Travel Diaries
19 Days in Portugal and Spain
by Christine FlynnMallorca and Ibiza had topped my bucket list for years, but the journey getting there was just as important. I love road trips, so instead of heading there directly, we took our time winding through Portugal and Spain, from the Algarve to Madrid and Valencia, before ferrying across to the Mediterranean coast. Along the way, we checked into six incredible luxury hotels. Portugal was a place I’d long wanted to revisit as a photographer, while it was my husband Niall’s first time there. Spain, meanwhile, was somewhere we’d each visited before—but never together. This is the route I’d recommend to anyone with 19 days to spare.
Days 1-5: Algarve
We touched down in Lisbon and wandered straight into Alfama, letting the Old Town’s maze of cobblestone lanes, colorful tiled buildings and vintage trams climbing steep hills set the scene. After breakfast at Magnolia beneath its Rococo-style ceiling fresco, we left the city behind and followed the road south to the Algarve, where sun-drenched beaches, rugged cliffs and sleepy fishing villages welcomed us into five blissful days by the sea.
What to do in the Algarve:
- Grab a couple of beers at Praia do Zavial and watch surfers carve through the Atlantic swells.
- Order the freshly caught shrimp, local clams and briny olives at Pont’a Pé in Aljezur—the kind of meal worth planning a return trip around.
- Step back in time at Silves Castle, where ancient stone walls and sweeping countryside views tell the story of Portugal’s Moorish past.
- Spend an afternoon at Praia de Carvoeiro, where golden sand, dramatic cliffs and turquoise water capture the Algarve at its best.
Where to Stay in the Algarve
Our first few nights at Vila Vita Parc couldn’t have been a better introduction to the Algarve. Perched high above the rugged Atlantic coastline, the Moorish-influenced resort instantly slowed us down with its sweeping ocean views and immaculately manicured gardens tucked around every corner. One of our favorite parts was the walk down to the beach, following staircases carved into the cliffs that led to secluded stretches of sand below, making even a simple beach day feel like an adventure. Mornings started with coffee framed by palm tree views before giving way to afternoons beneath thatched umbrellas overlooking the sea, spritz in hand, and dinners of fresh seafood at Arte Náutica Beach Restaurant, just steps from the beach.
For the second half of our Algarve stay, we headed inland, passing grazing cows and rolling countryside before arriving at Praia do Canal, where the scenery felt wilder with every turn. Surrounded by 220 hectares of protected nature, the hotel’s sand-coloured buildings seemed to disappear into the landscape, while floor-to-ceiling windows and bold architecture frame the outdoors. From our room, the view stretched across the Parque Natural do Sudoeste Alentejano e Costa Vicentina—one of Portugal’s largest protected coastal landscapes—with bougainvillea climbing outside the door and a huge marble bathroom I fell in love with. As a photographer, I loved wandering the grounds with my camera, capturing the dramatic coastline and local fishermen perched high on the cliffs above the Atlantic. Between delicious brunches, one of the best massages I’ve ever had and swims in the infinity pool, each day brought a new way to appreciate the beauty of this wild corner of Portugal.
Days 6-8: Madrid
Leaving the Algarve behind, we hit the road for Spain. The eight-hour drive took us across Portugal and into Andalusia, with a well-timed stop in Seville to wander the sun-soaked Old Town, admire its beautiful architecture and enjoy a glass of vino before continuing on to Madrid.
What to do in Madrid:
- Start the day with a stroll through Parque del Retiro, the city’s iconic green oasis and a UNESCO World Heritage Site filled with gardens, fountains and row boats.
- Wander the tree-lined streets around Mercado de La Paz, an exquisitely restored 140-year-old market, and pick up picnic essentials from its charming local stalls.
- Spend an afternoon at Museo Nacional del Prado, home to one of the world’s most celebrated collections of European art.
- Step inside La Dolores, a beloved Madrid institution since 1908, for traditional tapas served beneath original marble bars and old-fashioned interiors.
- Sip sherry at La Venencia, the legendary bar once frequented by Ernest Hemingway, where little has changed since 1922.
Where to Stay in Madrid
We checked into Nômade Temple Madrid in the heart of the city, lucky enough to be among the first guests to experience the newly opened hotel. Housed in a beautifully restored historic building, it strikes a beautiful balance between old and new, preserving its original architectural details while layering in rich materials and tactile textures throughout the space. The moody interiors, thoughtfully designed rooms and rooftop views (best enjoyed with a glass of vino, of course) quickly became highlights, but the evenings brought their own excitement. We even got a sneak peek at the hotel’s soon-to-open nightclub, before ending our nights with Negronis in the lobby, taking in the atmosphere of a space that felt every bit as stylish and full of energy as Madrid itself.
