Tailor-made Holiday · Portugal
7-Day Classic Portugal Tour: Lisbon, Porto & Sintra Highlights
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
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Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
This trips has been designed to introduce you to Portugal's highlights over a single week. Start in Lisbon, where the LGBTQ+ scene thrives in different parts of the city. The city's fado houses, cobblestone neighborhoods, and rooftop bars create a backdrop where you can be completely yourself. Alfama's winding streets lead to unexpected discoveries, and the view from Miradouro da Senhora do Monte is always a highlight.
The coast between Lisbon and Sintra delivers consistently. Estoril and Cascais have that effortless Portuguese elegance, while Sintra's palaces are genuinely impressive (not just Instagram-worthy). The Pena Palace's colors pop against green hills in a way that seems almost unreal.
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Porto shifts the energy north. The riverside setting and azulejo-tiled buildings create serious atmosphere, and the port wine tastings here go deeper than most places. You're not just sipping; you're understanding why this region matters to Portuguese culture.
The Vinho Verde region caps off the trip perfectly. The vineyard visits feel personal rather than commercial, and when local winemakers invite you to their table. These aren't staged experiences - they're how Portuguese hospitality actually works.
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: Arrival & Fado in Lisbon
Arrive in Lisbon, where a private transfer takes you to Heritage Avenida Liberdade, a refined boutique hotel blending history and elegance. In the evening, immerse yourself in Portugal’s rich culture with a traditional Fado performance in Chiado. This deeply moving musical tradition, recognized by UNESCO, captures the soul of Portugal. Enjoy an intimate performance accompanied by fine wine before returning to your hotel for a restful night.
Day 2: Lisbon’s Historic Wonders
Explore Lisbon’s layered history on a private guided tour, from the charming Alfama district to the grandeur of Belem’s UNESCO sites. Visit the Lisbon Cathedral, gaze over the city from Miradouro da Senhora do Monte, and admire the Jerónimos Monastery and Belém Tower. Discover Portugal’s Age of Exploration at the Monument to the Discoveries before enjoying leisure time to relax or explore more of the city. Return to Heritage Avenida Liberdade for the evening.
Day 3: Coastal Beauty & Sintra’s Fairytale
Journey along Portugal’s stunning coastline, stopping in Estoril and Cascais before reaching the dramatic cliffs of Cabo da Roca, the westernmost point of continental Europe. Then, explore Sintra, home to fairy-tale palaces and enchanting gardens. Wander its old town before visiting the vibrant and whimsical Pena Palace, perched high above the town. After a magical day, return to Heritage Avenida Liberdade for a final evening in Lisbon.
Day 4: Travel to Porto & Exclusive Wine Tasting
Board a train to Porto, where a private transfer brings you to the stylish Editory Boulevard Aliados Hotel. In the afternoon, enjoy an exclusive vintage Port wine tasting at Graham’s Port Wine Cellar, sampling exceptional vintages from 1994, 2000, and 2016. Savor gourmet cheese and fine chocolate truffles in an intimate setting before an evening at leisure to explore Porto’s riverside charm.
Day 5: Porto’s Cultural Icons
Uncover Porto’s UNESCO-listed historic center with a private guide. Visit the Porto Cathedral, enjoy panoramic views over the Douro River, and explore Batalha Square and Liberdade Square. Walk along Santa Catarina Street, famous for its lively shopping and historic cafés, before a stop in Ribeira Square. Savor a coffee and pastry in a charming Art Nouveau café, then return to The Editory Boulevard Aliados Hotel for an afternoon at leisure.
Day 6: The Vinho Verde Wine Experience
Venture into Portugal’s Vinho Verde wine region, where rolling vineyards and historic towns await. Explore Amarante, a medieval gem, before visiting a renowned vineyard to learn about the famous “green wine”. Follow the Romanesque Route, discovering ancient churches and castles, before heading to a boutique vineyard for an exclusive meal cooked by the winemakers. After this indulgent day, return to The Editory Boulevard Aliados Hotel for a final evening in Porto.
Day 7: Departure from Porto
Enjoy a seamless transfer to the airport, with optional assistance available. Reflect on a journey filled with coastal beauty, rich history, world-class wines, and soulful Fado music—a luxurious, inclusive adventure through Portugal’s most captivating destinations.
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.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.