How I Traveled to 50+ countries...and how you can too Visit50 TC Llama Machu Picchu 1600x

How I traveled to 50+ Countries…and how you can too!

When people find out I’ve already traveled to more than 50 countries, they often ask, “how do you travel so much?” And, “how do you find the time to visit so many places?” I’ll tell you the secret to travel more here! I’ll share how I traveled to 50+ countries, and how you can too!

We’ll cover how to save up for travel, how to get free flights, how to maximize vacation days, and how to save money on travel.

“How can you afford to travel so much?”

Are you rich?” Not yet.

Do you make a living off of Visit50.com?” Not yet!

Does your job / career send you on a plane to all of these places?” Nope! My first passport stamp ever was from my first job (to Australia!). I assumed that I’d be traveling for business throughout my career but my work is all local in the U.S.

What do you do for a living?” My career is in advertising, but that’s not related to my travel. Much of my travel was done before I was even successful in my career, and with very limited funds.

What’s the secret?” Fortunately it’s not a secret. In this post I’ll share how I travel so much and how I travel so often.

How to travel more often

This post will cover what I recommend in detail. In the meantime, here’s 5 strategies to help you travel more often:

  • Choose destinations that aren’t expensive, especially for your first trips. This helps you stretch your budget further.
  • Consider spending less money on lodging so you can travel more often. Take advantage of signup bonuses for free flights.
  • Research your spending habits to save money for traveling wherever you can.
  • Combine your vacation days with days you already have off, to maximize your vacay days.
  • Consider pausing your career to take a multi-month trip.

I’ll go through each in more detail below.

Visiting Iceland, my 50th country! Use these tips to travel more
Photo from Iceland, my 50th country visited!

How to find the time to travel more

I actually don’t travel that often – only about 1-2 international trips per year. I’ve twice paused my career to go travel, including a half year through Asia (yes seriously! I’ll explain below).

Want to know more on how I travel so often? Here we go!

Prioritize travel to travel more

After catching the travel bug, I decided to prioritize travel. Prioritizing it in every aspect is what will help you travel more often. That means so many different things to different people, so I’ll elaborate.

Save money everyday

Save money in your everyday life. Yes, you’ve heard this before, but find the aspect that helps you most.

When I first graduated from my university, that meant saving money wherever I could. That’s on both big and little things. There were times that I could barely afford my apartment rent (thanks to a commission-only job. Eek!). As you get raises, resist the urge to increase your spending significantly.

Live below your means, instead of “paycheck to paycheck” if at all possible. When you get a raise, resist upgrading your apartment to a higher rent immediately. And remember that little decisions add up.

Some people find it helpful to make a dedicated vacation fund that they contribute to every paycheck.

Research your spending habits.

Save whenever you can. It all adds up. Think about how much you spend on coffee, or every time you go to the bar and how often you go. Prices here in New York are crazy, and that some adjustments might help you find much more budget for travel. For example, a weekend out in New York can be a flight to my next destination.

For some that means cooking at home instead of going out, going to the bar less often, canceling cable and using Netflix/Hulu/Amazon Prime, limiting, reducing your Starbucks visits, reducing cigarette smoking (bonus, it’ll save your life too!), and more. Take a look at where your money actually goes. Everybody’s budget is different. Prioritize travel.

Planning the trip: Be flexible!

Are you ready to plan a trip? The number one recommendation is to be flexible wherever you can. That means considering flight/lodging costs before finalizing your destination. With flexibility, the laws of supply and demand can offer you savings to help you afford to travel more often.

me in Belize under a palm tree. Choosing cheaper destinations helps you travel more.
Don’t overlook Central America! This was from visiting Belize for my second time. I found a cheap flight deal and relaxed under a palm tree

Choosing your destinations

Once you have a travel budget, that’s when it gets fun. Think about where you’d like to go. Then realize that there’s so many amazing places in this world, and not all destinations are equally priced. If you’re on a tight budget, I’d encourage you to consider the less expensive places first.

Try not to commit yourself in to just one destination that you must find the best deal for. There might be a similarly appealing destination that’s dropping prices to attract visitors just like you!

Stay with friends!

My friends have moved all around the world. While that means you’ll see them less often, it also means you can visit each other! Thus, another way to save money on travel is to stay with friends. And host friends too!