Days 9-13: Mallorca
After a few days of city adventures, it was time to chase the Mediterranean. We left Madrid behind and made our way to Valencia, a scenic 3.5-hour drive away, where we spent the afternoon taking in the city before boarding an overnight ferry to Palma. Arriving just after 6:00 a.m., we were greeted by a spectacular sunrise that painted Mallorca‘s coastline and honey-colored buildings in soft golden light. Before setting off for our next hotel, we roamed Palma’s quiet cobblestone streets and fueled up at Fika Farina, where some of the best pastries of the trip were waiting behind the counter, including a cardamom bun that quickly became my favorite.
What to Do in Mallorca:
- Discover Mallorca’s hidden calas, making time for Cala Llombards, a quieter stretch of coastline that’s well worth seeking out.
- Follow the trail to Caló des Moro, where every step is rewarded with one of the island’s most spectacular shades of blue.
- Grab lunch at Restaurant Nautilus for fresh seafood served alongside Mediterranean views.
- Wander the postcard-perfect fishing village of Cala Figuera before stopping at Bon Bar Cala Figuera, where colorful boats bob in the harbor.
- End the day at Bar Blau Portocolom, pairing fresh seafood and local rosé with front-row views of boats gliding through the harbor.
Where to Stay in Mallorca
Somewhere along the way, we spotted a man riding a moped wearing a T-shirt with the words “Live Slow” printed across the back. It became our unofficial motto, and nowhere embodied it better than Sarena de Muro Resort Mallorca. Set on the edge of the Mediterranean, the resort felt as though it melted into the sea, with views that made it seem possible to step straight from the room into the water. Days drifted between walks along the white-sand beach and afternoons by the pool, rosé at the ready, stretched out on the hotel’s signature green-striped loungers. It was the kind of place that made doing very little feel like the perfect way to experience Mallorca.
Days 14-19: Ibiza
After soaking up Mallorca’s laid-back charm, we continued our island-hopping adventure with a quick two-hour ferry ride to Ibiza. While the island is famous for its nightlife, Northern Ibiza revealed a completely different side, one defined by wild landscapes, hidden coves, turquoise waters and sea-kissed days far from the crowds.
What To Do in Ibiza:
- Set sail on a private boat day to explore Ibiza’s most secluded corners, from hidden calas and crystal-clear waters to spontaneous swims in the Mediterranean.
- Join the sunset gathering at Cala Benirràs, where locals and travelers come together for a celebration of drumming, music and island tradition (and if you happen to be there for the Summer Solstice like us, even better).
- Book ahead for a lunch at Xiringuito Xuclar, a little sand-side chiringuito serving up some of the freshest fish on the island.
- If the timing lines up, catch a sunset DJ set at Cantera Can Coix, a former quarry where towering rock walls create one of Ibiza’s coolest concert settings.
- Don’t leave without trying the croquettes at Con Domo, where farm-to-table cooking and seasonal ingredients make every meal feel special.
Where to Stay in Ibiza
From the moment we arrived at Six Senses Ibiza, we knew it would be one of the defining stays of the trip. Tucked into the island’s rugged northern coastline, the resort feels completely at home among wildflowers, rocky cliffs and the endless blue of the Mediterranean. The infinity pool appears to spill straight into the sea, making it difficult to tell where one ends and the other begins, while every sunset painted the coastline in a different shade of gold. Mornings started with delightfully prepared breakfasts, before giving way to swims in the sea, afternoons stretched out by the pool and serene moments simply taking in the extraordinary beauty of this corner of Ibiza.
For the second half of our Ibiza stay, we remained in the island’s north, where the pace was calmer and the coastline felt magnificently untouched. Cala San Miguel Resort became our base for exploring rugged cliffs, secluded coves and the region’s wild beauty. Our room’s panoramic view was unforgettable, looking over a private cala that felt like a world away. Between swims in the resort’s three pools and afternoons by the sea, every moment revealed another reason to fall in love with this quieter corner of the island.
Until Next Time
Every great road trip eventually reaches its final stretch. The ferry back to Dénia marked the beginning of the journey home, but neither of us was ready to say goodbye. Driving through Portugal and Spain became one of the most memorable parts of the trip, with winding roads lined by ancient olive groves, rolling hills and landscapes that seemed to change around every bend. We left with thousands of photos, a long list of favorite meals and six extraordinary hotel stays, but also the feeling that we’d only scratched the surface. Northern Ibiza, especially, has an energy that’s hard to describe until you’ve experienced it for yourself. We’ll be back next year. I’m sure of it.
