I am pretty ambitious when it comes to traveling abroad and try to get the most out of every single trip. The vast majority of my trips abroad have included stops in multiple countries. And I am not alone. Over 40% of international travelers visit more than one country per trip. A few airlines are even making it less costly for you to do so. If you are one of those people that have thought about it but assumed you can only “handle” one country—this post will challenge that. The truth is, it’s often cheaper and easier than people think.
Think visiting two countries in one trip will be stressful, expensive, or is only for seasoned travelers? Let me prove you wrong. By the end of this post, you’ll have all the information and confidence you need to plan a multi-country itinerary that’s exciting, affordable, and totally doable—even if this is your very first time using a passport.
How to Visit Two Countries Even If It’s Your First International Trip
News flash! You don’t need to be a seasoned traveler to experience multiple countries and cultures in one journey. And you don’t have to be on a cruise ship to make it happen. Albeit cruise ships are a great way to accomplish the multi country vacation with very little effort but I digress. With the right planning, hitting two countries on a trip abroad can actually make travel easier, not harder. Here’s what you will need to process if a multi country trip is right for you.
Planning Considerations
1. Proximity and Transit Times
You don’t want to more than 4-5 hours in transit between destinations. That’s all in. The closer the destinations are to each other, the more transit options are likely available. This includes looking for countries with shared borders like France and Spain or major cities that are connected like Belgium and Paris. I use tools like Rome2Rio to help visualize routes and understand my options. If you are driving between two places, 5 hours can be a lot for a short vacation.
2. Visa and Entry Rules
Next, you want to consider entry requirements. U.S. passport holders can visit most European countries without a visa which makes it easier to select multiple destinations. But try going from Thailand to Vietnam and you’ll quickly learn that you need a visa that requires at least three days advance notice. Do your research to learn which countries offer visa – free or visa on arrival access. Those are the countries you want to focus on for your visit to multiple countries. Check out the US state department site for the most up to date details.
3. Budget Compatibility
Before you book, check price levels so your budget isn’t stretched. Going from Strasbourg to Geneva might seem like a great idea until you learn that the average price of a hotel in Geneva can be double what you find in Strasbourg. If budget is a concern, you may want to avoid pairing very expensive destination with affordable ones unless that is part of your overall plan. Or leverage airline stopover programs for some instant savings. I booked a trip to Seoul with a stopover in Taiwan that was significantly cheaper than just going to Seoul.
Now that the pre-planning is out of the way, let’s explore a few possible matches for a visit to two countries.
Finding the Perfect Match
After many years of exploring the world, I’ve found a few combinations that are beginner-friendly, easy to navigate, and full of unforgettable experiences. Here are a few perfect pairings that can help you level up your game for that first multi-country trip.
1. Spain + Portugal
These two Iberian neighbors share a relaxed pace of life and warm weather most of the year. The history, food, and architecture all have similar origins with each having it’s own unique flavor.
Lisbon and Madrid are both great entry points from the U.S., and you can experience different cultures while staying within a manageable budget.
Moving between the two cities is fairly simple as well. Hop a short 1 hour flight and you can be in either country in no time flat. Of course if you want to take the scenic route, you can rent a car and road trip it through Andalusia. In about 5 hours, you’ll can kick back and enjoy a entirely new vibe.
2. France + Italy
These two countries happen to be two of Europe’s most iconic —perfect for foodies, art lovers, and fashionistas. Paris and Milan are popular gateways and the route between them is well-trodden.
Each offers a different yet complementary vibe: romance and elegance in France, passion and tradition in Italy. Both with some outright amazing fashion. In Paris you can visit icons like Dior and Saint Laurent then head to Milan to get close to Prada and Versace.
It makes sense that there is easy transportation options between these cities. A train will have you there in about 6 hours but a 90 minute flight will have you spending all your hard earned money on some bespoke shoes you can only find at the flagship store. Low cost airlines like RyanAir and WizzAir will help you save your money for a cool shopping spree. Albeit you might have to buy new luggage to accommodate all of your finds and not to mention the extra baggage fees airlines now seem to charge.
