Our Vacation Planning Guide

Near Bandon Beach, Oregon

When Kristin and I met in 2009, Kristin had already traveled to six of the seven continents.  I had traveled to one (the same one I live on).  Kristin introduced me to a world of travel I never dreamed I could experience.  Our first vacation together was to Australia (Kristin’s seventh continent), where we hopped from town to town and managed to see some amazing sites (including the Great Barrier Reef).  After a few domestic vacations (Sedona, Florida, Big Sur), we headed abroad to Thailand, Cambodia and Nepal for our honeymoon.  Future travels took us to Scotland, Vancouver Island, San Diego, Italy, Portugal, Belize, South Africa, Wales, England, New Orleans, Oregon, Washington, Colorado, Belgium, and Alaska.  Next up is Northumberland, and then maybe New Zealand.  With each vacation, we learn a bit more about how to reduce stress and maximize enjoyment while traveling.  I wrote this guide to fondly reflect upon our travels, but I hope it is also useful to others who may wish to travel in similar fashion.

This would not be a good guide for someone traveling on a student budget.  If I were a student, I would still visit the same areas, but I would do so differently.  For instance, I would travel by train, not rental car.  I would tent camp or stay in hostels, not vacation rentals.  I would visit sites that are free or have low-cost entrance fees.  I would rarely eat out.  But for the most part, I would still see sites that are just as amazing, as educational and as transformative. 


How we prefer to travel…

Finding places to visit

Once we know which region, state or country we plan to visit, I create a customized Google Map for that area.  I search websites, using phrases like “Best things to do in…” or “What to see in…” or “Historical attractions in…” or “… off the beaten path.”  From these searches, I identify places that we may want to visit.  Here is a guide on how to build a Google Map.

I then add these possible visit sites to my Google Map using different icons for different types of places (i.e., one icon for museums, another for wildlife, another for historic site).  Usually this results in more than 100 possible sites to visit on any vacation.

If a site appears on all of the “best of” lists, then we are likely to NOT visit it, since we know it will be crowded.  As noted above, we may make an exception if the site is truly unique.

This mapping process allows me to see where numerous sites are clustered together.  Based on these clusters, we look for lodging close to the best sites, or in the areas with the most sites, or that have the most diversity in site types.

Here is our customized Google Map for our upcoming trip to Northumberland.

When visiting places with rich tourist infrastructures, we research convenience features.  For instance, the National Trust in the UK manages many historical sites, including castles, historic manor houses and cottages.  These sites generally charge entrance fees, which can add up quickly.  However, you can purchase an annual pass from National Trust, which pays for itself very quickly.  Likewise, if you go to Florence, you can expect very long lines for most of the museums and galleries.  If you purchase the Firenze card, you can skip the lines and you do not need reservations at most sites.  When we visited Rome, we visited the Coliseum.  But by doing a bit of research first, we discovered that the normal entry does not provide access to the underground level or the top level.  So, I planned ahead, bought my ticket online, and I was able to get a guided tour of these interesting places.

Finding lodging

We avoid staying in hotels whenever possible.  They are loud, crowded and overpriced.  Once upon a time, we enjoyed staying in Bed and Breakfasts.  They were comfortable, the breakfasts were generally delicious, and the hosts were informative.  However, BnBs have become much more expensive, and they are harder to find online than ever before (primarily because hotels that provide free breakfasts now also categorize themselves and BnBs on the popular reservation sites). 

Now we tend to stay in vacation rentals.  This is becoming more difficult to justify, as the prices are going up fast, and as the vacation rental industry is making it difficult for new home owners to purchase their first houses.  But for now, it’s still the best option open to us.

Having said that, we seldom meet all of these criteria.  We often have to sacrifice one or two, depending on the region we are visiting.  For instance, visiting Alaska is incredibly expensive.  In order to stay within our budget, we sacrificed most of the criteria and settled with lodgings in convenient locations.  When visiting Belgium and the Cotswolds, however, we were able to meet most of our criteria while staying under budget.  On the whole, vacation rentals in Europe are much cheaper than vacation rentals in the US.

We do make two important exceptions to our no-hotels rule.  When we visited Wales and the Cotswolds, we made the mistake of flying to Manchester, renting our car, and then driving five hours to our rental in Blockley.  We were exhausted from the flight and time-change, and we were driving on the left-hand side of the road.  We are lucky we made it without having an accident.  When we went to Belgium, we got smart.  We landed at the airport, got our luggage, and immediately checked into an airport hotel.  We got some sleep and had a few good meals.  The next day, we popped back over the airport, picked up our rental car, and then drove on to our first vacation rental. 

