So many people take advantage of holiday periods from work and school to be able to take vacations. Sometimes this can be very tricky to do with the number of people traveling to visit with family pushing the supply and demand on prices to their highest. Besides the prices being higher, space is more limited.

The best advice for holiday travel: be ready for anything. Flights can be cancelled or oversold, cruises will be packed with families, resorts may sell out. Maybe you planned to stay at a particular resort but it was sold out by the time you were ready to commit. Or your favorite cruiseline is charging more than you paid for your first car to book the broom closet room under the anchor for a 2 night cruise. Better yet, the only car rental option you can find costs more than the entire rest of your trip and is local operation that you worry may not be in business tomorrow let alone when you arrive. My personal worst case scenario, you go to the big amusement park to find out that they sold out right after you bought your tickets which means the park is at capacity and you can barely move. All of these things can stress you out, but they can be handled and it is still possible to have a great trip as long as you are willing to be flexible, mostly with your wallet.

I personally always battle with the decision of when to book a cruise. Is it better to try to book as soon as the sail date is made available, less than 30 days before sailing, or somewhere in the middle?

For a cruise during a holiday or other peak sailing time, I think you are better off to put a deposit down ASAP. Some of those sailings sell out completely well before final payment is due. The reality is, most people travel when schools are on break. That makes the demand be very high during these times.

If you are willing to be a little flexible, waiting is definitely an option. Some of the best prices I have ever seen were within 30 days of sail date. Odds are you won't have your choice of cabin but you could sail for under $50 per person per day so I wouldn't care in the least. I've seen as low as $199 per person for 7 days. It's all a matter of supply and demand.
 
I always go with: When you find a price you are comfortable with, BOOK IT! There's nothing worse than settling on a cruise and waiting for the better price to come along only to find it sold out.