Every winter, travellers from colder climates flock to southern Spain and Portugal to trade snow and grey skies for sunshine, seaside promenades and outdoor café culture. Long stays in these regions are incredibly popular – but many require you to stay in one location for weeks, organize your own sightseeing, find grocery stores, cook meals, or search for restaurants every day.
I wanted to create something far more relaxing, social and exciting.
This Travel With Bradley Long Stay Journey combines the comfort of extended stays with the ease and discovery of a fully escorted tour. We will stay in four uniquely different hotels across Spain and Portugal, explore historic cities, charming villages and breathtaking coastlines, and enjoy included meals every single day. No planning, no grocery shopping and no wondering where to eat – simply relax and enjoy the sunshine while everything is taken care of.
Our two coastal hotels are perfectly suited for long-stay living. Rather than large, glitzy resort properties that you find in some parts of the world, these welcoming seaside hotels focus on comfort, location and relaxed coastal lifestyle – exactly what makes winter escapes in southern Europe so enjoyable. Spending a longer time at two of the properties allows you to truly settle in and enjoy day-to-day Mediterranean and Portuguese life just like the many European travelers who return year after year.
Long winter stays in southern Spain and Portugal are hugely popular with travellers from the UK and Northern Europe, creating a lively and social atmosphere throughout the season.
With so much included – hotels, excursions, meals, experiences and full-time hosting – considering the tour length this journey offers outstanding value and a wonderful escape from the Canadian winter.
As a bonus, I can’t wait to share two of my favourite cities – Seville and Lisbon – with you on this incredible adventure.
Be sure to join me,
Bradley Walters
New Departure
Itinerary
March 7 – 28, 2027
TORONTO – MALAGA, SPAIN
Due to our evening flight, we are including a one-night post stay at a Toronto Airport Hotel when you return to Toronto on March 27. Receive complimentary parking at a Toronto airport hotel, plus a convenient shuttle to Toronto Pearson Airport. Our adventure begins when I greet you and assist with your flight check-in. Afterwards, meet your fellow passengers in the Plaza Premium Lounge for food and beverages prior to boarding our connecting overnight flight to Málaga. The excitement begins as we set off together for sunshine and warmer days ahead.
Meals Included: Dinner (D)
COSTA DEL SOL – MALAGA
Welcome to the Costa del Sol. After arrival in Southern Spain we explore vibrant Málaga, birthplace of Picasso and one of Andalusia’s most exciting coastal cities. With our guide we will wander historic streets lined with colorful buildings, lively plazas and charming cafés buzzing with local life. Palm trees, sea views and mild temperatures immediately remind us that winter in Canada feels very far away. We then transfer to Torremolinos on the famous Costa del Sol. For the next seven nights, our beachfront hotel boasts a prime location along the seaside promenade, steps away from cafés, boutiques, and scenic walking paths. The setting makes it easy to slip into Mediterranean life – morning strolls by the sea, relaxed afternoons in the sunshine and evenings watching the sunset along the waterfront. Tonight we gather for a welcome dinner to celebrate the beginning of our journey together.
