In EMS or larger daypack:
passport and/or driver’s license
all flight, hotel, restaurant, day tours and entertainment confirmations
Moleskine notebook with destination notes
guide book or photocopies of guide book pages
laptop/charger/card reader and external hard drive/charger
Crumpler 5 million dollar home with my Canon Rebel SLR and 2 lenses, filters, memory cards, charger
Canon G11 back up camera – or Canon D10 underwater camera in case w/charger
Cell phone/charger
Kindle or books
ziplock bags of liquids needed for flight (hand cream, Ayr Nasal Spray, chap stick)
pills in original containers
makeup
1-2 granola bars
sunglasses
no wallet – Cash/minimal credit cards in inner pocket of bag, or in a money belt, worn under clothing
phrasebook if necessary
insect repellent towelettes (if necessary for open air airports in tropical settings)
extra pair of underwear
bathing suit and sarong
pens
Water Resistant phone case:
Or waterproof key case:
small handbag
waterproof pouch for valuables while snorkeling/swimming
3 bottoms in addition to one worn on plane
5 nice tshirts
3 dressier tshirts
1 sundress
2 bathing suits
1-2 coverups
1 sarong
hat
1-2 pair matching flip flops
1 pair nice sandals
cosmetics (liquids still in 2-3oz Nalgene bottles)
Woolite packets
face and body suntan lotion
insect repellent
underwear
sleepwear
socks if any hiking involved
umbrella
folding bag for purchases
Eagle Creek cube with first aid kit, extra TSA lock, alarm clock, Tylenol, Tylenol PM, blister protection, travel laundry line and other assorted necessary items
zip lock bags and plastic shopping bags for bringing home liquids and wet items.
snorkel, mask and fins (optional) or your favorite sporting equipment
1mm wet suit (optional)
outlet adapters for international destinations
On plane – heaviest walking shoes (if necessary for hiking, or Keen amphibious sandals with heavy dark socks), loosest jeans, nice t-shirt, zip neck thermal long sleeved shirt and fleece. When leaving NYC in winter for tropical climates, I wear 3 layers instead of a coat, and bring a SpaceBag to condense them for packing. Especially for a multi-destination trip.
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