How to plan the perfect trip
Updated: Jun 27, 2021
When you’re longing for an international vacation, how do you determine where to go and when?
This may be the easiest of all decisions or your biggest first headache. Many people have a very specific wish list or a dream location which makes getting started pretty simple. Even then you will likely still be faced with some key decisions, say you dream of going to Germany but then what cities or regions do you visit when you get there? And then there’s the question of when – German Christmas markets in winter, the Black Forest during the fall, you get the dilemma. Some of the timing questions resolve themselves based on work and family/life schedules but how do you decide otherwise? And if you are like me, and you want to go everywhere on the planet, how do you get started? As I think of planning travel for later in 2021, I will share some tips and suggestions in this blog to help with these two questions.
A couple of disclaimers up front about what to expect in this advice. Most importantly, I really enjoy doing all the research. Many people just show up and play it by ear or prefer an organized tour, but that is not what I, or this blog, are about. I love learning about where I’m going, the history, what to do, what’s off the beaten path, where to eat, etc. My end goal with this blog and venture is to offer boutique travel advice. What I suggest here will likely be a lot more than most people will want to take on when planning their own travel. Also, I don’t have children so my advice will be more applicable to couples, groups of friends, or singles. I love history, culture, local points of interest, food, and the arts so there will be a bias towards those types of activities. Finally, my focus is on international travel. There are tons of wonderful places to see in the US (I’ve been to 42 states) but international travel is what’s more intimidating for many people.
So, if you know where you want to go already, great! You can skip this next part and jump ahead to the section where I write about when to travel below. We’ll also get into more detail about what to do in-country in a pending blog post. But what if you have no idea where to start?
First and absolutely foremost, what do you like to do at home or while vacationing in your home country? Your own passions and interests really should be the key drivers of all your decisions. Do you love chocolate – how about Switzerland or Belgium? Wine – France, Italy, Chile, and South Africa come to mind? Sports – how about the rich soccer (football) history in Europe and South America? Or Cricket in India? Or baseball in Cuba or Japan? If you are religious or interested in spirituality – visit India to learn about Hinduism, Southeast Asia for Buddhism, Germany for the birth of Protestantism, the Middle East to understand Islam better, or Rome as the seat of Catholicism. Love sportscars, racing, and gambling – head to Monaco or Macau. Big foodie? Visit the places of birth of so many great cuisines – France, Italy, Japan, China, Mexico, Vietnam and many others. Like to dance? Learn the tango in Argentina. Are nature and animals your thing? Try the gorgeous open spaces of Canada, South America, Africa, and Australia. Love history? – we’ve all been on this planet the same amount of time and there is so much rich history to learn in every country. I could go on and on with examples but I think you get the point. Whatever jazzes you up also happens all around the world and it’s so interesting to experience it from other point of view. As with so many things, the Internet is your friend here. Simply do a search for “best countries for XX” with XX being your interest (sports, beaches, chocolate, etc.) and you’ll quickly get a narrowed list from which to start.
Another consideration is where are the “top” places to go? You may want to flock to these or avoid them at all costs. Sites I like to consult are the New York Times 52 Places To Go annual review, TripAdvisor’s Top Destinations, and travel magazine specific sites, such as Travel and Leisure, Traveler, and Afar. These sites and articles not only give you what’s current in travel but also highlight key events that may be of interest – for example, Egypt was on the New York Time’s list for 2020 due to the opening of the Grand Egyptian Museum that year (since deferred to 2021). Going to the “top places” may be incredibly fun and exciting to keep you “in the know” or a terrible burden with crowds, inflated prices, and unrealistic expectations. The sites I noted are just a small few of the options worth exploring. I also like the book 1,000 Places To See Before You Die as a general reference. It contains highlights for almost every country on Earth, and while it’s probably best for when you’ve narrowed down where you want to go, it can help when you are in a toss up among a few different countries.
