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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 will not affect your price.

pretty sky view from a plane
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?

a pretty street in the oldest part of Stockholm, Gamla Stan
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 better than London 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 most museums are free!), Amsterdam, Berlin and pretty much any major city in the world.

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; game parks in Tanzania, Kenya or Malawi.

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

A lionfish in Jordan
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?

Choosing accommodations will also depend on your travel group. If you’re going solo, a hostel or Airbnb could be an excellent choice. I don’t sleep well in hostels but have had great luck renting rooms in private homes through Airbnb.

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.

My recommendations

Airbnb: (Note: This affiliate link works somewhat differently. If you click on it, I will get a small cut of what you spend, as with any affiliate link. However, you will also get a discount if it’s your first time booking through them.) Airbnb is good for renting a whole house or flat for the family so you can cook instead of using restaurants. Also good for solo travelers because you can rent a room in someone’s house and get a glimpse into a local’s life.

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.) If you are risk-averse and want to know exactly where you’ll be staying, is a more traditional accommodation booking agent. It’s the one I use most.

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

Flying: 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.

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.

parked planes at Schiphol airport in the Netherlands
parked planes at Schiphol airport in the Netherlands

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 Airbnb accommodation away from beaches, I wanted to do a lot of sightseeing, and the public bus system is very limited. So I drove.

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.

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 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.

a beautiful Costa Blanca view
amazing views at every turn

My recommendations

Skyscanner: I use Skyscanner in incognito mode.

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.

Car rentals: Hotwire can also get you cheap car rentals. 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!).

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

view of Japan Rail train tracks: what's your destination?
travel by train

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

  • 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;
  • exploring outside the city in Hong Kong or Singapore;
  • enjoying a short cruise on the Nile;
  • whale and dolphin-watching in Martinique;
the whale's tail above the water's surface on the Martinique boat trip
a shot of the whale’s tail off the coast of Martinique
Chateau Chaumont
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. Street food in Tokyo (delicious filling soups) or Singapore (Chinese, Indian and Malaysian food) or China. And cities like San Francisco, New York, London and Berlin have food from all over the world in astounding quality.

storefront, open to the street in Hong Kong, with large steam baskets holding a variety of dim sum.
I got breakfast every day from this very cheap and very good dim sum place.

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 sophisticated 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.

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.

I live in a really pretty great city.
I live in a really pretty great city.

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 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.

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 can 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:

  • The US
  • Canada
  • The Netherlands (and make sure to venture out of Amsterdam as well!)
  • The UK, including Scotland and Northern Ireland
  • Ireland
  • Sweden (and Norway sounds equally wonderful, though I haven’t been there yet)
  • Estonia, Latvia and Lithuania
  • Germany
  • Greece
  • Italy
  • Hong Kong
  • Singapore
  • Australia

Please don’t get 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, China, Japan, Guatemala, Guadeloupe) but that don’t seem to me to be quite as good places for a first-time independent traveler.

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!

Here are some other articles to help you plan your trip:

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  • Jane Dempster-Smith

    January 4, 2017 at 10:28 pm

    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.

  • Joanne Kaminski

    January 5, 2017 at 2:51 am

    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.

  • Suzanne Fluhr

    January 5, 2017 at 11:11 am

    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.

    • Rachel

      January 7, 2017 at 11:24 am

      Wow, that’s a big question, because it’s a big country! My favorite city in Italy is Venice. Just walk in any direction away from St Mark’s square and you’ll escape the tourist hordes. And check out the islands of Murano and Burano (not sure of the spelling…). I’m not a huge city fan, but Rome and Florence are pretty fascinating. I loved the countryside outside of Florence. Lots of people recommend the cinqterres (again, not sure of the spelling) area, but I’ve never been there. I wasn’t so thrilled with the lakes area in the north; it was very pretty, but in the summer absolutely overrun with tourists. But the Italian alps are gorgeous…

  • Ruth

    January 6, 2017 at 5:23 pm

    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

    • Rachel

      January 7, 2017 at 11:17 am

      All good advice. The best prices for flights are usually about 2 months ahead. I’m lucky as well in that I sometimes get to lead these workshops, which means I don’t necessarily travel somewhere I choose, but it does leave room for serendipity. The two I have coming up, Prague and Dubai, are both places I’ve been before, but it’s fun to go back and see whatever I missed the last time. And my trip to Lagos, Nigeria last year: that was a place I never would have visited otherwise!

  • Nancie

    January 8, 2017 at 4:36 am

    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

  • Michele {Malaysian Meanders}

    January 8, 2017 at 7:54 pm

    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.

    • Rachel

      January 8, 2017 at 8:59 pm

      We took a bit of a middle ground when we traveled in China. We were lucky in that our foster daughter could speak Mandarin. So what we did was booked all of the transportation and transfers and hotels, but did the rest ourselves. If we hadn’t had our foster daughter, we would have hired a guide for at least some of the places we went and used a guidebook for the rest. Getting dinner was easy; we just wandered into random restaurants and pointed out four random items on the menu. It was always good, if sometimes a bit mysterious!

      Anyway, satisfying teenagers is always difficult. I wrote about this on tentotwenty’s website:

  • Jenny Freedman

    January 9, 2017 at 2:32 pm

    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!

    • Rachel

      January 9, 2017 at 3:09 pm

      Me too! I especially loved the variety of food in China, Hong Kong and Japan. The only meal we didn’t like in China in a whole month was at a restaurant that catered specifically to western tourists. Every single other meal, either at randomly-chosen hole-in-the-wall places or at street markets, was wonderful and varied.

  • Victoria @The British Berliner

    January 9, 2017 at 4:18 pm

    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!

    • Rachel

      January 9, 2017 at 5:47 pm

      I would have included France except that so many people there don’t seem to speak English, and for a non-French-speaking first-time traveler, that’s intimidating. Otherwise it’s a wonderful place to travel! I’ve never been to Thailand so I couldn’t include that.

  • Debbra Dunning Brouillette

    January 10, 2017 at 6:54 am

    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!

    • Rachel

      January 10, 2017 at 1:47 pm

      Thanks, Debbra! Bonaire is wonderful for snorkeling and diving because all of the water around it is protected. You can just rent the equipment and go wade in wherever you like around the island. It was the first place we felt confident enough to dive without a guide.

  • Nathalie

    January 10, 2017 at 3:53 pm

    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.

  • Carole Terwilliger Meyers

    January 11, 2017 at 2:11 am

    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.

    • Rachel

      January 11, 2017 at 7:16 am

      It definitely does! I realized that a year or two ago when I kept checking a particular price, waiting and hoping it would go down, but it kept going up. Somewhere on line someone suggested incognito mode and, voila, the price went down lower than when I started to watch it!

  • Sue Reddel

    January 13, 2017 at 10:05 pm

    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.


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