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Tailor-made Vacation · Portugal

Spain and Portugal Tour: Barcelona, Madrid, Lisbon & Sintra

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Duration 9 days
From $8,060 pp
Trip type Tailor-made Vacation

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

A journey through two neighboring capitals and their satellite towns, taking in each city's own LGBTQ+ quarter along the way.

This luxurious journey through Spain and Portugal blends cultural discovery, world-class hospitality, and unforgettable experiences. The route moves between two capitals and the historic towns that shaped them, Toledo for Madrid and Sintra for Lisbon, tracing each country's golden age beyond its capital.

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Begin in Barcelona, where Gaudí's modernist masterpieces set the stage for the day, and an evening in the Eixample, one of southern Europe's most established LGBTQ+ neighborhoods, extends naturally from it. Beyond the city, Montserrat's mountaintop monastery offers a quieter counterpoint.

In Madrid, walk through the legacy of Spanish royalty, from Plaza Mayor to the Royal Palace, with Chueca, the country's LGBTQ+ hub since Spain's transition to democracy, a short walk away. Toledo follows, a UNESCO-listed window into the country's Christian, Jewish, and Muslim past.

Crossing into Portugal, Lisbon's LGBTQ+ scene centers on Príncipe Real, much as Chueca and the Eixample anchor Madrid and Barcelona. Explore the city's historic quarters before the coast: Estoril, Cascais, and Sintra's Pena Palace.

Five-star accommodations, private transfers, and curated experiences run throughout, returning you home with memories from two of Europe's finest countries.

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Day by day

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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 in Barcelona – A Warm Welcome

Upon arrival in Barcelona, meet your private driver for a seamless transfer to H10 Metropolitan, a stylish boutique hotel in the heart of the city, moments from Passeig de Gràcia and its run of modernist facades.

Your welcome package will be provided with all necessary travel documents, and a dedicated assistant will be on hand to guide you through check-in and answer any questions.

Spend the afternoon at leisure, soaking in the lively atmosphere of Las Ramblas, where flower stalls and century-old cafés line the boulevard down to the harbor, or unwinding at your hotel’s rooftop terrace as the city settles into evening.

Day 2: Barcelona – Gaudí’s Architectural Masterpieces

Embark on a full-day private tour exploring the visionary works of Antoni Gaudí. Wander along the elegant Paseo de Gracia, stopping at Casa Batlló and La Pedrera, two of Gaudí’s most iconic creations. Continue to the breathtaking Sagrada Família, where intricate designs and towering spires leave a lasting impression.

Explore Barcelona’s Gothic Quarter, admire the Roman walls, and stroll along the famous Las Ramblas. The day ends with a visit to Park Güell, where Gaudí’s colorful mosaics and imaginative structures overlook the city.

In the evening, the Eixample, a short taxi ride away, offers one of southern Europe’s most established LGBTQ+ neighborhoods for those who want to extend the day.

Day 3: Montserrat – A Sacred Mountain Retreat

Leave the city behind and journey into the Catalan countryside for a half-day visit to Montserrat, a sacred mountaintop monastery that has been a place of pilgrimage for nearly 1,000 years, its jagged peaks visible from Barcelona on a clear day.

Explore the Renaissance Basilica and view the twelfth-century carving of the Black Madonna, the patron saint of Catalunya, still visited by pilgrims who climb a narrow staircase behind the altar to touch the relic.

Take in sweeping views over the rugged landscape, where the mountain’s serrated silhouette gives Montserrat its name, before returning to Barcelona for an evening at leisure.

Day 4: Barcelona to Madrid – High-Speed Luxury & Historic Madrid

Board a high-speed train for a seamless journey to Madrid, arriving in just 2.5 hours. A private driver will take you to Hotel Atlántico, a refined hotel on Madrid’s famous Gran Vía.

In the afternoon, explore Madrid’s historic quarters on foot, uncovering the legacy of the Habsburg and Bourbon dynasties. Visit Puerta del Sol, Plaza Mayor, and the impressive Royal Palace, the largest in Western Europe.

Wander through medieval alleyways, discovering historic taverns and architectural gems before ending the day in the grand Plaza de Oriente, a short walk from Chueca, the city’s LGBTQ+ hub since the years following Spain’s transition to democracy.

Day 5: Toledo – A Journey into Spain’s Medieval Past

Travel to Toledo, Spain’s medieval capital and a UNESCO World Heritage Site, perched above a bend in the Tagus River that once made it nearly impregnable.

With a private guide, explore the city’s labyrinthine streets, visiting the stunning Toledo Cathedral, one of the largest Gothic churches in the world, the Santa Maria la Blanca Synagogue, and the formidable Alcázar of Toledo.

Learn about Toledo’s rich history as a melting pot of Christian, Jewish, and Muslim cultures, a coexistence known as convivencia, while admiring the city’s Gothic and Moorish architecture side by side.

Return to Madrid in the afternoon for an evening at leisure.

Day 6: Madrid to Lisbon – Arrival in Portugal’s Capital

Meet your private driver for an airport transfer and board a direct flight to Lisbon, crossing from Castile into a country with its own distinct rhythm and language.

Upon arrival, an English-speaking assistant will be waiting outside customs to greet you and accompany you to your hotel, Hotel Britania, a refined Art Deco-style retreat built during Lisbon’s 1940s heyday, in the heart of the city.

Receive a welcome package with relevant documents and tickets before settling in for the evening, perhaps with a glass of port to properly mark your arrival into Portugal.

Day 7: Lisbon – The City of Seven Hills

Explore Lisbon’s rich history with a private guide and driver. Visit Rossio Square in the heart of the city before venturing into Alfama, Lisbon’s oldest district, where winding streets lead to the Lisbon Cathedral and breathtaking views from Miradouro da Senhora do Monte.

Head to Belém, Lisbon’s monumental district, home to the Jerónimos Monastery and the Belém Tower, both UNESCO World Heritage Sites.

Conclude with a visit to the Monument to the Discoveries, a tribute to Portugal’s great explorers, before returning to your hotel. Príncipe Real, home to Lisbon’s LGBTQ+ scene, is a good option for the evening ahead.

Day 8: Lisbon, Estoril, Cascais & Sintra – A Coastal Escape

Enjoy a scenic drive along Portugal’s stunning coastline, stopping at hidden sandy beaches and historic fortresses built to guard the mouth of the Tagus. Visit the elegant resort town of Estoril, once a haven for exiled European royalty and wartime spies during the Second World War, and stroll along the Tamariz Beach promenade.

Continue to Cascais, a vibrant fishing village turned luxury retreat, before heading to Cabo da Roca, the westernmost point of continental Europe, where the Atlantic stretches uninterrupted toward the horizon.

In Sintra, wander through the old town’s charming boutiques and pastry shops before ascending to the magnificent Pena Palace, a whimsical fusion of Gothic, Moorish, and Manueline styles perched atop the hills in a fog that gives the town its particular, otherworldly character.

Day 9: Departure from Lisbon – A Graceful Farewell

Bid farewell to Portugal as your private driver transfers you to the airport for your onward journey, tracing the route back along the Tagus one final time.

If desired, an English-speaking assistant can accompany you to ensure a seamless departure experience, closing out a journey that carried you from Catalonia’s modernist ambition through Castile’s imperial past and into Portugal’s own age of discovery.

Our Experts

Dionne Charles
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.
Dionne Charles Luxury Travel Expert
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Maria Gardner
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.
Maria Gardner Luxury Travel Expert
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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.

Did you know?

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.

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Our charity partner

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.

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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.

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