As winter approaches, I’d love to head south to warmer waters and palm trees swaying in the breeze.

Bahamas sunrise

Sunrise in the Bahamas makes the long sail down the coast worthwhile.

Our dream of owning a Helia 44 would require a regular journey south for us... which is fine with me. We’d be moving our boat between the Chesapeake Bay and the Bahamas, to take advantage of two peak charter seasons. Not only would this add a lot of sea miles to our cruising resume, it would also allow us to get a nice cross section of inland cruising and offshore experience.

I’ve sailed this route before, and if you find the right weather window it’s a pleasant journey through historic towns and cities that can be done in as little as 7-10 days, depending on how many places you stop to enjoy. So here's the fantasy that's keeping me warm as cold weather creeps in:

We’d cruise south from Annapolis to Gwynn’s Island, Virginia on our way to Hampton Roads. I have a home here in the Middle Peninsula so it’s a great stopover to visit friends—and have the best pizza in Virginia, at Southwind Pizza.

Other choices to break up the sail to Hampton Roads could include anchoring off Smith or Tangier Islands.

From Gwynn’s Island, a half-day sail would put us in Norfolk or Portsmouth. With the Helia’s mast height, the Intercoastal Waterway isn't an option. So we’d have to wait for a good weather window... enjoying the sites before we head out again for some near-coastal sailing.

Once we get a good stretch of weather, we’d parallel the coast inside the Gulf Stream  and round Cape Hatteras. We'd drop anchor again in Charleston, a great city for sightseeing and enjoying authentic southern cuisine.

Next we’d head out across the Gulf Stream for some offshore sailing to Marsh Harbor in the Bahamas, where our Helia 44 would settle into her winter home.

Now we just need to get the boat! Until then, we’ll keep dreaming of heading south for the winter, just like the birds.

What's your dream escape boat and destination for this winter? Share it with us in the comments below.