Good walking shoes and lots of sunscreen
Toiletries and Medical Supplies: There are grocery stores and drug stores on the island so you can probably get what you don't bring.
Miscellaneous: Take a good map with you. They hand out free maps that are misleading, incomplete and not to scale. I did not find any reasonably priced maps for sale in Key West.
Key West is a walking town especially on and around Duval Street so comfortable, soled shoes or sandals are a must. Don't walk downtown in barefeet as the streets are likely to have either debris (glass, etc) that could cut up your feet. Also, in the heat, both streets and sidewalks heat up tremendously and you don't want to either burn your feet or have to purchase shoes/sandals from a downtown vendor.
Toiletries and Medical Supplies: Essentials if you plan do to the "Duval Crawl" include: aspirin, Tylenol, antacids, Pepto-Bismol, and Chaser.
You should also have available at your hotel or B&B at least some insect repellent, sunscreen & aloe vera gel.
Camping/Beach/Outdoor Gear: If you plan to do the beaches, bring a blanket and or chair and some sort of sun protection. The sun is brutal on skin not normally exposed to this heat and latitude.
Luggage and bags:
Bring a day pack for whatever you'll need while you're out.
Clothing/Shoes/Weather Gear: Your sweaty or wet feet need to dry. Sandals make a good choice, especially the kind that can go into the water. The only downside is the possible stink, but that's why you bring copious amounts of hand sanitizer to disinfect them.
Toiletries and Medical Supplies: * Hand Sanitizer (for the above mentioned sandal stench).
* Aloe and Moisturizer for burns.
* Antacids for the food.
* Painkillers for the hangovers.
Photo Equipment: * $15 disposable Waterproof camera for snorkling, etc.
* compact point and shoot digital camera for everything else.
Camping/Beach/Outdoor Gear: Bring a fancy, compact, hi-tech raincoat just in case. They roll up small, so you can bring 'em along every day.
Miscellaneous: If you're doing Key West properly, you should be wet about 50% of the time. This of course means you'll need:
* zip lock bags
* garbage bags liberated from your hotel room for putting wet towels etc. while you're out.
Clothing/Shoes/Weather Gear: Do remember Key West can be a rainy soggy misrable little stinking island. Do pack appropriate wet weather clothes, or suffer the wrath of locals as you walk around in a cheap tourist poncho (which looks suspiciously like an altered garbage bag).
Luggage and bags:
Carry lite. Pack little. Cool clothing, maybe a lite sweater for the evening by the water.
Clothing/Shoes/Weather Gear: sandals or tennis shoes
Toiletries and Medical Supplies: There are medical places around local
Photo Equipment: Bring your camera. You may get the best pictures of big scooners and a sunset.
Camping/Beach/Outdoor Gear: I think thers's a state park. It didn't look that crowded when we passed it. Looked pretty clean at a glance.
Miscellaneous: Lots of history here. You may run in to a golden Elvis or a statue of liberty walking around. They need tips too!
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Miscellaneous: Buy a copy of 'Key West & The Florida Keys' by June Keith before you leave . . . She lives in Key West and really knows her stuff . . . Can't go wrong with anything she suggests . . . See all books by June Keith @ http://cyberconch.com/june/index.html
Luggage and bags:
If you are flying into Key West, prepare to fly on an 11 seater prop-plane. The airport is too small for larger planes. Prepare to have large carry-ons checked and placed in cargo as you enter the plane.
Clothing/Shoes/Weather Gear: Key West in October is a bit tricky. In 2001, we needed sweatshirts and jackets in the evening. Most times, it is quite hot - especially in costume! Hmmm... maybe this explains the lack of material in some costumes. ;-)
Photo Equipment: Bring A LOT of film! Plenty of places to buy it if you don't, but it tends to a bit on the expensive side.
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