If you are wondering what to pack for Key West in May, prepare for heat.
We were lucky and had beautiful weather during our trip, with plenty of sunshine and no rain, but the temperatures were still intense. Most days were in the high 90s, and the real feel was often over 100 degrees.
The good news is that evenings cooled down into the mid-70s and felt wonderful. Mornings were also fairly comfortable until around noon. After noon, the heat picked up fast, so cold water, shade, and breaks made a big difference.
After spending several days walking around Old Town, eating through Key West, swimming, exploring, and taking a Dry Tortugas day trip, these are the items I was glad I packed and a few things I would do differently next time.
If this is your first trip, I would also read my Key West Travel Guide for First Time Visitors because packing makes more sense once you know how much walking, eating, sweating, and sunset-chasing is involved.
Key West in May is hot, sunny, humid, and very walkable if you pack correctly.
This is not a destination where I would bring a suitcase full of “just in case” layers. During our trip, I never needed a jacket, sweater, jeans, or anything heavy. I needed lightweight clothes, comfortable shoes, sunglasses, cold water, and hair ties.
Mornings were the easiest time to explore. We could walk around Old Town, get breakfast, visit attractions, or take photos without feeling like we were melting immediately.
By midday, the heat was much stronger. If you are planning a May trip, I would build your days around mornings, evenings, pool breaks, shaded stops, and indoor meals when possible. My Key West 3 Day Itinerary for First Time Visitors is a good next step if you want to see how I would structure the days without cramming everything into the hottest part of the afternoon.
Evenings were the best surprise. Once the sun went down a little, Key West felt so much more comfortable. Dinner, sunset, and walking around after dark were much easier than trying to do everything in the middle of the afternoon.
This is not the trip for heavy fabrics.
During the day, I mostly wore:
The humidity is no joke, and you will appreciate anything lightweight and breathable.
For a Key West packing list in May, I would focus on clothes that feel easy to wear in direct sun and humidity. Think cotton, linen, athletic-style skorts, breezy dresses, and tops that are not going to cling to you all day.
If you are wearing dresses or skirts in the heat, Thigh Society shorts are a good thing to pack.
This is also not the trip where I would pack a bunch of complicated outfits. You are walking, sweating, going in and out of restaurants, stopping near the water, and possibly changing for dinner later.
Cute is fine. Heavy is not.
For daytime in Key West, I would pack casual outfits that can handle heat, walking, and a little sweat.
Old Town Key West is very walkable, but that also means you may be outside much more than you expect. Between Duval Street, Mallory Square, the Historic Seaport, the Hemingway House, coffee shops, restaurants, and random wandering, we spent a lot of time outside.
A good daytime outfit for Key West in May would be something like:
I would avoid anything thick, tight, or fussy. If you are already questioning whether something will be too hot, it probably will be.
Key West is surprisingly walkable. Between Duval Street, Old Town, Mallory Square, the Historic Seaport, and all the restaurants, we walked a lot more than I expected.
I mostly wore flats because they worked well with my outfits, and they were fine most of the time. But there were definitely moments when tennis shoes would have been more comfortable.
The downside is that tennis shoes can feel hot during the day, especially in May.
If you are trying to balance comfort and style, a comfortable sandal or supportive flat is a great option. I would not pack shoes that need to be broken in, and I definitely would not plan to walk around Key West all day in anything uncomfortable just because it looks cute.
This is a walking destination, even if it does not feel like one when you are packing.
One thing that surprised me about Key West is how laid-back it feels.
Even at nicer restaurants, people were not overly dressed up. You can absolutely wear a cute dinner outfit, but you do not need to pack like you are going to a formal resort.
For dinner, I wore:
That felt right for Key West.
I did bring a pair of heels for a nicer dinner, but I ended up changing into them once I arrived at the restaurant rather than walking around Key West in them. That was the correct decision.
The sidewalks, heat, walking distances, and general Key West casualness do not make heels especially practical. If you want them for photos or a nicer dinner, bring one pair. I would not pack multiple pairs.
I did not use one.
Not once.
Not during the day.
Not at night.
Not in restaurants.
Many restaurants in Key West are open-air or partially outdoors, so I never encountered the freezing restaurant air conditioning that sometimes makes me want a sweater.
If you are visiting Key West in May, I would leave the jacket at home.
