What I take or purchased when I get there:

• Clothing/beachwear for 4 days.  I'll have plenty of time to do a batch of  laundry in the condo in 4 days time. I take 4 shirts, 3 pair of shorts and a skirt.  Your needs may be different.
• Depending on my plans for the trip, I take one nice outfit to go out in.  Your needs may be different.
• Sandals or shoes that can get wet
• Walking/hiking shoes
• Water shoes / Aquasocks
• Swimsuit
• T-shirt for snorkeling
• Wrap or swim suit coverup
• Pajama bottoms or something to lounge in at the condo
• Medications/vitamins/essential oils (Both the items I regularly or periodically take, plus some cold meds, just in case.  It's no fun to spend your vacation time looking for cold medicine.)  Take meds in their original bottles so that if you get stopped at the airport, you can easily verify what medication you have with you.  Also, have name/number of your physician or pharmacist in case you need a refill.
• Contact lenses (even though I wear glasses most of the time, I take contacts to wear while snorkeling)
• Personal hygiene items
• Tanning oil or sun block - You can get burned in just the first few hours
• Bug repellant, which you will need if out during sunrise/sunset.  My favorite is an essential oil blend  - it works much better than Deet or Off.
• A hat or visor to shade you from the sun
• Sunglasses
• Snorkel/swim gear
• Camera/film
• Cell phone/charger
• Portable CD player / music
• My favorite pineapple slicer
• Beach mats
• Laundry detergent tablets
• Little packs of condiments
• Games to play with the kids/friends at night
• Lots of plastic baggies
• Fanny pack or backpack to take hiking
• Collapsible cooler
• Guide books
• Novels/other books for enjoyment reading
• Addresses/stamps for sending postcards
• Umbrella
• Golf clubs & gear, if this is a golfing trip

Stored in my carry on bag:

• Reservations/confirmation
• Passport/ID (if not kept on my person)
• Money, credit cards, etc.
• 1 small change of clothes
• 1 swim suit
• A good book
• DVD player & Netflix movies
• Other items to entertain myself on the flight, including headphones
• Camera/phone and other items I do not want to pack in my checked luggage
• I keep coins in my pocket in the event I was separated from all my baggage and had to make a land-line phone call.

Before leaving home I remember to:

• Arrange with neighbors to watch the house & pick up mail
• Arrange any other security measures (lights/timers/visitors)
• Water my plants
• Most importantly:  Shut off the main waterline to the house (just one incident of having a broken pipe while you are gone will convince you to shut off your water before you leave.)