Additional important factors to consider are health, comfort, and safety. In general, I have found in my travels that people are more good than not and places that may seem scary are more hype than reality. That being said, this is a very personal factor and you must be comfortable in your decisions or your trip will not be as fulfilling as you’d hope. A few key considerations:
Health – not withstanding the coronavirus pandemic, you should assess any health considerations of the countries you want to visit. What are common illnesses there and what vaccinations or precautions do you need to take? The CDC has a comprehensive travel site with guidance and advice.
Ability – you should also factor in our own ability to enjoy the trip and participate in activities. My general premise is to visit places which require more vigor when you are younger. For example, I’ve been to Peru and visited Machu Picchu and it’s not something I would want to do as an older person (generalizing of course) – there’s a lot of transportation required, high altitude with the possibility of altitude sickness, lots of climbing and walking, etc. Think through your own abilities, the activities you want to participate in, and the maturity of facilities where you intend to go.
Logistics – some places are easier to get to and get around in than others. Even if you REALLY want to get to that small village in India, it may require multiple international flights, multiple domestic flights, multiple car or bus rides, etc. These modes of transportation may also only be offered on certain days of the week, only one way, or have other limitations. For some this may not be a concern, but it should be considered as you could lose a few days of your precious vacation time or at the very least be exhausted when you finally get there. Also check entry (visa) and passport requirements, some visa may take time to procure.
Safety – there are two factors here, general conditions in locations you are considering and safety concerns you may have as an individual. The general conditions are probably pretty clear – you probably don’t want to vacation in a country in the midst of a war or other conflict, areas with high terrorism concerns, high crime rates, etc. Most of these types of places you are likely aware of from the news or your own general knowledge but the US Department of State has a comprehensive travel advisory site. You can also register on the site when do you do travel so that you will receive travel notices from the Department of State and they will also have a record of you being in country to assist you in the event of an issue. The more individual concern relates to how you may be treated in the country. Many groups of people have special considerations such as: LGBTQ travelers, women (solo or in groups), people of color in certain countries (what level of discrimination you may face), people with diverse abilities, etc. It’s important to also do a little research (again the internet is your friend here) on what specific considerations apply for your situation. This research may not entirely deter you from traveling but it’s good to understand the situation on the ground so that you have realistic expectations and can adjust accordingly.
Language – you may be concerned about traveling to a place where you don’t know the language. I’ll never forget my first international trip when I was 18 and arrived in Paris’s Charles de Gaulle airport. Arriving in a new country where everyone is speaking in another language that you don’t (or marginally) understand is a surreal experience. But I’ve also learned that English is the international language of travel. I’ve never been to a country where I’ve not encountered people in the tourism economy who speak English. So, if you are sticking to the tried and true tourist experiences, you will likely be just fine in almost any country. But if you want to venture off the beaten path then you may want to stick to countries where English is the primary language or invest in some tourist-oriented language classes.
So now after you have factored in all (or none) of those items above, when do you go? As with picking a destination, this may be a very easy decision based on your own life factors such as time off from work, limitations such as school months for children, special event trips (birthdays, anniversaries), etc. Or your trip may be timed with a special event or season (reopening of the Pompidou Center in Paris, carnival in Rio de Janeiro or grape harvest time in Australia). If specific timing is less of an issue, below are a few other factors to take into consideration.
Weather – while you won’t be able to predict the weather, you should at least consider general seasons and what they bring. For example, when is it hot and dry in India vs monsoon season, when is it coldest in Patagonia, when should you be worried about typhons in the Philippines, or how many hours of daylight are there in Norway in January, etc.? Understanding these types of things can better help you pinpoint a comfortable and enjoyable time to travel to your chosen destination.
