How To Smartly Choose Your Next 3-Week Holiday Trip

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As a person who holds a full-time traveller, depending on where you are living or working, surely, you have limited time off from work. In my experience, many season travellers only have 2-4 weeks off a year from work and often use this time to travel to new destinations.

Having this very limited time, you want to make sure to spend it properly and smartly. I’ve met a guy from the UK who’s been doing it for almost five years, making sure his annual leave is out of the country and well-spent.

RELATED POST: How to write an itinerary for a 3-week trip

I, even though I work online and don’t have any bosses to answer to, I still find myself in situations like this. First, because I’m more productive if I don’t work while travelling and actually able to enjoy my trip without my laptop.

I often browse booking sites to find a good deal for a flight to a new destination and read about what to do and the costs of travelling there. I consider plenty of things before fixing or deciding on a specific destination.

This post will list the best places to spend your next 3-week holiday trip or how to choose one smartly. If it’s your first time travelling alone, we have an article that includes tips to stay safe while o holiday.


Below, you will find my favourite travel sites that I use when arranging my trips. I like to book some things in advance, such as hotels and flights. I want to make sure I get to book the accommodation I want at a fair price, while flight tickets are often much cheaper if booked as soon as possible.

However, when it comes to airport pick-up or even tours, I usually book those about three weeks in advance. The same goes for train tickets since those don’t book up unless it’s peak season or a national holiday in the destination I’m going to.



First, let’s get through the basics; what to consider before deciding on your next destination?

How much time do you have

The most important thing to ask yourself is how much time you have for this trip. Because, if you only have a week, flying to another continent is not worth it. You’ll end up feeling rushed and most likely will forget to enjoy. There’s a big chance you will spend 2 days in the airports, buses, trains, and planes (back and forth) instead.

Now, a week can go a long way if you live in Europe since flights are often short while trains and buses can be done overnight. A 2-week trip can bring you a lovely holiday and a 3-week trip is worth a flight across continents.

You need to remember to calculate how much it will take you to get to point B from point A. If it will eat up more than 30% of your holiday time, look for a closer destination to you where travel time (2-way will only take a few hours or a day).

If you have three weeks, you probably think, “Hey, I’m already flying half the world. I have to make the most out of it”. Now, “making the most out of it” doesn’t always mean seeing as many places as possible. The best way to interpret this is to enjoy as much as possible.

For example, if you want to explore the Philippines for 3 weeks from north to south under three weeks will be a nightmare. Instead of enjoying a lazy day on the beach or an extra day hiking, you will spend it on a ferry or cramped in a plane and you will forget to stop, look around you, appreciate where you are, and process every experience you will go through this trip.

How much is your budget

One of the most critical factors in choosing the destination for your next holiday is your budget. We all have been there, weighing two places, something we want to go and explore and another that fits best to our budget.


The advice when you’re tight on the budget but still want to go on a trip is:

  1. Go to the place you want to go only if it’s only a little more expensive than the other; flight tickets, hotels per night, and food costs are almost the same. Then only visit 2-3 places. Hotels and BnBs are often cheaper if you stay more than 2 nights. Moving less means spending less.
  2. Choose a cheaper destination and let yourself enjoy some luxury. For example, in Vietnam, 5-star hotels cost between $50 to $100/per night. By doing this, you can pamper yourself without worrying too much about breaking the bank plus, you can even see more places, join more tours, and enjoy more yummy food.

Imagine this scenario: You have $3000 to spend for the entire 3-week trip, including the flights, and you’re coming from the US or Canada. The flights to Southeast Asia vs Europe are almost the same nowadays so the deal-breaker would be accommodation costs, food and drinks, and expenses on tours. Your $3000 can go a looooong way in Thailand compared to Iceland. >> Europe on a budget itinerary.

What are the activities you want to do

This is very vital in your decision-making. If you want to go hiking or do some fun water activities, you want to ensure that a destination is a good place for that or that the season is appropriate.

A holiday where you imagine yourself to be in a wonderful resort, with a fancy swimming pool and white beaches can’t be done in Colombia unless you want to stay in just one area (Barranquilla or Cartagena). While a trip that is solely about hiking isn’t fit for a holiday in Denmark (it’s a very flat region).

The best thing to do is to list the activities you want to focus on making this upcoming trip and find which destination is best for it.

For example, a motorbiking trip is fun to do in Vietnam, Laos, Cambodia, or East Europe (during summer). A challenging trip can be done in Nepal, Tanzania, Vietnam, the United States, and Canada. For a beach and surfing destination, you have the Philippines, Indonesia, Sri Lanka, the Caribbean, East Africa, and even the Southern part of Italy, Spain, Greece, and Portugal.

Repeat or a new destination

When I started backpacking or travelling full-time, I wanted to see the world, and with that, I meant every country. But eventually, my preference changed and found myself visiting the same places twice if not three times.

