When riding long distances or travelling with an open-ended itinerary, one often does not know where one will stop for the night. Detailed planning quickly falls apart. This story from four years ago remains relevant today, in the middle of the travel season. I hope it helps. 

They sat at a picnic table across from the grocery store, passing a two-liter carton of orange juice back and forth. The bicycles lay against the gate of the closed campground behind them. At the end of the road, they could see an angry Adriatic Sea roiling onto the beach. The brilliant sun made for pleasant riding, but the wind had a bite. The tourists had gone home; the little beach town and the coast were all theirs. Swimming was out of the question this late in the year and so was camping.

“I figure we have maybe two hours till sundown,” he said. “We can make Rimini by then.”

The wind was whipping her hair across her face. She had her head down, tapping on her smartphone.

“This looks like a nice place.” She held the phone up for him to see. “What you think?”
“I like it, and the price is good, too. Let’s get it!”

She tapped out a few more steps on the screen. “That’s it. I noted that we would arrive about 5 PM.”

He looked at her, not trying to hide his admiration. “How do you do that so quickly? Do you have some kind of method — perhaps one that I could learn?”

She thought for a minute, with her eyes closed facing the warm sunshine.

“Well, I guess I do.”

“Is it different for the different booking services?”

“No, not really. Whether I’m looking at booking.com, bookingbuddy.com, hostelworld.com, tripadvisor.com or even kayak.com, I follow pretty much the same steps. After putting in the location, the dates, and the number of guests, I scan the search results for anything with a review score of eight or above. Anything below eight is going to have some kind of problem, or at least require more research. So far, we’ve been able to find affordable places with good scores almost everywhere we’ve stopped.”

“I would probably look at the price first. That’s what my mother would do.”

“It doesn’t cost that much more to get the best. Start with the best and then work down to what you can afford, if the very best is too expensive.”

“Then what?”

“Then I look at the pictures. All of them. Every time. No exceptions.”

“The pictures? I don’t trust those,” he said. “I figure that most of them are staged. I keep looking for what’s not in the pictures, or trying to second-guess where they put the camera and what they’re trying to emphasize or deemphasize.”

“You do that well, too.” She smiled. “It is one area where you have been very useful. But the pictures are important. Assume the hotel or B&B shows us pictures of its only decent room: if the picture does not look good, then the rest of the place is probably worse.”

“Anything else?”

“I always look at the location. Specifically, how far is it from where we want to be? Tonight, we just want a place along the route to Ravenna, but usually, we like to be in the historic center, so we can walk around and see the sights. Or near the train station, if that is how we are coming or going into town.”

He took the empty orange juice carton to a trash can. They walked to the bicycles, and strapped on their helmets.

“What if nothing got a score of eight or better?” he asked, leaning down to tighten his shoe straps.

“Then it depends on what you can put up with. Some of the scores come from people who are unhappy with the parking, or the sound of young people partying in the street. Some of the places with scores between seven and eight are actually quite nice, but then you have to look at all the review comments and see why they got the score they did. Sometimes other people’s problems won’t be relevant to what we need.”

“I’ve stayed in some pretty miserable places over the years,” he said. “I like your method. Thanks. Hey –!”

She was already 50 meters down the road and gaining speed. At least this time he was rested as he began the evening sprint to beat the sun to the horizon…

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This fictional vignette outlines one strategy for using online services to reserve a room along the way. It applies whether you’re living on your bicycle or traveling some other way. Here are some other things I learned, in no particular order of importance.

Price is a moving target. There are two times that you can get a good deal on a room: very early and very late. If you make reservations months in advance, the booking service will give you a very good rate, especially if you’re able to commit yourself to being there on the date that you reserve (or can give up the deposit or advance payment). On the other hand, after about noon on the day of arrival, the price begins to drop on any beds that are not reserved. The hotel owner would rather have somebody in the bed for half-price then have an empty bed. We learned not to look for reservations until two or three hours before we would arrive, partly because we were never sure when we would be where, and partly because of the afternoon price drop. This tactic works even in high-volume tourist areas, unless there is a very special event going on, like a rock concert or a papal visit. Even so, Cheryl was able to get us reservations when a Shania Twain concert was in town, although we stayed in a different hotel each of the two nights. The price drop might not be much on a Friday or Saturday, if the town has a regular weekend surge crowd.

Return reservations. If you’re going back to some place that you already enjoyed, try asking for a lower rate by calling them directly or using the hotel website. The various people providing accommodations pay about 18-20% booking commission to the various online services, which comes out of the rate that you pay. If you book directly with the hotel or B&B or campground, you could ask to split the savings.

Communicate with the host(s). Unless you’re staying at a full-service hotel with a 24-hour manned desk, you may or may not be asked by the booking service to provide a one-hour window when you will arrive. Often the proprietor is not at the lodging location, and needs to meet you. If you’re going to miss your expected arrival time, you should call or text/SMS ahead with an updated time. Every host that we encountered in our travels was using a mobile phone; they were able to send and receive texts/SMS, and get our number from our call. That one courtesy was clearly the most important thing we could do to ensure a pleasant stay. (Picture this: someone missing their child’s recital or soccer game, waiting for you to show up. They will never tell you that.)

If the booking service does not ask you for an arrival time, do make sure that the phone number you put in the reservation form is one that you are prepared to answer. The host might call you to find out when you’re arriving. The phone with that number should have a decent battery charge and not be in airplane mode!

Tipping. I grew up in a world where tipping was the rule, but in a world of prepaid online services and credit cards, I find that tipping is no longer expected everywhere. In Europe, this is partly because the various EU nations have cracked down on abusing (underpaying) the staff, and partly because the tax authorities take a dim view of cash changing hands without it being recorded on the fiscal receipt. I never even saw a place for the tip on any charge slip that I signed.

Taxes and other small charges. The booking service should send you a confirmation email that states what you will have to pay. The room rate will be a firm number, but there may be small print that mentions city tourist taxes, bed taxes, or other charges. Look for these, so you can ask the host about them. I never saw any that broke the bank, but there is no point is giving yourself an unwanted surprise. One hostel that I favor in Rome rents the towels and holds a five-euro deposit to be sure that they get the key card back. They also had a small charge for breakfast. The logic was solid: those little charges allowed them to keep the room rate way down, because they did not waste food or linens, or have to replace key cards.

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This week’s topic is not confined to bicycles or freelancing, but any kind of travel. Do you have any techniques or tips for finding a roof each night?

Until next time.

Smooth roads and tailwinds,

Jonathan