Catamount Imaging | Travel Planning

Travel Planning

August 04, 2013  •  Leave a Comment

When I corner someone and blab endlessly about how much I enjoyed our trip to Portugal, I sometimes get questions about how we planned the trip. Did we stay in hotels? How did we find and reserve them? Where did we rent a car? How did we decide where to visit?

They are interesting questions and I realize that we've come a long way in planning our trips. My first trip abroad was in 1999 when Meg and I traveled to Berlin, Poland and Prague. European travel was completely foreign - and frightening - to me. We communicated with hotels via the fax machine which we would hear printing in the middle of the night - we were in California then so either eight or nine time zones away.

Today of course, we're blessed - and cursed - with the internet which provides everything from an endless number of travel sites to travel photo sites to a myriad of booking sites. Planning a trip like this can be as much work as you let it become and you can be as fussy or as free as you like. Luckily Meg and I are of like minds about these trips. We tend to plan the structure of the trip quite thoroughly and leave the daily details more open so that we can improvise within that structure.

Our planning has a couple phases:

  • Deciding where to go in the big sense. What country or experience?
  • Deciding on flights.
  • Deciding where to go in the smaller sense. What cities? What sights?
  • Deciding on transportation there. Trains, busses, car rental?
  • Deciding on lodging.

For my mind, finding my way through all these decisions is a matter of reducing the number of variables one by one with each decision further reducing the options. In the context of planning, this turns out to be a good thing.


Deciding Where to Go.

For us anyway one of the things we know typically is when we want to travel. Sometimes it's because we're piggy backing on a business trip of mine or sometimes its just the normal ebb and flow of the year that dictates this. This is actually helpful as the time of year in different places dictates weather which can make decisions for you very quickly.

Case in point. We had been considering travel back to India this year but May is NOT the time to go to India. Very, very hot in most places. We'll be looking for a mid-winter timeframe for that trip.

Then there is cost. We've developed such a long list of places to go that we actually use that to our advantage. What's cheap at the time that we can travel? This is how we decided on Spain a couple of years ago. We found a non-stop ticket from Boston to Madrid for around $550 - an amount that seems almost mythical to me now. It made the decision easy.

Then of course as we get older, we begin to think about vacation trips versus trips of exploration vs. bucket list trips. Our list includes a safari to Africa which is a huge and expensive undertaking - not something that's easy to jump into. That said, we want to do it when we are young enough to do what we want to do on the trip without being overwhelmed by the physical demands of the trip. On the flip side if we don't have much time, then we look for a closer, easier to access destination. 

What kind of a trip are you taking? Is it a cultural site seeing trip or is it a get away trip? This makes a huge difference although we found in our trip to Portugal the opportunity to do a bit of both.

The key is to actually let your constraints help narrow the choices - then try it on and see how it fits. Does it feel right? Are you excited about the idea of going? Or not? Don't be afraid to try on a couple ideas and then go with your gut.

Side note: I follow a podcasting photographer named Martin Bailey who just returned from a trip to Namibia - he was there about the same time we were in Portugal. His travelog describing his adventures and pictures is most enjoyable. 

Deciding on Flights.

Once you've made at least a tentative decision as to where, the question becomes how to get there. I find this one of the most time consuming and least rewarding parts of planning. However, it also represents commitment; once you buy plane tickets, you've waded into the deep end.

Planning flights is tough because there are so many variables, so many little decisions to be made. The first one is cost: how much do you want to spend on your flight? As little as possible right? 

Maybe. Maybe not. Most travel web sites (like our favorite tend to prioritize flights by cost. However as time goes on we are paying more and more attention to other factors like:

  • Duration of the trip. Departure and arrival times. Layover duration.
  • Airport. We've had a number of poor experiences in Charles de Gaulle for example so we de-prioritize flights through Paris.
  • Which airline to fly and frequent flyer miles. Airline safety records - especially an issue when flying outside the US and Europe.

We tend to fly with Delta quite a bit these days because that is typically the airline I fly for business travel to Amsterdam and Gent. The miles pile up and Delta does pretty well by most metrics. On our recent trip to Portugal we bought our ticket from KLM (part of the SkyMiles alliance with Delta), flew on a Delta flight and then were denied miles because of the type of ticket we bought. My wife was, to say the least, annoyed and flying Delta may no longer be an option for us.

One added complication these days - or at least it's new to me - is the challenge of getting decent seats on your flight. On our recent Boston to Amsterdam flight, I paid extra for Delta's Economy Plus seating which ensured that Meg and I sat together in the Window/Aisle seats of the Airbus 330 configuration in row 17 (fairly forward in the cabin). I failed to upgrade or even reserve in advance seats for the return trip and we filled the center two seats in the four-across center section in row 37 or so. That said, Meg and I agreed the experience wasn't all that different and I'm not sure I'll be paying extra going forward.


