I took my first trip to the Caribbean with this deal in 2008, and not being an all-inclusive resort-type of traveler, I booked the independent boutique Silver Point Hotel. The hotel is nicely located in a residential area with plenty of rum shops and small restaurants within walking distance, served well-priced and actually decent food (contrasted with the expensive and mediocre food served at certain American chain hotels), and the staff was friendly and helpful. In 2008, I paid around $750 per person for the week of Labor Day with airfare and found it available for $777 in 2010. The previous deal had also included a $200 debit card to be used anywhere on the island, but the current promotion still represents a good savings. I calculated the hotel and airfare separately for the same dates and it worked out to over $400 more per person without the package.

The package is government-subsidized in an effort to increase tourism during hurricane season, though Barbados is one of the few Caribbean islands outside the hurricane belt and hasn't suffered a major storm in over 50 years. You may encounter a few rainy days in September, a good time to explore the travel nerdy Concorde Experience, check out a historical house, or just hunker down in a rum shop. Barbados is a former British colony and remains a high-brow but laid-back destination with a nice balance of beach, nature, and culture.

Full details: Book by August 31st for travel September 1 - December 18, 2010. You have to stay a minimum of either 5 nights at an all-inclusive or 7 nights at other hotels. You can book through a travel agent or online through Orbitz and the like, full partner list here.