I’ve also been lucky to meet some amazing people on my trips, some of which have become friends. What happens after you ask each other to keep in touch? Don’t just write catch up notes. Actually visit each other! Seeing countries from a local perspective is much different. I met Jesper and Louise while diving in Borneo, and later visited them in Copenhagen. They showed me why they loved it there, and soon I did too!

After my friend Jared moved to Tokyo, I stayed with him in Shibuya on my brief visit. Heather and I met in Laos and have connected in multiple cities around the world since, including my first San Francisco trip. I visited my friend Gabby in Sweden, after last seeing her when we were swimming with whale sharks. Raymond and I met in the Philippines and he’s since visited me in the US.

Save with less expensive destinations

If you’re used to Europe prices, Southeast Asia is ridiculously affordable (details in a future post). Within Europe, the Baltics will cost much less than Vienna or Oslo or Paris.

Avoid Cities

Avoid cities – they tend to cost more than non-city destinations. I live in New York, so I’m typically looking to avoid cities anyway.

I spent a half year in Asia. Loved it this much! SE Asia being so cheap is how I travel more often
I spent a half year in Asia. Loved it this much! Here’s me Jumping at Bayon in Angkor Thom in the amazing Angkor Wat

Consider less popular countries

Dreaming of the Caribbean? Realize it’ll often cost much less to go to Central America for similar weather and potentially more interesting experiences. There’s so many underrated destinations.

Destinations are not priced based on how amazing they are. They’re priced based on supply vs demand, and you might not have the precise same interests as everyone else.

Be flexible on which country

If you’re going to the Caribbean, don’t lock in a specific island. See which islands have low demand. Assuming it’s not because of a hurricane or rain season, some might have the same weather and much less expensive flights or lodging.

Be open to new destinations

There’s so many interesting destinations in the world – I started this travel blog to inspire people to explore new destinations that they hadn’t considered. Choosing less expensive destinations is how you’ll travel more often.

The 2 biggest costs are flights and accommodations, and I don’t finalize my destination until researching these. Next we’ll go over how to save on flights and lodging.

Save on Accommodations

Within a trip, accommodations is easily the place where I save money compared with most people. I don’t need 5-star accommodations. The stars aren’t even all for things I care about. I don’t need luxury shopping.

You might be picturing a hostel dorm with dozens of people sleeping in the same room, and while that exists, it hasn’t typically been the direction for me. There are plenty of ways to save money on your private room.

(and yes, if you wanted to, in Southeast Asia you can find less than $5 per day for hostels)

Lodging priorities

If I’m traveling solo or with a friend, I find lodging that’s safe/secure, clean, and somewhat near where I need to be. Most other elements are negotiable. Have I missed anything major?

These days Wifi is a requirement. In warm places, air conditioning too. But it’s a fairly short list of needs.

Hotels aren’t your only option.

There’s all kinds of lodging options – hotels, Bed and Breakfast, Airbnb, and more.

Hostels are often less expensive if you’re open to it, and are often much more social. Some hostels have private rooms for more money, giving you the privacy of your own room, along with the benefits of the social aspect.

If you’re comfortable with it, check out Couchsurfing. It’s not just for literally staying on someone’s couch. You might connect with new travel friends.

As I’ve advanced in my career, my budget and minimums for lodging have risen, but it’s certainly possible to keep it basic yet comfortable.

Negotiate for lodging deals

Did you know that you can sometimes negotiate lodging? In most of Southeast Asia this is actually common. The price listed is not always the lowest price they can offer. This is especially true for smaller privately owned hotels. Prices are set by supply and demand, just as much as perceived quality.

For AirBNB, for last minute bookings, some travelers kindly ask for a slightly lower price. If it’s nearly that day and the owner might not fill it, they may be inclined to offer you a discount. If their alternative is $0 for an empty room, a discount off their typical price might be enticing.

Consider booking upon arrival

This might make you nervous. It did for me! When you’re backpacking and have time, walk in to hotels and ask.

For example, when I was in Mui Ne in Vietnam I realized this new hotel by the beach was mostly empty. I negotiated ~60% off. They also added in breakfast.

It’s a risk/reward judgement. Assuming you’re not traveling in peak season, you can always book later.

For your first time, just booking your first night or two upon. You’ll have a hotel upon arrival, and then you can choose an area you want. That’s what I did in Bali. I realized other travelers were spending much less on lodging for similar quality. I found a more affordable hotel, and then got a 30% off discount with minimal effort, just for asking for the lower price.

how I travel so much - with a llama including Peru and Machu Picchu!
making a new travel friend in Peru at Machu Picchu – incredible experience!

