Tailor-made Holiday · Portugal
Luxury Portugal Tour: Porto, Douro Valley, Sintra, Lisbon & Alentejo
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
This isn't your typical Portugal trip. From the moment you land in Porto, everything shifts up a gear. Expect private transfers, world-class hotels, and access to experiences most travelers never see.
The Douro Valley delivers on its reputation as the world's oldest wine region, but you'll experience it from Six Senses Douro Valley, where vineyard views stretch endlessly and the spa treatments actually live up to the hype. The wine tastings here go beyond the usual tourist offerings - you're meeting the people who make these wines and understanding what sets this region apart.
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Sintra changes the pace entirely. The fairy-tale palaces are real, and staying at Tivoli Palácio de Seteais means you're living in one. This 18th-century palace turned hotel sits perfectly positioned for exploring Portugal's most romantic town without the day-trip crowds.
Lisbon shows its range, from Belém's serious maritime history to neighborhoods where locals still outnumber tourists. The private Tagus River cruise at sunset give you a an unbeatable view of the city.
The Alentejo region closes out the trip with a completely different energy. São Lourenço do Barrocal represents Portuguese luxury done right. Biking through their vineyards, tasting wines made on property, and using their private observatory puts you squarely in "how is this real life" territory.
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: Arrive in Porto – Settle into Portugal’s Second City
Your journey begins with an international flight to Porto, Portugal’s second city and a hub of history, culture, and incredible cuisine. Upon arrival, a private escort will transfer you to The Yeatman, a luxurious wine-themed hotel with panoramic views over the Douro River. Spend the afternoon at leisure, taking time to explore the surrounding neighbourhood, stroll along the waterfront, or relax with a glass of local wine. In the evening, perhaps enjoy a meal at the hotel’s Michelin-starred restaurant or head into the city to sample fresh seafood at a riverside eatery.
Day 2: Exploring Porto & Private Douro River Cruise
Begin your day with a guided exploration of Porto, combining walking and driving to experience its diverse architecture and lively neighbourhoods. Visit the historic Ribeira district, take in the intricate tilework at São Bento Station, and admire the imposing Clerigos Tower. Drive to the Foz do Douro, where the river meets the Atlantic, before crossing into Vila Nova de Gaia for breathtaking views from the Serra do Pilar viewpoint. Board a private boat for a scenic Douro River cruise, enjoying lunch onboard as you sail past Porto’s iconic bridges. The day ends with a private port wine tasting before returning to The Yeatman.
Day 3: Porto to the Douro Valley – Cooking Experience & Vineyard Stay
Bid farewell to Porto as you head into the rolling hills of the Douro Valley, one of the world’s oldest wine regions. En route, stop for an exclusive cooking experience in a countryside home, where you’ll learn how to prepare traditional Portuguese dishes before sitting down to a home-cooked lunch. After a guided tour of the property, continue your journey north to Six Senses Douro Valley, a five-star retreat renowned for its spa, vineyard views, and wellness focus. Spend the evening enjoying the hotel’s exceptional facilities, from wine tastings to a relaxing dip in the infinity pool.
Day 4: Wine Tasting & Vineyard Exploration in the Douro Valley
Spend the day uncovering the Douro Valley’s rich wine heritage. Begin with a private tour of a renowned port winery, learning about the centuries-old production process before sampling some of their finest vintages. Continue to a winery offering panoramic views, where you’ll enjoy a leisurely lunch paired with local wines. In the afternoon, visit another top producer for a final tasting before returning to Six Senses Douro Valley. Spend the evening at your own pace, indulging in the hotel’s spa treatments, enjoying dinner at their farm-to-table restaurant, or simply relaxing with a glass of wine on your private terrace.
Day 5: Journey from the Douro Valley to Sintra
Depart the Douro Valley and make your way south to the enchanting town of Sintra, known for its fairytale-like palaces and lush landscapes. Upon arrival, check in at Tivoli Palácio de Seteais, a grand 18th-century palace-turned-hotel. The rest of the day is yours to unwind—wander through Sintra’s picturesque streets, sip coffee in a historic café, or simply enjoy the luxurious surroundings of your hotel. In the evening, consider dining at a local restaurant to sample Sintra’s signature pastries and fresh seafood.
Day 6: Sintra’s Palaces & Hidden Gems
Step into a world of romantic architecture as your private guide takes you on a tour of Sintra’s most famous landmarks. Explore the whimsical Quinta da Regaleira, a palace surrounded by mysterious tunnels and gardens designed by an Italian opera set designer. Continue to the colourful Palácio da Pena, perched high on a hilltop with sweeping views over the countryside. Stroll through Sintra’s historic centre and enjoy lunch at a traditional restaurant before returning to Tivoli Palácio de Seteais for a relaxing evening.
Day 7: Sintra to Lisbon – Tasting & Sightseeing Tour
Depart Sintra and travel to Portugal’s capital, Lisbon. After checking into Tivoli Avenida Liberdade Lisboa, a historic luxury hotel, embark on a guided tour of the city. Wander through Lisbon’s vibrant neighbourhoods, sampling local delicacies such as pastéis de nata and bacalhau. In the afternoon, take a drive to the district of Belém, the historic launching point of Portugal’s great explorers. Visit the ornate Jerónimos Monastery and the iconic Torre de Belém before heading back to your hotel. The evening is free to explore Lisbon’s lively dining scene.
Day 8: Leisure Time in Lisbon & Sunset River Cruise
Enjoy a leisurely morning in Lisbon, revisiting your favourite sights or exploring new areas such as Castelo São Jorge or the trendy LX Factory district. In the evening, set sail on a scenic sunset cruise along the Tagus River. Relax with drinks and light bites as you take in the city skyline from the water, passing landmarks like the 25 de Abril Bridge and the Monument to the Discoveries. Return to Tivoli Avenida Liberdade Lisboa for a final evening in Portugal’s capital.
Day 9: Lisbon to the Alentejo – Roman Ruins & Wine Tasting
Travel east to the Alentejo, a region known for its rolling plains, ancient towns, and exceptional wines. Stop in Évora, the region’s capital, to visit its well-preserved Roman temple, impressive Gothic cathedral, and maze-like Moorish alleys. Just outside the city, sit down for a wine-tasting lunch at a prestigious vineyard before continuing to São Lourenço do Barrocal, a luxurious countryside retreat. Spend the evening exploring the sprawling estate or relaxing at the hotel’s award-winning spa.
Day 10: Relax & Unwind in the Alentejo
Enjoy a full day at leisure in the Alentejo. Take a bike ride through the estate’s vineyards and olive groves, indulge in a rejuvenating spa treatment, or simply relax by the pool with a good book. In the evening, dine at the hotel’s farm-to-table restaurant, savouring dishes made from fresh, locally sourced ingredients.
Day 11: Vineyard Tours & Stargazing in the Alentejo
Spend another day immersed in the beauty of the Alentejo countryside. Take a guided tour of the hotel’s vineyards, ending with a tasting of their signature wines. In the evening, embark on a private stargazing experience at the estate’s observatory, taking in the stunning night sky over the vast, open landscape.
Day 12: Farewell to Portugal & Departure
Say goodbye to Portugal as you journey back to Lisbon for your return flight home. If time allows, take a final stroll through the city or pick up last-minute souvenirs before heading to the airport. Your return flight will arrive the same day, marking the end of an unforgettable adventure.
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 specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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 travelling 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.
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