The “Season” – many places have a period of time when they are most popular (and therefore most busy and most expensive). A primary example of this is beach or other seaside locales, these are always most popular when the weather is warmest and the days are longest. In the Northern Hemisphere that is the summer months of June – August (it’s the opposite in the Southern Hemisphere). The “season” may also relate to events that you are interested in – sports and arts in particular come to mind. There are various seasons when different sports are played leading up to their respective championship competitions. There are also arts seasons – ballet, opera, festivals, etc. You should try to understand the prime time for the types of things that you want to participate in and plan around that. Consider the “shoulder season” which is generally the months leading into and out of the prime season – for example, ski season in Europe is generally December through March and November and April would be considered the shoulder season where it may be perfectly fine to ski depending on the specific location (say high in the Alps). You may also find the crowds to be smaller and hotels and restaurants to be less expensive. Finally, there is the “off season” which is usually the months directly opposite the prime season (i.e. winter for beach visiting). The off season may have its own charms but generally you will find many more limitations, such as restaurants being closed for the winter.
What’s Going On – this is a bit of the chicken and the egg situation, and I will talk more about planning what to do in country in a coming blog post, but you do want to do some research to understand what events are happening and when before you nail down your final travel plans. If you really want to see the Bolshoi Ballet in Moscow, you need to understand when the performances are. Great general sources here are national and local tourism organizations. Almost everywhere has some time of tourism organization that can help you get quick views of the top things to see and do and calendars of when things are happening. Here’s Russia’s for example. Two other website I absolutely love are The Culture Trip and Atlas Obscura.
Budgeting Your Time – lastly and before you book those tickets, you should assess if you are trying to do too much. This is a classic problem and one that I learned the hard way in my earlier travels. I’d have literally every hour scheduled and would be so frustrated when things got off track and something caused the schedule fall behind. I was too focused on doing it all and not enough on enjoying myself. Be careful not to try to take in too many countries in one trip depending on the time you have and also not jamming too much in each day. But it’s also a balancing act. A fantastic 2018 trip I planned included Lisbon (Portugal), Seville and Ronda (Spain), Gibraltar, and Tangier and Casablanca (Morocco) – but it was a two-week trip, the countries and all close to each other making transportation pretty easy and some places were only a day or less (Ronda, Gibraltar and Casablanca). I think having three or four days in a major city is the minimum and individual days should have two or three areas of focus with time built in for mistakes, long lunches, and unplanned detours. I also like to try to leave a day (or at least a half a day) as unplanned so that you have some cushion for things you maybe didn’t get to or want to add to the schedule.
Alright, so after all of that, where am I thinking of going in 2021? With Covid it’s still a little tricky to plan so I won’t be pulling the trigger on these just yet but I am looking at Southwest England and/or Greece in late summer or early autumn. I am a big history and culture fanatic so that is a major driver for these two locations. Some of my other rationale, using some of the criteria above, is:
Southwest England: I’ve been to England many times but have not been to this part of the country. Lately I’ve been reading a lot of novels based in Anglo-Saxon and Norman England (the Kingsbridge series by Ken Follett and the Last Kingdom series by Bernard Cornwell) and much of those stories take place in this part of the country with its rich history. It’s also generally a beautiful countryside with rolling hills, quaint towns, and charming seaside locations. England is easy to get to with lots of direct flights to London, good internal transportation (trains and car-rentals), minimal safety concerns and with shared values and language. Visiting in the late summer/early autumn would allow for pleasant weather with attractions still being open (I imagine most are year-round here).
Greece: I have not been to Greece so that alone is a big driver for this decision as part of my quest to visit as many countries as I can. The history of Greece is of course an obvious draw with its numerous important contributions to Western culture. Greece is relatively easy to get to (more limited direct flights so this could be a one-connection flight) and while I don’t yet know internal logistics, I suspect they are mature enough to get to the major locations and islands. The warm Mediterranean location is an appeal and I envision long and lazy seaside meals with lots of local seafood. Like England, there are no major health or safety concerns of note. Going in the autumn would allow me to take advantage of the should season and hopefully avoid big crowds but still enjoy nice weather. Greece also has a nice central location to add on potentially a side trip to Crete or Turkey.
Stay tuned for more details in my next blog post when I will share guidance on selecting transportation and determining where to stay and eat. I’ll also share more details on specifics for England and Greece.
Comments