Navigation: If you are planning on the eastern Caribbean, you have to get this book: "Gentleman's guide to Passages South" If you get to Luperon, DR make sure to look up Bruce as he is a great help and resource. (http://www.ThornlessPath.com)
If you have an iPad, I have come across a great, inexpensive app called "ISailor" that you may want to check out. I like it better as I understand it uses the real gps signals and not triangulated cellular signals so it will work when you are offshore.
Another great app for the iPad is SEAiq. It comes in two versions depending on if you need US or International charts. It has a one time fee of $10 and will interface with "Active Captain." These is also a website called http://www.eboatcards.com/ that works with Active Captain to help you track fellow cruisers and to see who is nearby. Check it out and use your iPad!
Weather Routing: Make sure to look into signing up with Chris Parker. He is a good friend that I knew in Miami and is fantastic in helping you with weather. His website is www.caribwx.com. You can communicate with him on the SSB will make the passages much more enjoyable. He can also send the information by email or offers a combo which uses both. He has also published a book on weather forecasting which I found very helpful.
Communication: For inexpensive (sometimes free) phone communication, sign up with Skype. A lot of restaurants & businesses along the way will have WIFI so you can get onto the internet to talk: (www.skype.com)
A single side band radio (SSB) really came in handy for staying in touch with other cruising friends and for getting weather. There are cruising nets that you can catch up on the latest, pick up radio broadcast and send emails (very, very slowly). I even spoke to friends in Grenada when we were by the Florida Keys on our return trip. Very nice.
Insurance: We were concerned about our health insurance when we were abroad and contacted Lifeboat Medical for foreign coverage: www.lifeboatmedical.com.
Boat insurance can also be challenging if there are only two of you on board. We used IMIS in Maryland and they were great. Contact them at www.imiscorp.net.
Miscellaneous: So that you can remember everyone along the route, you'll want to get "boat cards." Just like business cards but with your boat info. You can get a small order for free at www.Vistaprint.com.
How will friends and family share in your adventure? There is a blogging website called Get Jealous that is great to keep everyone up to date. www.getjealous.com
Photos: With digital cameras you will take tons of photos and after a little while most of the island photos will look the same. I made it a point to photograph the island/country's courtesy flag (the one you should fly when you remove the yellow quarantine flag down after clearing customs) so that I would know that all of the photos following were from that island or country. I also published a hardback book with the photos using a website called Blurb.com. It was a great way to display the photos and tell the story of our trip.
Cooking and Provisioning: Here is a great website to help you with provisioning and cooking while cruising: http://theboatgalley.com. It always seemed like it took so much time and effort to provision and yet the provisions were gone before you knew it.....
I've got a lot more tips that I will be happy to share if you contact me as I had a lot of hurdles to overcome before we "cut the dock lines."
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