My marina neighbors Matt and Carla shoved off Sunday morning and started a two-year adventure aboard their 34' Allied Seawind Escondida. They're currently headed east to Louisiana at which point they'll head south across the Gulf of Mexico to the Yucatan Peninsula. Apparently that route helps avoid a great number of shipping traffic and offshore platforms.
You can follow their updates at www.therumtrail.blogspot.com.
They don't have Internet on the boat, but they do have a Spot GPS tracker, so while updates to the blog itself won't be frequent, there is a link to the Spot page, which is charting their progress.