Planning for future travel. What accommodations should you be booking now?

I am asked all the time about “when should we book” or “how far in advance should we plan”. While I typically answer, “It depends, but the sooner the better”, I have tried to outline a simple guide.

A good rule of thumb for booking accommodations; the larger the group of travelers and the more popular the destination, then the more time you need to plan. Booking in advance ensures optimal availability and typically reduced pricing. Hotel and resort prices will typically rise with demand. Unless you are booking a low-demand property, then rates won’t drop as time nears for your travel.

Cruises (Boutique River and Ocean)
Book your cruise or expedition 12-18 months in advance. Sometimes 24.

Festive Season (mid-December through NYE)
Book your trip 10-15 months in advance when you’re traveling during the holiday season.

Peak Season (Caribbean mid-December through Spring Break)
Book your trip 8-12 months in advance for peak seasons, especially the Caribbean and Central America.

Peak Season (Europe June – August)
Book your trip 8-12 months in advance when you’re traveling to Europe for Summer Break.

Shoulder Seasons and all “other”
Book your trip 3-9 months in advance.

Weekend getaways or stay-cations
Book these quick adventures 1-3 months in advance but remember even weekend getaways and stay-cation destinations can be in higher demand and may require more time to plan.

In summary, what should your current calendar look like as Summer rounds out;

  • Fall Break – Booked (Smaller getaways should be in planning stages)
  • Christmas Break – Booked (Very limited availability, so book now if you can)
  • Ski Trips and Spring Break – This should be in the planning and booking stage currently
  • Summer 2020 – Planning 10-12 months out is ideal, especially if you have specific resorts in mind, want access to First Class international air tickets, or if you have a large group traveling.


Closing Pro Tip: Always purchase Trip Insurance to protect your investment from the “what if” and the unknown.

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