Four tips brought home from a motorcycle vacation in Portugal

As it turns out, not much did go wrong. If you've ever considered a fly-and-ride vacation, especially to Portugal, here are four things I learned from my experience that might convince you to take the dive.

1. Planning is overrated

To plan a week-long ride, I reserved a BMW F 750 GS from IMT Bike and — that's it. No route, no hotels, no must-see sights or must-ride roads.

I went in January, when it's very quiet. Every day the weather said there was a 33% chance of rain. Translation: Wake up and ride the two thirds of the country where it's not raining. Portugal is all winding two-lane roads, no matter which way you go, and I had them to myself. I got wet on the last day, when I was required to return to Lisbon.

Here is my morning routine: Get coffee, pick a direction, and head out. Follow whatever road looks interesting. At lunch — that's 2 p.m. local time — use Google Maps to find a hotel, maybe two or three hours away. Set Google to "Avoid tolls" or else you will catapult past all the good places.

In the off-season, hotels are no problem. I rented some great rooms for €40 to €60 per night. In the southern Algarve region, someone had to unlock the hotel to let me in. The towns were lively but not crowded, in that easygoing way that happens after the tourists have all left.

Only one detail requires planning: Bring an International Driving Permit, which costs $20 from AAA, or else you can't rent a bike.

2. Everyone wants to help you

After flying all night from New York to Lisbon, I found myself standing in front of a ticket machine at the airport metro station, trying to read Portuguese. Someone ushered me aside, pushed the right buttons, made sure I got my ticket, smiled, and walked away.

The whole trip went that way. An optometrist fixed my glasses for free. Countless waiters and bartenders brought me something, based on gestures, smiles, or intuition. An artist gave me wine in a water glass, and told me stories. I tried to tip a kid €1 for making me coffee in a rural roadside shack, but he ran after me to return the money. He thought I had paid him twice.

First thing out of Lisbon, I headed for a ferry to take me south down the Atlantic coast. I found the ferry terminal, but was on the wrong side of a median and couldn't get in line. A cop waved me to ride over it — my one GS-conquers-all moment — then they let me jump the line. Bikes board first.

Needless to say, the crew at IMT Bike would do anything to make the ride go well. They were there in case I needed them, but with the whole country helping out, there was no need to call.

3. Your gear matters more than your bike

I meant to spend a day walking around Lisbon before hitting the road, but I found this place called Scooteria that rents smaller bikes. I soon found myself buzzing up and down wet cobblestone streets on a Honda SH125i, in the rain, having a blast. I saw more of Lisbon than I could have any other way. I figured out how to work my way in and out of tiny alleyways. I got lost. For that day, a twist-and-go 125 cc scooter was the perfect ride. I highly recommend it.

For the rest of my trip beyond the city, however, my choice was less critical. My do-it-all F 750 GS was great, but I would have had as much fun on a Royal Enfield Himalayan. Portugal is the size of Indiana. On the BMW, I could bounce from one corner to the other in one long day. The Enfield costs around half as much and would make getting there more of an adventure. Bearing in mind that the F 750 GS was the most expensive part of the trip (around €100 per day, plus gas), I realized that I would have been as happy on pretty much anything with two wheels. Did I mention that I recently rode a Moto Guzzi V7 from Vermont to San Diego?

So I will ride just about anything, but my riding gear — Dainese Essential Tourer jacket and pants, winter gloves, base layers — is indispensable. I never regret bringing one layer too many. I keep chemical hand-warmers in my bag, in case I don’t have heated grips. If I had brought a heated vest I could have headed farther north. Anyway, I felt good the whole time, which came down to the gear more than the bike.

I carry my gear in a SealLine waterproof backpack that holds 120 liters. It’s bulletproof. You can throw it in the ocean, and someday your stuff will wash up, still dry and folded, somewhere on the Jersey shore. It holds twice as much stuff as the saddlebags on a BMW R 1250 RT. When you arrive, you sling it over your shoulder and head inside, instead of fumbling with hard cases. When the trip is over, check it at the gate and fly home. The fancy hard cases on the GS were a downgrade. On the Guzzi, I bungee my bag to the rack and go.

Most important: Bring a backup for your phone. The no-planning approach falls apart if you can't navigate or reserve rooms online, particularly in rural Portugal, where few people speak English. I took an iPad along for the ride. Any tablet will do.

4. Everything works

I used to spend hours figuring out how things work, in advance. Now I remember that Portugal has been there for a really long time, and if something didn't work, it would have been fixed by now.

Case in point: An American looking at the steep, wet, cobblestone streets of Lisbon or Porto might think, "I would be lucky to hike up that, never mind ride." Turns out the cobblestones drain instantly and grip pretty well. I bombed around on the Honda 125 trying to get the ABS to kick in. To do that, I had to ride on wet trolley tracks.

I woke up early on a Sunday in Coimbra, a university town since 1308, needing to do laundry. I found the laundromat, but for my life I couldn't find detergent. How do Portuguese people wash clothes without detergent? Turns out it's built into the washing machine.

The washing machine knows what to do. The ticket machine at the ferry terminal knows what to do. The tunnel that you wish would lead you to the beach actually does lead you to the beach. The ATMs try to cheat you with a bad exchange rate, but be stubborn and say "no" twice, and then it works.

I was stumped by the gas pump. First, the diesel nozzle is the same size as the gas. I snuck past that one. Next, there are five buttons: 10, 5, 1, L, €. I wanted to fill up, so I pressed 10 and L and bought 10 liters of gas. I needed 12. I did it again, and bought the other two. Turns out I should have pressed the “10” button twice. No harm done, and now I know the drill.

The bottom line is this: The more I try to prepare, the more I complicate things. I rode Portugal for a week without any preparation and had the time of my life.

So my final advice is this: If you are thinking of riding overseas, get an International Driving Permit and go.