Deciding Where to Go in the small sense. 

So once you decide to visit a place - how do you work out the details? What cities? What sites? How do you balance relaxation with sightseeing?

We tend to approach it by looking at what kind of trip experience we are looking for. If we visiting some place we've never been before (like for me Italy in 2010), it's very difficult not to do the big standard places like Rome, Florence, Venice etc. If by contrast we're returning to a place we've visited before, we feel more latitude to try visits off the beaten path. For example our next trip to Italy is likely to include some time in the Apulia region in the south east of Italy.

We also consider how much we want to move around once we arrive. We tend to try to visit several locations in the general area once we've made the trip. Last year we flew to Basel and then drove into Germany and France before returning to Switzerland staying in four different locations. The recent trip to Portugal was about the same for us. 

We have however developed a rule of never staying in one place for a single night. We did that in Baden-Baden and instantly regretted it. If it's worth going somewhere, it's almost always worth staying for a full day which means two nights generally. 

Lastly when we put together a list of places, we string them together and think in detail about what we want from each location, how we're getting from one place to the next. Visualize and test it out. Does it feel realistic? Does it feel hectic? Then we try to find a balance between seeing and experiencing everything we want to with overdoing it and exhausting ourselves.


Deciding on Transportation

The first couple of trips we took to Europe, we relied exclusively on public transportation and especially trains. There is no doubt that traveling by train - European trains - is a great way to travel - the recent accident in Spain notwithstanding. I've been especially spoiled the comfort, quiet and speed of the fast train from Paris to Brussels for example. Even regional trains have better comfort and of course a dining car. It's just so much more fun than traveling by plane.

The last two trips however, we rented a car and drove from location to location. I was severely apprehensive about this. I imagined the cars to be underperforming and unsafe. I imagined the rules of the road to be foreign and the signs incomprehensible. Turns out that I was imagining things. Driving in Europe has been much easier and more enjoyable than I ever imagined. 

That said, it clearly varies greatly country to country and I've never tried driving on the left hand side of the road. I've ridden in cars several times in Poland and I have no intention of ever driving there if I can help it. It is too aggressive and it is decidedly dangerous. But Germany, France, Switzerland and Portugal were all very doable.

While traveling by bus and train has it's own romance, there are simply things you do if you rent a car that you don't do otherwise. In Portugal we never would have been able to enjoy the rural Sagres area including Cape Vincent without a car. We never would have taken N120 through Odemura north towards Lisbon and we never would have seen the amazing Cromeleque dos Almendres near Evora.


Deciding on Lodging.

Lodging is obviously a very personal decision. Some folks like to leave this up in the air and let the wind take them where it may. Being locked down to reservations in certain places at certain times is no vacation for them. 

We are not like that. As mentioned above, the uncertainties of travel are mitigated for me by having a well defined structure to the trip which means reserving lodging ahead of time.

I suspect we spend a bit more percentage wise on lodging that most travelers but we don't go overboard. We are generally so busy on our trips and so tired when the day is done that the money spent for a clean, quiet, comfortable room is money very well spent.

We rely a lot on Trip Advisor. There is a lot of good information there though sometimes you have to dig a bit deeper to find it. I understand there always the capacity for fake reviews but I imagine I'm clever enough to notice them and filter them out. Reviews that tell you enough about the reviewer so that you can determine to accept or reject their suggestions are always helpful.

We've traveled enough now that I have developed a pretty firm set of priorities for hotels which starts with clean and is shortly followed by quiet. Other priorities include free wifi, workspace for two people, sufficient electrical outlets and proper quiet climate control. Many of these things are difficult to determine from the internet but you can get a sense of it.

Before we book we often contact the hotel with questions. Simply seeing whether and how the hotel responds to that tells you a lot about the place. We contacted the Bairro Alto Hotel in Lisbon before our Portugal trip asking for a quiet room on the upper floor with a view. Not only did they respond promptly but they referenced this when we checked in and we were very happy with the room and the view.

We've also used with good results. They too have a rating system and it's sometimes handy to compare information there to Trip Advisor and the hotels website. Finally we still rely on those staid old war horses: guide books. When we get ready to travel we will generally pick up a guide book from Rick Steves, Lonely Planet, or whatever seems to best fit our needs for the place we're traveling. 



There are many, many decisions in planning your own trip. We like to thoroughly plan the basic structure of our trip and try to do so without spending so much time on it that we're sick of our trip before we even go! We leverage our constraints to make some of the decisions, then carefully weigh - and talk about - our options before making the smaller decisions. Finally if we're unsure, we'll sit on a plan for a day or two, see how we feel about it and then go with our gut.

Happy traveling!











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