Southern Portugal – Lisbon & the Alentejo

Discover the beauty of Southern Portugal with a journey through Lisbon and the Alentejo, exploring vibrant cities, historic sites, and indulging in world-class wines with authentic cuisine.

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Exploring Southern Portugal on Our Small Group Tour

Take a sensory trip through Central and Southern Portugal, exploring the vibrant city of Lisbon and the picturesque Alentejo region. In Lisbon, wander through cobbled streets, savoring traditional Portuguese dishes like pastéis de nata and grilled sardines. Visit historic sites such as Belém Tower and Jerónimos Monastery, soaking in the city's rich cultural heritage. Then, venture into the Alentejo countryside, where vineyards sprawl across rolling hills. Sample exquisite wines like Vinho Verde and Alentejo reds, paired perfectly with local delicacies such as creamy cheeses and succulent cured meats. Immerse yourself in the relaxed pace of life, breathtaking landscapes, and warm hospitality of this enchanting region. Wine cultivation is thought to have been introduced to this land, now Portugal, during the Bronze Age. It was such a good idea that they never stopped cultivating it! The first wines came out of the Lisbon area, in areas where they still produce today, the Setubal and Azeitão regions. Portugal has over 250 native grape varieties and 15 different wine regions, two of which (Douro and Pico Island) are protected by UNESCO. This trip will introduce you to three (3) regions specifically: Colares, Setubal, and Alentejo.

  • When October 4 2025 - October 12 2025
  • Duration 9 days
  • Price $4,500 per person
  • Availability Limited spots

What's Included

  • 9 days, 8 nights
  • 4 nights in 4-star Hotel Lisboa Plaza, in Lisbon
  • 4 nights in 4-star Évora Olive Hotel, in Évora
  • Airport transfer to hotel on arrival day
  • Airport transfer from hotel on departure day
  • 17 meals, including multi-course meals with wines
  • Local transportation via luxury coach and dedicated driver throughout the itinerary
  • Dedicated expert Portuguese tour guide throughout the itinerary
  • Full-time tour leader and wine host
  • 4 private winery tastings in three (3) wine regions (Colares, Setubal, and Alentejo)
  • 4-hour Lisbon tour, walking and by tuk-tuk
  • Guided visit at Sintra National Palace
  • Walking tour in Evora city center with a local guide
  • 4x4 cork estate tour in the countryside outside Évora
  • Visit to Estremoz Puppet Interpretive Center
  • Porters (1 large luggage piece per person) at each hotel, arriving and departing

Your Itinerary

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Group transfer from Lisbon airport to the hotel. You will stay for the next three nights in a four-star hotel in the city center. Lisbon, the capital of Portugal, is one of the most beautiful capitals of Europe. It is a quiet city where you can enjoy walking in the narrow streets of the old quarter, resting in the elegant and busy esplanades of downtown, or taking the tram uphill. Here, you can visit impressive monuments of very different eras, Roman times up until modern days, not forgetting the era of the discoveries and the commercial contacts with Asia and India. Lisbon's history is not only in museums but in its streets and buildings. It is a great walking city. (Ladies are advised to wear comfortable shoes and avoid high heels) 05:30 pm – Meet Sam and our local tour host Inês for orientation at Hotel Lisboa Plaza, in Lisbon 06:30 pm – Dinner at a local restaurant within walking distance.

Accommodation Hotel Lisboa Plaza, in Lisbon Included Meals Dinner

10:00 am – Tuk-tuk and gastronomic tour around the city. A four-hour tour through the city gastronomy and culture, walking and by tuk-tuk, and visiting the most emblematic neighborhoods of Chiado, Baixa, and Graça. We will have the opportunity to savor Portugal’s gastronomy, get acquainted with our traditions, and learn about the history of the country and the city of Lisbon. The rest of the day is free. Dinner on your own. We will have restaurant recommendations.

Accommodation Hotel Lisboa Plaza, in Lisbon Included Meals Breakfast; gastronomic experience, including drinks.