3. Thailand + Cambodia
If exploring Southeast Asia is on your list then a combo like Thailand and Cambodia are ideal for adventure seekers. Bangkok and Siem Reap are major hubs that also offer an exciting mix of vibrant city life paired with ancient wonders like Angkor Wat.
It also helps that both are fairly inexpensive. You can stay at some pretty lux hotels for the price that you’d pay for a budget room in NYC.
It’s a short 1 hour direct flight between Bangkok and Seim Reap which makes it a perfect pairing. If you want to save a few coins, try a bus transfer. It will take roughly 6-8 hours on some pretty treacherous roads and I’m sure you’ll arrive wishing you had just paid for the flight.
4. South Africa + Zimbabwe
If Africa is on your list but you don’t want to spend all of your time on safari, then add a Cape Town and Zimbabwe trip to your destinations. Cape Town gives you the magic of city life, history and wine while Zimbabwe gives you nature at its best.
South Africa is enough on its own between wines, whales and the incredible scenery you’ll have plenty to keep you occupied. But if you want to experience the best of nature with the magic of Victoria Falls, then a stop in Zimbabwe is an easy addition.
In only a few short hours you can go from mingling with the big five on safari to living your best life in Cape Town. Flights between these two destinations is about 3 hours which honestly is the only logical way to travel efficiently here. A ground transfer would be too much.
5. Argentina + Chile
For those flying south to check out South America, Argentina and Chile offer stunning landscapes—from Patagonia to wine country—and contrasting vibes between the cosmopolitan Buenos Aires and laid-back Santiago. They’re neighbors, but each country is distinct.
I chose to go wine tasting in both countries which was absolutely amazing. The food and wine together certainly did not disappoint. Check out my blog on Discovering the Wines of Argentina and Discovering the Wine of Chile for some insight into my adventure.
If you plan to visit these two countries, you should know there is much more to enjoy besides wine. You could pop down to Patagonia and head to Antartica but that trip isn’t cost effective or easy.
Since you’ll be sticking to Argentina and Chile, you’ll find direct flights between Santiago and Buenos Aires that are around 2 hours. You could also choose the bus route see the Andes up close but who wants to spend 18 hours in transit. Unless you have nothing else to do, I would recommend seeing the Andes from above. It’s a better view anyway.
6. United Arab Emirates (Dubai) + Jordan
If modern glam and historic charm speak to you, then putting the UAE and Jordan together is what you need in your life. The UAE has long been a destination for the well heeled. You start to feel rich the moment you step off the plane in Dubai (and even before if you are lucky enough to fly Emirates).
Jordan makes you feel like you’ve stepped back in time. Archaeological sites like Wadi Rum and Petra have been designated a UNESCO World Heritage site making it even more fascinating to visit.
You can get a 3 hour direct flight from Dubai to Amman and go from a shoppers paradise to a history lovers dream all within a day.
7. England + France
If this is your first time out of the country and you are interested in doing a multi-country trip, I would recommend a beginner friendly destination pairing like London and Paris.
These two destination are very tourist friendly and are well connected to the US. In fact, this is where I take first time international travelers looking to travel with me.
The Eurostar train gets you between London and Paris in just over 2 hours. It’s quicker than a flight and easier than driving making it the preferred choice for this trip. You can see the changing of the guards at Buckingham Palace in the morning and drink wine under the twinkle of the lights from the Eiffel Tower at night.
My Perspective
If you’re not sure what you want to do but are dead set on a visit to two countries in one trip these destinations make it easy to accomplish. You don’t have to be a travel expert to plan a two-country trip—just smart and strategic. Focus on simplicity by picking countries that are geographically and culturally aligned. Most importantly select countries based on proximity, easy border crossings, and budget compatibility.
With these tips you are closer than you think to planning your international adventure—with two countries instead of one.
FAQs About Visiting Two Countries on Your First International Trip
Is it too ambitious to visit more than one country on your first trip abroad?
No, it’s completely doable with the right planning. In fact, pairing two nearby countries can make your itinerary more flexible and allow you to experience more without significantly increasing the cost or complexity.
What’s the easiest country pairing for first-time travelers?
One of the easiest options is England and France. These countries are connected by a quick train and offer similar climates and laid-back vibes—making them beginner-friendly for first-time travelers to Europe.
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