Cruises: The Earlier the Better
It's to your advantage to book a cruise when the schedule comes out. It's a win/win because you can book a refundable deposit and adjust your booking for any new promotions that are released between when you book and your final payment date.
  • Groups - If you book when the sailings are released, you can secure group rates if you plan to sail with at least 5 cabins. For instance, I'm working with a group who booked their November 2018 cruise in August 2017. They are paying hundreds less than the current rates.
  • Alaska -  If it's important to you to have the best cabin and best views, it's critical to book a year in advance because 50% of the cruise inventory is usually sold out by December for the next summer. 
  • Luxury and river cruises are good to book at least one year in advance and sometimes two years out because the ships are small and popular routes sell out. 

All Inclusive Vacations: 6 - 8 months in advance
Airfare schedules are released 330 days in advance. Southwest and JetBlue usually release their schedules a little later. This means it's hard to get accurate pricing for your total vacation cost before then.

Disney World Vacations: At least 6 months in advance
Disney World requires a lot of pre-planning.
  • If you want the best shot at the hard to get dining reservations, it's important to book at least six months in advance because that's when dining becomes available.
  • You definitely want to be booked at least 2 months in advance to secure your Fast Passes.

Last Minute Deals: Be Flexible
Your best chance at a last minute all inclusive deal is to be super flexible. One challenge with last minute deals is the flights.
  • The process that decides the pricing for flights thinks that anyone who books within 6 weeks of travel is likely a business traveler so price doesn't matter. The airlines will keep raising the prices as it gets closer to departure.
  • Two exceptions:
    • If you live in a city with vacation charter flights. These are flights specifically chartered to a popular all inclusive destination:  Cancun, Montego Bay or Punta Cana. Those cities are: Baltimore, Boston, Chicago, Cincinnati, Cleveland, Denver, Detroit, Kansas City, Lansing, Milwaukee, Minneapolis, Philadelphia, Pittsburgh, Rockford, and St Louis.
    • Viking Ocean Cruises - Viking currently has some deals with free airfare in November for Caribbean sailings. That's considered last minute in the luxury travel market.
For cruises, it helps if you can drive to the port to avoid the last minute airline prices. A good time to check is one month before departure.

When vacations are you dreaming about over the next year? Let's get started!