Vacation Values in the Caribbean

A recent snow squall got me thinking about winter breaks in the Caribbean. In this week's Sunday New York Times, the Frugal Traveler asked "How Low Can You Go For Some Sun and Sand?" He reported on the winner of his online search for the cheapest package, an all-inclusive resort in the Dominican Republic. The total cost for his three night vacation? $561.86, or about $187 per night. I thought I'd try to beat that price, for those of us who'd like to plan our own getaway.

A quick search revealed lots of options, including non-stop flights, roundtrip transfers, and 7 nights in an all-inclusive resort in Punta Cana for $1,169, or $167 per night. Similar deals are available for shorter stays, and other destinations. Here are my tips for maximizing the value for your next Caribbean vacation.

1. Try an all-inclusive resort. Food is expensive in the Caribbean. All-inclusive resorts have come a long way, with high quality food, multiple restaurants, and top shelf liquors. It's pretty nice to know in advance what you will pay, and not to receive a shocking bar/restaurant bill when you check out. Leave your wallet in the safe!
2. Look for a package that combines airfare, airport transfers, and hotel. Tour operators offer discounts when all elements are booked with them. Consider a charter air package - these are for 1 week vacations, and depart on weekends to Cancun and the Dominican Republic from Boston.
3. Be flexible with dates, if possible. Prices are lowest now until Christmas week, with the exception of Thanksgiving week. January and early February are good times to find the best deals. After February vacation week, you get into college spring breaks and Easter.
4. If you must travel during peak times, book as far ahead of time as you can. Flights are selling out quickly due to reduced capacity.
5. If you are willing to be surprised, consider a "mystery deal" from your tour operator. This deal allows you to select your vacation destination, dates, and star level of hotel. The operator then selects the property you will stay at. For example, you can specify you want a 5 star resort in Negril, Jamaica. In return for the ability to select the resort, you pay much less than if you booked direct.

So, dig those flip flops out of the back of the closet. The beach is calling you!