Should We Plan a Mediterranean Cruise? (Asking For Myself, At 11pm, With Seventeen Tabs Open)
It's 11:14pm. Jamie is asleep. I am not asleep. I am doing the thing where I open one cruise line's website "just to look," and ninety minutes later I have seventeen tabs open, a spreadsheet I didn't mean to make, and a very strong opinion about balcony cabins on the port side.
This is how it always starts. Not with a decision. With a spiral.
Here's the thing — we've actually done the Mediterranean before. A cruise with friends, years ago, before Reset & Roam was even a phrase I said out loud. We ate our body weight in bread. We got lost in a way that was charming for the first hour and character-building for the second. We came home different, in that quiet way good trips do that to you.
So you'd think going back — again by ship — would be the easy part. It is not the easy part.
Because now I'm the person who plans other people's dream trips for a living, which means I am incapable of just looking at a cruise itinerary and going "sure, that looks nice." I am looking at port days and mentally scoring them for pace. I am asking whether seven ports in seven days is a vacation or an endurance event. I am doing this at 11pm on a Tuesday for a trip that is not booked, not planned, and not even fully agreed upon.
Jamie's official position, when I bring it up over dinner, is "sure, let's do it," delivered with the same enthusiasm he'd use to agree we should probably clean the garage eventually. Supportive. Vague. Not actually helpful.
So here's where we actually are, honestly:
• We know we want to go back.
• We do not know if it should be a cruise or a slower land trip, round two.
• We do not know when — 2027 is spoken for with Alaska, so realistically we're talking 2028.
• We are considering if we do cruise it, wanting fewer ports with more hours in each one, not the itinerary that brags about hitting five countries before breakfast.
That last one is the part that actually matters. Because the question underneath "should we plan a Mediterranean cruise" isn't really about the Mediterranean. It's the same question that's underneath every trip I help plan: are we building a trip that fits how we actually like to travel, or are we building a trip that looks good on paper?
Gentle pace and an exciting trip aren't opposites. Tonight I'm saying it to myself, with seventeen tabs open, trying to believe it applies to my own vacation and not just everyone else's.
I don't have an answer yet. I have a spreadsheet, a sleeping husband, and a trip that's still just an idea we keep circling back to. That's honestly where most good trips start — not with a booking, but with somebody staying up too late, still curious.
If you want to follow along as we actually figure this out — cruise or no cruise, 2028 or someday — that's exactly what the Roam newsletter is for. I'll show my work, tabs and all.
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