I know there is always the little packing voice that says, “But what if I get cold?” I usually listen to that voice. In Key West in May, that voice was wrong.
This was probably my biggest packing mistake. I wore my long hair down during the first day and immediately regretted it.
Between the heat, humidity, and walking, I quickly realized fun updos, ponytails, braids, and messy buns were much more practical during the day. I still wore my hair down for dinner, but daytime was a different story.
If you have long hair, pack more hair ties than you think you need. Bring clips, scrunchies, a claw clip, whatever works for your hair. This is not the trip where I would rely on one tiny emergency hair tie at the bottom of your bag. The humidity will win.
Save this for later on Pinterest so you don’t forget it.
I used my sunglasses constantly.
Key West is incredibly bright and sunny, especially when you are walking near the water.
If you normally leave home without sunglasses, this is not the trip to do that. I would pack a pair you actually like wearing and maybe a backup pair if you are someone who loses things on trips.
Between the water, white buildings, sidewalks, boats, and full sun, your eyes will need them.
My Brita water bottle was one of my most-used items.
I would fill it with ice at the hotel each morning and then refill it throughout the day at restaurants and attractions.
Having cold water while walking around Old Town made a huge difference.
This seems basic until you are walking in Key West in May and realize how often you want water. Buying bottles all day gets annoying, and it is easier to stay hydrated if you already have one with you.
I would not do Key West in May without a refillable water bottle.
Even if you are not planning a beach vacation, once that hot heat hits you, you may change your mind. We did. Ha.
We ended up swimming every day, whether it was at our hotel pool or during our Dry Tortugas excursion. If you are curious about where we stayed and why the hotel pool was very much appreciated in May, I wrote more about it in my Hotel Marquesa Review: Is This the Best Boutique Hotel in Key West?
A swimsuit ended up being one of the most-used items in my suitcase.
Even if Key West is not a classic “lay on the beach all day” trip for you, I would still pack at least one swimsuit. If your hotel has a pool, you will probably use it. If you are taking a boat trip, snorkeling excursion, beach stop, or Dry Tortugas day trip, you will definitely want one.
For May, I would bring at least two swimsuits if you have room. That way one can dry while you wear the other.
If snorkeling is even remotely on your vacation wish list, bring your own gear. The Florida Keys are home to North America’s only coral barrier reef, and there are plenty of opportunities to get in the water.
We used our snorkel mask at Dry Tortugas, but there are many other snorkeling opportunities throughout the Keys as well. If you are planning that day trip, my How to Visit Dry Tortugas National Park: Everything You Need to Know breaks down the full experience.
Could you rent or use provided gear on certain tours? Yes. But I prefer having my own snorkel mask because I know it fits, I know it is comfortable, and I am not trying to figure it out for the first time once I am already in the water.
If snorkeling is a major part of your Key West trip, bring your own gear if you can.
Many Florida Keys beaches are rocky, coral-filled, or rougher than visitors expect. I was very glad I had water shoes.
They made entering the water much more comfortable and protected my feet from sharp rocks and coral.
This is especially helpful if you are used to soft sandy beaches where you can walk straight into the water without thinking about it. The Keys are different. The water can be gorgeous, but the entry points are not always soft and easy.
Water shoes do not take up much room, and I was glad I had them.
We packed a large quick-dry beach towel that was big enough for both of us. It took up very little room in our luggage and came in handy multiple times throughout the trip.
I liked having one large towel instead of packing bulky beach towels. It worked for pool time, water stops, and the Dry Tortugas excursion. A quick-dry towel is especially useful if you are trying to keep your luggage lighter or if you are changing locations during a Florida Keys trip.
A few smaller items also helped more than I expected.
For sunscreen, I like having both body sunscreen and face sunscreen because Key West is not a casual sun situation. Coola spray sunscreen is easy for reapplying during the day, and Supergoop face sunscreen is good if you want something that feels better on your face.
I would also bring a portable phone charger, especially if you are using your phone for maps, photos, restaurant reservations, and directions all day.
For bags, you do not need anything huge, but you do need room for sunglasses, water, sunscreen, and whatever random thing you bought because you walked into a shop for “just a minute.” A phone and wallet crossbody strap is also helpful if you want to keep your hands free while walking around, taking photos, or carrying your water bottle.
Yes. During our trip, the real feel was often over 100 degrees, so I would pack for heat, humidity, and lots of sun.
