In Port - If available Wireless Hot spots using external 802.11g USB adapter with USB extension cable--
While in developed countries I use an external wireless USB stick with an extension cable that gets it out the hatch on into the cockpit under the hard dodger. If the signal is weak I boost it with a metal pasta strainer acting like a satellite dish to focus the beam. It works great and even the skeptics have been adding it to their boats with great success. The only problem is in gusty anchorages where the boat sails at anchor. In Bum's Bay in Australia we focused our strainer at the hot spot 2 miles away and it worked great!! see here
for photo and link to blog
In Port - Internet cafés and carry a USB flash memory card.
I save web pages to the USB stick using the IE File->Save As options (use web archive (Single File) .mht if available for IE or File->Save Page As-> Web Page Complete from Foxfire). This saves reading time in the cafe, saves the info for later reference on the boat and allows me to compose messages or replies on the boat. At $7 an hour it's worth it.
At sea - Iridium Satellite Phone with Data Kit and Skyfile (free email)
I am not a ham so Sailmail was my only option. I had an older SSB radio which would not support the switching speeds of the Pactor modem, and I refuse to pay $800 for a modem.. it's pretty simple technology and you can't step off the boat with it. I bought a a used Iridium phone 9500 (the old style) for $500 and use the pre-paid option instead of monthly service. The cost is about $1 a minute and I use 1 minute a day to get all my emails and weather data, similar to Sailmail costs. The only problem is I have to buy 500 minutes a year and I don't typically use them but they roll over into the next year. You can the extra minutes to make voice calls and we do call home on the special occasions. Actual Internet access is also available but you can't really go searching and pages with graphics are almost impossible but it is possible to get pages emailed to you and skyfile supports attachments for files including pictures for weather charts. I know of some one who hit Chesterfield reef and lost his boat. He stepped off with the Iridium phone and called his wife who coordinated the rescue.
Don't forget a good computer backup system and a spare drive (or two)
For more details see www.creative-cruising.com/what_works.htm