Where should I travel? How to choose a destination

Sometimes it’s hard to choose a 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. You think “Where should I travel?” and the answer is just too big.

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.

looking out a plane window, a bit of the wing is visible at the bottom of the picture. The lower part of the sky is hazy white, but the upper part is brilliant blue. Far in the distance in the middle of the photo, a plane is visible, with its trail of smoke behind it.
Leaving on a jet plane …

I wrote recently 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. 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? Perhaps  you prefer exploring a country’s historical sites, cities, museums and cuisine? There’s even the option to stay longer and immerse yourself in a country by visiting one of the best countries to teach English.

a narrow street in the oldest part of Stockholm, Gamla Stan. Older apartment buildings on both sides, and a clock tower of a church visible down the street.
a pretty street in the oldest part of Stockholm, Gamla Stan

Once you’ve decided what style of vacation 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 and scuba diving the next. A place like Malta or perhaps Egypt would suit you well.

My recommendations

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 (where many museums are free!), Amsterdam, Berlin and pretty much any major city in the world.

The Night Watch is a large painting of a group of men in the 16th century. In front of the painting, a group of people, backs to the camera, obscure the bottom half of the painting. They are all coincidentally wearing blue jackets, and the wall around the painting is also blue.
The Night Watch, by Rembrandt

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

Natural beauty: the US, especially the Southwest, the Rockies and the coast of 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.

A lionfish in Jordan, seen against bright blue water with a few blurry vertical poles behind. The lionfish is striped brown and white, with elegant tails of fins along its back and on its side. The lionfish is facing to the right, where some bright red coral extends from the right side of the picture.
A lionfish in Jordan

2. Where should I travel? Consider your accommodations…

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 can you cut costs by staying in a simpler hotel a few blocks from the shore? 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 could also save a bit of money by choosing accommodations outside the city you’re visiting.

Choosing accommodations will also depend on your travel group. If you’re going solo, a hostel could be an excellent choice.

If you’re traveling with children, you might need a bigger room, or adjoining rooms, or a crib. Some beach resorts offer kids’ clubs, so you might want to choose based on that.

Pinnable image
Text: How to choose a destination
Images: above is a picture over an airplane wing onto fluffy clouds with blue sky above that. Below, on the left, Chateau Chaumont, all round towers and turrets, and on the right: a whale's tail sticking up out of the sea.

My recommendations

Hotwire: Use Hotwire to find hotels. 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’ll end up with a good deal. (Read my Hotwire tips here.)

Booking.com: If you are risk-averse and want to know exactly where you’ll be staying, booking.com is a more traditional accommodation booking agent. It’s the one I use most. Use the map below to search booking.com and Airbnb by location:

TripAdvisor: Another reputable site, and it offers lots of information about destinations too.

3. And consider your form of transportation when you choose a destination…


If you are traveling somewhere that would require flying, 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 “everywhere.” Add your dates of travel and you’ll get a list of the cheapest places to fly from your airport.

A row of KLM planes parked on the runway: Just their tails, in a neat row, are visible here, with one service truck parked under the nearest one.
parked planes at Schiphol airport in the Netherlands

When you do book, make sure to use incognito mode (control-shift-n on Chrome) or 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. The airlines offer more guarantees 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 first.


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.

a view over a highway with a few cars passing by
a highway near my home in the Netherlands

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

a beautiful Costa Blanca view over a valley. There are no buildings in sight. The valley is covered in low, scrubbly plants. On the other side is a ridge of exposed stone.
amazing views at every turn in the Costa Blanca

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 Paris or London or New York, where public transportation is excellent and parking is expensive.

Public transportation

In many countries, public transportation is the best, cheapest, and least stressful way to get around. 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.

A view in a Japanese railway station looking down the tracks, no trains in sight.
travel by train

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. In some countries, buses or taxis are really your only public transportation option (e.g. Guadeloupe and Nigeria), and how relaxing the ride is depends on the quality of the roads as well as the vehicle.

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, it’s usually worth figuring out what flight you want to book, but then 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 search engine. It might be somewhat more expensive, though, so that’s a judgement call you’ll need to make.

A view over an airplane wing onto fluffy white clouds. Above them, brilliant blue sky.

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. Make sure, if you are 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 and 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 choosing nearby walkable sights for your first sightseeing of the day.

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

A very full roadway, with, nearby, a group of motorcycles, some carryign two people. Only some of them wear helmets. The rest of the traffic appears to be cars and taxis, and they're not moving, judging by the fact that the motorcyclists in the foreground have their feet steadying their motorcycles.
traffic in Mumbai

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

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.

My advice

City cards: Many cities offer tourism city cards for a price that makes them worthwhile if you are planning to visit many sites in one city. Amsterdam has one, for example, called the Amsterdam City Card. You can look up these deals ahead of time on-line to see if they’re worth it.

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 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

A whale's tale sticks up out of the water in the center of the picture, with empty sea all around.
a shot of the whale’s tail off the coast of Martinique
The castle has a rounded tower on each side of the entrance, and each tower is topped with a pointed grey turret.
Chateau Chaumont

5. Consider food and drink…

How important is food to you? Your answer to this question will also affect how you choose a 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.

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.

storefront, open to the street in Hong Kong, with large steam baskets holding a variety of dim sum. The owner stands next to where the steam baskets are displayed and smiles for the camera.
I got breakfast every day from this very cheap and very good dim sum place.

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. 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.

A market stall with fruit on display. Several people face the fruit seller inside the stall. One of them holds a bicycle. An elderly couple walks down the row away from the camera. In the blurry distance, more of the market is visible, with a blurry view of a church tower beyond that.
I live in a really pretty great city in the Netherlands. This is our city’s market.