09:15 am—Today, we will take a minibus to Sintra, Portugal’s most romantic town, located close to the ocean, 40 minutes drive from Lisbon. Upon arrival, guided visit to Sintra National Palace. This is the oldest National Palace in Sintra. It was built over the centuries, probably in the 10th century, when Sintra was still a Moorish town. The king's presence in the palace was frequent over the centuries, not only because it was much cooler than Lisbon but also because hunting was abundant in the area. Today's palace is a mixture of styles, making it a great palace to introduce Portuguese History. The visit should end by 11:30 a.m. You will have free time to explore Sintra and the small local shops. Eventually, you will visit the Palácio da Regaleira on your own, a private palace with a mystic garden and park. You will have lunch in one of the local restaurants. 03:00 pm – Group meeting and departure to the Colares Winery, the oldest Cooperative Winery in Portugal, dating from 1931. Colares wine region is the smallest in Portugal. It is also one of the oldest demarcated wine regions, dating from 1908. Tasting of two of these unique wines, along with tapas from the region. 06:00 pm – Transfer back to your hotel in Lisbon. Meals included: Breakfast, wine, and tapas tasting. Dinner on your own. We will have restaurant recommendations.

Accommodation Hotel Lisboa Plaza, in Lisbon Included Meals Breakfast

09:00 am – Check out. Time to say goodbye to Lisbon and drive south. The first stop will be just 45 minutes south of Lisbon, in the region of Alentejo, for a wine tasting. The wine tables from this region are quite appreciated, but most foreign people will immediately recognize the Setubal Moscatel. We can choose to visit the José Maria da Fonseca Wine Cellar or the exquisite Bacalhoa Wines, which taste can be made in the beautiful Renaissance palace, surrounded by beautiful gardens and Portuguese tiles. Wine tasting will include tasting the delicious bread and cheese of the region. After this visit, we can drive directly to Evora, approx. 1h30 drive, or stop for a fresh fish lunch on our own at Setubal (not included). The drive to Évora is pleasant, on the highway, across the green plains of the Alentejo. Arrival to Évora: We will stay in a 4-star hotel in Évora's old town center for the next four nights. Minibuses are prohibited in the city center but can stop 200 m from the hotel door. We will have porters, but each guest is requested to take his/her hand luggage. 04:30 pm – Evening walking tour in the city center with a local guide. Évora is the capital city of the province of Alentejo, in the south of Portugal. Due to its well-preserved old town center, still partially enclosed by medieval walls, and many monuments dating from various historical periods, including a Roman Temple, Évora is a UNESCO World Heritage Site. It is also a member of the Most Ancient European Towns Network. The history of Évora is more than 2000 years old. It was known as Ebora in the period of the Celts; the Romans conquered it in 57 BC and expanded it into a walled town. Ebora became a flourishing city, as it lays at the junction of several main routes. During the barbarian period, the city declined. Still, with the arrival of the Moors in 715 AD, it slowly began to prosper again and developed into an agricultural center with a fortress and a mosque. The current character of the city provides evidence of this Moorish influence. In 1165, Évora was conquered by the Portuguese, which has had an important role in Portuguese history ever since. The walking tour will end in one of the small local restaurants, serving delicious local food. (sunset will be at 05:35 pm)

Accommodation Évora Olive Hotel, in Évora Included Meals Breakfast, Wine Tasting with cheese and bread, Dinner.

