Spending 14 days in Southern Spain and Portugal is the perfect vacation plan, offering a great way to explore some of the most iconic landmarks of the Iberian Peninsula while experiencing both countries in a single trip. Here’s the ultimate road trip itinerary to help you plan your holiday adventures like a pro.

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2-Week Southern Spain and Portugal Itinerary

Visiting Southern Spain and Portugal in one itinerary

Including Southern Spain and Portugal within a single 2-week itinerary is a fantastic way to explore some of the most unique landmarks of the Iberian Peninsula, while also experiencing the charm of two different countries in one trip. It’s absolutely doable – I’ve visited Southern Spain on multiple occasions and crossed the border into Portugal a few times myself, curious to see whether it would be too much to fit into one itinerary.

In my opinion, you could easily spend 14 days in Southern Spain (or Andalusia) alone and still not see it all, especially with so many incredible places to discover in this part of the country. However, I personally enjoyed combining it with Portugal. While Spain and Portugal share some cultural and architectural similarities, they are still distinct countries, and that difference adds a wonderful variety to any two-week -European adventure.

Best way to travel around Spain and Portugal

While the blog features plenty of itineraries for train travel in Spain, I mainly recommend trains for those planning to stick to major cities. For this particular 14-day Southern Spain and Portugal road trip, however, you’ll need to rent car to make the most of it. The route includes small towns and hidden gems where public transport – mostly buses – can be slow and infrequent, making it difficult to cover as many places in just 2 weeks as you could with your own vehicle.

How to Plan 2 Weeks in Spain and Portugal

I recommend starting this 2-week itinerary in Malaga, as it has a great international airport and high-speed train connections to Spain’s capital of Madrid. If you can’t find good flight deals to Malaga and consider arriving or departing from Madrid’s airport, you can also check out this complete article on potential road trips that can be started from Madrid.

Arriving directly in Malaga is the easiest option, as in addition to its train connection with Madrid, Malaga has excellent road links to every major landmark in Southern Spain, making any road trip through the region convenient. While starting in Seville is also an option, it’s less time-efficient. Starting your 14-day itinerary in Southern Spain and Portugal in Malaga allows you to explore the eastern gems of Southern Spain first (like Granada and Malaga), and then gradually make your way westward to Seville, Cadiz, and Portugal.

Best base for a Southern Spain Itinerary

While Malaga is one of the best places to start any Spain and Portugal itinerary, for this particular road trip, you’ll be actually choosing two bases in Spain: Malaga and Seville, and in Portugal – any small town in the Algarve region. This way, you can easily explore the rest of the landmarks via day trips while saving time on check-ins and packing.

To personalize this Southern Spain and Portugal itinerary or make it longer, you can find more detailed travel plans in the blog’s itinerary section, where I share my trips across Spain. Depending on your time and interests, you can combine this itinerary with a road trip through Extremadura, a getaway to Almeria, or even a Don Quixote road trip in Central Spain (starting from Cordoba).

14 Days in Southern Spain and Portugal: The Ultimate Road Trip Itinerary

Day 1: Malaga

Malaga is one of the most popular destinations in Southern Spain. This vibrant coastal city is known for its rich history dating back to Roman times, lively festivals, and delicious local cuisine.

It is the birthplace of Pablo Picasso, and visiting his museum is a top plan for all art lovers in Spain. However, the historic center of Malaga is full of stunning architecture, including the Alcazaba fortress. You can read more about Malaga in this post.

Day 2: Marbella and Castillo Colomares

The upscale town of Marbella is one of the most popular getaways from Malaga, known for the luxurious vibes of the Puerto Banus neighborhood. Its charming old town, with Plaza de los Naranjos and picturesque whitewashed streets, is perfect for a stroll.

On the way from Malaga to Marbella, you’ll find the small town of Benalmadena, known for its Castillo Colomares – a fairytale-like monument dedicated to Christopher Columbus. It is one of the most peculiar landmarks in Southern Spain, celebrated for its unique blend of Gothic, Romanesque, and Mudejar styles.

Day 3: Hike Caminito del Rey

Caminito del Rey is considered one of the most iconic hikes in Spain. It appears on every list of adventurous plans, as it is suspended along the steep cliffs of the El Chorro Gorge, and the views are jaw-dropping. I highly recommend prebooking a tour to El Caminito del Rey from Malaga, as it is one of the most popular activities in Southern Spain.

