How to choose a destination: Tips to consider before travel

Sometimes it’s hard to choose your next travel destination.

Let’s say you have only two weeks’ vacation, and you want to get the most out of it that you can. At the same time, if you’re like me, you want to see pretty much the whole world. You know that in just one lifetime, and in just a few weeks’ vacation a year, that’s simply not possible. There are just too many new places you’d like to see. If this describes you, you’ve come to the right place!

So how do you choose a destination?

Disclosure: This post contains affiliate links. That means I’ll receive a small commission on anything you buy through clicking the links. This post also contains a sponsored link from TTA, the TEFL Academy.

I wrote a a few years ago about choosing a destination in a time of terrorism. In this post I’d like to address some of the other factors to consider when you choose a destination. I’m working, by the way, on the assumption that you want to plan an independent trip, not a package holiday.

Here are some things to consider in deciding where to go on vacation, along with some general recommendations from my own limited experience:

1. You could choose a destination by type of travel.

People vacation for a variety of reasons. What kind of trip do you want? Do you want to just relax at a spa, by a pool or on a beach? Or do you want an active outdoor vacation with hiking or skiing or diving or whatever? Are you looking for a romantic destination to enjoy with your significant other? Perhaps  you most enjoy exploring a country’s historical sites, cities, museums and cuisine? Or would you rather stay longer and immerse yourself in a country by visiting one of the best countries to teach English?

Once you’ve decided what travel style you want, you can already start narrowing down possible destinations. For example, if you love to take long scenic hikes, enjoying natural beauty, you might like the Scottish Highlands or Iceland better than London or Rome and the Appalachian Trail better than Washington, DC.

Of course, you might want to combine more than one activity, visiting a historical site one day, scuba diving the next, and lying on the beach the next. A place like Malta or perhaps Egypt would suit you well.

My recommendations for your next vacation

First, a disclaimer: I can’t cover every possibility because a) I haven’t been everywhere and b) I don’t do every activity: skiing, for example, is unwise for a klutz like me. However, I can make some very general recommendations.

Museums: New York City, San Francisco, Washington, D.C. (where many museums are free!), Amsterdam, Berlin and pretty much any major city in the world.

Historical sites: Egypt, Israel, China, Japan, Spain, France, Greece and Italy.

Natural beauty: the US, especially the Southwest, the Rockies and New England; Canada, especially the Rockies and the west coast; the Alps in Switzerland, France or Italy; the Pyrenees; Sweden, Iceland, the coast of Norway, game parks in Tanzania, Kenya or Malawi.

Scuba diving: the Red Sea in Jordan, Australia’s Great Barrier Reef, Bonaire, and Lankayan Island and Sipadan in Malaysia have been my favorites.

2. As you make your travel plans, don’t see accommodations as an afterthought.

Of course, you have to consider cost in making this decision, and part of that is considering what is important to you. For example, is luxury right on a beach important to you or won’t that fit in your travel budget? Could you cut costs by staying in a simpler hotel a few blocks from the shore, or do you feel like that would ruin your vacation? Is fine dining important or could you save money by renting an apartment and cooking for yourself? Are you comfortable with less traditional forms of accommodation: couch surfing, hostels or Airbnb?

You can sometimes get the best deals by choosing accommodations outside the city you’re visiting.

What accommodations you book will also depend on your travel group. If you’re going solo, a hostel could be a great way to save money and to meet people at the same time.

If you’re planning a family vacation, you might need a bigger room, or adjoining rooms, or a crib. For young kids, some beach resorts offer kids’ clubs, so you might want to choose based on that.

My recommendations

Hotwire: Using Hotwire is one of the best ways I’ve found to get a great deal on a hotel, especially relatively last-minute bookings. It lets me stay at a fancier one than I can normally afford. Make sure to set your browser to incognito mode before you search (control-shift-n). Hotwire means taking a bit of a gamble in terms of location, but you’re likely to end up with a good deal. (Read my Hotwire tips here.)

Hotel booking engines: If you’re risk-averse and want to know exactly where you’ll be staying, use a booking engine like Expedia or Hotels.com. A tip: read the reviews! And pay attention to information about whether the booking is cancellable.