Save on flights to travel more often

The most expensive part of my trips is usually getting there. I use every trick and travel hack to save money on flights. I explore multiple meta searches, use flexible dates (rather than guessing where the best deals are), activate incognito mode, shop from the local airline sites, skip lag, creative itineraries, take an extended layover, take budget airlines, avoid checking bags, use email newsletters with limited flight deals, all of it. Let me know if you’d like me to share them all in detail in another post.

Miles = free flights!

Let’s start with free flights! I’ve taken so many flights for $0 (plus airport taxes)! Assuming you’re already paying your credit card bill on time, why not let your spending work for you. Pay attention to the sign-up bonus; most cards aren’t as valuable after that. You might even want to make the sign-up bonus miles your top factor for choosing a priority. I’ll dedicate a whole post to this, but many offer you thousands of free miles over a few months. I’ve taken so many trips from this.

My roundtrip flights to Asia for my half year trip was free on air miles. I used a credit card that offered 40k miles for spending $3k over 3 months. That gave me a big boost! It had a $100 annual fee, but I planned to cancel before then. They offered to remove the fee for year 2 so that I wouldn’t cancel.

There are some fantastic deals out there. Note that the one that’s best for you really does depend on your spending habits. I’ll do a full writeup eventually. In the meantime, my last few were the Chase Sapphire Reserve, Capital One Venture. Also, look consider cards that give bonus miles to a specific airline. I’ve used the United Explorer and American Airlines AAvantage.

Assuming you’re paying your bill in full, look to see which purchases can be done on your credit card instead of cash. This also assumes there’s no extra fee to use a card. That would defeat the purpose of using it.

This all assumes you’re paying your bill in full. If not, disregard the bonus and this entire strategy. This isn’t for you.

Cycling new cards does hurt your credit rating a tiny bit, but not significantly. If there’s no annual fee, keep it open indefinitely.

Meta search to find travel deals

Assuming you can’t get your flight for free, let’s look at how to save money on your flight. Consider the tools from meta search like Google Flights or Kayak. You can look at where’s cheap at any given time. You can look at when are the cheapest months or cheapest days to travel. They’ll also use historical data to tell you if the flight price is high or low, and if it’s likely to rise or fall by waiting. This is super helpful. That brings us to the value of flexibility and timing.

Book months in advance to save on flight prices

Do those searches well before you’re ready to travel. Booking in advance can really save money. Take a look at the indicators to see if it’s a good price or not. Airlines often reward you for booking ahead.

How early to book in advance?

The stats cited are between three weeks and four months in advance. The average number cited is 70 days.

Why booking ahead of time saves you money

The logic is simple. They have wide open inventory 8 months out. If you first book a month out, you’ll suffer from price spikes from more projected demand than supply.

Occasionally booking late can offer savings, but it’s risky. It’s typically better to book ahead. Note, location flexibility will still save you more here.

Save $$ on flights and lodging based on seasonality and day of the week

There’s a huge difference in prices from Peak versus off-peak for a given destination. If you have flexible timing, avoid peak months when everybody else wants to travel.

If you have flexibility on days, consider going on a Tuesday or Wednesday, to see if prices drop. So many people have a really tight schedule that demands it being a weekend trip. If you have flexibility to travel in the middle of the week, explore it.

But how to find enough the vacation time?

For most of my adult life I’ve received just 2 weeks vacation (10 business days), plus holidays. That’s it. And you typically can’t use them together for a 2-week trip. If you take a week off for a trip, that means you can’t go very far in any one trip, so it’s crucial to maximize your days.

Typically that means most of my trips are about 9 days long (5 weekdays plus 2 weekends) these days.

How to maximize your vacation days

To maximize these precious vacay days, I typically combine my trips with holidays that we already get off. If you get a day off combine it with holidays and stretch it further. Thus the math changes – now 4 vacay days can mean a 9-day trip.

For example, in the US that means you can take a trip in late May during the week that has Memorial Day off, use 4 vacation days, and you have 9-day trip. I like this timing because it’s just before summer price hikes. This is how I did my trips to Peru, Barcelona and Copenhagen.

Or even better, if you’re not with family during the two days off in the winter (Thanksgiving or Christmas in the US), then just 3 vacation days means a 9-day trip. That’s less than a third of your total! Many of my trips took advantage of this – Cartagena, Tulum, Turks & Caicos, Nicaragua, and more.