The other time we use hotels is on the back end of our trips.  If our flight out of a country leaves in the morning (usually from a large airport in a metropolitan setting), we check into a hotel near the airport the night before.  This allows us to get as much sleep as possible that night, improving our resistance to germs and travel delays.

We tend to find our vacation rentals on one of four sites:

Check out this comparison of vacation rental sites.

Here are some very legitimate concerns about vacation rentals. 

Planning itineraries

For each day, I usually plan a default itinerary of places to visit.  Based on our location and the sites near us, I plan one or two sites each day.  This plan may seem like it is written in stone, but usually it is not.  While there are some must-see sites in each area (for instance, seeing the puffins in Wales or the bears in Alaska), most of the sites are interchangeable (like the fascinating Little Moreton Hall in England).  With wifi, we have access to the Google Map I created for the area, so we can quickly change our plans based on weather, emerging interests, or advice from the locals. 

We usually build in a few relaxing days, where we will visit only one site, or maybe just lounge around a particularly nice vacation rental. 

Weather can change our plans quickly.  To see the puffins on Skomer, you have to arrive at the boat dock early (we arrived at 6 am), stand in line until 8 am when the ticket counter opens, purchase your tickets for that day, and then take the boat over to the island at your assigned ticket time (we were early enough to make the 9 am crossing).  You cannot purchase your tickets for Skomer in advance or online.  So, if you arrive at 6 am, and then wait until 8 am for the ticket office to open, it’s entirely possible that they will tell you the water is too rough for the crossing, so visit cancelled.  We knew this going in, so we planned Skomer for the first day of our visit in the area, with backup plans in case of bad weather.  Using this approach, if the crossing was cancelled the first day, we would visit our backup sites, and return to try again for Skomer the second day.  Likewise, when we visited Brooks Falls, we planned to visit for two days instead of one, in case the weather knocked one of the days out.

If you are new to travel, never show up expecting easy access to a site you most want to see, or one that is off the beaten path.  Always research the site first.  Many sites are open only five days a week, or are open only during limited hours.  Some popular sites are open on a first-in-line basis, while others require you to purchase tickets in advance.  For each place you want to visit, check the website for hours and notifications, and then check the TripAdvisor page to read reviews and advice.  It makes for a bad vacation to drive two hours to see a wondrous site, only to find it closed.  And yes, we have made this mistake more than once.

Florence, Italy

Little Moreton Hall, UK.  National Trust Site.

Planning meals

Since we usually stay in places with kitchens, and we often have rental cars, our meals tend to look like this:

Since we only eat out once per day, our first stop in any area is the local market.  We pack reusable bags on our trips (the ones with zippers are the best for car travel), and we have a shopping list before going in.  Cookies are rarely on our list, yet somehow almost always make it into our basket.


Driving abroad

Driving abroad is not for everyone...  

The signs can be confusing, the roads can be narrow, the rules can be slightly different, and multi-lane roundabouts can be downright frightening.  For many travelers, driving abroad is simply not worth the hassle.  But if you feel comfortable in your driving skills, and you are prepared in advance, it is great to have the level of freedom that self-driving affords.  We have love driving in Europe, Canada and Australia, but we would not drive in Asia.  We would drive in Mexico and South America, but have not had the opportunity to do so yet.  Other travelers love driving in Asia, so it’s really a matter of your comfort level with chaos and uncertainty.  The best driving advice we received was from a tour guide in Italy… “Slow and Brave.”  This means that when approaching a crazy intersection without stoplights, go into the intersection slowly, predictably and bravely.  If you wait for an opening, it will not come.  Just edge your way in, and others will give way.  That worked like a charm, though it was a bit harrowing.

Our first rule in driving abroad is that side-seat-driving is not only allowed, it’s required.  Four eyes are better than two when driving in unfamiliar places.  So, if I am driving, and Kristin points out an obvious danger up ahead, I can’t say “Yeah.  What, do you think I’m blind?”  Instead, I need to say “Thank you for pointing that out.”  I know it may seem silly, but this little rule has helped us avoid many an expensive accident.

Car Insurance...

Because we book our cars on a travel Visa card, we have fairly good car insurance without having to buy any from the car rental company.  However, if you get into a scrape (and we have, several times), then it can be a pain to process the paperwork from Visa.  Purchasing comprehensive coverage from the rental car is usually much more convenient, but also much more expensive.  So, if the rental car company insurance is cheap or required (as in South Africa), then we purchase it there.  Otherwise, we go with our Visa coverage.

GPS...

