The longest I’ve been on the road is two months. Living out of a single suitcase, you start missing the stable life. You miss your bed, your neighborhood cafe, even your loud hallmate who can’t stop shouting. Then you’re on the train again and you remember the thrill you get from thinking about the potential adventure up ahead. “I could do one more city,” you tell yourself, and so the cycle repeats. Chain-traveling, or as the industry calls it, multistop traveling, is to travel what a marathon is to the run. It doesn’t treat the weak easy but it rewards those who give it the preparation and initiative it requires. I’m not the most nomadic of the lot (I’ve met folks who’ve been on the road for more than two years) but I’ve picked up some useful thoughts and tips to those who want to plan their first chain-travel trip.

Why Chain-Travel?

There’s a number of reasons why you’d decide to do a multistop trip instead of a single destination. Most of the time it’s a combination of factors but here a list of good reasons to chain-travel instead of doing a single-destination:

1. You’re visiting a new region far away from your home base and you’re not sure when’s the next time you’ll be back. This could be due to cost, time, opportunity etc.
2. You have a long break and you can kill time. Staying in one city for two months could be useful if you’re trying to learn a language or skill but if not, you may choose to keep moving instead.
3. You’re in location A and you need to get to location B in a couple of weeks. Why not hop around in between and inch your way towards your destination?

I’ve chain-traveled for all of the reasons above and it’s been a great decision. You have great value for money and you also get to have a more fluid and holistic understanding of the region you’re in, rather than of just a single city or location. Of course, you can do chain-traveling between regions too (think China-Southeast Asia or South Europe-Middle East)  but you’ll find that the benefits still apply. There’s definitely a time and place for single location traveling, especially if you don’t have the energy or mindset for a chain-travel, so don’t discount it from your options.

How does one maximize the benefits from chain-traveling? Here are some easy tips to follow:

TIP 1: PLAN AHEAD, OR DON’T

This is a bit of a tough one but it’s probably the most important. You have to decide your style of traveling. I’ve mentioned before that I’m more of a planner, but that’s because I’m more cost and time conscious. If you’ve saved up and ultimately are just traveling around for a gap year or so till you run dry, then definitely feel free to explore a city as much as you want and then move on when you feel like it.

If you are like most other people, however, and are trying to squeeze your trip for all its value, a plan is going to help. I’m going to go ahead and share a template I use for most of my trips, especially when I’m traveling with others. This tool has helped me make sure I’m conscious of the time I have in a day to do what I want and also watch my budget as I add costs to it. I’m sharing this tool mainly because I’ve gotten so much value out of it. In fact, I’m in the process of building a better tool I can share with my friends and readers that would make chain-traveling so much easier but for now, this will have to do. Here’s the tool: CLICK HERE.

What you’ll see is that immediately you get a visual understanding of your trip both in terms of time and costs. You can also add comments or notes for yourself or your travelmates, and keep updating your plans easily.

Here are my step-by-step instructions for filling up the sheet:

1. Choose the first city you want to fly into. This is normally a function of cost and date. Choose the city with the cheapest flight to it because transportation from there onwards tends to be cheap anyway.
2. Choose the last city of your trip. This could be the city you’re ultimately ending up in, but if it’s not, this too will normally be a function of cost and date of the flight out.
3. Now’s the fun part. Look in between the two cities you’ve chosen and then choose the cities and spots you want to visit in between. A good guide is to divide up the duration of your travel into the following blocks:
   • one night in a small city or remote spot (unless you want to do natural activities or day trips in the area)
   • two nights in a medium-sized city
   • three nights in a large city or a city with a lot of day trip opportunities
4. Choose your transportation options in between those cities. Here you’re going to need to balance costs and dates, and may need to move things around or change your spots in between.
5. Make sure you have all of your transportation costs down now. Look for your accommodations and put down those costs too. The bulk of your costs should come from these.
6. Now, decide what you want to do in each city. This is where the cost calculator helps a lot. You can keep adding activities and average meal prices until you hit your budget, ensuring you don’t go overboard.

It’s a methodical process that has given me the biggest bang for my buck.  Of course, feel free to modify it according to your own style and habits – I’d love to hear any ideas to improve or change the template or method.

TIP 2: THINK THEMATICALLY

If you stay within a region, this tends to emerge naturally. History tends to be regionally focussed and so a lot of culture and stories tend to span across multiple cities. Cuisine does differ between sub-regions, which would provide some variety in your trip but it would be a good idea to look at visiting cities and regions that have some relation to one another. For example, doing an ex-USSR bloc trip adds to your overall understanding of how the ex-Soviet nations found their own identity after the collapse of the regime and how different countries have evolved differently.

This form of contrast and juxtaposition adds to the value of traveling in understanding the places you visit. Each location has value in its own right, because of the people in it and the cultures maintained but there is another layer of appreciation when you can see countries and cities in relation to others, especially those that are just nearby. You realize the value of good governance, community culture, education and environmental upkeeping in promoting a good quality of life.

Of course, you could also plan a trip based on many other arbitrary themes. A seafood-tasting trip along the Mediterranean is well within your rights or an adventure trip through the United Kingdom could make sense too. Whatever the case, do yourself a favor and make some sense of what you’re trying to achieve with your trip. The discovery process doesn’t mean you have to go in blind, there’s still a lot to learn when you have a vague understanding of your overall theme.

TIP 3: KEEP A REGULAR TEMPO

This is the advice I wish someone told me when I was starting to chain-travel. Recognize that the intensity of your day’s itinerary affects your energy and ability to enjoy your trip. A good gauge is to plan one low-intensity day for every five consecutive high-intensity days. Go to the beach, take a break at a cafe or bookstore, or just sleep in your accommodation. You’re allowed to take care of yourself, even when you’re traveling. Of course, it’d be at an advanced level to plan your rest day somewhere cheap because that requires another step of strategic thinking, but you’ll get the hang of it as you chain-travel more.

Diversify your trip as well. Spend some time in big cities and fill up the days in between with smaller cities or nature spots. Treat yourself to some fine dining once in a while but then eat street food as much as you can. Party on your Friday and then go to a cultural music show on a weekday night. Don’t let yourself get bored by your travels – it probably means you’re not thinking about your travels right. The world is a multi-colored multi-textured tapestry and you’ll never run out of stuff to be amazed by.

___

Do you have any additional tips for chain-travels? Maybe you have questions you’d like me to answer in relation to my experiences? Let me know in the comments and I’ll answer them. Chain-traveling looks like a hard challenge for a lot of new travelers, and sometimes it even gets intimidating for a more seasoned traveler like me too, but with the right attitude and some looking ahead, you’ll be on the path towards an amazing experience. That’s the reward to keep in mind.