City Escape to Alentejo: Vineyards, Medieval Villages & Viewpoints
8 hours
Day Trips
Lisbon
Choose one of 15 locals available
Experience hosted by Luis, Rui & other locals
Private Tour
Carbon Neutral
Imagine this: a scenic road trip from Lisbon to explore the enchanting Alentejo region, filled with medieval villages, stunning viewpoints, rolling landscapes, vineyards, and cultural treasures. Sounds like a dream? No, it’s possible on a Withlocals day trip with a local host leading the way!
Destination
Lisbon, Portugal
Category
Day Trips
Duration
8 hours
Transport mode
Car
Available languages
English, Português, Español, Română, Русский, Deutsch, Français
Included
Private Guide
Transport by Car
All Withlocals Tours are Carbon Neutral
Excluded
Entrance to Attractions
6 reasons to book this tour
Discover the region off the beaten path
Check out the Roman Temple of Diana & Cathedral of Evora
Connect with a local & discover their culture
Take in breathtaking sceneries & panoramas
Enjoy the freedom to make stops along the way
Can be 100% personalized to your wishes
What you can expect
Maximize your trip by experiencing the treasures of Alentejo! Discover the region’s beauty as you explore a mix of highlights and hidden gems along the way.
Forget crowded tourist buses — let a local host guide you through Alentejo, your way! Spend the day uncovering the incredible sights that lie just outside Lisbon. Trust us, they're worth it! Your knowledgeable host will lead you on a scenic road trip, with frequent stops to take in the surprises this region offers. Visit iconic sites like the Roman Temple of Diana, the Cathedral of Évora, and the Monsaraz Castle, while enjoying breathtaking views throughout the journey.
Alentejo is also known for its exceptional wines, and if you’re interested in a wine tasting, your host can arrange one for you! Simply contact your host in advance to personalize the experience.
With a convenient pick-up and drop-off/meeting point, all you need to do is sit back, relax, and enjoy the ride. To make the experience even more special, you can choose your local host for the day. Each host will craft a unique journey based on their passions and expertise, while also considering your interests.
Our local hosts are natural storytellers, each with a different background ranging from arts and history to real foodies. They can't wait to share some of their unique stories and let you connect with their culture in an enjoyable and inspiring way! Feel like changing the route a bit? No problem, the hosts will be happy to personalize the tour to your wishes.
Choose your local
Get to know these 15 passionate locals, each bringing unique perspectives and talents. Choose your favorite, check their availability, and book to create an unforgettable adventure tailored to you.
Luis
The Local Guide
4.9435 reviews
Deutsch・Français・English
Rui
Lisbon wonders
5.04 reviews
English・Português
Bruno
In love with the country, let me show you!
5.03 reviews
English・Español・Português
Mauro
The Comedian Guide
5.0
English・Español・Português
Miguel
The Portuguese Buddy
5.031 reviews
English・Español・Português
Stasea
Travel enthusiast
5.010 reviews
English・Română・Русский
Carlos
Your eclectic guide
5.0
English
Joao
Local Private Guide & Friend
5.03 reviews
English・Português
Luis
History, Architecture and good food!
5.08 reviews
English・Español・Português
Tiago & friends
The Unconventional Historian
5.0
English・Español・Português
Rui
The Personalized Tour Guide
4.51 review
English・Português
Alfredo
The no stress host...
5.0
English・Português
Miguel
Professional Friend for a Day
5.0
English・Português
André
The All Around Guide
5.025 reviews
English・Português
Diogo
The Urban Beatboxer
4.9254 reviews
English・Español・Português
This is the plan
Check out the plan below to see what you'll get up to with your local host. Feel free to personalize this offer with the host of your choice.
Meeting point
Meet at - Lisbon to start your journey
Itinerary
This is what our experience could look like, but it’s not set in stone! Once you book, you can chat directly with your host to make small tweaks to suit your preferences.
Convenient Pick-up & Drop Off
On the day of your day trip, your local host will pick you up from your accommodation or an agreed location. Once the day trip comes to an end, they’ll drop you off at your accommodation
Scenic Trip
This full-day trip is arranged for you, so all you have to do is enjoy the sights as your host takes you through Alentejo while telling you incredible stories and insights
Only You & Your Host!
