Southern Portugal - Lisbon & the Alentejo

Lisbon, Portugal

CW
Crush Wine Experiences
  • Email address verified
17 reviews
Oct 4 - 12, 2025
Group size: 1 - 16
Southern Portugal - Lisbon & the Alentejo
Lisbon, Portugal

Crush Wine Experiences
  • Email address verified
17 reviews

Oct 4 - 12, 2025
Group size: 1 - 16

About this trip

Overview:

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. 

What’s included

  • Lodging
    4-star Hotel Lisboa Plaza, in Lisbon, 4-star Évora Olive Hotel, in Évora
  • Airport transfers
    Airport transfer to hotel on arrival day & departure day
  • Meals
    17 meals, including multi-course meals with wines
  • Ground Transportation
    Local transportation each day on private luxury vehicle
  • Local expert guide
    Dedicated expert Portuguese tour guide throughout the itinerary
  • Wine tastings
    4 private winery tastings in three (3) wine regions (Colares, Setubal, and Alentejo)
  • Local Expert Tours
    Guided walking tours in Lisbon and Évora
  • Special Attractions
    Guided visit at Sintra National Palace, Visit to Estremoz Puppet Interpretive Center
  • Cork Tour
    Cork estate tour via 4x4 vehicles in the countryside outside Évora
  • Farewell Dinner
    Farewell dinner in Avignon at La Maison de Celou, 3 courses with wine included
  • and much more!

What’s not included

  • Airfare
    Flights to/from Lisbon

Available Packages

Double Occupancy
Deposit: $1,350
Available until September 4, 20254 left

See full itinerary here

$4,200
Deposit: $1,350
Single Occupancy
Deposit: $1,560
Available until September 4, 2025Only 2 left

See full itinerary here

$4,900
Deposit: $1,560

Available Add-Ons

Pre-night stay at Hotel Lisboa Plaza
$315
Only 1 left

In Lisbon. Room type: Lisboa Room (18m)



Your Organizer


CW
Crush Wine Experiences
17 reviews
Experience small group, multi-day tours off the beaten path. Our food, wine, and cultural excursions span the world's most interesting regions, and include an American wine host/Sommelier along with charismatic local guides.

Reviews

Sam & Alicia (sp?) were incredible tour guides, and the trip was diversified…mixing interesting experiences w/unbelievable wineries/tastings, underground city tour, buffalo mozzarella farm, Pompeii…couldn’t have been any better! The three hotels we stayed in were lovely. The last one was really not going to open everything up until June 1, so it seemed somewhat “shut down” in some respects. I would tour w/Sam & Alicia again…definitely! And it was fun to have my winemaker, Miro & his fun wife, Molly on the tour as well. Could not get over how fun (& crazy) the participants were…we all got along so well! Great, memorable trip…thank you! *lynn
By Lynn C for ZAP! Naples, Amalfi Coast & Campania Tour on May 25, 2025
Thank you so much, Lynn! We’re thrilled to hear you enjoyed the tour. It was a pleasure meeting you and Dom and having you with us. Alice and I loved sharing the experience with such a fun, adventurous group. We’re delighted the mix of wineries, culture, and cuisine made it memorable. We’ll pass along your kind words to Miro and Molly too. Hope to see you on another adventure!
By Crush Wine Experiences on May 26, 2025
CW
This trio had a lot of his and downs but ultimately the price we paid did not meet our expectations. We felt hotels were of low quality, wine and food provided were low quality, sequence of events were poor. Highlights being a great wine and food experience, the local guide Alice was wonderful, and the people on the group were nice. We felt back to back lunch’s at wineries were not planned well, quality overall was low, the elderly couple on the trip was taken care of by guests, price did not match the low quality. A lot of time spent on travel as well, not experience.
By Nick K for ZAP! Naples, Amalfi Coast & Campania Tour on May 18, 2025
Dear Nick, Thank you for taking the time to share your feedback on the ZAP! Naples, Amalfi Coast & Campania Tour. We’re genuinely sorry to hear that the experience didn’t meet your expectations, and we appreciate both your praise and your concerns. This tour is a bit different from others we host in that a portion of the price supports Zinfandel Advocates and Producers (ZAP), a California non-profit organization dedicated to preserving and promoting Zinfandel. It also includes the presence of a California-based winemaker, which we believe adds a unique dimension for wine lovers, though we understand that this may not have been apparent in the overall experience. Regarding the hotels, our accommodations are all 4-star properties that we’ve carefully selected for comfort and location. While we recognize they may not meet the standards of 5-star luxury resorts, they are consistently well-rated and chosen to support an itinerary filled with daily excursions and activities. These same hotels have been used in all our past Naples, Amalfi Coast & Campania tours with positive feedback. (This includes a version of this itinerary from just last month.) As for the wine and food, we’re a bit puzzled by the contrast in your review—on one hand noting the quality as low, while also highlighting a great food and wine experience as one of the tour’s strengths. We’d truly welcome any specific feedback you’re willing to share so we can better understand and improve. In Irpinia, the wine region of Campania, our visits are structured to maximize the day by including two wineries in the same general area, separated by lunch. Travel time is kept to a minimum, with no leg longer than an hour or so. We aim to strike a thoughtful balance between exploration and relaxation. Lastly, we want to address your concern about the elderly couple. Throughout all group activities—walking tours, winery visits, meals, and transportation—both Alice and I were attentive to their needs and safety. While we can’t accompany guests during their free time, we regret that it felt like their presence affected your experience, and we thank you for your compassion toward fellow travelers. We sincerely appreciate your candid feedback and are always working to refine our tours. Thank you again for traveling with us. Warm regards, Sam Kimball Crush Wine Experiences
By Crush Wine Experiences on May 19, 2025
CW
It was a wonderful vacation. Our organizer Sam, tour manager Sergio and various city tour guides made sure that everything went well. The itinerary was a perfect mix of activities, sights, free time, wine tastings and food. Plus we had an incredible group of people who came together on this trip to experience southern Italy.
By Norma F for Exploring Puglia & Matera on May 15, 2025
A fantastic trip! Well organized, great tours and activities with free time each day as well. Highly recommend traveling with Sam!
By Robin G for Exploring Puglia & Matera on May 14, 2025
We had a great time! Great people to share the experience with, great food and wine, and good accommodations! I definitely recommend this tour and look forward to doing more in different areas in the future. We have our eye on the New Zealand tour early next year. :-) Cheers! Robert
By Robert C for Exploring Puglia & Matera on May 14, 2025
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