Alentejo, Portugal 2024


Wednesday September 25 to Saturday October 3, 2024 (departing from Toronto on Tuesday September 25) *new date, with one night and dinner in Lisbon included. SOLD OUT

Personal concierge services of Kato Wake and Billy Munnelly • 10 nights Ensuite Accommodation • ALL Dinners with wine, including one Michelin • 4 Lunches with Wine • 10 Breakfasts • Winery Visits and Private Tastings • Tasting and Tour at an Organic Wine Producing Farm •  Organic Olive Oil Tasting • Visit to a Tile Museum • Artisan Cork ‘Factory’ visit • History Walk of Evora • Ferry to Tavira island • Private Tour of a Marble Quarry • Fado Concert • Private coach travel throughout • Bocce Tournament • Interactive Cooking Demonstration • Transportation for return official flight to Faro airport … and a few surprises!

“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 tour starts officially in Lisbon at our chosen hotel at 6pm, with a meet and greet, stroll of the “hood” and a wonderful dinner. The nextt 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. For some, the real star may be our first winery visit that showcases 12th century and contemporary architecture, and delicious, authentic food. 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 guide 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!


“To steal their words, the trip is planned in the spirit  of delivering the satisfaction of an engrossing four act play. It offers a sparkling variety of experiences, each chosen to compliment and enhance that which went before.  The pace is relaxed and thoroughly in tune with vacation energy flow. We visited beautiful wineries in unusual locations – first stop off the plane was glorious luncheon in a restored castle winery which served to kickstart the whole experience. I won’t offer details because a large part of the fun was the surprises each new day offered, but suffice to say there were castles, olive groves, ancient wineries, music, beaches, picnics, marble, cork, contemporary art, vibrant history lessons and warm and loving reception from the people offering us their hospitality. I like to design my own trips but honestly I will eagerly sign on again for another trip curated with the creative sensibilities of Kato and Billy. They do it RIGHT.”  R. Dunsmore, Stratford ON


As we travel south we’ll have a fabulous lunch at a beautiful/arty winery. Every Alentejo visit should include a stay at a country farm estate, and we have a beautiful one reserved for you. Imagine sipping a chilled Rosé by the pool – as you soak up the rural charm.  Dinner will be 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. Just in time for lunch and a stroll on the beach (and a swim in the Atlantic!) before checking-into our magnificent bright yellow hotel in a former convent. Next day you may want to take in one more castle, a stroll on the cobble-stone streets, or do some last-minute shopping. Before we gather for a final dinner at one of our favourite restaurants – you’ll be treated to a Fado concert that will surely impress. You too may want to move to Tavira!


Billy and Kato have hit another home run, indeed a series of home runs, with their new offering of Alentejo 2022!!  The food, the wine, the accommodations, the castles, the beautiful cities and the quiet countryside…..all were top notch and I would recommend to anyone. In an area steeped in history, it is like travelling through time where you can imagine everything from Roman centurions to medieval knights and their magnificent horses, rattling up the hill to the castle gates. At the same time, you can be amused/amazed as cars and buses thread their way through seemingly impossibly small entrance ways. To say I enjoyed myself would be a complete understatement.  Thank you, Kato and Billy!!!”  Grace C, Prince Edward Island, Canada

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.


“Beyond expectations” doesn’t do justice for what Billy and Kato achieved with this tour! Scrumptious food, phenomenal wines and amazing places we would never have found on our own! Every detail taken care of – just pack your bag and go – that’s what we’re planning on doing again!” D. Pasquino, London, ON



Wednesday September 25 (tour starts at 6pm at the Lisbon hotel) to Saturday October 5, 2024 SOLD OUT

Personal Concierge Services of Kato Wake and Billy Munnelly
10 nights Ensuite Accommodation
ALL Dinners with wine, including one Michelin
4 Lunches with wine
10 Breakfasts
Winery visits and Private Tastings
Organic Olive Oil Tasting
Tile Museum visit
Tour and Tasting at an Organic Wine Producing Farm
History Walk of Evora
Artisan Cork ‘Factory’ Visit
Ferry to Tavira Island
Private Tour of a Marble Quarry
Fado Concert
Bocce Tournament
Interactive Cooking Demonstration
Transportation for return flight from Faro airport
Private Coach Travel throughout
…and some value-added surprises and events!

Best Bottles Inc reserves the right to make minor changes in the itinerary.

A few lunches
Travel and medical insurance
Any additional transfers before or after the tour that are not part of the tour schedule


CDN based on double occupancy, taxes included
Single supplement $1,995

NOTE for friends travelling together: Our Lisbon hotel does not have rooms with two beds. For the first night in Lisbon there is a small surcharge of $150 CND to cover the cost of each having your own room.

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


The tour starts in Lisbon on Wednesday September 25 (at 6pm at our Lisbon hotel) and ends Saturday October 5, 2024 after breakfast.

We aren’t recommending an official flight for getting to Lisbon. If you would like to explore Lisbon before the tour starts (and not have jet lag), we can give you our Lisbon recommendations – our favourite places to eat and favourite things to see.

Our recommended RETURN FLIGHT is Air Transat TS233, departing from Faro at 13:35 and arriving in Toronto at 16:45.

Our tour ends in the Algarve (Tavira), ideally located to get to Seville by bus, or explore the Algarve. Taking a train to Lisbon is easy and not expensive from Tavira too. We are happy to help you coordinate your plans!



Email with ALENTEJO 2024 in the subject headline.
Once your spot is confirmed we will give further instructions regarding your $500 non-refundable deposit.

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 120 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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