Luxury Portugal Vacations & Tours

Why should you travel on a luxury Portugal vacation with us?

Come for the dramatic, cultured coast of the Iberian peninsula. Stay for the Pastéis de Nata.

In 2005, we began charting the world as Black Tomato. In truth, we added destinations on an almost ad hoc basis – of those with which we had the strongest emotional connection. Portugal – we’ve consulted the notes, tattered as they are – was country no. 5. Why? Because of its unlike-nowhere-else cuisine, for the baroque-seaward cities of Lisbon and Porto, for its earthy, heavy-hitting wines and its gorgeous, easygoing hinterlands. Since those early days, we’ve built cast-iron connections with a host of local guides, partners and contacts; the same people who’ll ensure your luxury, bespoke trip to Portugal is as memorable as it first was for us.

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What to see and do in Portugal

Use this page as inspiration, then get in touch and together we’ll plan your perfect Portugal vacation.


Sitting snug in the crevice between Spain and the warm tides of the Atlantic, Portugal has all the vibrancy of its neighbor to the east, but with fewer crowds and a number of added hidden gems. Exuding a quiet confidence, a luxury vacation in Portugal lifts the lid on centuries worth of history and accompanies it with a side of delicious simplicity and beautiful scenery.


Wine production isn’t the only thing that Portugal’s Douro Valley does tantalising well. It’s a mecca for the romantic, thanks to its off-the-grid feel, charming mountainside towns and high-end boutique hotels. Whether you stay put in one of the region’s glamorous resorts or opt to cruise down the river and land in the dazzling city of Porto, a vacation to this region of Portugal will be bursting at the seams with phenomenal sunsets, personalized spa treatments, and private winery tours.


Lisbon has some sort of hypnotic essence about it. Sitting under the shadows of Castelo de Sao Jorge, the city smells of salty air, sounds like approaching cable cars, tastes like freshly baked pastel de nata, and embodies everything we love about the European lifestyle. For history lovers and sun seekers alike, our luxury tours of Lisbon include an insiders glance at both the city’s cultural sights and gastronomic delights, as well as a private venture to fairy tale Sintra.


From its expressive cities to its sun-drenched beaches and all of the lush valleys in-between, Portugal currently reigns as our most desirable and attractive Mediterranean country. In part due to its mouth-watering cuisine and partially due to our love affair with traditional fado music, we have this country to thank for welcoming zest and simplicity back into a sun soaked European vacation. A private tour of this seductive country will see guests discovering the Portuguese lifestyle and history from a handful of vantage points.


While Lisbon, Porto, and the Douro Valley may seem to be on everyone’s bucket list, Black Tomato doesn’t want you to limit your imagination. Thanks to our on-site experts and private local guides, the country’s more unspoilt and rural secrets can be yours to unearth. If you need convincing, a quick search of Portugal’s Alentejo region should do the trick.

The best of Portugal


Baroque stylings, steep hills, and clattering trams.

Lisbon is an adventurous, historic city. Hilly, labyrinthine, and culturally fascinating, our Black Tomato highlights are many. The 18th-century Four Seasons Ritz. A local historian to teach you about the iconic Seven Hills. A trip to the Grand Monastery, and a descent into the cellars of its Port District – where we’ll serve you a two-star Michelin meal, listening to the melancholic tones of live fado music.

Porto & the Douro Valley

Welcome to port country.

For over 2,000 years, the locals have been producing port in this stunning valley. And it has fed the city of neighboring Porto, too (the clue is in the name). You’ll set sail down the valley of Douro in a private yacht, with local wine tastings and visits to bucolic vineyards. In the city itself, enjoy an absolutely jaw-dropping meal at the Yeatman Hotel. It’s one of life’s major accomplishments, we think.


Sprawling. Traditional. Delicious.

This enchanting, traditional hilltop village – and its surrounding region – are a welcoming heartland for Portugal’s most traditional cuisine. Rolling, craggy hills, palaeolithic carvings, and Roman ruins stand side-by-side. Pork, game, bread, cheese, wine and seafood are its staples. And believe us when we say the locals know exactly what to do with them. It’s probably one of the world’s best surprises.

Bairro Alto Hotel, Lisbon

Step into Bairro Alto Hotel and take a moment to feel the energy of this city pulsating around you. A love letter to Lisbon, the…
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Sublime Comporta

Take a step back in time to Comporta and discover a picture-perfect paradise seemingly frozen in time. Set against silky white sand beaches and a…
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Sao Lourenco do Barrocal, Alentejo

Set in the rolling landscapes of The Alentejo, amid ancient holm trees, olive groves and vineyards, São Lourenço do Barrocal is a step back in…
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