When Should You Book

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 SeasonShoulder/Off SeasonBook
CaribbeanMid- December- mid-April. Most expensive is Christmas/New Year and Spring BreakMid-April through Mid-December, especially when school is in session.Peak Season & school holidays- 6-8 monthsSpring/Fall-3-4 months
EuropeJuly-AugustAfter Easter through early JuneSeptember through NovemberPeak Season-6-8 monthsShoulder Season-4-6 months
HawaiiMid- December- mid-April. Most expensive is Christmas/New Year and Spring BreakApril/MaySeptember/OctoberPeak Season & school holidays- 6-8 monthsSpring/Fall-3-4 months
AlaskaMid May through AugustLate April-Early MayFirst half of SeptemberPeak Season- 6-8 months
DisneyAll holidaysNoneBest weeks for crowds are probably:First 2 weeks of SeptemberFirst 2 weeks of MayWeek after Thanksgiving through second week of DecemberTo 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.