Category Archives: Travel Tips

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” 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

Subscribe to this blog on the top left.

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!

Visit 50 Travel goal: 50 countries by age 50

Take the Visit50 Travel Challenge! I named this travel blog after the “Visit 50” travel goal.  I want to inspire you to visit 50 countries, by age 50.  It sounds ambitious, but you can do it!

First we’ll define the Visit 50 travel goal. Next, we’ll explain what counts as a country, and what counts as a visit. Finally, strategy tips on how you can visit 50 countries.

What is the Visit50 Travel Goal?

Lots of people say “I want to travel more.” However, that’s a desire, but that’s not a goal.

By definition, a goal needs to have 5 things. Goals need to be S.M.A.R.T.  That stands for Specific, Measurable, Ambitious, Realistic/attainable and Time-targeted. That last part means it has a specific have a time limit.

Hundreds of travelers are keeping track of their travel progress against this Visit50 travel goal. They want to visit 50 countries by age 50 as well, but ask how how it works. Feel free to play along!

How to measure your visit 50 travel goal

To measure your Visit 50 travel goal, you need to determine two things. Firstly, you’ll need to decide what counts as a visit. Then, you’ll need to decide what counts as a distinct country. To get started, below are how it works, and hopefully answers the most common questions.

Visit 50 Travel Goal: What counts as a visit?

A visit means you had an experience in the destination.

You need to leave the airport or the highway. You need to actually do something in that country or destination for it to count.

As a simple guideline, can you tell people a story about the time when you visited this place?  Do you have photos from your experience there?  Can you tell us about that delicious or terrible meal you had there?

Do you have a good answer if a friend asks, what did you do in that country? If you can tell me about that time that you visited that country, you visited, even if it was just for a day.

There’s no minimum amount of time. I’ve had lots of experiences in countries for just a day. For example, I visited Guatemala on a day trip have all

Also, there’s no minimum amount of the country that needs to be visited to count in this game. There’s something amazing that I missed in nearly all of the 50+ countries that I’ve visited. Some I just didn’t have time for, while others I didn’t know about until I left. In a few rare cases, the amazing thing wasn’t discovered when I visited (for example, Rainbow Mountain in Peru).

These are my rules, but it’s your game too. You can make play by any rules you’d like.

The surprisingly more difficult question is what counts as a country. This seems straightforward I’ve already had to recount along the way. Here’s how you count what’s a distinct country.

Visit 50 Travel Goal: What counts as a country?

Use the Visit50 country list! There are 198 countries according to…me.  Here’s how I arrive at that number.

Firstly, let’s count all 193 United Nations member countries in the world. Next, let’s add both (2) UN observers (Vatican and Palestine). That brings us to 195. Finally, we include the three (3) additional countries that are recognized by most other countries (Taiwan of course, plus Kosovo, Western Sahara) even though the UN doesn’t.

The above summary has exceptions. Some examples:

  • For example, if you visit London, spend a few days in Wales, then over to Ireland, and finish in the Cayman Islands, how many countries have you just visited?
  • Does Puerto Rico count as a country? It’s officially a US Territory, although many people treat it as its own country.
  • Are the Cook Islands a country or part of New Zealand?
  • If you visit mainland China, Taiwan, Macau, and Hong Kong, how many countries have you visited?  That last one’s a real example, as I’ve now visited all 4. I count Taiwan as a country, and the rest as part of China (including HK & Macau).

Which list to use for what’s a country:

As you’ll notice, there isn’t really not a comprehensive and credible list that’s all inclusive. It’s more challenging of a question than I thought.

You can’t just go by UN’s list of 193 countries, because Taiwan’s not listed and the world clearly recognizes them as a country. For proof check they have their own Olympic team, so clearly the world recognizes them as their own country.

Wikipedia’s List of sovereign states.

It  includes 193 member states of the United Nations, two states that are not UN member states but are either a UN observer state or a member state of a UN specialized agency (Vatican and Kosovo), and nine other states (includes Taiwan, Palestine).

