Alentejo 2023



September 25 to October 4, 2023

Tour departs Toronto Sunday September 24, Arrives Lisbon in the morning September 25
Departs from Faro airport direct to Toronto Wednesday October 4. Flights to be confirmed in October, 2022.

“There is something profoundly invigorating and liberating about the Alentejo landscape; its endless open countryside, gently undulating plains and wide blue skies. The landscape mingles with the vines to create an ever-changing canvas of colour.”

The Portuguese have a love affair with their province of Alentejo. “You must go,” they keep telling you. No reasons are given. “Go and you will see.” So we went, and loved everything from the landscape, to the endless space, the immensity of the rolling plains with cork trees, the soft rolling hills and vineyards, the faded-green olive trees, the towering eucalyptus trees, the black pigs munching on acorns, and the wide sky with an immaculate blue horizon. We enjoyed a daily menu of bird song, sunshine, tranquility, great food and wine. Everything felt welcoming and unpretentious and rooted in the surrounding culture. It was good for the soul.

The Alentejo province is a huge area south of Lisbon stretching from the coast to the Spanish border. Visiting feels like travelling back in time – a walking museum of 2000 years of civilization that is now sprinkled with wineries set in country palaces, or striking contemporary structures. The food experiences also vary from hearty traditional to tasty modern. Old hilltop towns, craft galleries and historic sights are a must see – if only to experience the landscape on which they sit. These are proud people who valiantly cling to their local crafts, and centuries-old farming traditions.

The first three days of our tour are based in and around Estremoz – staying at a former Royal Palace perched high above the city. From there we will visit other ‘perched’ towns such as the postcard perfect Marvao, and the everything-made-of-marble town of Vila Viçosa. Both of these places will amaze you as will the Berardo Tile Palace in Estremoz. But for some the real stars may be meals and visits to Fita Preta and Dona Maria wineries – think beautiful palaces! One dinner we are keeping as a surprise, while another may land you in jail!

After this we move to Evora, the historic capital of the region. So much history to absorb, but our guides will help. Outside the town, we will visit a cork craft centre and have an intimate lunch in the old farmhouse of one of Portugal’s best olive oil producers. You’ll not find him on Trip Advisor!

Every Alentejo visit should include a stay at a winery and ours will be at the beautiful Herdade do Sobrosa. On arrival we recommend a chilled Rosé by the pool, the pond or patio – as you take in the rural charm. Close to Sobrosa we will have a lunch at the beautiful/arty Quetzal winery, and a dinner between-the-giant-amphoras at a rustic village taberna. A surreal experience for sure! Making and ageing wine in amphoras is part of the tradition here, as is drinking lots of a white called Antao Vaz. You’ll not miss Chardonnay!

For our final chapter we move south to the Eastern Algarve and our home town of Tavira. Horray! And just in time for lunch and a stroll on the beach – before checking-into our magnificent bright yellow hotel in a former convent. Next day you may want to take in a Fado concert, one more castle, a stroll on the cobble-stone streets, or do some last-minute shopping – before we gather for a final dinner at our favourite river-side restaurant. You too may want to move to Tavira!

Next morning, Faro airport (and your direct flight to Canada) is just a thirty-minute coach ride away.

The Portuguese are right! Alentejo is a “must go”, and like all special places it cannot be explained, it must be experienced. We are looking forward to showing you around this dreamy, ancient world that’s long on charm and short on crowds. While it’s one of the quietest places in Europe, it’s also one of the most up-and-coming. Now is the time to visit.



September 25 to October 4, 2023 (departing Toronto September 24)

9 nights ensuite accommodation
8 fantastic dinners with wine
7 lunches or picnics with wine
9 breakfasts
Several winery visits and private tastings
Olive oil tasting
History walk of Evora
Entrance fees to galleries, museums, attractions
Lisbon airport pick-up
Transportation for return flight to Faro airport
Private coach travel throughout
…and some value-added surprises and events!

Two lunches and one dinner
Personal items and drinks
Travel and medical insurance


based on double occupancy, taxes included
Single supplement: $1,695

This is a LAND ONLY TOUR beginning in Lisbon. TICO #2392471

GROUP SIZE: 18 persons


The tour will start at Lisbon airport and depart from Faro (both direct flights with Air Transat) and will be confirmed end of summer, 2023



Email with ALENTEJO 2023 in the subject headline.
Expressing interest does not automatically guarantee a spot. We will keep you informed by email.
Once your spot is confirmed we will give further instructions regarding your $500 non-refundable deposit.
Should you be interested and have emailed us, we will confirm your spot (one way or the other) by the end of OCTOBER 2022.

We expect everyone to be in good physical shape – able to easily walk for a few hours a day – and to participate in every daily excursion.

We work with Ellison Travel and Tours, our official partner with TICO #2392471
Billy’s Best Bottles reserves the right to make changes in the itinerary.


Your $500 pp deposit is non-refundable.
Final payment is due 90 days prior to the tour, and is 100% non-refundable.

FYI: Tours will be cancelled or postponed if Canadian “˜Do Not Travel’ advisories apply to the destination, or if Ellison Travel & Tours deems it unsafe to travel, in which case, all monies paid will be transferred to a future travel credit.



We must start by telling you that we never set out to conduct tours. However, after a few trials with friends we sensed that there was an interest in our style of travel. Found a niche as they say. Original and generous were the two most used words we heard to describe what we offered, and not surprisingly as our itineraries were of our own making. We did not see the point of taking people to over-crowded ‘guide book’ places. It is impossible to catch the feeling of a place when you’re lost in a sea of fellow travellers. We still deliver WOWs, but without the hassles and crowds. And generous might have something to do with how much wine we were pouring.

