Tailor-made Vacation · Portugal
10-Day Portugal Tour: Porto, Douro, Lisbon, Sintra & Alentejo
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At a glance
This itinerary traces Portugal's story from its founding to its golden age of exploration, with serious food and wine discoveries along the way.
Start in Porto, where the Romans first established Portus Cale, the settlement that gave Portugal its name. The city's azulejo tiles tell stories on nearly every building, a tradition dating back to the 13th century when Portuguese sailors brought the technique from North Africa. The port wine cellars across the river in Vila Nova de Gaia hold wines that have been aging since the 1800s.
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The Douro Valley reveals Portugal's oldest demarcated wine region - officially established in 1756, making it older than Bordeaux or Champagne's classifications. These terraced vineyards were carved by hand over centuries, creating what UNESCO now recognizes as a World Heritage landscape.
The Alentejo region holds Portugal's most mysterious history. The Cromeleque dos Almendres stone circle predates Stonehenge by 2,000 years, making it one of Europe's oldest astronomical observatories. This region's wines remained largely unknown until the 1990s, when international attention finally discovered what locals had known for centuries - that Alentejo's clay-limestone soils produce exceptional reds.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: Porto
When you arrive at the airport your driver will meet you and transfer you to your hotel.
Day 2: Porto
Today you’ll set out on a tour of Porto exploring its old town, the Neoclassical Palacio da Bolsa and the wine bars. In the afternoon you’ll set out on a cruise down the Douro River. Later, you can explore Porto’s famous wine caves.
Day 3: Covas do Douro
Today you’ll explore the best wine region of the Douro Valley and also visit Guimarães, a UNESCO World Heritage Centre associated with the birth of Portugal. It was, after all, the birthplace of Portugal’s first King. Exploring Guimarães, it can feel like your stepping back in time to the Medieval period.
Overnight in the Duoro Valley.
Day 4: Covas do Douro
Today you’ll tour some of the best wineries of the Douro Valley. You’ll then take a cruise down the Douro River and have lunch at another winery. More wineries await, so you may wish to go full throttle Eddy and Patsy.
Evening at much-needed leisure.
Day 5: Sintra
Today you’ll take a day trip to Sintra, a popular resort town not far from Lisbon. You can head into the hills and visit the Castle of the Moors. You’ll also find yourself strolling through Arabesque courtyards, and also the elegant Pena Palace.
Day 6: Lisbon
Today you’ll transfer to Lisbon and check into your hotel.
Day 7: Lisbon
Take a tram to Belém. Here you can explore Europe’s biggest plaza, the Jardim da Praça do Império, taste some classic Portuguese pastires at Pasteis de Belém, and also learn about the Age of Exploration at Museu Nacional de Arqueologia.
Day 8: Lisbon
This morning you’ll head north to Estremadura. At Batalha, you’ll visit the Tomb of the Unknown Soldier, the Gothic Batalha Monastery and, supposing you’re feeling adventurous, you can explore the Grutas da Moeda caves underground.
Day 9: Évora
You’ll be heading east to Alentejo. Here you’ll visit the megalithic stone complex, Cromeleque dos Almendres. This ancient stone circle dates back to 6000 BC.
When you’ve explored the site you’ll check into your hotel in Évora.
Day 10: Moncarapacho
Today you’ll continue you’ll head to the Algarve coast and check into your new hotel. Evening at leisure.
Day 11: Moncarapacho
After breakfast you’ll head to the market with a local chef, buy some ingredients and then head to a cookery class. With some new Portuguese recipes under your belt, you’ll return to your hotel.
Day 12: Moncarapacho
You’ll be avoiding the tourist trail and exploring the less well known – but more authentic – stretches of the Algarve coast. Try some of the grilled fish associated with this area, and also the sparkling green wine (vinho verde).
Day 13: Departure
Today you’ll be transferred to the airport for your return flight.
Our Experts
If you like food, surfing or simply sightseeing, Portugal is somewhere you just have to visit. I personally adore Lisbon for its booming culinary scene and colourful backstreet bars and cafes.
Porto is my absolute favourite place in Europe and I've been too many times to count. It's super-inclusive and is also perfectly paired with a trip to Morocco.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.