Planning to: Extended Travelling

Updated: Mar 7

With so much time on your hands, your retirement is the best time (and maybe even your last chance) to finally visit those places on your bucket list. Now that you don’t have to worry about the number of days of leave you can take, you’re free to travel for as long as you like, wherever you like.

But for those who are only familiar with taking short weeklong vacations, travelling for an extended time - while it can sound exciting - can seem like a daunting feat and also a planning nightmare!

According to The Travel Camel, extended travel is defined as travel over eight weeks. However, as long as you’re planning a holiday that’s over two weeks, we think that some of these tips will be useful to you too.

We may not be a travel website, but the team at Ready or Not? has taken the time to scour through some of the travel guides out there and have compiled a list of travel tips, ideas and resources below for your own reference and planning. (Note: each of us has experienced living overseas for a few months, so you can count on us that we only share what we believe!)

There are many, MANY different types of long-term travelling - backpacking, going for an overseas programme, volunteering or working overseas, etc. This goes without saying, but how you structure your trip will affect many things, from packing to budgeting to travel logistics, so it is important to have a rough idea of what your trip will look like.

Please remember to check on your visa requirements, especially for extended travel, and ensure you include ample buffer time for the whole process. Visas can take weeks or even months to be ready; you don’t want to run in the situation where the visa is not ready on your departure date!

Also, beware of scams - it is well worth conducting extra checks before you purchase a visa, as many scam websites look legitimate and may even be the top search on Google.

Travel insurance is not just an extra add-on you can afford to miss. I repeat: it is not just an extra add-on you can afford to miss. If you’re going to be travelling for a few months, you’re bound to face some kind of crisis and it will be very unwise to take that gamble with the universe!

Travel fatigue is a real problem, y’all.

If you’re travelling for an extended period of time but at the same pace as on a shorter holiday, you’ll find that you’ll quickly become exhausted. The excitement of visiting some place new also quickly wears off, which is not what you want - after all, travelling should be about enjoying your experience, not just about crossing the place off your bucket list!

Take a vacation off your vacation - as ironic as it sounds, that’s exactly what it is. You can’t be going out to sightsee every day for a month! Set aside time to decompress and relax during your travels. Don’t feel guilty for allowing yourself some downtime to recharge - it’s important so that you have the energy to enjoy the rest of your travels.

Since you’re already setting aside more time for your travels, you should also consider slow travelling. Instead of trying to visit a city every few days, why not consider staying in one place for a week or even longer? Not only is it cheaper, but it also allows you to gain a deeper understanding, connection and appreciation of the place.

If your trip is more than a month-long, we would encourage you not to have too detailed an itinerary - imagine how much time it would take to plan everything out in full! The best way to plan for your long term travel would be to first decide which regions you would be visiting, and roughly how long you would stay in each region. Then, plan out your itinerary for the first region, and only start planning in detail for the second region once you have reached the first region. Of course, everyone’s planning and travel styles are different, but the point is to not put too much pressure on yourself when planning for long haul trips, and to take it one place at a time!

Don’t be afraid of the hole that long-term travelling might leave on your wallet. As long as you do your due diligence of proper budgeting, you can travel for an extended period of time cheaply, or even spend around the same amount of money as you would for a shorter holiday.

Of course, travelling in countries like Switzerland, Iceland, or Nordic countries like Norway can be really expensive, while travelling in Southeast Asian countries would be a lot more affordable, so do take this into account!

While it would be difficult to estimate the exact numbers, you can check out Indie Traveller’s rough breakdown of how much it would cost to travel for one year, including monthly figures, based on the different travelling styles (travelling frugally vs travelling lavishly) and the different types of countries (cheap or expensive).

Here are some tips you can consider to minimise your expenses:

1. Eat out less Once you start cooking your meals, you’ll find that it really makes a big difference financially! This is especially so for European countries where groceries are cheap, while eating out can cost around 10-15 euros per person per meal (S$16-24). Opt for Airbnbs or apartments that provide kitchens for you to cook.

2. Opt to walk instead of taking public transport This tip is especially helpful if you’re visiting countries with very walkable city centres, which Europe is a great host for. Of course, it is not always possible to get around on foot, but when you can, you’ll find that you can explore so much more of the city as compared to when you’re travelling around on a car, bus or train. Free walking tours are also a fantastic option where you can learn about the country’s history and culture that you wouldn’t otherwise learn by yourself. (And of course, it’s free! Although, you should always tip your tour guide).

3. Stay in hostels Hostels may sound dangerous, or something that only young people would opt for. However, they actually have numerous benefits that many tend to overlook. Besides the affordable price tag that is a big plus, the experience of meeting other like-minded travellers and the knowledge you’ll gain from them would be the main draw that you won’t get from staying on your own. No doubt, you’re also sure to feel young again!

If you're uncomfortable with the idea of sleeping in the same room with strangers, you can also opt for private rooms that many hostels offer. Although hostels are relatively safe, it is still very important to stay vigilant and not forgo safety precautions, like ensuring your valuables are secured properly. When choosing a hostel to stay at, ensure that you are staying at a safe location that is close to the centre of where you want to be. Do also remember to read the reviews and do your proper research before booking - opt for trustworthy websites like Hostelworld or

As much as you can try to plan for your trip, the important thing to bear in mind is that with all things in life, not everything can be planned. But that’s the beauty of long-term travel; learning as you go! As the cliche would go: it’s all about the journey. Have fun and go at your own pace - you can finally afford the time to, anyway!

Also, remember that all good things will ultimately come to an end. As much as we want it to, travelling just isn’t a sustainable retirement option. Don’t forgo planning for your life in Singapore as well - check out our other articles for more suggestions related to work, volunteering or lifelong learning that you can do in your retirement!

Do also check out our other article here where we covered some general travelling tips you can consider.

(Source: Investopedia, The Travel Camel, Practical Wanderlust, Indie Traveller)