However, keep in mind that if you are visiting the region with kids, you might need an alternative plan, as only children aged 8 and above are allowed on El Caminito del Rey. Another great option for a day trip from Malaga is visiting one of the famous white villages of Southern Spain, also known as pueblos blancos, such as Setenil de las Bodegas or Frigiliana.

Day 4: Ronda and Juzcar

Another iconic day trip from Malaga is the town of Ronda, considered a must-stop on any Southern Spain and Portugal itinerary. Known for its iconic bridge, Puente Nuevo, Ronda often appears on lists of storybook locations in Spain.

After exploring Ronda, its bridge, and the famous bullring, I also drove in the afternoon to the nearby village of Juzcar – Europe’s only blue Smurfs village – considered one of Spain’s most colorful places. You can read more about my visit to Juzcar here.

Day 5: Granada

Granada is one of the most famous places in Spain, known for housing one of the country’s most iconic landmarks – the Alhambra Palace. As a UNESCO World Heritage Site and one of the world’s greatest architectural wonders, visiting the Alhambra requires booking a tour at least a few months in advance. It is definitely a must-do on any Spain bucket list.

However, I have to admit that I’ve never gone back (at least not yet): getting in is always a hassle, and it’s usually so crowded that, on my first visit, it was honestly hard to enjoy. Last year, my parents visited Southern Spain and managed to get Alhambra tickets just a week before their trip. I’m mentioning this for last-minute travelers who haven’t booked in advance but want to see the Alhambra – there’s still a bit of hope. My mom kept the official booking website open all day, refreshing it regularly until she saw a few last-minute tickets become available. She grabbed them right away – and this was during a regular week in spring.

Granada also has a charming old town and some of the most authentic flamenco shows in Spain. But if you’re visiting the Alhambra, plan to dedicate at least half a day to it. Once you have your ticket, it’s wise to make the most of your visit – especially since I know very few travelers who would go through the experience again, despite the landmark’s undeniable beauty.

Days 6-7: Seville

Seville is one of my favorite Spanish cities, often called one of the country’s most charming and romantic destinations. While I often share tips on making the most of just one day in Seville, I usually recommend spending at least two days in the vibrant Andalusian capital. The city’s biggest highlights include the majestic Seville Cathedral, which houses the tomb of Christopher Columbus, and the Real Alcazar, a stunning palace featured in Game of Thrones.

I have to admit, I personally enjoyed the Real Alcazar of Seville even more than the famous Alhambra of Granada, not only because it was less crowded, but because the whole experience felt more relaxed. Real Alcazar felt smaller and more intimate, yet definitely one of the most storybook-like spots in Spain, transporting you straight into the pages of One Thousand and One Nights.

Seville is also a great place to experience some of the trendiest flamenco shows in Spain. You can read more about my two days in Seville and the best time to visit in this post.

Day 8: Cordoba

Cordoba was once the capital of Moorish Spain, and it is one of the easiest and most popular day trips from Seville. Its breathtaking Mezquita-Catedral is one of the most unique religious sites in Spain, and its history is filled with mysterious legends.

I really enjoyed spending a day in Cordoba and always recommend including it in any Southern Spain itinerary. You can check out my full itinerary in this post.

Day 9: Cadiz

Despite being called one of the most underrated Spanish cities, Cadiz is a unique destination when it comes to ancient history, as archaeologists have discovered the oldest settlement in western Europe here.

Besides its charming Old Town, iconic La Caleta Beach, and beautiful cathedral, the most popular activity in Cadiz is climbing Torre Tavira. You can check out my full Cadiz itinerary in this post.

Day 10: Tarifa

Tarifa is another one of my personal favorites in Southern Spain. Known as Europe’s southernmost point and a haven for windsurfers, it’s a popular gateway to Morocco. Beyond its endless white-sand beaches with the African continent as a backdrop, Tarifa is where travelers can take a one-hour ferry to Tangier for a day trip to Morocco. You can read more about Tarifa in this post.

Tarifa is a vibrant destination if you visit it during the summer months, full of quirky restaurants and bars. In the off-season, it is still beautiful in terms of nature (personally, I have visited in winter and enjoyed the lonesome vibe, but I admit that many travelers might find it a bit empty).

