Only a few hours into my first stop in Cuba, it hit me: I had done this all wrong.

Santa Clara was incredible, and I was meeting tons of people. On the flip side, I was beginning to hear that Varadero, my next locale, was touristy and overblown. Why hadn’t I stayed in Santa Clara longer? By that point — due to a prepaid hotel in Varadero with an unkind cancellation fee — it was too late.

For trips, it’s hard to know when to nail down plans and when to roll with the tide. I generally make that decision following a few guidelines (except in this case, on assignment for the newspaper, I ignored them).

Part of the choice depends on whether I’m traveling alone. Staying spontaneous with other wanderers — especially more than one — can be tricky. Can you agree on what the vibe of the trip should be and allow some give-and-take with the planning? If your friendship is the type where you often battle about which restaurant to go to, it’s smart to work through any disagreements on familiar ground, before you head out.

I also consider how familiar I am with the destination. If I understand the lay of the land and what I want to do, I might go ahead and make plans. But if I’m walking into a total adventure, I prefer to line up a schedule as I go, based on what a place has to offer and any info learned once I get to a place.

It’s also important to look into lodging. If I’ve got my heart set on exploring a remote island with a handful of huts, it’s too risky to wait. If I’m staying in an Airbnb, I often search for apartments from home with only one or two days’ notice.

Be aware that floating along this way can be more expensive, too; transportation options such as train and airfare can be significantly cheaper when booked in advance. If you’re set on a certain standard, you could pay more for lodging as well. But you just might be rewarded with a detour to a thrill you would otherwise miss.

 

Amelia Rayno covers food and travel for the Star Tribune. Follow her on Twitter and Instagram at @AmeliaRayno