3 Tips for Planning a Last-Minute Trip

It was a long winter at home. I live year-round in a beach town on the very edge of Cape Cod, so after spending the entire season in a nearly empty and frozen town, I was hungry to get away. When spring arrived and brought with it the opportunity to snag $250 roundtrip mistake fares to Portugal, I pounced. I’d listened to my friends rave about Portugal, but honestly, I’d never looked into what the country has to offer beyond port wine and seafood.

It was time to get planning. But time was exactly the problem. The flight left in less than a month. I manage two businesses, host a weekly podcast, and have a family, plus I’m organizing a tour to Patagonia this November. All of a sudden, I found myself with a pending trip to somewhere new and virtually no time to plan. A good problem to have, yes, but a problem nonetheless.

Under different circumstances, this might be okay. I’ve shown up to more difficult places, like Oman or New Zealand, with no course of action, no accommodation, no way to get around – and it’s always worked out. But with a family in tow, I didn’t have the flexibility to freewheel it. And besides, this is not how I wanted to spend my week in Portugal. I wanted, and needed, to make my week count.

Related: One Week in Portugal in a Rental Car

Usually, I’m the type to really geek out on trip research. By the time I arrive, I’ll know where to eat, what to drink, who’s the hottest chef in any city, the best affordable-yet-fancy boutique hotels for your money, and how to get anywhere by car or public transport. I’ll pour over paper and digital maps, make lists, visit my favorite sites, read travel blogs, and create my own city guides. I love the process because it’s like getting a head start on exploring without any risk of getting lost. Before I even leave, my imagination runs wild with possibility, and imagination and possibility are what travel is all about.

However, sometimes, there’s just no time. That was the case with this very last minute trip to Portugal, a country I knew very little about. In fact, all that I knew was that you can drive the entire coast in a week on a budget and something like that sounded like my travel style.

Here are the steps I took to plan my last-minute, one-week road trip in Portugal:

1. Find Your Unique Experience

The first step to any great trip is to check in with the people you know, like, and trust to lead you to your best experience. This certainly works most effectively if you know a local whose opinion or taste you trust, but for most of the world, we don’t know the people who live where we’re going. Instead, we have to look to the travelers. The benefit of actually following the chronicled lives of travel bloggers is that you begin to get an understanding of their style and where they’ve been. For example, I knew Jackie had road tripped the Portuguese coast last year. I also wanted to check out a few other favorites that cover the sites, the food, and provide a sophisticated perspective. It’s particularly magic when you find a local perspective that matches your style.

From a handful of my favorite blogs, I knew I had to spend time in the sleepy, coastal region of the Algarve, to spend time hunting down authentic fado in Lisbon, and that Sintra, Obidos, and the fishing villages in-between were not to be missed. I knew where I wanted to stay in Lisbon and the Algarve. What wines to try where, and where I might get to try the world’s best grilled octopus.

Lisbon Portugal
Lisbon, Portugal © Nathaniel Boyle

2. Use TripCreator

Without the luxury of time, I needed something that could cut down on my travel planning time significantly. I needed a car, a route, places to stay, and an idea of things to do along the way. More importantly, I needed it customized just for me. Enter TripCreator.

Input your destination, dates, number of travelers, and hit “Let’s go!” Then it’ll ask you for your start location and end location, and two simple, yet important questions: “Do you have a specific budget for your trip?” and “How busy do you want your schedule?”

The last step is to enter your “traveler type.” You can choose from a number of categories such as, “Adventure,”  “Cultural,” “Family,” “Historical,” “Nature Explorer,” “Relax and Romantic,” “Wine and Dine,” and so on. Unlike nearly every other travel site out there, TripCreator doesn’t just crowdsource everyone to make blanket suggestions on the best things to do. Instead, TripCreator asks you to define your travel style on an individual trip basis (after all, our travel styles change based on the destination, right?) and makes suggestions from that. This way, it won’t recommend a museum to someone who prefers nature and nightlife, for example.

I chose Adventure, Family, Nature Explorer, and Historical (because I’m a castle nerd) and clicked on “Create trip.”

A few seconds later, I had an entire itinerary, mapped by day, laid out on a calendar by the hour, with suggestions for a rental car and hotels in ideal destinations. Magic.

Trip Creator
Traveler type

Tolls in Portugal

On the highways of Portugal, tolls add up. To drive from Lisbon to Porto, it can cost you around 20 Euros in tolls alone. To complicate matters, Portugal recently instituted a (hotly contested) electronic toll system on most of their major highways (A1, A2, A3, etc.). This means you need a transponder on your windshield and your rental car agency can likely include one as an add on. On the electronic toll roads, every couple of exits, you’ll drive under a scanner and your transponder will beep.

On the bright side, locals do not seem to use these roads. They are virtually empty so you never hit traffic and can always make great time by using them. The toll roads are empty because it’s too expensive for locals and there’s a mandate that there needs to be an alternate route that runs parallel enough. That’s especially comforting for anyone hesitant to drive in a foreign country.

The electronic toll roads are fast, smooth, empty, and easy to drive on; however, they’re expensive and, honestly, a bit boring. I drove from Porto, in the north, to the Algarve, the southernmost region, and avoided the toll roads by taking alternate routes along the eastern border. While driving through beautiful farmlands added a couple of hours to the already long trip, the scenic route was a highlight I hadn’t found while driving on the electronic toll roads.

Unfortunately, there’s no convenient way to find alternate routes. Google or Apple Maps always suggests you take the electronic toll roads, so you have to either use them to chart points between shorter distances (not at all ideal) or use old fashioned paper maps. However, here’s a handy resource for every electronic toll road in Portugal.

Castle in Portugal
Sintra, Portugal © Nathaniel Boyle

It’s true that getting off the highways and taking the scenic route can be intimidating, but that leads me to my last point.

3. Don’t Be Afraid to Get Lost

In as little time as possible, we’ve done a lot of research. How much is too much?

People often ask me how much they should plan and how much they should leave open for spontaneity, serendipity, or the unexpected. They’re afraid that if they over-plan, the trip might be too busy, go too fast, and by the time it’s over, they’ll have missed out on the fun of exploring.

It’s true when you’re looking for the freedom in travel, it’s easy to confine yourself to your itinerary. So I say, “Fill your mind, not your time.” There’s a key difference between planning your time and researching your destination. If you can inform yourself of where you’re going, you just might find the confidence to get lost.

That’s when the real magic happens.

Nathaniel Boyle
Cabo da Roca, westernmost point of continental Europe © Nathaniel Boyle

By Nathaniel Boyle

This post is part of a sponsored collaboration with TripCreator. All opinions are those of the author.