I understand that some travellers like to check off places on their list, and that’s not a problem. Ask yourself, do you want, to explore a new place or revisit the same place and explore the area you missed on your last visit?

Visa and travel documents

One more thing to consider is the visa and legal documents you might need. If you hold passports from the US, UK, Canada, or you are an EU citizen, there’s a big chance you shouldn’t worry about this more than half of the time.

However, in the past years, many governments where the economy heavily depends on tourism decided to implement evisa (electronic visas) instead of offering visa-free to maximise their profit.

Europe travel visa
Schengen/Europe visa sticker

Often, eVisas are easy and very quick to obtain, sometimes, they can be pricey but too much. In contrast, there are countries like China, Russia, and even India which will require you to apply for a visa way in advance since the process can take weeks and require a lot of travel documents.

If you only have a month to spare to gather your documents or apply for a visa, I recommend you choose a destination that doesn’t require a visa for your passport or where an evisa is easy to get online or else, a tedious, stressful holiday might turn into a nightmare.


The season is a very important factor when deciding on where your next 3-week holiday should be. For example, many travellers who take annual leave during winter prefer to go to a warmer destination.

On the other hand, travelling during some specific seasons can mean that it can be pricier. If you want to explore Europe from June to September, expect the hotels, flights, and tours to be more expensive compared to during the winter season or the low season. Check out our packing list for a 3-week holiday.


When discussing accessibility, I’d look into the language barrier and easiness to travel for PWD.

Personally, I never take into account the language barrier since there are many translation apps out there and in my own experience, dealing with locals who work in the tourism industry is pretty easy since most of them do speak English. The challenge will be found when communicating with the locals, taxi drivers, or even public bus or train stations.

But I do understand if some people would feel unease to head to a place where language can be a big challenge to enjoy their trip. For example, many Chinese, Korean, Russian, and Japanese tourists go on a group trip since it’s everything is arranged on their behalf plus, they travel with tour guides who serve as their translators 24/7.

On the other hand, for PWD, accessibility in terms of the possibility to move around with wheelchairs, canes, animal support, etc, can be a deal-breaker.

For example, in the Philippines, even in its capital city Manila, a person in a wheelchair will have difficulty getting around. The streets, stoplights, public transportation, some hotels, and even tours or activities are not wheelchair friendly.

While if you head to Scandinavia or North America, many stoplights make a sound when the light is green or buses can deploy a ramp so a wheelchair can board.


Here is my personal recommendation for the best destinations if you have a 3-week holiday trip. These destinations are the places I’ve travelled to in under three weeks or places I’ve travelled longer than that or shorter, but I know a 3-week trip would be suitable. We also have a round-up post of the best destinations to spend your 3-week vacation.


I’ve travelled and lived in Vietnam extensively. I think it’s one of the best places to spend a 3-week trip. The country’s land geography is straightforward. There’s only one way to travel the country, either going north or going south, it’s very easy when it comes to decision-making.


It’s also bordered by Cambodia and Laos, which means you can spend 2 weeks in Vietnam and 1 week in Cambodia or something along the line. There are short flights between these countries or you can take a 6-hour bus from Vietnam to Cambodia and a bit longer from central Vietnam to Laos.

Vietnam is a great destination for many reasons. It’s popular to do an epic motorbike trip, hike on the rice paddies or the highest point in Indochina (Fansipan), amazing beach holiday since it’s a coastal country, a foodie haven, perfect for those who love to learn history and culture, and the best part is, it’s the cheapest place you can spend a holiday. >> Check our itinerary for Vietnam for a 3-weeks vacation.

  • Pros: Hotel and BnB accommodations run between $10-$20/night for two people, dorm beds are at $3-$7/night, and 5-star hotel rooms are at $50-$100/night for two people. Organised day tours are from $6-$25 including transportation, food, and an English-speaking tour guide. The world-class Vietnamese can be enjoyed at $.50-$4.
  • Cons: Communicating in English with older locals can be a challenge but most young people and locals who work in the tourism industry speak very well.

South Africa

I spent 18 days in South Africa, I honestly could spend more days here but when I had to catch my flight home, I felt very satisfied with my trip, the places I saw, and the things I did.


During my 3-week trip in South Africa, I explored Kruger National Park for 5 days and 4 nights and did a self-drive Safari trip which was the highlight for me. I also managed to spend 3 days in Jeffrey’s Bay (JBay) which is a good surfing spot, 2 days in Port Elizabeth, 4 days in Johannesburg, and 4 days in Cape Town, where I visited Table Mountain, saw the African penguins and enjoyed too many local wines.

In general, I found South Africa mid-range when it comes to travel expenses. It’s not as expensive as Denmark but not as affordable as Southeast Asia. The most expensive part would be the flight there (I flew from Asia), next to it, it’s probably the Safari tour (the entrance fee and accommodation inside the park is not cheap), while domestic flights, food, and tours are reasonable prices. The wine is the cheapest cost but is very high quality.