While booking through these sites is easy, it sometimes pays to book directly with the hotel on their own website. Because they pay the booking engine a commission, they prefer you to book direct and will often offer incentives for direct booking, such as room upgrades or free breakfast. It’s worth checking.

In poorer countries, book locally-owned hotels as much as possible, rather than international hotel chains. The money you pay is more likely to stay in-country and circulate in the local economy, rather than getting transferred to a corporate office somewhere else.

3. Consider your form of transportation when you choose a destination.

Flying

If you are thinking of international travel or traveling within a large country like the US, you’ll probably need to fly. Choose some possible dates and look up how much it would cost to fly there. This might help you decide between possible destinations by choosing the cheaper one. Skyscanner has a nice gimmick: type in your home airport and then click “Explore everywhere.” Add your dates of travel and you’ll get a list of places to fly from your airport. The cheap flights will be listed first. In Google Flights you can do the same thing: type in your departure airport and click on “Explore.” 

Don’t fall for flying to places that are relatively nearby, though. You can just as well take a much less polluting train or car.

Keep in mind a few things before you decide to fly for your next trip:

• It will essentially take two days off your vacation time – the first and the last day of your trip. If you don’t have much vacation time, it might be better not to travel so far afield.
• You’ll need a passport, which might take some time to get, and possibly also a visa. Depending on your nationality, visas can be the sort you get automatically on arrival or they can take months to obtain. They can also be expensive. Do your research before you book your flights!
• Notice flight times. The really cheap flights tend to have extremely early departure times. If you’re considering this, make sure you can get to the airport that early without having to spend on an extra night’s hotel stay. Is the destination and the lower priced tickets worth the effort of getting there that early?

When you look up flights, make sure to use incognito mode (control-shift-n on Chrome). Otherwise, you might see higher prices than when you first checked. Cookies allow the sites to see that you’re particularly interested in those flights and raise the rates in response.

Figure out what flights you want to book, then go to the airline’s website to actually book them. (When you do a search in Skyscanner, the resulting list will allow you to choose jumping to the airline’s own website. Choose that.) The airlines offer more service when flights are cancelled or delayed, so it’s safer to book directly through them.

Before you book, read this article about sustainable air travel.

Driving

Do you feel comfortable driving in the destination you’re considering? In some places, you really have to drive if you want to do any sightseeing. My trip to Guadeloupe is an example. I stayed in an accommodation away from beaches, I wanted to do a lot of sightseeing, and the public bus system is very limited. So I drove.

Another example is my quick trip up into the Sierra from San Francisco. It would have been possible by bus, I think, but would have taken much longer.

I’ve had a great time on road trips together with my husband: 

• Driving in Romania allowed us to visit some very off-the-beaten-path UNESCO sites. 
• Driving in the Costa Blanca in Spain was breathtaking. 
• One of our best trips ever was a three-week road trip around Iceland.

On these road trips, driving became part of an enjoyable travel experience. In other places, driving would, to me, be very stressful: Dubai, for example, where I could take the metro or a taxi easily and fairly cheaply. Cairo, where the traffic is pretty crazy. Amsterdam, where all the bicyclists and pedestrians seem to be on suicide missions. Or any big city like Singapore or Paris or New York, where public transportation is excellent and parking is expensive.

Public transportation

In many countries, public transportation is the best and least stressful way to get around, and it doesn’t cost much money. The great advantage of traveling by train or bus is that you get to relax and just enjoy looking out the window in this new and interesting place you’re visiting. It allows glimpses of a new culture too: observe the behavior of the people around you closely and you might learn something about local customs.

Of course, it depends on the country. In places like Japan, the Netherlands and South Korea, the trains are well-maintained and run on time. Or, in some places, city public transportation can be excellent even when inter-city options are minimal, such as in many US cities like San Francisco or New York City. In some countries, buses or taxis are really your only public transportation option (e.g. Guadeloupe, Saint Lucia, and the US outside of big cities). How relaxing the ride is depends on the quality of the roads as well as the vehicle.

If you’re deciding on a destination and you can’t or don’t want to drive a rental car, you essentially have three choices: 1) choose somewhere with good public transportation, 2) plan a road trip nearby your home, using your own car; or 3) go somewhere where you stay in one place the whole time like a resort.

My recommendations

Skyscanner: I use Skyscanner in incognito mode to look up flights, then book through the airline’s website (also in incognito). Google flights has similar features.

