We’re currently SOLD OUT of the trip but you can still join our waitlist by adding your name to the form below. Be the first to know if a spot opens up or hear about future trips!
Point of the Bluff presents
An insider’s view of Southern Portugal, the Alentejo
April 13-19th, 2026
Join Point of the Bluff and friends for an international wine tasting tour in Portugal this April!
Come find out why Travel & Leisure Magazine, the Wall Street Journal and many others are falling in love with Portugal. With the UNESCO World Heritage town of Évora as a base for 6 nights, we will venture in all directions exploring the gastronomic and cultural treasures of the Alentejo. We will visit the fairytale walled village of Monsaraz, the marble town of Estremoz with its bustling Saturday market, a prehistoric megalith that predates Stonehenge by 2,000 years, all the while discovering the wines and dishes that are putting Alentejo on the map.
Jordan Harris, Winemaker at Point of the Bluff, and his wife Jen, a Certified Sommelier, will be joining you on this adventure. Jordan has been recognized as one of Canada’s top up-and-coming winemakers, a benchmark producer in Virginia, and now a leading winemaker in the Finger Lakes, where his wines have earned over 75 awards and accolades in Wine Enthusiast, Wine Spectator, and more. He was named a Top 40 under 40 Tastemaker by Wine Enthusiast and recognized as one of the Top 100 Most Influential Winemakers in the USA by Intowine.com.
You will also enjoy the exclusive opportunity to taste a selection of Jordan’s first vintage of Point of the Bluff wines, available for the first time only in Portugal, alongside Jordan and Jen’s expert guidance.
- Accommodations in a five-star hotel
- Breakfast daily
- Daily long lunch or dinner (includes food, wine, gratuity)
- Wine tastings – all, generally including tapas
- Transportation – all
- Admission and entrance fees – all
Does not include:
- Airfare
- Trip insurance, if applicable
Cost per person: $3,700
Single travelers welcome. If you prefer a single room, additional charge is $600. 6 nights in the Alentejo. Limited to 20 participants.
Additional Information
Pick up and drop off in Lisbon
All of the flights into Portugal from the United States are overnight flights. Please plan to arrive in 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.
To secure a spot on the tour, please use the following payment link:
Current Itinerary
Day 1 – The UNESCO world heritage city of Évora
Our private group bus will meet you at our pickup location in central Lisbon at 10am and to take us to Évora (approximately 1h20m minute ride).
Prior to lunch, we will visit the famous Bone Chapel of Évora. We will then wander the maze of narrow streets of Évora before arriving at our lunch destination.
Wine tasting & lunch: We will dine at one of our favorite restaurants in Évora. The family has been serving traditional Alentejo gastronomy for close to 40 years.
After lunch, we will visit the 800 year old Cathedral of Évora followed by the 1,800 year old Roman temple, before making our way to your hotel – a 5-star property located within the walls of the town.
Each evening you can enjoy the common areas of the hotel with its commanding view of the 16th century aqueduct or wander the streets of Évora.
Fala Português? If you like, you can begin each morning with a fun informative half hour Portuguese lesson.
Day 2 – Cork, the Montado & Portugal’s Stonehenge
Cultural stop over: You will learn why cork is such an incredible sustainable resource. We will visit a cork forest led by the always jovial, interesting Andreia. You will never look at a wine cork in the same way again!
Lunch & wine tasting: We will then stop at Senhor Daurindo’s for a super traditional Alentejo feast accompanied by some very local wines.
More culture: On the way back to our home base, we will stop by at the pre-historic megalith, Cromeleque dos Almendres: a stone circle that predates Stonehenge by 2000 years.
Day 3 – Portuguese Royalty & Howard’s Folly Winery
Cultural stop: A guided visit to the royal summer palace in Vila Viçosa.
Wine tasting: Howard’s Folly. Funny name, serious wine. Lead winemaker David Baverstock is better known for running the wine operation at Esporão. But Howard’s Folly is a new, small venture by David’s good friend, Howard who lived for 30 years in Hong Kong.
Lunch: Innovative Chef Bernardo creates perfect dishes to pair with Howard’s wines.
Day 4 – Portugal’s best hilltop village
Cultural stop over: the fairytale village of Monsaraz. One of the best-preserved villages in the country. If it were anywhere else, it would be mobbed with tourists year-round. We will stop in the pottery town of São Pedro do Corval along the way for some shopping.
Lunch: We will have a lovely lunch on the covered patio facing the lake and the Spanish frontier at good friend Joao’s family restaurant in Monsaraz.
Day 5 – Roman Villa & Quetzal Winery
Wine: Visit our friends at Quinta do Quetzal who love both art and wine. Our visit will be led by winery head, Reto Jorg.
Lunch: João Mourato, head chef at Quetzal, may receive a Michelin star one day. You will not believe he is only 27!!
Cultural highlight: the Roman Villa of São Cucufate has been standing for over 1,800 years.
Day 6 – The Estremoz Saturday market and Monte Branco Winery
Cultural stop over: We will visit one of the oldest outdoor markets in Europe in the marble town of Estremoz.
Winery tasting: Owner, winemaker Luis Louro of Monte Branco was practically born into the wine business. Luis has strong opinions about winemaking and looks forward to sharing them with you. It also helps that his tasting area overs a glorious view of the countryside.
Lunch: We will have a lovely lunch in the barrel room while continuing to try some of the Monte Branco wines.
Day 7 – Boa viagem
Early breakfast, check out and transfer back to Lisbon airport. Most of you will be departing on a noon flight that day, therefore you will be leaving the Évora hotel at around 8am. If you are staying in the country, breakfast is at your leisure. We can help you in booking transfers at other times and to different locations.
