Hello, Reader!

As I’m writing to you today, we’re about halfway through our Mediterranean adventure.

We started a week-and-a-half ago in Crete (our first time in Greece), then spent a whirlwind day and a half in Venice before landing here in Ibiza.

Three very different places. Three very different ways of getting around. Three sets of hotels, flights, transportation, reservations, and logistics to figure out. The planning sometimes felt like an adventure in itself.

And now that we’ve actually navigated all three, I can tell you that some things have gone smashingly well… and a few have been a little more challenging.

So today, I thought I’d take you behind the scenes of how we planned this trip and share a few things we've learned along the way that might help with your next adventure.

The pre-trip planning

We started earlier this year with a blank slate, knowing only that we wanted to go somewhere near the ocean. That’s Todd’s love (and not a bad direction to tag along).

Having loved our time in Sicily and Malta last year, we set our sights on the Mediterranean.

As luck would have it, we found rooms available through our Hilton timeshare in both Crete and Ibiza, with nearly (but not quite) perfectly aligned check-in dates.

That’s where Venice entered the picture. We needed accommodations for two nights between Crete and Ibiza, so why not Venice? It was roughly in the middle after all. 😊

Then came the flights.

I used Kayak to piece together an itinerary that got us where we wanted to go without breaking the bank.

The biggest challenge turned out to be that while our flights to and from the U.S. were both on British Airways, the two flights in between were booked on smaller, local airlines. And not the same ones.

That meant three different airline apps for check-ins and travel information, plus three different sets of baggage requirements to keep track of.

And that brings me to my biggest planning mistake of the trip.

In Crete, I was overly concerned about our “excessive” baggage weight compared to what I believed the limits were on Aegean Airlines.

So I paid the overage fees.

Only AFTER I paid them did I realize my mistake.

In the U.S., our checked bags are measured in pounds. In Europe, they’re measured in kilograms. Which meant that not only were we NOT overweight... We were actually significantly UNDER the weight limit. 🙃

So what happened to those excessive baggage fees I paid?

Well…

Looks like we might have to make a return trip to Greece someday to use the baggage credits we now have. I mean, we can’t let those go to waste, right?

Boots on the ground

Once we arrived, we took a completely different approach to exploring each location.

In Crete, we relied on public transportation and excursions that picked us up and dropped us back at our hotel.

In Venice, we arranged a water taxi from the airport and explored almost entirely on foot. Until it was time to leave...

That’s when we encountered our biggest transportation challenge of the trip so far: figuring out the vaporetto (public water ferry) and bus system with luggage in tow. More on that another time. 😉

And here in Ibiza, we decided to rent a car so we’d have the freedom to explore all parts of this tiny island.

There are pros and cons to each approach, but looking back, I’m not sure I’d change much about how it all came together.

We pre-planned some things.

We scheduled others once we were there.

And we left plenty of room for decisions to be made in the moment.

You might be a traveler who loves structure and wants every detail of every day planned before you leave home.

Or maybe you’re the kind of traveler who likes to see where the day takes you.

Both can make for an amazing trip. Which is probably why we’ve settled into a hybrid version. It gives my left-brain tendencies enough structure to be happy, while leaving room for our more relaxed sides to be spontaneous.

That’s become our sweet spot.

A few of the tools we actually use

When people ask how we manage to plan trips like this, these are some of the tools that make it easier.

We don’t use every one on every trip, but they’ve become part of our travel-planning toolbox, and they may be useful for your next adventure, too.

​Kayak: Kayak has been part of my travel-planning routine for years. For this trip, I used the multi-city option to build our entire itinerary in one search: the U.S. to Crete, Crete to Venice, Venice to Ibiza, and Ibiza back to the U.S.

What I love about using it this way is that Kayak compares the available flights for each leg and helps identify the best options based on things like price and schedule. It made it much easier to see the entire trip at once and find a combination that worked for us without having to search for each flight separately.

For a complicated itinerary with multiple destinations, I definitely recommend giving the multi-city option a try.

​DiscoverCars.com: This is a relatively new addition to our travel-planning toolbox, but one that many others in the travel creator world recommend. We’ve now used it twice when renting cars abroad, and both experiences have been easy.

I like being able to compare rental companies and vehicles in one place rather than visiting a dozen different websites.

If you’re considering a road trip or simply want the freedom to explore beyond the usual tourist areas, this is one I’d check before booking directly with a rental company.

​Viator: This is one of my go-to sites when I’m looking for things to do in a destination. I like being able to search by location, activity, length, price, and reviews, which makes it easy to compare options before deciding what fits our trip.

We’ve booked activities all around the world through Viator and have had great experiences. In fact, the Crete tour I wrote about last week was booked through Viator.

If you’re planning a trip in the U.S. or abroad and want to add a food tour, day trip, cooking class, guided hike, boat excursion, or something completely different, it’s a good place to start looking.

​GetYourGuide: I use GetYourGuide for much the same reason: it’s a great way to see what experiences are available in a destination and compare your options.

On this trip, we used it to pre-arrange our water taxi from Marco Polo Airport directly to the dock at our hotel in Venice. Having that transportation taken care of before we arrived made a travel day that much more enjoyable.

But it isn’t just for airport transfers. You can find everything from walking tours and museum tickets to day trips and unique local experiences.

And maybe that’s the biggest thing I’ve been reminded of during this trip:

Good travel planning isn’t about planning everything.

It’s about figuring out the things that will make the trip easier, more enjoyable, and less stressful, and then leaving enough room for the unexpected.

Because sometimes the best parts of a trip are the things you never could have planned. And sometimes the things you did plan go completely sideways.

Either way, you still get the story and memories to last a lifetime.

Until next time,

With love,

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