Hopper: Enter your dates of travel into the Hopper app. It’ll not only tell you the current prices for the trip, it’ll tell you whether the prices are likely to go up or down. Then you can set it to send you a warning when the prices are unlikely to drop any further.

If you use a flight search engine like Skyscanner or Hopper or any of the other ones, do follow my advice above about booking it on the airline’s own website. If the flight gets changed or cancelled or whatever, you’ll have more recourse than if you book through a booking site. It might be somewhat more expensive, though, so that’s a judgement call you’ll need to make.

Car rentals: Check out the deals your credit card offers to get a decent price on a car rental, or the offers you get from your airline once you book your flight. Discover Cars allows you to compare rates from all the big rental car companies.

Make sure, if you’re going to rent a car, that your hotel or other accommodation also includes parking. Get collision insurance if it’s not already included on your credit card. Check the car very carefully before you leave the parking lot to make sure you don’t get blamed for any dents that are already there (This has happened to me!). Take photos of the dents before you leave and tell the attendant to mark them on their record.

Public transportation: Don’t assume that whatever tourist transport pass a city offers is necessarily the cheapest. Think about how much you’re likely to use it. Do the research to find out what the best deal for you might be. A ticket like the locals use could end up cheaper. Avoid the local rush hour by sleeping in or by choosing nearby walkable sights for your first sightseeing of the day.

Omio is a useful site for looking up train and bus schedules.

4. Or you could choose a destination by type of activities.

As I mentioned before, the activities you want to do might be the way to a destination choice.

Whatever the purpose of your trip, make sure to factor the cost of activities into your plans. Some activities are more expensive than others. Museum admissions can add up fast, as can renting equipment for scuba diving or skiing. Hiking is usually free, but many other outdoor activities like skiing, snowboarding, sailing, bungee-jumping, or whatever activity you have in mind, cost money. Even on many beaches you have to pay for a lounge chair or an umbrella. Check these things out ahead of time and budget them in. You don’t want to end up regretting that you couldn’t do a particular activity because you couldn’t afford it. Better to choose a different destination that you can better afford, or else to wait until you’ve saved up enough.

My advice

City cards: If you want to see a lot of popular sights in a single city and you have a tight budget, a city card might be a good idea. The cards are valid for a limited number of days and give you admission to all the most popular sites as well as discounts for restaurants and other businesses. Amsterdam has one, for example, called the Amsterdam City Card. For other popular cities, try GoCity , which offers passes in 30 different cities. Look up these deals ahead of time online and do the math to see if they’ll save you money.

Package deals: Similarly, scuba clubs often offer packages of a number of dives over several days that end up cheaper than renting equipment for one dive. The same goes for many other activities like skiing or visiting Disney parks: multi-day packages can save you money.

Pre-booking: Many of the most popular sights now allow or require pre-booking, which is often slightly discounted and, more importantly, allows you to skip waiting in a long line. Disney parks, for example, fall into this category. In Amsterdam, the Van Gogh Museum and the Anne Frank House come to mind. I didn’t book ahead for the Dali Theatre-Museum in Figueres, Spain, and wished I had!

Favorite activities I’d recommend

• Scuba-diving and/or snorkeling in Israel, Egypt, Jordan, Australia, Bonaire or Malaysia (especially Sipadan)
• Taking a walking tour in pretty much any city; I loved the ones I did in Athens, Barcelona and Berlin.
• Climbing a volcano in Guadeloupe
• Walking on the Great Wall of China
• Hiking in Iceland
• Exploring outside the city in Hong Kong or Singapore
• Enjoying a short cruise on the Nile
• Whale and dolphin-watching in Martinique

• Taking a longboat trip into the ancient rainforest of Brunei
• Taking a cruise up the coast of Norway
• Visiting World War II-related and Cold War historical sites in Berlin
• Touring chateaux in the Loire Valley in France
• Taking a road trip through beautiful scenery in the Costa Blanca, Spain or the Scottish Highlands or the Rocky Mountains in the US or Canada or on the ring road around Iceland.