Therefore, if you’re planning these 14 days in Southern Spain and Portugal during the off-season, you might consider making a day trip to Jerez de la Frontera, known for its iconic horse shows and sherry wineries. For history lovers in Spain, I would recommend the famous ruins of Baelo Claudia near Tarifa.

Day 11: Columbus Landmarks in Huelva

On the way to Portugal from Seville, many travelers make a stop in the lesser-known region of Huelva, home to several Christopher Columbus landmarks. While the area is also famous for its Doñana National Park and birdwatching, I personally enjoyed visiting La Rabida Monastery, where Columbus stayed before his voyage, and the Muelle de las Carabelas, known for replicas of his ships (the Santa María, the Niña and the Pinta).

While there are more Columbus-related landmarks you can find in Southern Spain to channel the Age of Discoveries vibe (check out this detailed post), both La Rabida Monastery and Muelle de las Carabelas are the easiest to include on any Southern Spain and Portugal itinerary, as they are literally on the road.

Days 12-14: Algarve

While the Algarve in Southern Portugal is one of the most iconic coastal destinations in Europe, I visited it on a weekend break from Southern Spain and absolutely loved it. After a jam-packed itinerary in Southern Spain, full of iconic landmarks and historical insights, it felt refreshing to explore the small fishing villages of Algarve.

The cliffs of Algarve make you feel like you’ve reached the end of the known world. Plus, it’s an amazing destination to enjoy all kinds of seafood – I was so surprised that the platters were almost twice as cheap as in Spain. While travelers typically stay in the Algarve for 5-7 days, two days was perfect for getting a great first impression of the region. You can check out my full Algarve itinerary in this post.

If you can add a few extra days to your 2-week Spain and Portugal trip, most travelers drive from Algarve to Lisbon to spend a few days in the city and visit the famous Sintra. However, since the drive takes around 3 hours, Southern Spain is usually just combined with Portugal’s southern region of Algarve.

Is it worth visiting Spain and Portugal on a single road trip?

In my opinion, visiting both Spain and Portugal on a single trip is a great travel plan as long as you fully understand that you won’t be able to see everything in just 14 days. As someone who visits both destinations frequently, I would say that this is not necessarily a bad thing – you can always get a first impression and return on another trip to explore more.

While it’s easy to spend two weeks solely in Southern Spain, I enjoyed combining it with the Algarve, as it was really close and felt like a great way to experience two different countries in one trip. For me, Southern Spain was definitely more about unique architecture and landmarks, while the Algarve was a beautiful coastal destination to enjoy small Portuguese villages, stunning coastal landscapes, beautiful sunsets, and delicious seafood dishes. Therefore, I have enjoyed combining both on the same 2-week itinerary.

Best time to visit Southern Spain and Portugal

I have always enjoyed visiting Southern Spain and Portugal in late spring and early autumn, as the temperatures feel very comfortable and there are fewer people compared to the peak summer season. Most of the photos in this post were taken during my visits in May and October, and as you can see, all my outfits are straight from the summer Spain packing list.

Average daytime temperatures during these months range between 20 -26°C (68 – 79°F), which makes exploring cities and landmarks much more enjoyable. I have also visited Southern Spain during both summer and winter, and each season has offered a unique experience. Winter is ideal for budget travelers, as accommodation prices drop slightly and the weather is mild – typically around 12–17°C (54–63°F). It’s also a good time for those who prefer to avoid high temperatures.

Summer, on the other hand, can be overwhelming, especially in Seville and Cordoba, where temperatures are often around 38°C (100°F) – 45°C (113°F), and popular landmarks get very crowded. That said, I understand many travelers only have time off in summer, and it’s still absolutely worth it visiting Southern Spain or Portugal – the iconic landmarks of both are just as incredible year-round.

Yet, if I had to repeat this 14-day Southern Spain and Portugal itinerary, I would choose May or September. If you’re planning to visit Southern Spain in April, keep in mind that it’s the time of many local Easter-related festivities, like Semana Santa in Malaga or Feria de Abril in Seville. These events are fascinating if you’re traveling for the cultural experience, but the region gets packed with locals on holiday, and some places may be closed – making it less ideal for traditional sightseeing.

Map of this 2-week Spain and Portugal Itinerary

You can check out this 14 days in Southern Spain and Portugal Itinerary on Google Maps here.

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