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.

Four dishes, seen from above, on a blue and white batik tablecloth. Top left, chicken with cashew nuts. Top right: some sort of greens. Bottom left, beef, I think, with red peppers and tomatoes. Bottom right: three small dumplings, all different, and a fourth one that is a stuffed flower.
What we cooked in Yangshuo

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 or this one via an app in Singapore, 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.

Parma hams in net bags hanging to dry on a rack.
Parma ham in the factory

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

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 are feeling, I would suggest starting with an “easier” destination. 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:

Please don’t be offended if your country is not listed; I haven’t been everywhere 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, Guatemala, Guadeloupe) but that don’t seem to me to be quite such good places for a first-time independent traveler.

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:


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.


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.

Do you have any advice to add about how to choose a destination? How do you choose? And do you have any places to add to my list of “easy” countries to visit? Please add a comment below!

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Text: Where to go? Tips on how to choose a destination
Image: a dim sum seller in Hong Kong poses with his steam baskets on display


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about Rachel

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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Great article Rachel, you covered all options for travellers planning their next trip. So much to consider and choose from when planning your holiday for the year. Some great tips as well in regards to airfares and accommodation.

Super post Rachel, as retired 25-year travel agent veteran – I give this article a wholehearted thumbs up!

I love airbnb. I just took my family to Six Flags in Maryland on our way home from my mom’s in Massachusetts. I looked at hotels and they were going to charge a $150 cleanup fee because we had a dog. We stayed at an airbnb on the bottom of a yacht instead. No cleanup fee, dog welcomed, and everyone had a good nights sleep before we finished our ride home.

You have a ton of great tips here on how to choose a great place to travel. Sounds like you have been everywhere.

I liked the approach you took with this post, particularly the list of your favourite activities as I am always looking for more unique things to do.

My sister and her family used AirBNB the last time she came to Philly to visit us and was very happy with the experience. One of our sons is a digital nomad and uses AirBnB almost exclusively when he travels. One other thing I’d consider when planning a trip is the current exchange rate vis-a-vis one’s own currency. For years, this made Europe quite pricey for Americans. That situation is reversed at the moment.

These are great travel suggestions. I haven’t travelled much in Europe so I’m looking forward to exploring the continent this year. Do you have any recommendations for Italy?

This post is loaded with information! I devoured every word.

In terms of choosing a destination, a lot of times I go where the deals are. I have a list of places I would like to visit and start checking what the airfare costs on different dates. Last year, we flew to Budapest because that was one of the cheapest options. Turns out a new route on a budget airline opened.

My advantage is that I want to visit a thousand places and do not have to ask for permission to take time off (if you have the hours, you are good to go). Anyway, I start to look into prices three months (or before) ahead of my desire travel date. If you are going to move in Europe by train, I recommend booking tickets in advance (you will save money).

And, for activities, I recommend getting into the free tours bandwagon. I discovered them last year and am hooked. #TPThursday

Great tips and resources, Rachel! I would add Eastern Canada to your list. I know I’m biased because it’s my home 🙂 I snorkeled off of Sipidan, and it was incredible! I do a lot of Airbnb and lately, have had great luck. When I was in Portugal, last year I rented an apartment for a month, and that was very affordable. Once my immediate commitment of getting the condo finalized, I plan to head back to Europe. I want to experience more of Portugal, and Italy is also high on my list. I go for the scenery, the museums, the food, cooking school, and just about whatever strikes my fancy. I love walking everywhere I go, rugged hiking not so much. Thanks for co-hosting this week. #TPThursday

Excellent suggestions! The ones about public transportation are especially useful. The “trouble” with my family is that the kids are now old enough to have strong opinions, and we end up with a wide variety of Wants to satisfy when trip planning. We usually do independent travel but did a guided tour in China. I know that it is possible to do China independently, but it seemed that all my friends who took that approach ended up unsatisfied with their trip whereas those who had a guide raved about China.

A great article Rachel. With so many places to visit and types of holidays to choose from it’s always hard trying to decide where to go. I must admit that food always plays a huge part in our decisions!

These are great points Rachel. I like the way that you have specified countries for first-time travellers which is very important when you’re nervous about what to expect.

Having said that, I would indeed include France as a great destination to go to, and Thailand for the exotic factor. Wonderful with children although Singapore and Hong Kong are by far superior re Western standards lol!

I tend to choose by location either because I haven’t been there before, or simply because I have!! I love going back to countries that I’ve been to, a million times before!

I see you are a scuba diver! I am, too, and because of that, choosing a travel destination where I’ll have the opportunity to dive often enters in. You mentioned Bonaire, which I visited many years ago and is a place I would love to return. I agree with all the things you mention re: choosing a destination. Lots of good information here!

Some really great information here, we often will use a Flight Centre travel agent to help us find the best prices as they don’t have the problem of prices changing when they search.
I especially like your recommendations of destinations for first time travelers.

Anyone who is having trouble deciding where to go should find some help here! The hint that I am most interested in is:
When you do book, make sure to use incognito mode or 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.
I’ve always suspected this goes on.

Very comprehensive article, well done! Especially agree with your list of choices for new travelers.

You did a terrific job highlighting how to choose destinations that would be right for the traveler. There’s always so many things to consider. We mostly look at cuisine and growing seasons for our trips.

Wow; what a fantastic and comprehensive guide to travel! I am going to keep this url handy for future reference. You certainly gave me several ideas for future travel! Thank you!

Where should I go now? And is this you?