• Going on safari in Tanzania or Malawi.
• Taking a Boat Bike Tour on canals and rivers in Europe.
•  Skiing in the Alps (in Switzerland, France or Austria) or the Rockies, but there are other popular destinations like the Pyrenees too.
• Leaf-peeping in New England in the fall.
• Visiting historical sites in Greece, Germany, Israel, Egypt or Lebanon.
• Touring temples in Bangkok, Thailand.

5. Consider food and drink.

How important is food to you? Your answer to this question will also help you choose the right destination. If it’s important, make sure your budget accommodates high-end restaurants. On the other hand, if you enjoy exploring food that the locals eat, choose a place with a rich tradition of street food, like Hong Kong, Singapore or Thailand.

If food is just a matter of sustenance for you, you can choose a destination that is not particularly highly regarded for its food. Or you could rent an apartment and cook your own quick meals to save money. Or choose a hotel with an all-inclusive or half-board deal and eat from the buffet.

In some countries – France, for instance – lunch in a restaurant is very similar to dinner, but the prices are often lower. Make lunch your main meal and pick up sandwich ingredients to make your own dinner in your hotel room.

My food and drink recommendations

Where to travel for good food: France, just because, well, it’s French. And Italy because it’s Italian. Hong Kong has amazing food from lots of Asian countries; make sure to try dim sum. Street food in Tokyo (delicious filling soups) or Singapore (Chinese, Indian and Malaysian food from “hawker centers”) or China are all wonderful. And cities like San Francisco, New York, London and Berlin have food from all over the world in astounding quality.

Speaking of street food: Don’t just assume that street food is either unsafe or of poor quality; it depends on the country. I was amazed at how delicious the street food I tried in Tokyo was. And street food markets in Singapore and China are remarkably good, cheap and safe, since all the food is either boiled or cooked over very high heat in a wok. Check the internet ahead of time for safety advice on the particular country or city you’ve decided to visit.

Haute cuisine: On the other hand, if you want to enjoy haute cuisine every night, you might want to choose a destination accordingly. France is an obvious choice, especially Lyon. So is Italy, especially Bologna. Tokyo has the most Michelin-starred restaurants in the world – remember to reserve ahead! Any diverse big city will have a wide range of different national foods; Berlin, New York, San Francisco, Vancouver, Los Angeles, London or Melbourne are all good examples.

Alcohol: Don’t go to Scandinavia if you want to drink a lot. Alcoholic drinks are particularly expensive there. Anywhere else, try the local brews instead of spending lots more on whatever is familiar to you.

Vineyards and wineries: If you’re a wine connoisseur, you’ll love the wine regions of California, France, Italy, or pretty much anywhere else where wine is produced. Vineyard landscapes are beautiful and you can take wine-tasting tours as well. For obvious reasons, I suggest taking a tour rather than driving yourself.

Markets: Wherever you go, check out both the local market and the local supermarket. Both will offer insights into the food culture in the country you’re visiting.

Cooking: If you can, take a cooking class. We did this in Yangshuo, China, and it was worth every penny. Cooking classes will often start at a market, so you learn something about local ingredients as well.

Food tours: Many cities have food tours, which you’re sure to love if you’re a foodie. I enjoyed a guided tour in Krakow and one in Bangkok, both of which allowed me to try a range of local traditional foods. Some tours are more about food production than consumption, like the full-day tour I took in Bologna to learn about how parmesan cheese, balsamic vinegar and parma ham are produced.

Here’s another way you could choose a destination: follow your DNA.

6. The timing of your trip may affect your travel choices

To some extent this is obvious: if you’re going skiing, you’ll need to travel in the winter. If you want to see the Christmas markets in Germany, you’ll need to travel in the month before Christmas. The question is: do you have some leeway as far as the time of year you travel? 

My recommendations for school vacations

If you are traveling with kids or you’re a teacher and need to stick to school vacations, you’re going to see the highest prices and most crowds at popular sites. Avoid them. Instead, the perfect destination in the peak season is somewhere less well-known, which generally just means outside the big cities. Choose a small town outside of London rather than London itself. Do a road trip in Italy, but avoid the big cities like Rome. While the beaches of Croatia or the south of France might be mobbed, you’ll find the sights inland much less so. Take a safari in Malawi rather than Tanzania or South Africa. Spend time in Hokkaido rather than Tokyo.

