The short answer is always “As early as possible.”
Below is a table that can serve as a guide for you as you begin to look forward to 2020 and beyond to map out your vacations.
All of these are general guidelines. It all depends on how flexible you are.
|Peak Season||Shoulder/Off Season||Book|
|Caribbean||Mid- December- mid-April. Most expensive is Christmas/New Year and Spring Break||Mid-April through Mid-December, especially when school is in session.||Peak Season & school holidays- 6-8 monthsSpring/Fall-3-4 months|
|Europe||July-August||After Easter through early JuneSeptember through November||Peak Season-6-8 monthsShoulder Season-4-6 months|
|Hawaii||Mid- December- mid-April. Most expensive is Christmas/New Year and Spring Break||April/MaySeptember/October||Peak Season & school holidays- 6-8 monthsSpring/Fall-3-4 months|
|Alaska||Mid May through August||Late April-Early MayFirst half of September||Peak Season- 6-8 months|
|Disney||All holidays||NoneBest weeks for crowds are probably:First 2 weeks of SeptemberFirst 2 weeks of MayWeek after Thanksgiving through second week of December||To secure coveted dining reservations- 6+ months Otherwise- 3-6 months|
You need to plan EARLY, if you have:
- a family larger than 4 people
- specific dates that cannot be flexed
- a tight budget
- specific flight preferences
- room preferences, particularly suite/villa-style
HOWEVER, if you have the opportunity to travel last minute and you have some flexibility with the dates and location, there is a chance you can find something great.