Forget about cramped touristy buses, on this private day trip, you’ll have all of your host’s attention. Get the chance to speak 1-1 and get all of your questions answered for a personal experience that will make this trip more memorable
What’s in Store for You
Check out from viewpoints, nature, and cultural gems such as Roman Temple of Diana, Cathedral of Evora and Monsaraz Castle plus other stops your local host has prepared for you along the way
Optional Lunch
Along the way, your local host will recommend you typical and local places where you can stop to have lunch and catch a break. Lunch is not included in the price
Make it yours
Want to tweak the itinerary? Book directly & chat afterwards with your host to adjust highlights, skip stops, or make small changes to fit your preferences.
Book risk-free: Cancel within 24 hours for a full refund.
Need something special? Personalize your experience for more time, alternative locations or a completely tailored plan.
Flexible cancellation policy
Feel confident booking
Cancel within 24 hours for a full refund. Even up to 7 days before your experience, you’ll receive a refund, minus the service fee.
Change of plans?
Reschedule your experience to a date and time that works best for you.
Loved by travelers worldwide
Simple and flexible – your plans, your way.
Reviews from guests
Joy
(About local )
22 April 2025
We highly recommend Luis. Luis took us on a 3-hour walking tour of Lisbon the day we arrived, and then he took us on two one-day tours on subsequent days to several neighboring towns. He was flexible, accommodating, and congenial. Luis was very knowledgeable about the country, region, sites (touristy and off the beaten path), and history. He made great suggestions on what to do and was responsive to our inquiries. His car was clean and comfortable, and we felt very safe in his hands. In all, a delightful, stress-free way to get to know Lisbon and Portugal. We highly recommend Luis
Irini
(About local )
21 April 2025
We had the pleasure of touring with Rui through WithLocals, and it was truly an unforgettable experience. Rui is incredibly polite, friendly, and made us feel at ease right away. With over 20 years of experience as a guide, he impressed us with his deep knowledge of history and culture—he had something interesting to share at every stop. He drove us from Óbidos to Nazaré and then to Fátima, making each destination come alive with stories and insights. His enthusiasm and passion turned each day into a unique and memorable experience. Thanks to Rui, our trip was not just sightseeing—it was a meaningful journey. Highly recommended! Easily 10/10Great trip to Nazare and Fatima with Rui
Todd🇺🇸 United States
(About local )
12 April 2025
My wife and I enjoyed a wonderful day trip to Sintra with Luis! Although we endured some rain during the first half of the day, Luis made the best of it and enabled us to enjoy all of Sintra and the surrounding area. Luis' deep knowledge of Portuguese history is amazing, which brought the diverse background of Sintra to life for us. I cannot recommend Luis more for a visit to Sintra or anywhere else in the Lisbon area!Fantastic day in Sintra!
Marsha
(About local )
12 April 2025
Sofia knows and loves Sintra! She met us at our hotel and we had a wonderful day. We went to her favorite local seafood restaurant and had sea bass caught that morning. Fantastic! A storm one week before we arrived caused major damage to trees and roads, so she had to adjust the itinerary, and took us to other beautiful spots along the coast. We even got to visit a local winery and craft beer brewery. What fun! Thank you, Sofia!!Great intro to Sintra!
David🇺🇸 United States
(About local )
9 April 2025
We loved our trip to Evora with Luis. First, Evora is a beautiful walled city with great character. The roman ruin, churches and cathedral were a great draw, but it was walking the streets and seeing the shops we loved the most. It was also wonderful to be outside of Lisbon for a day and see the countryside.
Second, Luis was a terrific guide for us. From the car ride first thing in the morning until the return trip in the afternoon he was filled with information. He weaved together questions we had from other tours with new information about our visit to Evora and really helped us form a more complete picture of Evora, Lisbon and Portugal (people, places, culture and history). He is a wealth of knowledge that flows in conversations and stories and kept us engaged all day. We highly recommend him for any tour and appreciate that he made our day very fun.Evora Day Trip with a Great Guide
Faith
(About local )
7 April 2025
Our guide, Stasea, was really helpful and knowledgeable. She guided us through each destination and also gave us ample self time for pictures. The small group size of 6 made it optimal to learn more about the place and get to know each other better. I have done many small day tours before and I must say this is one of the best I've had. Highly recommended!Highly recommended!
Gail
(About local )
7 April 2025
Our travel guide (Migel) was excellent. Friendly, helpful and knowledgeable.
Sintra & Cascais & Quelez was fabulous! Only disappointment was the weather on the day as it was cloudy & raining intemittantly, this meant that we could not go to Pena Palace due to poor visibility. This was extemely disappointing as Pena Palace was the main reason I wanted to go to Sintra. Anyway, the rest of the tour was fabulous.Tour of Sintra, Cascais & Quelez Palace
Alessia
(About local )
4 April 2025
Miguel is a great guide!! Enjoy a beautiful and consigliata excursion! Abbiamo riso, scherzato and è super preparation in your land!Miguel is a great guide
Unknown
(About local )
2 April 2025
Amazing tour, very beautiful places and Stasea is an amazing guide, his knowledge about these places made the tour even more interesting. Thank you!A beautiful and interesting walk
Lenade
(About local )
31 March 2025
Ótima! O guia Miguel maravilhoso, uma pessoa muito culta.Ótima!
