How To Plan Your Multi-City Dream Portugal Trip

The best ways to spend 10 days in Portugal— from must-sees to hidden gems.

By Paul Jebara

5 September 2019

How To Plan Your Multi-City Dream Portugal Trip

Portugal has been trending heavily over the past few years—and for good reason. Five times smaller than its Iberian neighbor, Spain, this nation is even more accessible in one trip, from glorious cities like Lisbon and Porto to bastions of Portuguese food and wine culture in the countryside. Best of all, this Southern European nation has welcoming weather all year round.

Our epic 10-day itinerary focuses on Portugal’s greatest highlights, and how to visit them one day at a time. But remember—this is just a sample. Every Journy itinerary is built entirely from scratch just for you, taking into account your tastes, preferences, priorities, budget and more.

Plan My Trip To Portugal

The Essential Portugal Itinerary for First Timers

Lisbon For The Romantic

Nearly everything about Lisbon is swoonworthy. This seven-hill city is geographically blessed at the mouth of the Tagus River. During the day, the bells of tram cars bounce off Baroque buildings in the cobblestone streets. In the evening, you’ll hear a fado chanteuse belting her heart out al fresco. And the food? From sweet to salty, the specialties are all delightful. For all the above reasons and more, Lisbon may be Europe’s most idyllic capital city.

Porto For The Culture Seeker

Portugal’s second city comprises a UNESCO-designated historic district along the Douro River, Romanesque architecture in moody granite and blue-painted tiles, and a thriving culinary scene. Plus, proximity to one of the world’s leading wine regions (see below) means your glass will never be empty.

Douro Valley For The Wine Lover

East of Porto is the Douro Valley, one of the most revered viticultural regions on the globe—and the birthplace of Port, the queen of fortified red wines. Equal parts sophistication and wilderness, the Valley is an underrated destination for outdoor adventure, small town exploration and, of course, major wine tasting.

Algarve For The Beach Bum

With well over 300 days of annual sunshine, Portugal’s southernmost region doubles as the sunniest corner in Europe. And with the country’s best beaches, characterized by golden cliffs and turquoise waters, the Algarve is unmissable for Mediterranean flair on the Atlantic shore.

The Essential Portugal Travel Guide: Lisbon, Porto, Douro Valley, Algarve

Get ready for 10 days of pure hedonism that blends the best of Portugal, including its most cosmopolitan cities to the swoon-worthy countryside. From start to finish: discover the country’s beating heart in Lisbon, then get seduced by Porto and the Douro Valley before ending with your toes in the sand of the Algarve.

Want an itinerary just like this customized to you? Talk to a Portugal expert and get a FREE, no-obligation travel offer with your travel route, flights, transportation, and hotels.

Lisbon (Three Nights)

Sample Day 1: Lisbon’s most exciting neighborhoods

Lisbon, Portugal

Start your day early for a full day in the oldest part of the city: the Alfama. This district’s cobblestone streets and alleyways are best explored on foot, so meander leisurely, pausing to marvel at the ceramic azulejo tiles and pastel-colored buildings. After finding a bakery for some coffee and pastries, make the steep climb (or take the tram numbered 28) to one of the famed tourist attractions in the Moorish Quarter, Saint George Castle. You’ll pass several miradouros, or lookouts, along the way, but the ultimate panorama will be atop the citadel.

“It’s SO useful! The price is definitely worth it to save me the time of researching everything."



Plan My Trip

Make your way down with Uber to Belém, a district on the city’s western fringe Your one true purpose here is to savor the iconic custard pastries from Fábrica de Pastéis de Belém, which are truly legendary (and worth a potentially long queue). Grab your pastéis de nata to go and enjoy them on the steps of the medieval Belém Tower, right on the river.

Just before dinner, pop into Embaixada, a concept store housed in the historic Ribeiro da Cunha Palace. Stay in the buzzing Principe Real neighborhood for dinner, specifically at Peruvian-inspired A Cevicheria (sip on their Pisco Sours streetside as you wait for your table). Continue to the old red light district to bar hop, or head straight to Pensão Amor for stellar cocktails.