09:00—Departure by minibus. Today, we will discover how much the Romans and the Moors' presence has influenced the local culture over the centuries. This is true in the architecture, with the small, white-washed houses, and in agriculture, wine production, and crafts. A 40-minute drive will take us to a small village known for its traditional pottery. We will then visit some pottery workshops. Continue to another small town where the millenary wines of Talha are produced the same way as the Romans did. Visit a local winery and tasting of this unique wine. Lunch at a local restaurant. After lunch, visit the factory where the traditional wool rugs and blankets are handmade, using the same artisanal methods they used when they first started in the 16th century. 03:30 pm — We should be ready to visit the small medieval walled village of Monsaraz, which is on top of a mount and offers amazing views over the plains and the artificial Alqueva Lake. Monsaraz has nice craft shops and some bars, where people can sit and relax over a glass of wine. It is a great place to watch the sun fade before returning to Évora. (sunset 05:36 pm) The trip back to the hotel should take approx. 50 minutes. Meals included: Breakfast, wine tasting, lunch

Accommodation Évora Olive Hotel, in Évora Included Meals Breakfast, wine tasting, Lunch

09:00 am – Departure to a wine and cork estate located 40 minutes away from Évora. Upon arrival, we will be greeted and taken on a 4x4 tour around the property, which will explain all about wine and cork. Wine and local product tasting. After this tasting, our hosts will take us to a local restaurant for a delicious local lunch. After lunch, we will proceed to Estremoz, a beautiful town with a castle on top of a hill. Time to visit the Estremoz Puppet Interpretive Center (small clay figures, representing the local culture and professions) or just wander on your own. Before leaving for our hotel, time for the last wine tasting of the day, a local producer in this region. We will not visit the winemaking area, only the cellar and the shop. Transfer back to the hotel will take approx. 40 minutes. Meals included: Breakfast, Wine Tasting, and lunch.

Accommodation Évora Olive Hotel, in Évora Included Meals Breakfast, Wine Tasting, Lunch.

10:30 am – Departure from your hotel. 11:30 am – Arrival to Herdade do Sobroso. Wine tour and light lunch with wine pairing. Return to Évora after lunch to allow free time in the city for last visits or shopping. Dinner in a local restaurant.

Accommodation Évora Olive Hotel, in Évora Included Meals Breakfast, Lunch with wine paring, Dinner

10:00 am – Departure to Lisbon 11:30 am – Arrival to your hotel in Lisbon. The rooms will be available only after 03:00 pm. This day will be a holiday in Portugal, but most shops will be open. You can use this day to visit Belém Monuments on your own. 07:00 pm – meeting at the hotel lobby for our farewell dinner. Meals included: Breakfast, Dinner

Accommodation Hotel Lisboa Plaza, in Lisbon Included Meals Breakfast, Dinner

Group transfer out to Humberto Delgado Airport (LIS)

Included Meals Breakfast

Your Organizer The Crush Wine Experiences Difference

We create curated experiences around 4 things: wine, food, entertainment, and culture. We are steeped in the world of winemakers, distillers, and artisan food creators in each destination. We are a family-owned & family-run enterprise–hospitality is at the heart of everything we do.

Architecture, History, and Culture Lisbon

  • Historic Charm: Lisbon’s cobblestone streets, ancient buildings, and iconic neighborhoods like Alfama and Bairro Alto bring the city’s rich history to life.
  • Vibrant Culture: Known for its traditional Fado music, colorful tilework, and lively festivals, Lisbon offers an authentic cultural experience.
  • Scenic Views: With its seven hills, Lisbon has countless viewpoints and terraces (miradouros) overlooking the Tagus River and cityscape.
  • Gastronomic Delights: Lisbon is a foodie haven, famous for fresh seafood, pastel de nata (custard tart), and unique Portuguese wines.
  • Unique Architecture: From the medieval São Jorge Castle to the gothic Jerónimos Monastery, Lisbon is home to fascinating architectural landmarks.
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Portugal’s most romantic town Sintra

  • Sintra is special for its fairy-tale landscape, blending natural beauty with rich history and architecture. Nestled in the hills of the Sintra-Cascais Natural Park, the town is renowned for its romantic palaces.
  • Sintra’s lush forests, misty mountains, and dramatic coastline create a magical atmosphere that has inspired poets and artists for centuries.
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Vast landscapes, rich history, and distinctive wines Wineries of the Alentejo

  • The Alentejo wine region, known for being in the “breadbasket” of Portugal, has a warm climate and diverse soils, creating ideal conditions for viticulture.