If you’re thinking that sounds crafty, but still inadequate, you’re not alone. You can’t go very far in a week, meaning most of the world is off-limits. How can you travel for much longer?

how I traveled to Europe starts with discounted flights
check out multi-month Eurotrip! Photo is from Crete. Loved it!

Save for long-term travel. It’s amazing!

When you’re in between jobs, take a multi-month trip. Travel longer than you’ve ever traveled. Save up for that moment. It might be the best time of your life!

My philosophy: there’s no rush to get a new job immediately. Save for a rainy day, and use the time you’re in between jobs as an opportunity.

Don’t let the amount of vacation days you get limit how many days you travel. Your time in between jobs can be when you finally get to go to that country on the other side of the world.

My two-month trip Europe backpacking trip included a bunch of these strategies. I used discount airlines to get there, spent lots of time in the Baltics which it costs less, and then visited the Greek Islands during down season. Loved it!

Best half year trip ever!

All of this saving can be for little annual trips, but you can only go so far in a week. Twice I’ve paused my career to travel for multiple months at a time. Sometimes you need to prioritize life (over career), and it was important to me to save enough to do that when I was ready.

I started this Visit50 travel blog when I traveled for nearly a half year through mostly Southeast Asia (plus the Middle East). Loved it! Most posts on this blog are from that half year, and there’s so much that I still need to share. This was a huge decision for me, and I’ll share more about it in a later post.

I then worked for 3.5 years, and after leaving that company, I took another few months to travel, this time through eastern and central Europe (see my Eurotrip post).

Long-term travel isn’t for everyone but I loved it!

Think of it like a career sabbatical – use the time to get new experiences that will impact you for the rest of your life!

Did you find any of these ideas helpful? Does this all sound crazy? You can do it!

What to do next

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Follow me on Instagram and Facebook, and book your next trip!

Have you tried any of these strategies? Please let me know in the comments below!

59 thoughts on “How I traveled to 50+ Countries…and how you can too!”

  1. Love your blog. I think it’s informative for people to understand how to be able to travel and get the most out of it.

    1. Thanks Victor! I think it’s going to take a long while, but it’ll eventually bounce back. I’m hoping it forces some innovation and attention to germ issues too.

  2. Really enjoyed reading your blog! Many tips that I learned from this blog. Thanks a lot for sharing it with us. I’m impressed and really love your blog! Keep it up

  3. I totally agree! Once you catch the bug it’s definitely possible and you shared my favorite strategies!

  4. Fantastic!! Thank you so much for sharing your tips! Very inspiring and now I can’t wait until we can travel again to explore the world
    Very nice blog! I want to know more and more

  5. Great tips! Thank you for sharing them!
    I think we have to prioritize the projects in our lives and have a balance. I also believe that traveling is a personal thing, I love to explore the cities, to admire the architecture for instance. Other people love the exotic beaches and having fun in casinos… so it all comes to what you want most and go working for it!

  6. What a great informative article! Thank you for sharing those invaluable tips! I am especially interested in how to sign up for free airfare. Though I travel a lot (and loving it) I was never able to get any benefit from that.

  7. Great piece! I practice a lot of these too. They’re definitely the best ways to travel as much as possible. Whenever I’ve gotten the questions you include in the beginning my answer is also ‘priorities’. I hardly go out or eat out on my day to day so that I can travel instead, it’s crazy the amount of money you can save like that. I need to practice more searching for cheaper destinations though..

  8. Great post Todd. Specially the point on – Pausing one’s career for a multi country travel. I did the same. I took a 3 month career break and it was the best time of my life.

  9. Cool. I didn’t know that on google flight you can get info on if the price of a flight might increase or drop. Very useful

  10. Fascinating! Fun to read and so well written! Looking forward to reading all past posts and keeping up with future !

  11. I wish we had the mileage system here that you guys have in the States! It doesn’t even compare.
    But it’s all about making travel a priority! Exactly. Thank you for sharing!

  12. Great post! I can really relate to the things you wrote about as I travel in a very similar way! Keep it up! This looks awesome!

  13. Todd, this is a great list!! My husband and I have done some of the things mentioned. In fact, theres also a site where if you watch someones pet, theyll let you stay at their place for free. My brother visited Bulgaria for a whole month this way!

  14. Very well written, detailed and informative…good to understand from your perspective as you have done so much travel

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