Sample Day 2: Sintra

Sintra, Portugal

Today you’ll embark on the most popular day trip from Lisbon: Sintra. This UNESCO World Heritage Site feels like the set of a fairytale movie with its extravagant estates tucked into the lush Sintra mountains, all about 30 minutes by train from the capital. Arrive to Pena Palace first, before the crowds, to witness a remarkable example of 19th century Romantic architecture.

Migrate from Pena Palace’s opulent interiors and through the manicured gardens to the Castelo dos Mouros, which was built in the Middle Ages to guard Sintra from invaders. Descend the hills to visit Monserrate Palace and Quinta da Regaleira, two other displays of Sintra’s magical castles.

Return to Lisbon for dinner at Atira-te ao Rio, near the emblematic 25 de Abril Bridge on the other side of the Tagus. Take the cross-river ferry just before sunset to this waterfront restaurant for outstanding authentic seafood with views to match.

Sample Day 3: Cascais

Cascais, Portugal 

Craving the beach yet? Another ideal day trip from the capital is the golden sands of Cascais. A train ride from Lisbon’s Cais do Sodré station will transport you there in about 30 minutes for just under €5 round-trip.

A few beaches are reachable by foot from the Cascais town center, like Praia da Ribeira or Praia da Rainha, with sand dune beaches like Praia da Cresmina a bit farther out. Rent a bike for a coastal cruise until you locate your preferred sandy stretch.

Then stop for an al fresco seafood lunch at one of the buzzing restaurants of Cascais’ Old Town. The vibrant streets are also filled with boutiques, and sometimes street performers.

Upon return to the Cais do Sodré station in Lisbon, cross the street to the Time Out Market in the Mercado da Ribeira. With over 40 vendors serving both traditional Portuguese specialties and global fare, including a multitude of dessert options, it’s the perfect casual and convivial dinner. Take it easy tonight before your early morning flight or train ride to Porto.

Porto (Two Days)

Porto, Portugal 

Transportation to Porto: Take the train from Lisbon’s city center to Porto’s in under three hours, or book an affordable 50-minute flight on Ryanair or TAP Portugal.

Sample Day 4

Spend the day weaving through the narrow streets of Porto’s Old Town, a UNESCO-listed destination. You’re sure to find the mosaic of red-tiled roofs, Baroque churches, and medieval alleys an irresistible introduction to Portugal’s second city. Elaborate displays of azulejo tiles can also be spotted throughout this district. Getting around Porto is super easy thanks to an outstanding metro and light rail system.

Porto is also known for six bridges that span the Douro River—and if you can’t cross them all, just head to Dom Luís I for a stroll on its upper promenade. At the time of its construction, the double-decker structure was the longest of its kind anywhere in the world. Nearby is Guindalense, a low-key rooftop pub tucked away from the bustle of Old Town that doubles as an unofficial miradouro.

Sample Day 5

Of Porto’s many famed churches, these two are mandatory to visit: the mammoth 12th-century Porto Cathedral and the Church of St. Ildefonso. Then swing by São Bento Railway Station for its incredible azulejo panel, totaling over 20,000 individual tiles. Extend your binge of art and architecture with contemporary art at the Serralves Museum, the rotating exhibitions at the Portuguese Centre for Photography or the millenia-spanning artifacts at the Museu Nacional Soares dos Reis.

Pepper your day with drop-ins at Porto’s lively eateries, like Mercador Cafe on Rua de Floras, or Cafe Piolho, which has been open since the turn of the 20th century.

After an afternoon siesta—you’ll need one midway through this jam-packed itinerary—treat yourself to a night on the town along Rua Galeria de Paris, a storied alleyway that comes alive at night with cafes, bars and shops. Warning: this is a spot that could easily tempt you to stay out until the early morning hours.

Douro Valley (Two Days)

Douro Valley, Portugal

Transportation to Douro Valley: Join an incredibly scenic river cruise up the Douro River from Porto to the center of the valley.

