October 10 to 19, 2022 SOLD OUT

(NEW DATES as of March 2022)

Tour departs Toronto OCTOBER 9, Arrives Lisbon in the morning October 10
Departs from Faro airport to Toronto Wednesday October 19

“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 and 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. The old hilltop towns, craft galleries and historic sights are a must, 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.

We are SUPER excited about our new tour to Alentejo. Any tour we offer takes time (years!) to put together – so trust is required by those interested in coming on our inaugural Alentejo jaunt (but then again, trust is actually a prerequisite for all our tours). Although we have been to Alentejo twice to research, we will be revisiting next spring to explore more. By the spring of 2022 we’ll have all the wonderful details in place.

The schedule in the works consists of nights in a former Royal Palace, an old-world Country House winery, a lavishly converted former convent and a charming, chic boutique hotel. We’ll be drinking Antao Vaz white wine, reds that have been aged in amphoras, and a slew of other novel varieties. Daily outings will include not only wineries, but other interesting stuff such as studios still practicing hand woven floor rugs, and tapestries, marble from the bottom of a quarry, and a town where even the park benches are marble, a cork factory, spectacular walled villages, and 25,000-year-old cave drawings. Let’s not forget a picnic lunch on the beach.

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.


October 10-19, 2022 (departing Toronto October 9)

9 nights ensuite accommodation
7 dinners with wine
8 lunches or picnics with wine
8 breakfasts
Several winery visits and private tastings
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!

One lunch and two dinners
Personal items and drinks
Travel and medical insurance


$5,795 based on double occupancy, taxes included
Single supplement: $1,495

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

GROUP SIZE: 18 -20


as of MARCH 2022
The tour will start at Lisbon airport and depart from Faro (both direct flights with Air Transat)

DEPARTURE FROM TORONTO Flight TS 480 departs Toronto Oct 9 Sunday @ 21:30, arrives Lisbon Oct 10 Monday 9:35am
RETURN TO TORONTO Flight TS233 departs Faro Oct 19 Wednesday @12:30, arrives in Toronto 15:50 (3:40pm)


Email with ALENTEJO 2022 in the subject headline. Kato will be in touch!
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 due on September 1, 2021 and 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 – 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 litres of Pepsi are not a fitting image beside a French bistro.



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.




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