The Portuguese Trilogy
11-Day / 10-Night
September 21 - October 1, 2026
Welcome to IOJ’s 2026 Portugal Trip: The Portuguese Trilogy – Lisbon, Tomar, and Porto.
This journey winds through Portugal’s most evocative landscapes—vineyards, hilltop villages, ancient forests, and the quiet spaces in between.
Uncover layers of history shaped by explorers, mystics, and monarchs. From the maritime legacies of Magellan and da Gama to the hidden traces of the Knights Templar, every stop invites a deeper connection—with place, with culture, and with the spirit of travel itself.
Along the way, something golden unfolds, and it all begins in Lisbon.
The Portuguese Trilogy
Day 1 - 4: Lisbon
Day 1.
Your centrally located hotel offers the ideal base for discovering Lisbon—a city of light, hills, and rhythm. Step outside into a mosaic of lively neighborhoods, historic trams, grand plazas, fine art, and unforgettable cuisine—all set to the sounds of soulful fado. Settle into your room, your home for the next four nights. In the evening, gather with fellow travelers for a wine and cheese reception, a preview of the days ahead, and a warm welcome. Together, we’ll depart for an orientation tour and an upscale welcome dinner. It’s sure to be a stirring introduction to Portugal.
Day 2.
Begin the day with a guided walking tour as we explore Belém, where Portugal’s Age of Discovery comes to life. With our local guide, visit the majestic Jerónimos Monastery, the iconic Belém Tower, and sample the city’s most beloved pastry, the Pastel de Belém. Enjoy a free afternoon, your first chance to explore the vibrant streets on your own.
Day 3.
After breakfast, we journey to Sintra, a fairytale town nestled in the forested hills. Our focus is the Quinta da Regaleira, an estate layered with symbolism and myth. Wander its lush gardens, climb turreted towers, and descend the spiraling Initiation Well—believed to echo the rites of the Knights Templar. Enjoy the afternoon at your leisure—whether continuing to explore Sintra or relaxing with a view. Later, we return to Lisbon.
Day 4.
This morning is yours. Stroll a museum, shop the boutiques, relax at a café, or simply enjoy the calm of our elegant hotel. In the afternoon, we head west to the seaside town of Cascais. There, we’ll explore its coastal charm and share a seafood meal with a view of the Atlantic.
The Portuguese Trilogy
Day 5 - 7: Tomar
Day 5.
This morning, we depart Lisbon and make our way north into Portugal’s storied interior. Our destination is Tomar, a city steeped in medieval mystery and once home to the Knights Templar. Upon arrival, we’ll take a brief orientation walk to get our bearings and introduce you to the hotel and surrounding area. The rest of the day is yours to explore at your own pace—wander the quiet streets, visit a local café, or simply rest and take in the slower rhythm of this historic town.
Day 6.
After breakfast, we set out on foot along a gentle hillside trail to the Convento de Cristo, a UNESCO World Heritage Site and the former stronghold of the Knights Templar. Here, the layers of Portugal’s medieval history come vividly to life. We’ll continue to the Castelo de Tomar and the Church of Santa Maria do Olival, a sacred resting place for Templar knights and a quiet emblem of Tomar’s enduring spiritual legacy.
Following a free afternoon to rest or explore, we’ll gather again for dinner together at a local favorite.
Day 7.
Today invites you to explore at your own pace. Linger over coffee at a local café, visit the charming Matchbox Museum, or discover more about Saint Irene of Tomar, the town’s beloved patron. For those eager for something more, your guide will happily offer suggestions for hidden corners and unique experiences.
The Portuguese Trilogy
Day 8 - 11: Porto
Day 8.
After breakfast, we depart Tomar by private coach and travel north to Porto, Portugal’s vibrant city along the Douro River. Along the way, we will stop at a winery for a tour, tasting, and lunch. After settling into our Porto hotel, the afternoon is yours to relax or wander.
Day 9.
Enjoy a quiet morning at your leisure before we embark on a carefully curated food tour around midday. Taste your way through Porto’s culinary heritage, from bustling markets and specialty shops to storied cafés and traditional kitchens.
Day 10.
Your final full day in Portugal is yours to savor. Shop for mementos, capture photographs, linger in a café, or simply find a moment to write and reflect on the journey you’ve taken. In the late afternoon, we’ll reunite for a scenic river cruise, seeing Porto’s beauty from a new perspective, before gathering for a farewell dinner—a golden final memory together.
Day 11.
After breakfast, it’s time to continue your journey, whether homeward or onward. We part as friends, carrying the stories, tastes, and moments of Portugal with us. Until we meet again…
What’s Included
Accommodation in 4-star hotels.
Breakfast every day.
All listed tours, including entrance fees.
6 included meals.
Full porterage for one 24″ bag per guest.
Private transportation through Portugal from the first to the last hotel.
Expert insights and guidance.
Gratuities for included meals, guided tours, and activities.
Services of local guides, travel coordinators, and more!
What’s NOT included
Air fare
Transfer from the airport to the first hotel and transfers out of the last hotel.
Any passport fees.
Trip, cancellation, or medical insurance policies.
Food and drinks, unless specified.
Informal group activities.
Pricing, Terms, and Conditions
$5,000 + Air per person,
based on double occupancy.
Optional single supplement: $1,250.
A $750 deposit is due on booking to hold your place. Tours are intentionally small, so space is limited.
Deposit is due upon registration.
Final payment is due March 20, 2026.
Please note the itinerary is subject to improvement and changes.
Meet your guides
Lisa Steckley
Co-Founder, Travel Coordinator
With 100,000s of air miles to amazing destinations, Lisa found the best trips were ones that changed her perception.
She is not a fan of what she calls ‘hop on, hop off’ tours-where the bus pulls up for an hour visit to a museum then off the next destination.
In her experience, skimming the surface misses the opportunity to harvest the unique moments found only in travel. Her vision for IOJ Travel is to serve the world using the potential of travel to shift perception. And the way they do that is to create an experience that allows the participants time, space, focus and safety net to explore life that is different from their own. “Ah ha” moments are not only remembered, but are potentially life altering.
Keith Light
Travel Coordinator
I’m your IOJ guide, here to help you discover the beauty, depth, and richness of Portugal.
With a background in Politics/Philosophy/Economics and a lifelong passion for travel, culture, food, and storytelling, I am delighted to lead you on a journey through Portugal. A journey that moves beyond checklists and into connection: connection with people, landscapes, traditions, and yourself.
I’ve traveled throughout Western Europe, and I bring both personal insight and local relationships to every itinerary. Whether it’s securing a private tasting at a vineyard you’ve never heard of or timing your visit with a centuries-old festival, my role is to quietly open the door to the extraordinary.
The Steps to Portugal
Step 3: Complete your liability waiver
Please print, sign, and return a completed liability waiver.
Step 4: Watch your email
As the trip approaches, we will provide you with lot’s of information about our destinations, point’s of interest, hostory of Portugal, suggested reading, movies, and music. You won’t want to miss out on this.
Step 5: Book your flights
Once you have booked your flights, please let us know your Lisbon arrival day and/or time.
Stap 6: Pack and Travel
As the trip approaches, we will provide a recommended packing list.