Meals Included: Lunch, Dinner (L/D)
TORREMOLINOS
Today is all about easing into the relaxed rhythm of southern Spain. Our hotel sits just steps from Bajondillo Beach and the lively promenade, perfect for seaside walks, browsing boutiques and enjoying coffee cafes under blue skies. Winter visitors from across Europe fill the terraces, creating a lively and social atmosphere that makes long stays here so enjoyable.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
RONDA & SETENIL DE LAS BODEGAS
We journey into the dramatic Andalusian countryside to Ronda, one of Spain’s most breathtaking towns, perched high above a deep gorge. Its famous stone bridge spans the canyon and offers spectacular views that never fail to impress. After exploring Ronda’s historic streets, we continue to Seteni de las Bodegas, a remarkable white village where homes and cafés are built directly beneath towering rock cliffs. Walking through its narrow lanes feels like stepping into another world and enjoy a typical “tapas” luncheon in a charming, local restaurant.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
COSTA DEL SOL
Two wonderful days to embrace the Mediterranean lifestyle. Wander the palm-lined promenade, discover seaside cafés, browse shops or simply relax and soak up the sunshine that draws winter visitors from across Europe year after year. Long-stay travel is about enjoying life at a gentler pace – and these days capture that beautifully.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
GIBRALTAR
Don’t forget your passport, today we visit the Rock of Gibraltar. This British Overseas Territory offers panoramic viewpoints overlooking the meeting of the Mediterranean Sea and Atlantic Ocean (two continents of Europe and Africa). This unique southern tip of Spain is full of fascinating history and spectacular scenery.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
COSTA DEL SOL
Another perfect day to enjoy the seaside atmosphere, relaxed pace of life and mild winter climate that makes this region such a beloved winter escape.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
COSTA DEL SOL – SEVILLE
We travel inland stopping in historic Antequera before arriving in Seville for a two-night stay in a centrally located hotel near the historic heart of the city – perfect for evening strolls and soaking up the lively atmosphere. Seville is one of my absolute favorite cities and I’m so excited to share it with you.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
SEVILLE
Seville is known for their orange trees, and the fragrant blossoms fill the air in March. Today we explore the historic center including the magnificent cathedral, the old quarter, romantic plazas and lively tapas bars creating a magical atmosphere that capture’s hearts.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
SEVILLE – PORTUGAL/THE ALGARVE
We cross into Portugal and arrive in the beautiful Algarve for a relaxing 7-night coastal stay. Our welcoming, locally owned hotel is located within a 5-minute walk to the beach and within walking distance of a charming village center filled with cafés, shops and scenic coastal paths. Like many long-stay properties in southern Europe, this hotel offers a friendly, informal atmosphere focused on comfort, location and relaxed coastal living rather than glitz and glamour – exactly what makes winter stays here so enjoyable and why travelers return year after year.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
THE ALGARVE
A relaxing day to enjoy the surrounding village, browse local shops, enjoy coastal walks or relax at a café and watch daily life unfold in the Portuguese sunshine. The choice is yours!
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
LAGOS, SAGRE & SAO VICENTE
We explore the dramatic western Algarve beginning in historic Lagos, once a center of Portugal’s Age of Discovery. Continuing west, we reach Sagre and Cabo São Vicente – the southwestern tip of Europe. Admire cliffs with waves crashing below and endless ocean stretching toward the horizon. Truly unforgettable!
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
ALBUFEIRA
Today we visit the lively seaside town of Albufeira, famous for its whitewashed old town and golden beaches. This afternoon experience the Algarve from the water on a scenic boat cruise past dramatic rock formations, hidden beaches and spectacular sea caves – one of the region’s most memorable experiences.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
THE ALGARVE
Another beautiful day to enjoy sunshine, ocean views and the relaxed coastal lifestyle that makes this region such a beloved winter destination.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
SERRA DO MONCHIQUE MOUNTAINS
We journey inland into the lush Serra do Monchique Mountains where charming villages and scenic landscapes reveal a different side of Portugal. Bring your camera at this time of year; the hills are often covered in almond trees and yellow flowering mimosa. A visit to a local distillery includes tastings and panoramic countryside views.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
THE ALGARVE
The beach is a short walk away while nearby shops, cafés and seaside paths invite exploration. Enjoy another peaceful day in the Portuguese sunshine.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
THE ALGARVE – LISBON
We journey north to Lisbon stopping in the UNESCO-listed town of Évora to visit a cork factory and a bizarre attraction that I’m keeping a surprise. We arrive in Lisbon for a three-night stay in a stylish centrally located hotel that is rated one of the finest in the city. Lisbon is another of my favorite cities and the perfect finale to our journey.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
LISBON
We discover Lisbon’s historic neighborhood, elegant squares and scenic viewpoints on a guided walking tour at a comfortable pace. Expect a tasty surprise treat or two.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
LISBON
Enjoy a final day shopping, sightseeing and soaking up the atmosphere of this beautiful city. The choice is yours, but plan on meeting up with your fellow passengers for our group luncheon and farewell dinner.
Meals Included: Breakfast, Lunch, Dinner (B/L/D)
LISBON – TORONTO POST-STAY
We depart for home, filled with wonderful memories and new friendships. Welcome back to Canada. After collecting your luggage we’ll transfer to the Toronto Airport Hotel for a one-night stay.
Meals Included: Breakfast (B)
HOMEWARD BOUND
Travel at your leisure this morning. Thank you for travelling with Bradley.
