I have been to Cuba 4 times since 2008 and have a good idea on how to get the best deals for an all-inclusive resort trip to Cuba. The times of year I have been to Cuba is May and November to early December. The January to March period is generally the most expensive time to book a trip in Cuba while the August to Mid-November period is the hurricane season so I would recommend avoiding it. To me its pointless to go in June or July as that is the prime summer season for North Americans and Europeans so I recommend the April-May or November-December periods as the times where you will get the best deals while still greatly enjoying your Cuban vacation.
November-December is the off-season for vacations to Cuba so you can expect to pay as little as $500 for a 4 star or greater hotel and should not be paying more than $700 for a week long visit unless there are extra perks involved beyond the traditional all-inclusive vacation of drinks, food, use of resort facilities, and travel arrangements. For May, the acceptable range is from $600-$900 depending on where you go and the rating of your hotel.
The lowest price I have ever heard for a Cuban vacation was from someone who paid $500 with Red Tag during my November 2010 trip. Be particularly careful if you are to go to a wedding in Cuba. I stumbled upon wedding guests who paid $1,600 per person for a week, nearly 3 times greater than what they should have paid with no special treatment beyond what other guests of the resort paid. People generally do not shop around when it comes to wedding plans and it looks like travel agencies know this fact too.
Here are some specific steps to take and other key points to get the best deal when booking your Cuban vacation:
1. Do online comparison shopping. Once you have determined your desired Cuban location, length and period of stay, hotel star rating and type of room you want, look for the best two or three deals.
2. Once you have determined these top 2 or 3 travel agency offers, call them to see what their price is. Often the prices vary between their online offering and what they say over the phone. Pick the cheaper quote.
3. If you are travelling with someone who is not a significant other, see if you can get your own room as opposed to sharing a room, if you wish. Sometimes, but particularly in the off-season where there is space in the hotel, you will be charged the same for booking two people in two different rooms as you would be when sharing the same room.
4. There is a myth that you get the best deal by booking just a few days in advance. There seems to be no correlation between how far in advance someone books their trip and how much of a deal they get. Particularly in the case of the next point.
5. Review the terms of your agreement with your travel agency once you have booked your trip. Some, but not all agencies have a clause in the agreement where if you see the agency offer your same trip for less money than what you paid 30 days or less BEFORE your time of departure, you can request the same deal and get it. This also throws out the idea that booking last minute like in point 4 saves you money. You may end up with the same deal anyways if you ask for it.
6. Do not cheap it out too much. It is not worth the $50 in savings if you are going from a 4 star to a 3.5 star hotel. Look for the best combination of quality and price so you will enjoy your trip as well as not break your bank.
Refer to my other articles on travelling in Cuba if you are interested in information about: