When you’ve traveled as much as I have things tend to blend together. There’s that famous travel quote, “I’ve seen more than I can remember and I remember more than I’ve seen”. I can say that’s pretty accurate. However, some trips are more memorable than others. Here are my 10 most memorable trips.
1. Reaching the South Pole
When people hear me say the South Pole was my most memorable trip they kind of brush it off as “ok cool”. I totally get that because they don’t know the back stories of the trip and how hard it was to do and that I failed once when Prince Harry prevented me from reaching the South Pole. That said, when I stood at the bottom of the world with my good friends, it was as if I had conquered a great foe. It was definitely one my most memorable trips, probably right at the top, and one I still think about every day.
If you’re interested in going to the South Pole email me through the contact form on my website. Plus, if you’re interested in taking a once in a lifetime trip to the spectacular Ross Sea with my friends at Oceanwide Expeditions, use my discount code LEE1000GIFT to get an additional $1000 off an already discounted rate!
2. Study Abroad in London
I’ve said it a million times: studying abroad was the best decision I ever made in my life. It changed everything for me from my mindset to my future. It really opened my eyes to the world and I had the greatest time ever. I lived with one of my best friends and we lived right smack dab in the middle of the West End in London. We had no idea how lucky we were and we made the most of our opportunity. Those are some of my most precious memories that I will cherish forever. It was my first and certainly one of my most memorable trips!
3. My First Trip to Australia, New Zealand and Fiji
In 2002, I quit my Wall Street job for the first time to travel. I convinced one of my other best friends to quit his job and we decided to go to Australia, New Zealand and Fiji for a long time and that’s exactly what we did. We spent months in each place seeing just about every possible town and doing every single activity in each country. It was an amazing experience and after September 11, it was exactly what I needed to get my head straight. To this day I joke, that if I knew I was going to go to every country I would have taken that year to do a ton of them instead of just 3. But man, did we do those 3 well!
4. Living in Margarita Island, Venezuela
In 1999, I started a business in Margarita Island after going there to work for a tech company as an intern. That summer was the best summer of my life and changed a lot of things for me. I made friends for a lifetime who I still talk to everyday to this day. I learned more about the real world and making money that summer than you can imagine. Not to mention I got to see some amazing islands in the Caribbean, travel around mainland Venezuela and just really experienced life in a way that few ever will and if I told you, you wouldn’t believe me. I’m forever grateful for that experience. It was surely one of my most memorable trips.
5. Climbing Mount Kilimanjaro plus Safari and Zanzibar
Climbing Mount Kilimanjaro for me and one of my best friends was an epic adventure. We had never done something like that and weren’t even sure if we could. I actually celebrated my 28th birthday on Kili. When we made it to the top, it was the only time in my life where I’ve literally burst out into tears of joy. It was very hard, very cold and we had some altitude issues we overcame. At the time we called it our Everest. It was so exciting. After the climb, we spent another few weeks camping in the Serengeti, Ngorongoro Crater and then just chilled out in Zanzibar for another week or so! It was a memorable trip for sure and this was the trip that really fueled my desire to travel to every country!
6. The North Pole
Reaching the North Pole this past April was beyond exciting and an amazing feeling of accomplishment knowing I was one of the very few, like single digit people I believe, that have visited every country and both poles. It was a hard trip with a lot of delays and it was memorable for the delays, the way in which we arrived at the pole itself and the Russians who got us there. I was again fortunate to be with great friends and we will never forget the experience. It was one of my most memorable trips!
7. West Africa
From December 2008 to February 2009, my good friend and I went from Mauritania to Nigeria and some 14 West African nations in between. It was an epic trip that we certainly didn’t plan out. We did everything on the fly and did much of it overland via local drivers or however we could manage. It was an exhausting, eye opening, thrilling, saddening yet triumphant trip that I will not soon forget. Plus in that amount of time, even with getting stiffed for money in Liberia, my friend and I never argued once in 2+ months. That’s a common theme for me, you have to be chill and go with it when you’re on the road with others.
8. Egypt to Russia to Scandinavia down to Italy and back up to Iceland
In 2000, this was my college graduation backpacking trip to myself with my cousin and several friends along the way. We started in Egypt, Jordan and Israel before heading up to Russia, across Scandinavia, down through Central Europe, back up Western Europe to the UK and out to Iceland! Wow what a trip that was! I can’t remember the exact route but we visited some 20-25 countries in 3-4 months and had the time of our lives doing it. There’s nothing better than traveling when you’re young. You don’t know anything and you don’t care, you just have fun and enjoy the ride. I know I did!
9. Libya to Complete Visiting Every Country in the World
In 2011, Libya was the last country for me to visit every country. It was never something I really set out to do but I just kind of did it along the way. 2011 was the year of the Arab Spring and revolution was all around the region. My original trip to Libya that year was scheduled for March or April but was pushed back because of the war. When I finally did go in August, we got caught in a firefight as we basically got smuggled into the country in a minivan by a UN dissident I met at the airport. To say this trip was memorable is an understatement. It was so exciting!
10. The South Pacific
Back in 2010 I took a massive trip around the South Pacific to dozens of tiny islands, nations and World War II sites. I can’t possibly remember the route I took or how many planes I took or how many times I was in and out of Fiji but I remember a few spots pretty vividly. My disastrous boat to Tokelau was to this day the worst trip I’ve ever been on. Midway Island was a very exciting trip to a famous WW2 battlefield that you really can’t get to anymore. Guadalcanal was awesome for the same historic reason. Plus I visited super random places like Wallis and Futuna, Tuvalu and several others. Sadly, that trip ended for me in Papua New Guinea as I got the news of my grandmothers passing on a remote island and immediately flew home. So that trip was one of the most memorable trips I’ve taken but bittersweet in many ways.
