Winter Destinations
 

Hi! I'm going to start a contract on a cruise ship soon, and want to do some extensive traveling in my time off. With the contract being anywhere from 6-8 months, I'm looking for ideas of places to go in my few weeks off after that so that I can start planning (and saving) now. That would mean that my time off would land anywhere from December to February. I'm open to all ideas, and definitely would like to travel for a minimum of 3 weeks, so several destination is also an idea. I should say, the only thing I am not that interested in, is someplace that will be bitter cold. I'm from Chicago, so anything warmer than that! :)

Thanks for the input!

Mexico
Hawaii
Jamaica

Ideal time as far as weather is concerned for South East Asia - Cambodia, Laos, Thailand and some parts of Vietnam. 3 weeks would be enough time to see at least parts of a couple of countries.

Where are you cruising? Presumably you will want somewhere different? If you provide some info on your interests e.g. Temples, food, culture, adventure sports, laying on a beach etc. It will enable people to provide better targeted response. A rough idea of budget or travel style ( e.g. Backpacker or luxury hotels) would also help.

Where does your last cruise end? Are you going back to Chicago or straight to vacation mode?
If starting from Chicago I'd hop on the "City of New Orleans" at 8PM and be in Memphis in the morning. Spend 24 or 48 hours there and then take the CONO to New Orleans.
There are some cruises that leave from New Orleans too.
Three days a week the Sunset Limited leaves New Orleans bound for Los Angeles. If you have the money by all means get a roomette instead of riding coach.

Or consider riding in a Pullman car:

http://www.nytimes.com/2014/05/18/tr...-the-past.html

India, specially in Himalayan regions

Budget?
Nationality? (for visas)

With all due respect, it's unlikely that the Indian Himalaya, in winter, is what the OP had in mind.