The holidays can be a challenging time for those of us who find ourselves alone. Whether it’s an empty nest, the loss of loved ones, or simply a phase of life where others are busy with their own plans, the festive season can feel isolating. But what if being alone didn’t have to mean feeling lonely? Solo travel over the holidays offers the perfect antidote: the excitement of exploration, the joy of shared experiences, and the opportunity to create new memories to cherish.
This New Year’s, I’m hosting an intimate group - just eight travellers or fewer - for a magical journey through Portugal. It’s a dream itinerary filled with everything I love: incredible food, hidden gems, hands-on experiences, and the thrill of discovering new places.
Lisbon: The perfect start
We begin our adventure in Portugal’s capital, Lisbon, a city that balances historic charm with modern flair. For two days, we’ll soak in the sights, explore its iconic neighbourhoods, and indulge in culinary delights at cozy, hole-in-the-wall restaurants. From the lively streets of Alfama to the majestic Praça do Comércio, Lisbon is the kind of city that warms the soul, even in winter.
A coastal drive to Porto
From Lisbon, we’ll journey along Portugal’s dramatic coastline. Along the way, we’ll stop at Nazaré, famous for its towering waves and rugged cliffs, and the enchanting town of Óbidos. A medieval village with cobblestone streets and whitewashed houses, Óbidos is the perfect spot to wander and let the festive spirit sink in.
Then it’s on to Porto, a city often named one of the world’s most beautiful destinations. Porto’s charm lies in its rich history, picturesque riverside setting, and vibrant culture. We’ll stroll through its winding streets, marvel at the iconic Dom Luís I Bridge, and enjoy wine tastings in the birthplace of port wine. This dreamy coastal city is a feast for the senses, especially for food and wine enthusiasts.
Into the Alentejo
After Porto, our journey takes us to the Alentejo, an emerging gem of a region known for its rolling plains, vineyards, and olive groves. We’ll stay in a historic pousada, steeped in charm and character, where the slow pace of life and incredible cuisine will soothe your soul. Alentejo is a food lover’s paradise, and we’ll savour every bite—whether it’s a hearty traditional dish or a creative twist on local flavours.
Ending in the Algarve
Finally, we’ll head south to the Algarve, where the air is warmer, and the views are postcard-perfect. This region is known for its golden beaches, dramatic cliffs, and quaint fishing villages. It’s the ideal spot to relax and reflect on our journey before heading home. The trip concludes in Faro, where you can fly directly to Toronto with Transat. The convenience of this route—and the reasonable airfare of around $1,400 - makes it an excellent option for Canadian travellers.
Why join This trip?
This holiday escape is designed with solo travellers in mind. Whether you’re sharing a room for $3995 or enjoying the privacy of your own for $5,400, you’ll be part of a close-knit group experiencing the best of Portugal together. The cost includes many meals, a New Year’s Eve banquet, a cooking class, wine tastings, transportation, and accommodations that range from luxurious to delightfully historic.
As your travel companion and floating concierge, I’ll be there every step of the way to ensure your journey is seamless, fun, and unforgettable. Oh and you don’t have to be single to join us, Im bringing Keith after all...
An invitation to share the holidays
If Christmas feels daunting, I’d like to extend a personal invitation to join me at my own dinner table in Ireland before we depart for Portugal. The holidays are about connection, and if you’re feeling the weight of spending Christmas alone, I’d be glad to welcome you into my home. Together, we can enjoy good food, warm company, and the excitement of our upcoming adventure to Portugal.
Don’t be alone this New Year’s
If you’re looking for something to look forward to this holiday season, why not make it Portugal? A week of indulgence, exploration, and camaraderie awaits. Whether you’re sipping wine in Porto, learning to cook local dishes, or wandering through a charming village, you’ll be creating memories that will last a lifetime.
Don’t be alone for New Year’s—come join me in Portugal. Together, we’ll make this holiday season one to celebrate.
For more details or to reserve your spot, reach out soon. Space is limited, and this magical journey is one you won’t want to miss.
Email me at lorraine@lorrainesimpson.
Check some travel info at www.conciergetravelgroup.ca
Or just check out some stories and videos at lorrainesimpson.com
