Why My Bucket List Is Still Full

My September Travel Dilemma - Part 1

GENERAL

7/9/20263 min read

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Here's something nobody tells you about being a travel creator: I have a bucket list that's probably longer than yours. I've been to maybe 40 countries—Zanzibar, Cape Verde, Costa Rica, Belize, Panama, Brazil, Mexico, the Philippines, Thailand, Raja Ampat, Java, Sulawesi, the Cook Islands. They're all on my mind. Yet in September, with one week off, I still can't fit any of them in.

It's not because I don't want to travel; it's because travel planning is a logistical puzzle, and most of the pieces don't fit.

The Constraints Nobody Talks About

Let's break it down. My week off is strictly from Monday to Sunday, which sounds good in theory until Ryanair,Jet2, Easyjet don't fly to my destination that Monday morning. Or the Sunday return flight leaves at 4 p.m., forcing me into the airport by 2 p.m. on my last day. Suddenly, my "week trip" becomes five days on the ground.

For someone who travels constantly, five days doesn't feel like enough. It feels tight, rushed, and chaotic. If you're already fighting flight schedules before you reach your destination, you’ve essentially lost before you’ve begun.

The Math That Breaks Your Bucket List

So here lies the real issue: everything on my bucket list is long-haul. Zanzibar requires ample time to justify the flights. Costa Rica shouldn't be rushed into a week. Thailand? At least two weeks to really experience its beauty. Panama, Brazil, Mexico, Indonesia— these are easily 3 week trips to enable as much coverage of the Country as possible for our travel guides. You can see why we often need multiple trips to create a guide.

This leaves me with two choices every time I book time off:

  • Option A: Pick a destination that works logistically (easy flights, fits the Monday-Sunday window), thus leaving my bucket list untouched.

  • Option B: Pick somewhere from my bucket list and try to extend the trip.

The Creative Strategies

So, how do I tackle this dilemma? One tactic is the red-eye strategy. Instead of leaving Monday morning, I take a Sunday evening flight—a red-eye. This way, I gain an entire day and experience seven actual days instead of five. Sure, people might think I'm nuts for sacrificing sleep, but it’s well worth it.

Another approach involves bank holidays. I either use these as bonuses, squeezing in 4-5 day trips into long weekends without touching my annual leave, or I arrange my time off around a bank holiday to stretch my leave from seven days into nine or ten. But this requires planning months in advance, can often cost more and doesn't resolve the long-haul dilemma.

So why does my bucket list remain so full? Simple: It comes down to constraints. When travel isn't yet your full time job and you have a family; you don't get to choose based on pure passion; you choose based on flight times and logistics. When your bucket list is made up of long-haul destinations, a fixed calendar, and the recovery time post-flight cutting into your trip, nothing quite works out.

Therefore, my travel aspirations stay on the list—not because I lack desire, but because I’m stuck juggling the practicalities of scheduled flights and work commitments.

Sound familiar??!

The Reality Check

Travel creators make it look effortless. Like we just book a flight and go. The truth is messier. We're juggling constraints, choosing practical options over dream destinations, waiting for bank holidays, taking red-eyes on Sundays.

Sometimes our bucket list just sits there. Waiting for the logistics to line up.

If you've had this exact frustration, you're not alone. The best trips aren't the ones that fit perfectly into your calendar—they're the ones worth rearranging your calendar for. But sometimes, you're choosing between your bucket list and your actual life.

This is Part 1 of a series. Next week: the short-haul options I'm actually considering for September (and why even those don't quite fit). Then: why every single item on my bucket list needs 3+ weeks.

Subscribe to the newsletter below to see how this plays out—and get the Travel Log Method freebie if you're wrestling with the same constraints. It won't solve the Monday-to-Sunday problem, but it'll help you make the most of whatever time you do have.