11/09/2026
It’s September 2026, and we’re already planning well into 2027 and 2028. For some trips, even 2029 is beginning to come into view.
The big milestones are driving it. Significant birthdays, anniversaries, one last summer before the kids head off, the trips that mark something. Those deserve the best rooms, not the leftovers, and the best rooms go early.
A few dates already on our radar:
The Eclipse of the Century, August 2, 2027. The path of totality crosses destinations including Cádiz, Málaga, Tangier, and Luxor, and accommodations in prime viewing locations are already in demand. Nile sailings around that date require especially early planning.
The Los Angeles Summer Olympics in 2028. The most desirable places to stay will be spoken for long before the torch arrives.
The 2030 World Cup, hosted by Spain, Portugal, and Morocco, with centenary matches in Argentina, Uruguay, and Paraguay. If there’s a soccer fan in your household, this is the kind of trip that benefits from a serious head start.
And then there are cruises. Some of the most sought-after sailings for 2028 are already filling, particularly for destinations with limited seasons and departures. The same is true for festive travel, sought-after safari camps, and peak cherry blossom season. Limited inventory and fixed dates mean these trips often need to be planned much further ahead than travelers expect.
Tell us the milestone, and we’ll tell you its real planning timeline.