Lucas
(About local )
30 March 2025
Guia Miguel muito atencioso, conhece a região e a história do lugar. Muito bom e muitas dicas boas também.Guia Miguel muito atencioso
Fabrizzio
(About local )
30 March 2025
Foi ótimo do do início ao fim! Pontualidade, segurança, transporte e o guia gente boa pra caramba!!! Indico muito!Foi ótimo do do início ao fim!
Alexis
(About local )
30 March 2025
This was a wonderful tour and our guide Stasea was very pleasant. She spoke in detailed ways about the historical aspects of the place we visited. I felt like I learned so much from her. She was friendly and flexible while still keeping everybody on schedule. The van we traveled in was very nice and comfortable. Highly recommend!This was a wonderful tour
ELI🇦🇺 Australia
(About local )
29 March 2025
Rui was the best the overall experience was way beyond what I thought it would be could not recommend more highly thanks for a great day out 👍What a great day out
Yvette
(About local )
26 March 2025
Se eu pudesse dar 10 estrelas a esse passeio, eu daria! Miguel foi tão bom! Ele deu muita história e informações incríveis sobre Sintra, Cascais, Regaleira, Portugal e Lisboa! Ele é um residente de Sintra, nascido e criado e isso fica evidente! 100% recomendaria isso para quem pensa em fazer uma viagem de um dia!Meu passeio de um dia favorito! 10 estrelas!!!
Manuella
(About local )
26 March 2025
Great experience, the guide Miguel was very attentive, helpful, excellent!Great experience
sallyv69
(About local )
25 March 2025
We had such an amazing day with Rui as our tour guide
Very helpful and extremely informative about the area
Definitely recommend with Rui
********** starsWonderful tour in sintra and cascais
Maria
(About local )
25 March 2025
I just did my first day tour with a guide and I LOVED it! I travel a lot, but always without a guide. This time my friends and I decided to book a tour and we couldn't be happier with our experience. A huge thank you to tour guide Stanislava! She did an exceptional job planning our tour of the beautiful cities of Portugal. Her knowledge of Portuguese history, culture and cuisine is unbelievable.
I would definitely recommend her without hesitation to anyone planning a trip to Portugal.An incredible unmissable tour!
Anthony
(About local )
25 March 2025
Miguel was a very good guide who was able to speak French and pick us up from our place for the day tour. He was very kind and flexible and thanks to him we got to see a very nice and lovely place. Thank you very much Miguel :)Miguel was a very good guide
Andrea
(About local )
24 March 2025
A very well organized tour. Would like to commend our tour guide Stasea. Tour was flexible depending on the weather conditions as the day started out with foggy conditions. The guide also helped us to avoid the massive rush of peoplewell organized tour
Juan
(About local )
22 March 2025
Today’s trip was a refreshing and well-organized experience, blending stunning sights with smooth logistics. The highlights included engaging moments of discovery and relaxation, leaving a lasting impression. Overall, it was a day filled with great memories and inspiration for future adventures.
Great Experience
Elizabeth
(About local )
20 March 2025
Miguel was the perfect tour guide for us! This was our first trip to Portugal, and we have fallen in love! The scenery is beautiful, and the people are the friendliest we’ve encountered anywhere. Miguel spent the day with us touring Sintra and Cascais. He is an awesome tour guide, extremely knowledgeable of the Portuguese history and arts. His English is flawless. Best of all, he was able to customize our tour based on our interests. Highly recommend this tour.Sintra and Cascais, A Perfect Day
Susy
(About local )
17 March 2025
Luis was incredibly kind and well informed! I learnt a lot from the tour, although conditions were windy we were grateful to have had an informative guide to help us brace the winds! Not having to queue for the attractions was also a big plus!Amazing guide Luis
Deena
(About local )
14 March 2025
Oliver was an excellent guide - very fun, kind, and knowledgeable. He was flexible with our day and made sure we saw what we were interested in. Great experience - highly recommend!Sinta, cascais, cabe da roca day trip
Linda
(About local )
11 March 2025
⭐️⭐️⭐️⭐️⭐️
Diogo was absolutely the star of our tour! Not only did he tell us everything we needed to know about Lisboa, but he also took us to places we would have never discovered on our own. His enthusiasm, humor, and charm made the experience unforgettable.