  • Pros: I think travelling to South Africa will give you an outstanding balance of things you can do. I did a Safari, a beach holiday, road tripping, and learning the culture and history of South Africa, and I enjoyed the cuisine a lot. It’s straightforward to get around since everyone speaks English.
  • Cons: It’s pretty far if you are coming from East Asia, Oceania, North Europe, and anywhere from the Americas.

Georgia – the country

I’ve travelled around Georgia for a little over two weeks and I wish I had more time. Unfortunately, my time was up, and so was my budget. To be transparent with you, Georgia is a very affordable destination, it was just at the end of my trip and Georgia was a last-minute decision, so it wasn’t estimated on my budget.


Anyway, a very lovely, quiet, and curious country Georgia is. It’s a perfect place to explore vineyards, go hiking, do paragliding, and enjoy challenging yourself out of your comfort zone. The flights might not be cheap if you are coming from North America or South America. But from Europe, the flights are very good, while from Asia, the ticket costs are decent.

There are plenty of things to do and places to see, I only managed to see Tbilisi (the capital), Batumi, Kutaisi, and Gudauri. I wish I had more time to explore more areas and spend more time.

  • Pros: visa-free to most nationalities while evisa can be done online, the food and drinks, accommodations are very cheap, the people are super welcoming, and the crowd is not very big even during the peak season.
  • Cons: English-speaking locals can be hard to find but those who work in the tourist industry and business in touristy places can communicate well. The weather is not the best as it’s often cold here, even during summer, however, the winter is not as hard as in Northern Europe.


Poland is a pretty big country for Europe, while its land geography is round and its transport system is pretty epic. This means that travelling around the country can be done in a dozen ways.


Rich in history, amazing Polish dishes, and very friendly locals, Poland is a great destination for three weeks. While many flights from different continents fly directly to Poland making, the travel time should be no problem and tickets affordable.

I only spent less than a week in Poland where I focused on Krakow, a lively, interesting, and historical destination. If you want to spend 3 weeks here, you won’t get bored. For a nice beach trip, you can visit Krakow and Warsaw if you love history and Gdansk. If you think 3 weeks in Poland is too long, you can also do a 3-weeks in Central Europe and add Germany or Czechia to your itinerary.

  • Pros: Affordable destination compared to other popular European destinations, tasty beers, warm locals, and very easy to get around; either by train, plane, and bus. Plus you can easily take a bus or train to a neighbouring country in just a few hours.
  • Cons: A visit during winter can be brutal however, Christmas markets in Poland are pretty brilliant. Not the cheapest destination in Europe, but a lot cheaper than the Netherlands, Scandinavia, and countries in the central and south of Europe.


The last destination on this list of places to go on a 3-week trip holiday in Peru. I spent an entire month in Peru but 90% of it was just in Cusco, the town close to Machu Picchu. I feel a bit regretful now that when I went to Peru, I knew I wanted to see Machu Picchu and I don’t mind not seeing any other parts of the country.


I wish I had explored more since I had the time because I missed a lot. Although I visited many fantastic places around Cusco, just imagine the other regions that surely would be remarkable as well.

Peru is the home of one of the world’s oldest cities that’s still standing today – Machu Picchu. Even the UNESCO and the Peruvian government are doing their best to protect this Citadel. Many experts think that in the future, Machu Picchu might have to be closed to the public. Before that happens – don’t miss your chance to visit.

Peru is a great destination for many activities; it’s a great place for easy to expert hiking, sandboarding, food tripping, and even for travellers who love to visit lakes. We have a 3-week Peru travel itinerary.

  • Pros: Peru has diverse activities to enjoy, interesting cuisine, and the oldest traditions today not to mention the indigenous tribes who are directly from the line of Andean and Quechua.
  • Cons: If visiting Machu Picchu is your main reason to come to Peru, make sure you book your train tickets and tour tickets in advance because there visitors per day that are allowed to enter are limited, and the tickets are often sold out months in advance.


I think deciding the place to spend your precious 3-week annual holiday and not to mention your hard-earned money is not always an easy choice. Wherever you decide to go, I hope you’ll have a fantastic time and a relaxing holiday.

I hope this post has been useful for you and that we helped you make a smart decision for your 3-week holiday trip. If you have more tips or questions, or suggestions, let us know in the comment section below.


Choosing where to spend a 20-day trip involves considering personal interests, budget, and time of year. Research potential destinations, looking for a mix of cultural, natural, and recreational opportunities. Consider the climate, accessibility, and local events. It's also helpful to seek recommendations from friends, family, and travel forums. With careful planning, you can choose the perfect destination for an unforgettable trip. via @threeweektraveller

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