The first time we traveled to the UK, I had color-coded maps and a road atlas with our routes highlighted in yellow.  Then we spent 45 minutes trying to find our way out of Heathrow Airport.  Our first stop after finding our way to freedom?  An electronics store, where we bought a GPS.

These days, if we’re driving, we’re GPSing.  You can easily use the maps/directions feature on a cell phone, but we like the GPS option better.  Before we embark on our vacation, I load our lodgings and nearby markets onto my Google Map for the area.  Then I export the map as a KML file.  I then import this file onto our GPS (not all GPS units have this feature, so be buy one that does).  We use a Garmin Nuvi 2559LMT North America and Europe.  

When we pick up our rental car, our first step is to set up the GPS and plug it into the cigarette lighter.  With the GPS up and active, we simply open up our bookmarked locations, pick the one we want to go to, and drive off to adventure.

This approach has three distinct advantages over maps.  First, it allows both of us to watch the road, rather than one of us staring at a map.  Second, the GPS tells us which lane to be in (this is great on the freeway).  Third, we miss fewer turns, which reduces stress while driving.  It’s important to note, however, that letting the GPS do our thinking can get us into trouble.  On one memorable drive in Portugal, the road kept getting narrower and narrower as we followed the GPS directions into a village.  Then suddenly, the road became a sidewalk, not wide enough for the car.  Backing up was not an option, since we had driven over bridges barely wider than the car.  So we had to turn around in a very tight corridor.  It took us ten minutes to make the turn, with me driving and Kristin directing from outside.  It must have been quite the spectacle, since we attracted a crowd of onlookers, some of whom were taking pictures of us.  But it made for a great story to tell later! 

Another GPS consideration is parking.  When we set off for a castle in Wales, we found ourselves on a small one-lane side road, and then suddenly the GPS said “navigate off road,” meaning, presumably, drive up the side of the hill through the forest to reach the castle.  It turns out that I had marked the location of the castle on my Google Map, and not the parking lot for the castle.  So, the GPS took us as close to the castle as possible (which was not the parking lot), then told us to get out and walk from there.  Consequently, when I build my Google Maps now, I always add in the parking lot if it is far from the actual visit site. 

Other ways to get around

Travelling the countryside is difficult to do by train.  For instance, while you can presumably take a train from London to Ffairfach, you would still be 11 miles away from Castell Carreg Cennen (one of our favorite castles from that trip).  It was along the drive to Castell Carreg that we stopped to watch wild ponies on the moors.  You may be able to catch an Uber or cab from the train station, but then again, you may not, and you would likely not have the opportunity for impromptu stops along the route.  So travelling by train limits the sites you can visit.  For many travelers, this is not a problem.

We have found trains much more useful when visiting cities.  For instance, rather than staying in Florence, we rented a lodging outside of the city, and took the train in each day.  When we visited Belgium, rather than driving to Bruges on the last day of our vacation, we took a train from our airport hotel in Brussels.  And sometimes, we just take trains because they go through some amazing scenery (for instance, the train from Vancouver to Seattle).

On rare occasions, we have hired a car/driver combination.  For instance, when we visited Rome, we wanted to see the catacombs and a few other sites far from the train lines.  So, we hired a driver and car.  Likewise, when we visited Thailand, we hired a car, driver and guide to take on a four-day journey through the mountains north of Chiang Mai.  In Rome, the car/driver was expensive and not that great.  In Thailand, the car/driver/guide was affordable, and the driver and guide were amazing!

Some travelers love to bike or hike through the countryside, but we don’t have the knees or stamina to explore in that fashion.

When we reach the age where we no longer feel comfortable driving abroad, we will likely switch to organized tours and/or train travel, losing the freedom to go anywhere, but keeping the ability to travel to amazing places!

We have occasionally travelled by boat or ferry, though not by cruise ship (we would like to try a river cruise soon).  In Scotland, we took a ferry to the Orkney Islands, and in Alaska, we took a ferry from Juneau to Bellingham, Washington.  We have taken numerous site-seeing boat trips on our travels, including one from Key West to Fort Jefferson (where Kristin said “Yes” to my proposal, to my delight!).  Travelling by boat usually requires pre-planning, though not always.  When we took the ferry to Quadra Island in British Columbia, we just showed up and drove on.  But the ferry to the Orkneys and in Alaska required pre-booking.  Kristin tends to get seasick, so we also acquire medication for rough seas before we leave Albuquerque.  The Alaska Ferry is sparse, compared to a cruise ship, but we absolutely loved it!  It was comfortable and affordable, and the people we met were friendly and happy.