He really went above and beyond 😉. If you’re booking a tour, make sure to ask for him—you won’t regret it! 🎉Amazing tour! Amazing guide!
Anne
(About local )
11 March 2025
was a great day. Miguel is positive, helpful and knowledgeable. The toughest part was the traffic out of Lisbon - but after that- smooth sailing. And we set the pace. Miguel is very accommodatingit was a great day
Scott
(About local )
9 March 2025
Miguel was our guide. He was on time to meet us at our hotel. He is personable. His English is excellent. He planned the day so we seemed to be ahead of any crowd. He knew how to balance guided time and time on our own at each site. He obviously knew in depth information about our destinations and told us a lot about each. He was not a clock watcher in a good way. He let us set the pace of the itinerary. He even added a stop that we asked about that was not on the tour, but on the way. We recommend this tour in general and Miguel in particular without hesitation.Miguel was our guide
Rosemary
(About local )
4 March 2025
Great day spent visiting the Pena Palace Gardens, Sintra, the coast and lastly Cascais. Great time spent with our friendly, knowledgeable and interesting guide, Miguel. He kindly adapted part of the tour to suit our needs and made great suggestions for coffee and lunch. All in all an amazing day. Highly recommended.Great day
Victoria🇺🇸 United States
(About local )
4 March 2025
We spent the day with Luis who took us to Sintra and the Pena Palace. It was a wonderful day; he was informative, friendly, thoughtful, and pivoted to accommodate some weather changes to pack as much into the day as possible. His knowledge about Portugal history is worthy of an historian! We would love to have another tour with him in the future and highly recommend him.Fantastic day
Tom
(About local )
4 March 2025
The trip was really good and would highly recommend the tour but for me, Miguel was
an absolute gentleman and just an all around lovely bloke, never left a review for anything before but genuinely just strongly wanted to say if there are a few opinions for various tours, pick this oneThe trip was really good and would highly recommend
Jerry
(About local )
2 March 2025
Rui is an amazing tour guide. He is kind & knowledgeable; and makes even a rainy day, a fantastic experience.
We got to see three unique towns of Portugal; which gave us another opportunity to understand the culture, landscape, and history of the Portuguese people. I would highly recommend this tour as an addition to your stay in Lisbon; and the experience wouldn’t be complete without Rui as your guide. A great experience
Emma
(About local )
2 March 2025
Este passeio foi fantástico, Miguel é um excelente guia. Dia inteiro, Hotel pegar no 745, pequeno tour, parou para fresco, local, Pastel de nata em caminho para o Palácio da Pena. Chegou antes das 9, bateu as filas e as multidões. Miguel nos deu a história e tempo para ver tudo. Próxima parada, cidade de Sintra e Quinta a Regaleira. Mais uma vez, Miguel nos deu a história, e permitiu tempo para ver tudo. Quinta a Regaleira, era bonito, muito calmo e pitoresco. Iniciação bem é uma obrigação. Cidade de Sintra, teve tempo suficiente para visitar a área judaica e o Palácio Nacional de Sintra, sem se sentir apressado. A próxima parada é a cidade costeira de Cascais. Na praia, este foi um destaque para nós, recomendaria que as pessoas ficassem aqui em vez de Lisboa. Grandes vibrações, belos bares e restaurantes, variedade de lojas, um hangout local, trens diretos para Lisboa até 1 da manhã! ! Regressou ao hotel às 17h. Obrigado Miguel, definitivamente recomendaria que você esteja visitando qualquer pessoa que visite a área de Lisboa!
Saiba mais sobre - Visita de grupo pequeno a Sintra, Pena Palace, Regaleira e Cascais - https://www.viator.com/pt-BR/tours/Lisbon/Small-group-tour-to-Sintra-Pena-Palace-Regaleira-and-Cascais/d538-41021P1?mcid=56757Este passeio foi fantástico
Barbara
(About local )
1 March 2025
Highly recommended tour. Miguel is an excellent guide, very knowledgeable about all aspects of the trip and fantastic customer service. I had a great day.Highly recommended tour.
Dana
(About local )
1 March 2025
The best trip in Portugal! Amazing views! Miguel, is one of the best guides we had. Thank you for the amazing time we spent together!The best trip in Portugal
Dee
(About local )
1 March 2025
What a wonderful way to see Lisbon. I took this tour with my family including my parents (almost 80). Luis was fantastic, so knowledgable and interesting, ready for every question we had. Luis was able to adapt the tour to suit us and went exactly at the pace we needed. Couldn’t recommend this enough. Thank you Luis
Super tour! Make this the first thing you do!
