" (shirt-jacket) or cardigan. They are heavy enough to block the wind but stylish enough to wear to dinner over a sundress. For the guys? A quarter-zip pullover is non-negotiable.
In my experience this is mainly in December and January. November and February can be pleasant but that doesn't mean it can't get chilly after dark!
On my travel days I'll wear a tank top, joggers and a light jacket. That keeps me warm up north, on the plane and then I can shed the jacket once I hit the southern temps without carrying around a bulky jacket.
2. Respect the Wind (Especially Cruisers)
This is where most people fail. If you are on a cruise ship, you are on a moving object traveling at 20 knots. If you are up on the pool deck at night watching a movie, or even just walking to the theater, the wind chill is real.
The Math: 70°F air temp + 20 mph ship speed = It feels like 55°F.
Pack a windbreaker or a structured hoodie. The ocean breeze after dark cuts right through cotton.
3. The "Heated Pool" Trap
"Oh, I don’t need warm clothes, I’ll be in the pool!"
Yes, the pools in Florida and on cruise ships are heated. But the air outside them is not. The most dangerous walk of your vacation is the 500 feet from the heated pool back to your hotel room.
The Fix: Do not rely on a thin sarong. Bring a thick, terry-cloth cover-up or even a light bathrobe. You need something that dries you off and keeps the wind out.
4. Yes, You Need Pants
I know, you didn't go on vacation to wear pants. But in Orlando and the Bahamas, morning lows can hit the 50s. If you are rope-dropping a theme park at 8:00 AM, shorts are a miserable choice.
Pack "Vacation Pants": Leave the heavy wool at home. Pack linen trousers, maxi skirts, or lightweight joggers. They cover your legs but breathe once the afternoon sun hits.
The Cold Hard Stats
Don't believe me? Here are the average winter lows (what it feels like when you're going to dinner) for popular hot spots.
Destination | Average High (Day) | Average Low (Night) | The Reality Check |
Orlando, FL | 72°F | 51°F | That is jacket weather. Period. |
Miami, FL | 76°F | 60°F | Breezy and cool near the water. |
Nassau, Bahamas | 78°F | 64°F | Windy evenings make this feel colder. |
Cozumel, Mexico | 82°F | 68°F | Warm, but boats and decks get chilly. |
Caribbean Cruise Deck | 75°F | "55°F" | Wind chill factor is high on open water. |
Note: These are averages for Jan/Feb. Cold fronts can push these even lower!)
I've traveled many times in the winter months. Minimally you need a sweatshirt for the morning and evening - it may warm up enough in the day so shorts are fine. Other times you may need pants and a jacket all day! So always check the local forecast before you leave and pack appropriately.
The Bottom Line
You are going to have an amazing time. You will swim, you will tan, and you will escape the snow. But the difference between a good trip and a great trip is comfort.
Pack the hoodie. Bring the comfy pants. Throw in a scarf. Better to have it in your suitcase than to buy an overpriced souvenir sweatshirt you’ll never wear again.
Melissa Lenox specializes in concierge vacation planning. Helping busy parents plan dream vacations. Where to go, when to go, daily recommendations for your trip and even assistance while you are away so the entire process is seamless and stress free.
My specialties are theme parks, all inclusive resorts and ocean cruises. I am a Senior Travel Advisor with Coasters & Castles Travel and Blog Editor of Main Street to the World.
Follow me on my pages below or contact me at mlenox@travelcnc.com to plan your next adventure!