Organized tours

We have never travelled on a multi-day organized tour, though these will become more appealing as we get older.  However, we have had great luck with day-trip tours.  These often come in two forms: private tours and group tours.  We use viator.com to find most of our tours, though we sometimes use local websites as needed (for instance, regional tourism sites often list local tour companies).  

In Portugal, we joined a group tour (approximately 6 other travelers) to paleolithic sites, led by an anthropologist.  The tour company provided the van and the guide.  In Italy, we hired a private guide to Pompeii and Herculaneum, led by a local archeologist.  For that tour, we provided our the car.  In France, we hired a private tour of some fascinating sites near Verdun, again using our own vehicle.  In Cambodia, we hired private guides with cars to take us to the outlying temples of Angkor Wat.  In all of these instances, we visited places we would not have been able to access alone, and our guides pointed out things we would have never seen.  Local tour guides are amazing.  We recommend them wherever possible.  In fact, there are several places where we regret not hiring guides (for instance, Florence).

Travel insurance

Travel insurance is a tricky thing.  Here is a great guide to travel insurance.  Travel insurance is more expensive in the US than in Europe or Asia, presumably due to our high medical expenses.  There are many reasons to get travel insurance, including emergency evacuation benefits.  When we travel abroad, we always purchase insurance (usually through squaremouth.com).  When we travel in the US, we are less likely to purchase the insurance.  When we do purchase travel insurance, we try to get “cancel for any reason” coverage, if it’s within our budget.


Packing

We are the worst packers in the world.  We pack for every contingency, no matter how unlikely.  As a result, we each have one suitcase (usually close to the 50 pound airline limit), one backpack (usually way too large and too full) and one rolling carryon bag.  I take a ton of camera and computer gear, in addition to my plethora of other stuff.  Traveling with this much luggage is a pain, and if we travelled by train instead of rental car, we might pare down a bit.  But if you’re looking for packing advice, look elsewhere.  We’re the last people you should ask how to pack lightly. When we visited Siem Reap (near Angkor Wat), our hotel sent a tuk tuk to pick us up from the airport.  When the driver saw our luggage, he took a step back and had to think about how best to tackle it.  The other tuk tuk drivers were laughing.  So yeah, we’re THOSE people.

Tour guide at Angkor Wat

Tour guide in Pompeii

Camera and computer gear

I tend to edit and my photos while we are on vacation, rather than waiting until we return.  This will not work for everyone, but since Kristin enjoys reading in the evenings, it works well for us.

I travel with several cameras, depending on the situation.  For most trips, I take one camera body (a Nikon D500 or Nikon D7500), and two lenses (an 18-140 general purpose lens, and a 10-20 wide angle lens).  If I will be photographing wildlife (for instance, the Big 5 in Kruger National Park, or Brown Bears or Whales in Alaska) then I will take a long zoom lens.  Depending on the weather, I may also take a point-and-shoot waterproof camera (I also use this when taking pictures in cities).  Sometimes I take a 360 degree camera.  I always take spare batteries and SD cards (lots of them).  I usually take along some time of tripod or monopod.

I take my laptop, a mouse, a mousepad, and an SD card reader.  I use Adobe Bridge, LightRoom Classic and Photoshop for my editing.  I will sometimes take a portable memory device and a small battery charger.

In New Mexico, I tend to take landscape pictures of desert scenes.  But when we travel, I also take pictures of wildlife, waterfalls and beaches.  Different pictures require different camera settings.  But since I don’t shoot these subjects often, I don’t always remember which settings to use.  So, I create flashcards for different photography situations.  This saves time when photographing, since I don’t need to stop and think through what settings to use.   I have a set of flashcards for each trip.


I imagine you might be thinking “that’s a lot of prep work for one vacation!”  If so, that’s correct.  It would be much easier to head to an all-inclusive resort hotel and lounge on a tropical beach for two weeks.  Indeed, that is the perfect vacation for many travelers.  But for us, the joy in travel comes from learning new things together, experiencing different cultures, seeing amazing sites and imagining history through new lenses.  We are not interested in seeing the most popular sites, just the sites that are most interesting to us.  So, doing the prep work up-front means that our time on vacation is spent seeing and experiencing, not planning. This approach has served us well.

Here are some amazing travel planning sites:

How to plan a trip: The ultimate practical planning travel guide.  Excellent travel advice for younger travelers who pack much lighter than we do.

16 (Easy) step guide on planning your next trip.  A very comprehensive travel planning guide.

How to plan your UK trip - a step by step guide.  Excellent resource for visiting the United Kingdom.