Tamyris
(About local )
28 February 2025
Foi um passeio de um dia maravilhoso que fizemos em família, para Fátima, Nazaré e Óbidos. Escolhemos fazer o tour com o João Xavier, melhor escolha que fizemos. Foi um dia super agradável, ele levou em todos os pontos turísticos, tivemos tempo de ver e visitar tudo. O preço foi o mesmo do que cotamos com outras empresas, e mais barato que fechar pelo site ou aplicativo de fora, então valeu muito a pena!
O João é super simpático e acolhedor, nos explicou a história por trás de cada ponto histórico e nos acompanhou nos passeios, o que foi ótimo! Recomendo demais fechar o passeio com eles.MELHOR OPÇÃO DE PASSEIO PARA FÁTIMA, NAZARÉ E ÓBIDOS
Kim
(About local )
26 February 2025
We hebben een super mooie geweldige dag gehad. Onze gids Miguel was echt geweldig en nam de tijd voor ons en regelde als helemaal top. we hadden overal super veel tijd om alles te kunnen bekijken en beleven! Het was een top dag, dank je wel Miguel.We hebben een super mooie geweldige
Rafiah
(About local )
15 February 2025
Miquel fez a viagem incrível!! Bela experiência e recomendoMiquel fez a viagem incrível
Alessandria
(About local )
13 February 2025
Our guide was phenomenal! So knowledgeable, funny, and patient with our large group. I highly recommend a tour with Stasea!Highly recommended!!
Susanne
(About local )
9 February 2025
What a great day of touring wineries, markets and title factory!! Oh and also great food! João our guide was absolutely fantastic and on of the best tour guides we have had! I highly recommend this tour and guide!!Amazing Tour!
mabellev
(About local )
7 February 2025
Amazing trip. Stassia was a great tour guide. We're able to see the village of the shepherd's children in Fatima which my favourite part of the tour.Amazing trip
Marcela
(About local )
1 February 2025
Fue increíble! Miguel hizo todo con mucho cariño y es súper simpático, atento, divertido y hizo un excelente trabajo. Me encantó y cuando vuelva a Portugal repetiré con el mismo guía. Y el paseo todo increíble!!!Fue increíble!
Klaudia
(About local )
1 February 2025
Foi uma ótima viagem! Miguel é um guia incrível e nos divertimos muito! Eu recomendo!Foi uma ótima viagem!
Clare
(About local )
28 January 2025
Miquel was very informative and lovely to chat with. Our trip to Pena Palace was cancelled but he took us to other places. Our day wasn’t spoilt by this and Sintra is beautiful. Really enjoyed the day!!Miquel was very informative
Raul
(About local )
27 January 2025
Luis is a very knowledgeable guide with a lot of knowledge about the history, architecture and events that we visited. He kept us informed and entertained at all times. The cakes were delicious and are part of the tour. You don't just eat them, he also takes you to see how they are made. Thanks again Luis for a special day.Luis is a very knowledgeable guide
Amee
(About local )
26 January 2025
Tivemos um tempo maravilhoso visitando esses locais e nosso guia turístico foi incrível! Ele foi muito útil e divertido estar por perto.Tivemos um tempo maravilhoso...
Joel
(About local )
17 January 2025
Miguel is EXCEPTIONAL!! We loved our tour so much!!! He is very knowledgeable, engaging and absolutely WONDERFUL!! Highly recommend this tour to see some of the most BEAUTIFUL places you can imagine!!! Thank you Miguel for making this tour the absolute highlight of our entire trip to Portugal!!
Exceptional tour with an AMAZING tour guide, Miguel
Raymond
(About local )
16 January 2025
Miguel was a fantastic tour guide. He studied history so very informative. He was also funny and has a very positive vibe with good energy. Like hanging out with an old friend. He gave us plenty of time and options. Highly recommended.Miguel was a fantastic tour guide.
Miguel
(About local )
16 January 2025
Best Tour I had in Portugal. Me and my wife loved everything. The guide was amazing. Very friendly and he knows a lot. He also avoid all the touristic places. It was a very relaxing day. With so many tours to Sintra for sure this was the bestBest Tour I had in Portugal
Sindy
(About local )
3 January 2025
El guía Miguel ha sido muy amable, con recomendaciones pertinentes y siempre solucionando todo. Muy puntual y correcto, realmente lo recomiendo.El guía Miguel ha sido muy amable
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