for the lowest price on a long-term charter may not be the best strategy. It's not the same as shopping
for the lowest price on, e.g., an automobile or giant TV set.
Having done a number of long-term charters over the years (3 weeks to 2 months) I would suggest that the most important thing is to get a boat you'll be comfortable with located in an area you'd really like to explore
. Even if you get a fantastic price on a fantastic boat
located in a not-so-desirable location you'll be cheating yourself and your family/guests.
December is high-season in the Caribbean
, so don't look for exceptional bargains. However, you can save money
by shopping the reputable
companies and getting recommendations from those who've dealt with them recently.
Unless you have a very specific itinerary in mind, I'd focus on the Virgin Islands
-- USVI and British -- because there are more boats available and a wider choice of boats, and some of the best sailing/cruising in the world. A 30-day charter would be enough time to explore, e.g., the Spanish Virgins and even St. Martin if you're so inclined and the charter company agrees. If you're not so venturesome, stay in the BVI
...there's plenty to see and do and you'll be guaranteed a wonderful time.