Alentejo,

Portugal

October 20 - 26, 2025

Join John & Marialisa, along with their friend and expert tour guide Peter, on an unforgettable journey through Portugal’s Alentejo wine country. This intimate trip is designed for a small group of just 22 participants, ensuring a relaxed pace and a truly personal experience.

Over the course of a week, you’ll explore the rich culture, cuisine, and breathtaking landscapes of the region, all while visiting hand-selected wineries. Much like Rappahannock Cellars, each estate you’ll discover is small, family-owned, and dedicated to craftsmanship and tradition.

From the UNESCO World Heritage town of Évora to the rolling vineyards and charming villages, you’ll enjoy authentic hospitality, memorable wines, and the joy of traveling with a close-knit group of fellow wine lovers.

This trip includes:

• Accommodations in a four star hotel inside the walls of the city of Évora

• Breakfast daily

• Daily long lunch or dinner (includes pre-dinner drink, food, wine, gratuity)

• Wine tastings – all, generally including tapas

• Transportation – all

• Admission and entrance fees – all

Does not include:

• Airfare

    • Howard’s Folly – Winery tour and tasting, paired with a leisurely lunch.
      howardsfollywine.com

    • Quinta do Quetzal – Estate visit and guided tasting, followed by lunch with spectacular vineyard views.
      quintadoquetzal.com

    • Adega do Monte Branco – During our first-day walking tour of Évora, we’ll enjoy lunch at a local restaurant featuring their wines, especially their celebrated reds. On occasion, winemaker Miguel joins us at the table.
      adegamontebranco.com

    • Quinta do Mouro – A classic Alentejo estate with bold, expressive wines.
      quintadomouro.com

    • Herdade da Maroteira – After our cork forest tour, we’ll enjoy their wines at lunch, even though we won’t be visiting the estate itself.
      maroteira.com

    • Cartuxa – One of Alentejo’s largest and most famous wineries. While it isn’t part of our tour, you’ll have evenings free in Évora, where you may visit their tasting room and restaurant at your leisure.
      cartuxa.pt

  • Pick up and drop off in Lisbon

    All of the flights into Portugal from the United States are overnight flights. Please plan to arrive into Lisbon no later than the Sunday before the tour begins.

    On Sunday, we will drop you off at Lisbon airport at 9:30 am.

    We can help you arrange a different drop off location and/or time.

    Arriving early or extending your stay

    Lisbon is an enchanting city that can easily be explored on your own. You can easily spend a week in Lisbon if you have the time. If you would like to extend your trip or arrive early, our travel partners at Tinto Travels are happy to assist with hotel recommendations and things to see and do.

  • Day 1 – Arrival in the UNESCO World Heritage City of Évora

    Our private coach will meet the group in central Lisbon at 10:00am for the short drive (about 1 hour 20 minutes) to Évora. Before lunch, we’ll visit the famous Chapel of Bones, followed by a stroll through Évora’s maze of narrow streets.

    Lunch & Wine: Enjoy traditional Alentejo gastronomy at a family-run restaurant that has been delighting locals and visitors for nearly 40 years.

    The afternoon continues with visits to the 800-year-old Cathedral of Évora and the 1,800-year-old Roman Temple, before checking in at our 5-star hotel inside the historic city walls.

    Evenings are yours to explore Évora at leisure or relax in the hotel’s inviting common areas. Each morning, you’ll also have the option to start the day with a short, fun Portuguese lesson.

    Day 2 – Cork, the Montado & Portugal’s Stonehenge

    Discover why cork is one of Portugal’s most treasured sustainable resources. We’ll visit a cork forest with the lively and knowledgeable Andreia as our guide.

    Lunch & Wine: A true Alentejo feast at Senhor Daurindo’s, paired with authentic local wines.

    Cultural Highlight: On the way back, we’ll visit the prehistoric Cromeleque dos Almendres, a megalithic stone circle that predates Stonehenge by 2,000 years.

    Day 3 – Royal Palaces & Howard’s Folly Winery

    Step into history with a guided tour of the royal summer palace in Vila Viçosa.

    Wine & Lunch: At Howard’s Folly, you’ll meet a winery with a playful name but serious wines. Lead winemaker David Baverstock, famed for his work at Esporão, now crafts unique wines here alongside founder Howard, a longtime Hong Kong resident. Lunch features inventive pairings from Chef Bernardo, who creates dishes designed to elevate every sip.

    Day 4 – Portugal’s Hilltop Gem

    We’ll spend the day in Monsaraz, a fairytale hilltop village and one of Portugal’s best-preserved towns. Along the way, we’ll stop in São Pedro do Corval, renowned for its pottery.

    Lunch: Savor regional dishes on a terrace overlooking the lake and the Spanish frontier at our friend João’s family restaurant.

    Day 5 – Roman Ruins & Quinta do Quetzal Winery

    At Quinta do Quetzal, art and wine come together under the leadership of Reto Jörg.

    Lunch: Rising star Chef João Mourato (just 28 years old and already tipped for Michelin recognition) will prepare an unforgettable meal paired with Quetzal wines.

    Cultural Highlight: Explore the Roman Villa of São Cucufate, standing strong for over 1,800 years.

    Day 6 – Estremoz Market & Monte Branco Winery

    The morning begins at the lively Saturday market in Estremoz, one of the oldest outdoor markets in Europe, set in a town built on marble.

    Winery Visit & Lunch: At Monte Branco, winemaker Luís Louro—a passionate voice in Alentejo winemaking—welcomes us for a tasting with spectacular countryside views. Lunch will be served in the atmospheric barrel room, with wines flowing throughout.

    Day 7 – Departure (Boa Viagem!)

    After an early breakfast, we’ll check out and transfer back to Lisbon airport. For those on noon flights, departure from the Évora hotel will be around 8:00am. If you’re extending your stay, breakfast will be at leisure, and we’ll be happy to help arrange transfers at alternate times.

  • Pricing & Booking

    This all-inclusive journey (excluding airfare) is $3,800 per person.

    To reserve your spot, a $1,000 deposit is required at the time of signup. The remaining balance is due 30 days prior to departure.

    All bookings are managed through TintoTravels in partnership with Rappahannock Cellars.

Travel. Adventure. Wine. Friendship.

Travel. Adventure. Wine. Friendship.