Tailor-made Holiday · Portugal
Discover Lisbon and Porto: A Tale of Two Cities
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Experience Portugal by exploring it's two most famous cities, Lisbon and Porto.
Rebuilt after the devastating 1755 earthquake, Lisbon emerged as one of Europe's most livable capitals. The city's neighborhoods each tell different stories: medieval Alfama with its fado houses where Portugal's signature music was born in the 1820s, party-central Bairro Alto, and maritime Belém where Portuguese explorers once planned their world-changing voyages.
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Fado music captures Lisbon perfectly. This haunting style expresses saudade and hearing it in an authentic casa de fado connects you directly to Portuguese culture.
Porto built its reputation on trade and hasn't forgotten it. The Romans called it Portus Cale, giving Portugal its name, and that practical spirit lives on. The UNESCO-listed Ribeira district's narrow medieval streets lead to the Douro River, where port wine caves hold vintages dating back centuries.
Port wine itself started by accident - 18th-century British merchants added brandy to preserve wine for the journey home, creating one of the world's great fortified wines. The azulejo tiles covering Porto's buildings aren't just beautiful; they're practical weather protection that doubles as storytelling art.
The Perfect Pairing
The three-hour train ride between them reveals changing Portuguese landscapes, but the real journey happens within each city. Lisbon's international energy balances Porto's regional pride. Both cities welcome LGBTQ+ travelers with genuine warmth, offering vibrant scenes alongside centuries of history.
This two-city combination works because it tells Portugal's complete urban story - from maritime empire to modern European nation - in two great cities.
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: Lisbon
When you arrive at the airport your driver will meet you and take you to your hotel. Once you’ve settled in you’ll be heading out to enjoy dinner at Adega Machado in the Bairro Alto district. Here you’ll discover Portugal’s great tradition of Fado music.
Day 2: Lisbon
Today you’ll embark on a guided walking tour of Lisbon. You’ll stroll through Praca do Comercio, Lisbon’s most iconic square. You’ll visit both the National Palace and the Gardens of Queluz – a remarkable example of the harmonious link between landscape and palatial architecture in Portugal.
At the Av Fontes pereira de Melo you’ll see the most photographed street art in Lisbon.
In the evening, dine at La Brasserie de L’Entrecote; a one of a kind restaurant inspired by the famous Cafe de Paris in Geneva.
Day 3: Lisbon
Wake up bright and early and take a half hour train ride to Sintra, a beautiful small town. Here you’ll find a lot of striking architecture.
Although Sintra is small it boasts considerable cultural riches. You’ll want to visit the ancient walls of the Castelo dos Mouros, a castle built by the Moors around a thousand years ago. At the Palacio Nacional, you’ll discover a stunning residence inhabited by Portugal’s aristocracy during the golden age of exploration.
After a traditional Portuguese dinner you’ll return to Lisbon.
Day 4: Porto
Take an early morning train to Porto. As its name suggests, Porto is a city known for its Port. When you arrive at the station your driver will meet you and transfer you to your hotel.
You can explore the city at your own pace. You’ll no doubt want to visit Cais da Ribeira – a pier with lovely views and plenty of bars and restaurants. This would be a good time to sample some of the city’s famous port.
Day 5: Porto
Take a trip to Ribeira Square, a UNESCO World Heritage Site. Visit the Igreja do Carmo, a historic church that showcases Portugal’s unique tile art. Then, take a boat across the river for a tour of Porto’s famous port caves.
Day 6: Porto
Head to the Vinicola Ramos Pinto winery for a tour of the vineyard and a wine and port tasting session. You may wish to purchase a bottle or two to take home.
If you have the time visit Farol Molhe do Douro. You’ll be greeted with beautiful views of the sea meeting the river, offering a quite reprieve from city life.
In the evening, head to A Bolina, a riverside restaurant serving traditional tapas.
Day 7: Departure
Once you’ve done some last minute shopping your driver will transfer you 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 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.