 It’s also extremely hot in the summer vacation months in many of the most popular destinations worldwide. Think, for example, of Disney World in Florida, but also Paris or the south of France or Spain or Italy. Instead, travel in cooler places: Norway, Sweden or Finland, for example, or Iceland or Canada. Try Switzerland rather than France or Maine rather than Mexico.

During a summer vacation, small kids are easy to please with nothing more than food, a place to sleep and perhaps a place to swim, so you might be considering camping in the US. If so, I’d avoid the National Parks, since they get very crowded in the summer. Instead, look into state parks.

My recommendations for those traveling without kids

If you can travel outside of the Christmas holidays, spring break, and July and August, you’re in luck. Look at the typical weather patterns for wherever you’re thinking of traveling. Make that your starting point and choose your destination and timing based on that. Don’t visit a monsoon-prone place during monsoon season, but whatever the “shoulder season” is in that part of the world will have decent weather and fewer crowds. Check to find out if a potential destination has a rainy season, then choose the month just before or just after. You may still get some rain but you’ll avoid the tourist hordes.

Spring and fall are the best times to travel pretty much anywhere in Europe or North America. Popular destinations will be less crowded but the weather will still be good. Flights will be cheaper too, as will hotels.

Traveling in the off-season, i.e. in the winter to a summer destination or in the summer to a ski resort, can make the place seem like an entirely new destination even if you’ve been there before. Check ahead to make sure things like restaurants and attractions will still be open though. 

Some suggestions for newbies for choosing a destination

I already discussed concerns about terrorist attacks in my earlier post, but sometimes other worries come up. If you are an inexperienced traveler, you might look at independent travel with some trepidation. If that describes how you’re feeling, I would suggest starting with an “easier” destination: one that’s closer to your comfort zone. In my mind, that means it should have:

1. a stable, well-functioning society;
2. good quality, comprehensive public transportation and/or a well-maintained, well-signposted road network;
3. an English-speaking population, whether as a first or second language;
4. safe drinking water, so that you can eat whatever you want, even if it’s uncooked vegetables.

My recommendations for people who are just dipping their toes into independent travel:

• The US
• Canada
• The Netherlands (and make sure to venture out of Amsterdam!)
• The UK, including Scotland and Northern Ireland
• Republic of Ireland
• Scandinavia: Norway, Sweden, Finland and Denmark
• Iceland
• The Baltic states: Estonia, Latvia and Lithuania
• Germany
• Greece
• Italy
• Malta
• Hong Kong
• Singapore
• Australia

Please don’t be offended if your country is not listed. I haven’t been everywhere – all of South America is still, I hope, in my future – and I don’t feel comfortable recommending a place where I haven’t been. I’ve also left out lots of places I loved (France, Spain, Malawi, Egypt, Israel, Romania, China, Japan, Lebanon, Guatemala, Guadeloupe, Thailand) but that don’t seem to me to be quite such good places for a first-time independent traveler.

If this article has been helpful to you in deciding on a destination,
please buy me a cuppa tea!

Other circumstances

Some personal circumstances add another layer to the decision about where to travel. Here are some websites that can give you better advice than I can:

Disabilities

If you are mobility-disabled in some way, read this article on Curbfree with Cory Lee: The Best Disability-friendly Places to Travel in the World.

This article on Travel Pulse lists 25 disability-friendly cities around the world.

LGBTQ+

Travels of Adam is a great resource for LGBTQ+ travelers.

This tool by Destination Pride allows you to type in a city or country and get a graphic that shows the state of marriage equality, anti-discrimination laws, civil rights, etc. in that place.

And Million Miles Secrets has a lot more links related to LGBTQ+ travel.

Traveling while black or brown

While Oneika the Traveller focuses primarily on traveling while black and female, much of her advice would apply to any brown or black person.

‘N a Perfect World has an article listing places that welcome black and brown people: 10 African American Friendly Destinations and a sequel that lists more: 10 MORE African American Friendly Destinations.

This list of the 8 worst countries for black people to visit was an eye-opener for me; having enjoyed visiting many of the places it lists, I became more acutely aware of the privilege I’ve enjoyed due to my white skin.

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Hi, I’m Rachel!

Rachel’s Ruminations is a travel blog focused on independent travel with an emphasis on cultural and historical sites/sights. I also occasionally write about life as an expatriate. I hope you enjoy what I post here; feel free to leave comments! Read more…

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