Our expert, Derek Krantz, picks the places you should explore together on your multi-country Europe vacation.

Our expert, Derek Krantz, picks the places you should explore together on your multi-country Europe vacation.
Europe’s allure, steeped in history and culture, speaks for itself—several European countries are among the most visited destinations in the world. If you want to get the most out of your Europe vacation, combining two or more countries is a great way to experience more of the continent’s diverse delights in a single trip.
With this in mind, we’ve curated four of our favorite country combinations, each of which offers a distinct perspective of Europe’s captivating charm. The best part is that they’re all just a short train ride or flight away from each other, allowing you to spend more time immersed in discovery and less time traveling.
This is one of our favorite pairings! Spain is one of the most visited destinations in Europe, while Portugal is ideal if you’re looking to combine it with something off the beaten path. Together, they tick all the boxes for a truly enchanting vacation – rich history, fascinating cultural traditions and beautiful landscapes.
Spain, being the larger of the two, offers a more diverse mix of destinations, each with its own unique charm. Madrid is the seat of Spain’s royalty, and is renowned for its lively boulevards, museums like the Museo del Prado, and its fast-paced nightlife. The more laidback city of Barcelona is the epicentre of the country’s Catalan culture, and Seville’s architecture is a fascinating mix of Moorish, Gothic and Renaissance influences.
Portugal, while smaller, has a range of equally alluring attractions. The historic river city of Porto is known for being the birthplace of port wine, and is the gateway to the world-famous vineyards of the Douro Valley region. Sintra, a popular retreat nestled in the foothills of the Sintra Mountains, is home to some very interesting monuments such as the colorful Pena Palace and the impressive National Palace of Sintra. If you love the outdoors, you will be mesmerized by the turquoise waters and dramatic cliffs of the Algarve region. Its beaches are also regarded as among the most beautiful in the world.
Our customizable Portugal and Spain: Iberian highlights allows you to experience the best of Portugal’s wines, landscapes and history, and the distinct culture of Spain’s Catalonian and Andalusian regions. If you’d like to go a little more off the beaten path, then Portugal and Spain: Historical Wonders, is the one for you.
This is a true Roman holiday in every sense of the word! Italy was the heart of the mighty Western Roman empire, while Greece was a key province of the Eastern Roman Empire. Italy is high on many travel bucket lists, and with good reason! The country is renowned for its magnificent cities—Rome, Florence and Venice—fabulous art, and iconic landmarks like the Colosseum and the Leaning Tower of Pisa. Its culinary delights, ranging from pizza and lasagna to tiramisu, make Italy a top destination for food lovers as well.
The idyllic islands of Greece, with their more laidback atmosphere, amazing beaches and beautiful landscapes, are the perfect complement to your breathtaking exploration of Italy. They also offer a more authentic experience of Greek culture through scenic hikes, walking tours and cooking classes. Crete is famous for its ancient ruins, and you can delve into Greek island life at the traditional villages of Naxos. The charming towns and Cycladic architecture of Paros make it an alluring option. If you prefer something more lively, you can always head for Mykonos, the famous ‘party island’!
Our recommended route blends a more active exploration of Italy with a leisurely, offbeat Greek island sojourn. You can begin your journey in Rome and move on to Florence. If you want a break from the city experience, you can stay at a quaint property in the scenic Tuscan countryside and make day trips to Florence. This is an especially great customization if you love food, wine and the outdoors.
Next, delve into Greece’s rich history at Athens, before heading for the serenity of the Greek islands. Unwind on one of their amazing beaches, embark on scenic boat trips to discover secluded coves, and tour their vineyards and olive oil groves. You should definitely try Greek wines during your time here. Fun fact – Most wines produced in America use French and Italian grapes, while Greek grapes are rarely used.
Enjoy hiking through the countryside, stopping at charming villages to chat with the locals and savor the region’s cuisine. At Naxos and Paros, you can also experience a traditional cooking class and learn how to prepare a few Greek delicacies under the guidance of an expert chef.
Note: At the time of writing, Santorini has been experiencing earthquake-like tremors. Our experts can advise you further while planning your visit.
This pairing is a fabulous blend of history, culture and landscapes. From the majestic Palace of Versailles and the incredible art collection of the Louvre to the grand chateaus of the Loire Valley, France is a treasure trove of architectural and artistic delights. Its museums, culinary traditions and historical sites are a testament to the pivotal role France played in shaping Europe’s heritage.
Switzerland’s stunning natural beauty makes it a paradise for outdoor enthusiasts and a great choice to round off your vacation after a wonderful week spent exploring France’s culture. Whether you are seeking serenity or a little adventure, you will be enchanted by the country’s towering Alpine mountains, pristine lakes, and charming villages. Despite its small size, Switzerland is also quite culturally diverse, with three linguistically distinct regions – German, French and Italian.
We recommend starting your journey in Paris. In addition to uncovering its rich history at landmarks such as the Palace of Versailles, there are a lot of interesting day trip options to choose from. You can visit the infamous World War Two beaches of Normandy, the elegant castles of the Loire Valley region, and the vineyards of Burgundy. Next, head for Lyon, the culinary capital of France, where you can enjoy traditional cooking classes and personalized food tours.
From Lyon, it’s a short hop to pretty Geneva and then incredible Interlaken. We can recommend some beautiful properties in the Swiss countryside that are close to both of these destinations, where the crowds are fewer and the views are just as breathtaking. Soak in the beauty of your surroundings on leisurely hikes and boat trips. If you are feeling more adventurous, you can try rafting and night sledding.
If you are a history lover and feel like exploring a side of Europe that few others visit, this is the one for you! This multi-country European tour takes you through three of the continent’s hidden gems- Hungary, Austria and the Czech Republic.
Budapest originated a Roman settlement, was in and went on to become an important hub of the Austro-Hungarian empire. The city is home to fabulous landmarks such as the grand Buda Castle, the iconic Chain Bridge, and the majestic Parliament Building. It is divided into two distinct parts by the Danube. Buda’s medieval buildings and cobblestone streets give it a historic charm, while Pest is known for its cultural institutions and vibrant nightlife. During your time in Budapest, we recommend visiting one of its famous ‘ruin bars’, which are bars that operate out of old abandoned buildings!
Vienna is a fabulous showcase of Europe’s rich cultural heritage, imperial history and grand architecture. The former capital city of the Austro-Hungarian Empire brims with historical landmarks like the magnificent Schönbrunn Palace, the majestic Hofburg Palace, and the stunning St. Stephen’s Cathedral. Some of the world’s most famous composers – Mozart, Beethoven and Strauss, produced many of their finest works in Vienna. The city also has a vibrant coffee house culture, where you can savor traditional pastries and a steaming cup of coffee while watching the world go by.
Prague is known as the ‘City of a Hundred Spires’, and its skyline is dotted with Gothic, Baroque, and Romanesque buildings. Its location made it a key part of the Holy Roman Empire. Prague went on to become the capital of the Bohemian Kingdom, and it was also a major power centre during the Austro-Hungarian Empire. Its most famous landmark is the massive Prague Castle, which is among the largest ancient castles in the world. There is also the historic Charles Bridge on the Vltava River that connects the Old Town with the Lesser Town.
Derek studied European history at university, and his stints in the hospitality industry have given him an enviable knowledge of the continent’s culture and wines. When he isn’t crafting vacations as unique as his guests, Derek can often be found immersing himself in a podcast or a book on Europe’s rich heritage.
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