We have sought out parts of a country that offer a sense of the whole, thereby delivering the experience without long travel times. Spending less hours on the road attempting to see it all gives us more quality time in towns, galleries or cafés. Feet on the ground as opposed to bum on a bus, seeing better over seeing more.

Most of the experiences we offer are either not available off-the-street, or would require a lot of work to secure.

We love the time at table so most evenings we all dine together, at a hand-picked restaurants where we have arranged something special ““ for an experience not available to the general public. You can expect everything from gourmet to rustic with seating in small groups for an intimate experience. But we’re not opposed to a little rowdiness! We stay at smaller, non-chain hotels away from the tourist bustle.

Have to admit we are not huge history buffs, but we do allow enough free time for those who want to visit churches and museums. Think of us as the anti Trip Advisor – seeking instead the alternative, the unexpected. The kind of tour you’d imagine from a local, as opposed to a Tour company. If you have never travelled with a group before, fear not. Think of the possibilities for fun with a group – ‘adult camp’ as Kato calls it. It may be the best party you ever attended.

Expect to eat and drink too much – and love every minute of it.

In each of our destinations we concentrate on the things that are special or unique: rural pubs in Ireland as they are the hub of a community, historic grandeur combined with sleek contemporary design in Portugal, and the effortless, indescribable sense of style in France. Crafting beauty in everything is Italy’s great skill, and that includes food and wine. We ask that our travellers take the time to know something of, and respect the culture we are visiting – your comfy Adidas and litre of Pepsi might not a fitting image.



Those with a love of adventure and social interaction are obvious candidates. On the physical side, good walking ability and drinking stamina are not only essential, but mandatory. Meals are on the European clock – starting late and finishing late – celebrating time at the table. Basically we invite people who are interested in stepping outside their comfort zone and embracing a European experience. Filling the eyes, bellies and imagination with things unfamiliar. We welcome people who come hungry for activity and participation. Please do NOT come with us if you want a conventional sightseeing tour with no participation on your part.

Finally a word on why we do not publish detailed, daily itineraries. One reason is we like to remain flexible and work around weather and local events. But more importantly, we believe that the best travel experiences are built around daily surprises – a trust between the host and the guests. Those who have travelled with us have said that they enjoyed the surprise element as it kept them in the moment. We ask that you greet us with enthusiasm, a trusting open mind, good health, and an empty wine glass (not for long!).

Every tour we’ve run has sold out and many guests are repeat offenders.




“From the moment we arrived, we were treated to first class food, accommodation and hospitality. Every day was a new adventure from hiking through a vineyard to dining in a winemaker’s cellar. By far the best organized trip that we’ve been on ““ well-paced and the perfect group size.” B & H Purvis, New Hamburg, Ontario

“Had been to Italy several times. But this was my first small group travelling ever. Piemonte came vividly alive with Kato and Billy. Relationships, food, wine, learning, and conversation — all rooted in local ambience and warm personalities. Did someone say there’s a Portugal trip too?” Bill Roberts, Prince Edward County

“Doesn’t matter which tour you choose, they are all unforgettable! Just returned from our 4th trip with Billy and Kato, our 2nd to Piemonte! If you want to really experience food, wine (and other assorted libations), first rate accommodations, people, territory, history and downright fun, then join one of their adventures.” Wendy & Wayne Rider, Stratford

“Absolutely fantastic trip. Billy and Kato are the perfect hosts ensuring unforgettable wine tastings, meals and local experiences. The element of “surprise” around the daily activities added to the fun. Great way to meet and make new friends. After 2 months we are still raving to friends and family about how wonderful everything was from start to finish. Would highly recommend this trip.” The Culhanes, Ottawa

“I can say without qualification, that my experience of your Italian Wine tour far exceeded anything I could have imagined. Just outstanding in every way. Congratulations!” Wally Anderson, Simcoe

“This was our 15th professionally conducted wine trip, and while the previous ones were all fabulous, none were better than our Piedmont trip with Billy and Kato. They are a fun and caring couple who do everything to ensure you have a good time. We would highly recommend them.” The Chapmans, Oakville

“Kato and Billy took us to parts of Italy in the Piedmont wine country which I would never have discovered on my own. We stayed in top-notch accommodation, and the beautiful rolling hills of vineyards topped by ancient castles were a sight to behold! We saw it all ““ including grape harvesting, VIP winery visits, and a fantastic 3 course cooking class. I had a superb time with a wonderful group of people. Thanks to Billy and Kato ““ our imaginative, inclusive and generous hosts!” D Troop, Prince Edward County

“Again, what a wonderful trip – the Barolo Tour was our second trip with Billy and Kato. Travelling with B&K is not a tourist trip, but an experience that you don’t forget – great food, great wine, and you see and do things that tourists don’t get to do. Most of all, have lots of fun with new found friends.” Don and Sue Scott, Ottawa

“The Italian Wine Tour was FIRST CLASS! Billy & Kato thought of everything. It was interesting & fun filled. I’d go again in a heartbeat.” Mary Anne Perkins, Milford

“Exceptional all round gastronomical, cultural and just plain fun tour. I can’t think of a better way to experience the Piedmont wine country than joining Kato and Billy. The variety of wine tastings and daily activities are a testament to their thorough advance research and genuine desire to assure a wonderful memory for all. La dolce vitae indeed.” Brenda Smith, Ottawa

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