  • The region is famous for its full-bodied reds made from indigenous grape varieties like Alicante Bouschet and Trincadeira, as well as elegant whites from Antão Vaz and Arinto.

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Historic capital of the Alentejo region Évora

  • Rich History: A UNESCO World Heritage site, Évora boasts well-preserved Roman ruins, medieval walls, and the stunning Roman Temple of Diana.
  • Architectural Wonders: The city’s Gothic Sé Cathedral and the eerie Chapel of Bones showcase a blend of cultural influences and intriguing designs.
  • Charming Atmosphere: With its cobblestone streets, whitewashed houses, and vibrant town squares, Évora offers a picturesque and authentic glimpse into traditional Portuguese life.

(Photo: Patrick Nouhailler)

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Intricate pottery and vibrant rugs from the Alentejo Ancient Craft

  • Preserving Cultural Legacy: Both pottery and rug making are deeply embedded in Alentejo’s cultural identity, with local workshops and artisans dedicated to preserving these ancient crafts. Visitors can explore these traditions firsthand, gaining insight into the region’s rich history and the skills involved in producing these timeless works of art.
  • Pottery Heritage: Alentejo’s pottery craft dates back centuries, with artisans in towns like São Pedro do Corval renowned for their hand-molded, brightly painted ceramics. This traditional craft continues today, with skilled hands shaping unique pieces passed down through generations.
  • Rug Weaving Tradition: The village of Arraiolos is famous for its exquisite hand-embroidered rugs, an art form that originated in the 17th century. These rugs are known for their intricate patterns and meticulous craftsmanship, blending Moorish influences with Portuguese artistry.
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A blend of Mediterranean seafood, rustic meats, and farm-fresh ingredients The cuisine of southern Portugal

  • Mediterranean Influence: Southern Portugal’s cuisine is rich in Mediterranean flavors, featuring fresh seafood like sardines, octopus, and clams, complemented by olive oil, garlic, and herbs. Signature dishes include cataplana, a seafood stew, and grilled sardines, often enjoyed with locally produced bread and wine.
  • Rustic Tradition: Alentejo’s culinary heritage is rooted in simple, rustic ingredients like pork, lamb, and bread. Specialty dishes such as porco à Alentejana (pork with clams) and migas (a bread-based dish) highlight the region’s emphasis on resourceful, flavorful, farm-to-table cooking.
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Meet Our Expert Sommelier & Tour Leader

Sam Kimball is a WSET-trained sommelier and co-founder of Crush Wine Experiences, the NY area’s #1 food & wine experience company. He travels to Europe frequently on cultural and wine excursions to some of the continent’s leading wineries. As a wine professional who owns a wine retail store in the U.S., he knows the wines, culture, and local cuisine of Southern Portugal. Before each trip, Sam performs a careful inspection of each stop, not stopping until he finds the most unique places with a true wow factor for moments that surprise and delight. Over the years, Sam has established himself as an insider at each destination to give his guests exclusive access and VIP treatment. Each authentic experience leaves no stone unturned–curating every last detail so you don’t have to! It’s not just about the places themselves, it’s about immersing yourself in the culture. With Crush Wine Experiences, Sam will take you behind the scenes to see each place in a never-before-seen light.

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Pricing

Double Occupancy Private Room $4,500 p/person

Includes:
  • 4 Star Hotels
  • Transportation
  • Local Expert City Guides
  • Winery Visits and Tastings
  • 4x4 tour and Cork Farm experience
  • Visits to sellers of traditional pottery and wool rugs/blankets
  • 17 meals

Single Occupancy Private Room $5,200 p/person

Includes:
  • 4 Star Hotels
  • Transportation
  • Local Expert City Guides
  • Winery Visits and Tastings
  • 4x4 tour and Cork Farm experience
  • Visits to sellers of traditional pottery and wool rugs/blankets
  • 17 meals
Boutique, small group tour experience

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