3 more sources?

Until recently I was largely relying on these 3 sources:

– If the US State department lists them as a country (righthand column of page). I like the US’ list but part of it is political. Again, Taiwan is clearly a country. The US State department’s list of A-Z countries and regions is a great resource for other info too.

– If they have their own Olympic team (there’s 205 National Olympic Committees).  It sounds ridiculous to use this as my official list, but this shows that the international community recognizes them as a distinct country so it’s worth considering.

– If they’re recognized on the list of United Nations member states – there’s 193 of them. This seems like a fairly official list, but again, like the US State department list, politics often play a role. 

What makes it a country?

Two key factors make me want to include a destination as a country for my visit 50 travel goal:

– They’ve declared independence and are often regarded as having control over a permanently populated territory.

Other sovereign states recognize them as a sovereign state. In other words, it’s a country if most of the world’s countries treat it as if it’s a country. For example, Taiwan is officially recognized by 23 nations.

Indicators – States often have their own immigration/visa policies, which differ from the nation that claims them.
It doesn’t require your own distinct language, currency, or culture.

International law has 4 criteria

If you were wondering, international law has 4 criteria: the place must “possess[es] the following qualifications:
(a) a permanent population;
(b) a defined territory;
(c) government; and
(d) capacity to enter into relations with the other states.”


Count mainland China, Hong Kong, & Macau as one country, and Taiwan as a separate country. That brings the total to 198 countries. You’re welcome to count them anyway you’d like!

Do you have a suggestion on the best list to determine which countries count?  I’m open to feedback here.

Visiting 50 countries by age 50 seemed like a nearly insurmountable challenge, but I made it, and you can too!

Where I’ve been: For those of you keeping score at home, I’m at 26 states and now 54 countries as of June 2020 (in the past 5 years added 13 countries in Europe, Turks & Caicos, Nicaragua, Honduras, Colombia, Iceland, Italy, Netherlands, BVI, and Antigua & Barbuda). For an updated full list of where I’ve been, head over to the Where I’ve Been page, with the countries listed by region. I’ll also link to posts about each as I add them to the site.

Map of my visits

Here’s my map as of July 2018 after hitting 50 countries. There’s still so much more to explore!

map of the 54 countries I've visited
54 countries visited as of May 2020. There’s so much more to explore!

Visit 50 Travel goal – other ways to measure your traveling prowess:

UNESCO World Heritage Site List –

This includes 936 properties forming part of the cultural and natural heritage which the World Heritage Committee considers as having outstanding universal value. These include 725 cultural, 183 natural and 28 mixed properties in 153 States Parties. As of June 2010, 187 States Parties have ratified the World Heritage Convention.

Wonders of the World

I always thought there was one agreed upon list. There are actually dozens of lists. By definition they’re subjective, and I disagree with many of them. For the New 7 Wonders, locations were selected by voting, thus are certainly biased by political and economic factors . Listed determined by internet voting often hurt places in countries with poor internet access).  For example, Mexico’s Chichen Itza is an interesting site of Mayan ruins, but not even on the same level as Teotihuacan (also in Mexico).  Chichen Itza is near Cancun so many more people have been exposed to it, thus swaying votes. Is it really just a popularity contest among those with strong internet access?

How many countries have you visited?

Mapping your progress:

There’s a bunch of decent sites that will map the countries/places you’ve visited. I set mine up using this site. Note, this isn’t a great source for counting countries.

Do you have a travel goal?

For a full list of Where I’ve Been, head over to the Keeping Score page, with the countries listed by region.

world map - visit 50 travel goal
visit the whole world!

Strategy to visit 50 countries by age 50

Try to visit one country per year for most years.  And plan a long term trip.

There are plenty of inexpensive countries. For example, take a look at Central America, Southeast Asia, and eastern Europe all have interesting places that are values.

The ultimate guide to help you travel more often here.