Sample Day 6

No trip to Porto is complete without a visit to the Douro Valley, the world’s first demarcated wine region. You could certainly sample all of UNESCO-listed region’s famous products from a bar in the city, but there’s nothing quite like drinking it from the source. From your river cruise, you’ll take in a dreamy landscape of undulating hills covered with terraced vineyards and olive trees. Enlist your Journy trip designer to choose a cruise from Porto that has a wine tour included so you can spend the afternoon sipping reds, whites and fortified Port wine while passing through quaint villages nestled in the valley.

Book a night at Quinta Nova de Nossa Senhora do Carmo, a boutique hotel in an 19th-century mansion, or splurge at the Six Senses Douro Valley for some major R&R.

Sample Day 7

Take the morning off to enjoy a poolside breakfast at your hotel, then consider renting a car to explore deeper into the valley.

One option is to tour of the Douro Valley’s centenary olive groves, familiarizing yourself with the region’s other main export: olive oil. Madural, Verdeal, Cordovil and Galega are the main olive varieties grown here, each producing a unique flavor.

Another great choice is to drive up to the Braga, one of Portugal’s religious centers (about an hour north by car), for its ornate Baroque churches, lovely piazzas and bustling bistros.

The Douro Historical Train is a great car-free way to see more of the valley in a vintage carriage with live music and tasty treats.

The Algarve (Two Days)

Algarve, Portugal

Transportation to Algarve: A scenic drive or public train from the Douro Valley down to Portugal’s south can take up to six hours. Ryanair also has daily flights from Porto to Faro, Algarve’s regional hub. If you opt for the scenic drive, be sure to venture to the cities of Obidos, Coimbra, Evora or Tomar for a full Spain countryside experience.

Hear from fellow journy travelers

“Using Journy was hands-down the best travel decision we made. All the recommendations were excellent—food, activities, timing, etc. We would have never been able to organize the itinerary the way our trip designer, Lorinna, did for us. It felt like the recommendations came from a good friend who really knew us and cared about our experience.”



Plan My Trip

Sample Day 8

No matter how you get to the Algarve - car or public transportation, opt to stay in Lagos for its central location between the coast and some other towns worth exploring.

Since you’ll arrive in the late afternoon, spend the evening casually wandering the 16th-century Old Town, stopping at the Ponta da Bandeira Fortress for some photos. For an upscale dinner, reserve a table at the popular Avenida Restaurante and order the catch of the day. Nightlife in Lagos is surprisingly robust, so head to ZanziBar or Nox Club for a nightcap and dancing session.

Sample Day 9

Spend the entire day at one of the Algarve’s famous beaches that are walkable from town, like the much-photographed Praia do Camilo or sprawling Meia Praia. If you’re more adventurous, walk the two-mile coastal path from the lighthouse at Ponta da Piedade to the sandy beach below framed by 70-foot sandstone peaks and arches. A boat or kayaking tour can also be arranged to get up close to the towering.

Back in Lagos, opt for dinner and a view at Luca's Rooftop Restaurant overlooking Dona Ana Beach.

Sample Day 10

Renting a car will open up the Algarve’s cragged western coastline, where even more cliffs and caverns form a truly dreamlike landscape against the impossibly blue waters. Unlike the southern coast, this area is comparatively underdeveloped with more traditional beach towns and miles of secluded shoreline.

Make sure to end your drive at Cape St. Vincent, continental Europe’s most southwestern point. Round back through the town of Sagres, the site of a 15th-century nautical academy founded by fabled figure Henry the Navigator. A few whitewashed fortress walls are all that remain.

On your way back to the hotel, pass through Faro for dinner in the Cidade Velha, or Old Town. It’s ideal for strolling at golden hour before landing at Tasca do Ricky for codfish croquettes and a platter of fresh-caught shellfish.

Looking for more multi-city European itineraries? We've got you covered.

And if you're searching for another popular wine destination in Europe, consider Liguria, Italy, which has the stamp of approval from this sommelier.