I did not need a jacket at all. Not at night, not during the day, and not inside restaurants. If I visited Key West in May again, I would leave the jacket at home.
I would wear lightweight, breathable clothes. Shorts, skorts, tank tops, casual dresses, rompers, and flowy outfits all worked well. For dinner, Key West still felt laid-back, so I would bring cute but comfortable outfits instead of anything too formal.
Yes. Even if you are not planning a beach-heavy trip, I would still pack a swimsuit. In May, once the heat hits, pool time becomes very appealing.
I would bring them. They made rocky and rougher water entry points much more comfortable.
If I could give one packing tip for Key West in May, it would be this:
Pack for heat.
Then pack for even more heat.
The key is staying cool, comfortable, and hydrated while you are out exploring. Lightweight clothing, comfortable shoes, sunglasses, a refillable water bottle, and a swimsuit will get far more use than anything fancy you bring.
And if you have long hair like I do, learn from my mistake and pack plenty of hair ties.
If you end up booking anything for your trip, using my affiliate links helps support my blog at no extra cost to you. I spend a lot of time researching and writing these guides, so I really appreciate the support.
If you are flying into Key West or comparing nearby airport options, start with Skyscanner and then read my Key West Airport Guide for First Time Visitors.
For hotels, compare prices on Booking.com or Hotels.com. If you are still deciding which part of the island makes the most sense, my What Areas to Stay in Key West guide will help you narrow that down.
For activities, you can compare options on Viator or Get Your Guide. My Best Things to Do in Key West guide is a good place to start if you are still building your itinerary.
For Key West in May, the things I would prioritize most are a Brita water bottle, water shoes, a snorkel mask, and a quick-dry beach towel. If you are debating the Dry Tortugas day trip, read my Dry Tortugas Ferry vs Seaplane guide before you book.
Booked this Bryson City yurt for the ‘ber months and it’s already my top fall pick this year. 🍂
The Junaluska Yurt sleeps six but feels more like a stylish cabin than a yurt, two real queen bedrooms with actual doors, a full kitchen, and a private bathroom with a walk-in shower. Check-in is just a door code texted to your phone, no lobby, no waiting.
The real win is outside: wraparound porch, private fire pit, free firewood, a gas grill, and Smoky Mountain sunsets that stop you mid-sentence, picture all of that with October color on the ridgeline. Heads up, the last stretch in is a gravel road, so skip the low-profile rental, and there’s no restaurant onsite, you’re minutes from Bryson City, Dillsboro, and Sylva for dinner.
Two to three nights is the sweet spot. (We actually stayed in the dead of winter and it was still stunning, fall just takes it up a notch.) Full review linked in bio.
Italian food felt like the last thing I expected to find in the middle of the Appalachian Mountains... until I sat down at Ilda in Sylva.🍝
They call it Italian-Appalachian, and that’s not just a tagline. Homemade pasta, craft cocktails, local ingredients pulled straight from the mountains around it, this is the kind of meal that makes you forget you’re two hours from the nearest city. It’s cozy, it’s a little upscale, and it is not a walk-in kind of place, call ahead, because tables go fast on weekends.
It’s not cheap, and it’s not trying to be. But if you’re already making the trip out to Sylva, this is the one reservation worth planning your day around.
Full write-up, including what to order, link in bio.
Booked my fall cabin before September even started, and I’m not sorry about it. 🍂
These are the stays that make you actually want the cold to hurry up fireplaces, mountain views, the kind of porch you don’t leave. Not every one of these is going to fit every trip, but if a cozy fall getaway is on your radar, this is the roundup to start with.
One of my favorite travel seasons is almost here, and I have zero chill about it. 🍁✈️
There’s just something about fall trips cooler air, apple orchards, that first flannel of the season, food that actually makes sense with the weather again. I’m already mentally packing for it before September even starts.
If fall is your favorite time to travel too, tell me where you’re headed... I’m taking notes for the list.
Pack your bags... ✈️🧳My hiking and road trip gear shop just got a refresh, and this is everything that actually earns a spot in my bag. The dry bag pulls double duty for beach days and trail days, the Osprey backpack is the one I grab for anything motorcycle or day-hike related, and the GoPro comes with me literally everywhere at this point.
Nothing on this list is filler it’s all stuff I’ve used, packed, and repacked more times than I can count. Full shop linked in my bio if you want to build out your own kit before your next trip.
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