There’s so many more I could pick and I’ve been so fortunate to take so many amazing trips to all corners of the Earth with so many amazing people. But these ten trips are without question some of the most memorable trips of my life.
Disclaimer: I have a business relationship with Oceanwide Expeditions and receive financial compensation.
Any one of these 10 trips > Any trip I’ve ever taken
Happy birthday!
Thank you Esra! I appreciate that and I’m sure your trips are wonderful too!
Reading these trips is like an NFL player playing against Pop Warner kids! They’re so amazing!
Haha I love that analogy and thank you! I miss Pop Warner!
Sounds like some epic trips. I love following your Instagram and snapchat. Happy birthday and thanks for sharing your life with us.
Thanks Maria always nice to hear that!
Of all these trips, the one that surprised me the most was your Graduation backpacking trip. Most college Graduates usually go to Europe or Southeast Asia either because of cheaper travel or easier to get around when first starting out with International travel. I love how you pushed the boundaries further by including the Middle East, Russia, and Iceland in the mix. Plus, having an epic trip in the Year 2000 has a nice ring to it!
Now that you have finished visiting every country and have nearly visited every country on the TCC list, are there any more epic trips that you foresee yourself doing that you haven’t done yet in the past due to either time or money? How does one get that level of “excitement” or appreciation that you had with these past 10 trips at this point in your life, anyway?
Ray, thanks a lot, I always love your insightful comments! Yes that trip back in 2000 was just pieced together randomly because I had done much of Europe during my time abroad in 1998 and I took a massive trip to Asia, not mentioned or written about here in 1999 plus I traveled some of South America and Caribbean when I was in Venezuela. I always wanted to go to Russia, Egypt and Israel plus Iceland and I was meeting friends in Amsterdam a month later so went the scenic route through those countries plus added a few on plus Scandinavia which was decided last second. From Amsterdam we did a lot of the standard backpacker places because my friends hadn’t been to many of the standard spots but I went off on my own twice to do some countries in Eastern Europe and some of the smaller countries like San Marino, Liechtenstein etc that they didn’t want to go to.
As for excitement, there are different things that excite me now at this point in my life. I don’t foresee long backpacking trips for obvious reasons but theres’ still a lot to do and I love repeating places-I do it all the time! I love hotels now and estimations. I love to do them differently and luxuriously as opposed to when I was younger and hosteled them. It’s fun for me to see the difference. However, I have a pretty cool Central Africa trip coming up in September and then next year I’m doing a boat to some remote Atlantic islands I haven’t been to. I’m not super excited for the boat ride but looking forward to the destinations assuming we reach them all! Plus I have some mountains to climb which really excites me, especially Mount Vinson in Antarctica…great comment and thanks buddy.
One other thing is that it’s the trips I do with friends and people I care about that resonate best with me. Of these trips, the only one I did mostly solo was #10 the South Pacific trip although I did meet up with people for portions both planned and people I met along the way.
Wow! You really did make the most of your time during your University with all these trips around the world. I especially respect the fact that you had no qualms travelling solo to some countries because your friends had no interest in going. And what’s even more remarkable is that all this travel you did during University was all done in an era before Social Media became mainstream. Sure, we had the beginnings of the Internet around Y2K to help you get some basic idea of where to go and how to get there. But, we didn’t have the benefit of blogs, Twitter, Facebook or Instagram at the turn of the Millennium to help each other travel longer and cheaper. My hat’s off to you, Lee!
And I totally get you on the travelling with friends and family comment as I feel the same way. Travel is really about the people you are with or that you meet along the way. Every single connection you make will teach you something very important about yourself and life in general.
Looking forward to hearing more about your Central Africa trip as it starts to come together. Hope you are able to include some crazy sports experience in their, too, whatever it may end up being!
I would kill to do just one of these trips. You’re very lucky Lee.
Thanks Alex but as I always say it’s not luck! But I am very fortunate!
Awesome!!!!!! South Pacific. Favorite…..HAPPY BIRTHDAY!!!
Thank you! Great place and that trip didn’t even include my favorite pacific islands!
Happy Birthday Lee!! You inspire me to travel more! I am turning 33 this year, but I’ve been only to 18 countries so far and still counting.
Trish, thanks so much and congrats on all your travels that’s a huge amount! Best of luck and thanks again!
Totally epic, Lee! I Based largely on what I’ve read on your site, I have put down the deposit to climb Kilimanjaro and booked a flight to Uyuni, Bolivia to see the salt flats with Tunupa Tours! Happy birthday!
That’s so exciting! Congrats on your adventures!!!
What an incredible fete! Amazing! So now what, Mars? ????
Mars no…space very possibly!!!
wow, You\’ve been to Fiji? I\’ve always loved that place.
Recollecting memories and seeing photos of where you have been will always be one of the most rewarding and priceless things you can have in your life! Amazing journey and I hope you will still keep on travelling and bringing us more interesting adventures!
Wow interesting article LEE.
I think I really have to start preparing for my world tour asap. Your stories plus posts are so amazing, lovely, beautiful and challenging. Thanks for making time sharing. Cheers!!