Come explore Portugal with Dan and Deb
Portugal and Madeira September 2025
An 11-day Cultural Immersion Excursion
4 and 5 Star Hotels
September 8-18, 2025
Optional: 4 days in Magical Madeira
September 18-22, 2025
A journey into Portuguese culture, history, food, and wine.
Kent and Kelsey on our Croation Coast tour … a great partnership.
We could not be happier!
For the fourth time we are pleased to partner on our Portugal / Madeira 2025 trip with Kelsey and Kent, owners of Flights Wine Bar in Bend, Oregon. They have joined with us three times in the past two years with an 11-day Croatian Coast tour (pictured on the left), a Puglia, Italy tour, and an Umbria, Italy in Spring 2025. Kelsey and Kent’s love of adventure and their style of travel mesh perfectly with our vision of immersion experiences. Their knowledge of wine is a valuable addition as well. We happily extend a special invitation to all Flights patrons. Of course, all of our friends are welcome to join our Portugal and Madeira tour.
Escape to Portugal & Madeira
A Journey of Beauty and Discovery
Picture yourself exploring a land of rolling vineyards, winding rivers, and welcoming communities. Portugal offers a rich blend of history, culture, and incredible cuisine, where every meal is a delight, and each glass of wine has a story to tell.
Over the course of nine days, you’ll stroll through charming villages, cycle through sunlit vineyards, and cruise along peaceful riverbanks—experiencing the country at a relaxed and enjoyable pace. Then, continue your adventure on the stunning island of Madeira, where dramatic coastlines, lush forests, and fresh ocean breezes create the perfect setting for exploration and relaxation.
Join Deb and Dan on this thoughtfully designed journey filled with great food, wonderful wines, and unforgettable experiences. Let Portugal and Madeira leave a lasting impression.
Lisbon: A City of History and Charm
Lisbon, Portugal’s vibrant capital, is a city where history, culture, and scenic beauty come together. Set along the Atlantic Ocean and the Tagus River, its hills and historic neighborhoods tell the stories of centuries of exploration and discovery.
One of the best ways to experience Lisbon is with a walk along the Tagus River, where the salty breeze carries a sense of the past. Follow the waterfront to the striking Monument of the Discoveries, a tribute to the explorers who once set sail from this very spot. Along the way, stop at Pastéis de Belém, home to Portugal’s famous custard tarts. These delicious pastries, with their flaky crust and creamy filling, have been a local favorite since the 1800s.
For a taste of Lisbon’s vibrant food scene, visit the lively Time Out Market, where top chefs and local eateries serve everything from traditional Portuguese seafood to modern culinary creations. This bustling marketplace is a great way to sample the city’s flavors in one place.
As you explore, you’ll see Lisbon’s signature azulejo tiles decorating buildings, churches, and quiet alleyways, adding bursts of color to the city’s streets. Step inside historic cathedrals filled with intricate details, reflecting centuries of craftsmanship and tradition.
At the end of each day, unwind at your 5-star hotel, a peaceful retreat in a charming neighborhood, yet close to all that Lisbon has to offer. Whether you’re discovering its history, enjoying its cuisine, or simply soaking in the atmosphere, Lisbon is a city that leaves a lasting impression.
Hotel details Lisbon: 5 – Star property. If you would like to upgrade to a Superior room, the cost is $128 per person per night. Suites must be requested. Suite prices can vary as can availability. Request this thru us. We will find the details and relay back to you.
Sintra is a magical wonderland of fairy-tale castles, opulent palaces, and enchanting villas surrounded by lush, dreamlike gardens. Steeped in history and mystery, this centuries-old gem is one of Portugal’s most breathtaking destinations—a place where every winding street and misty forest feels like a scene from a storybook. As a UNESCO World Heritage site, Sintra is a treasure trove of architectural marvels and romantic landscapes, ready to sweep you off your feet!
The heart of this trip: 4 nights of 5-star magnificence in one of the most spectacular wine regions in the world: Douro Valley
Words fall short in describing the Douro River wine region, but photos come close. The photo above right shows the breathtaking 5 STAR resort we will be enjoying for our stay in this stunning river valley.
Steeply sloping mountains with ancient terraced vineyards stretch to the sky on both sides of the river.
Wine has been produced in the Alto Douro region for 2,000 years. Since the 18th century, its main product, port wine, has been world famous for its quality. But port is not the only offering… tinta roriz (same as Spain’s tempranillo), tinta bastardo, rabigato, viosinho, and green wine.
Cruising on the river while sipping Portuguese wine is an experience you will never forget.
We will spend four nights at our 5 star hotel set in the middle of the terraced vineyards overlooking the river valley…. Glorious.
Our hotel in Duoro Valley is a 5 – Star property. There are no upgrades possible.
Porto: The Historic Heart of the North
Porto, Portugal’s second-largest city, is a captivating blend of history, culture, and modern energy. Set along the scenic Douro River, it is known as the “Granite City” for its striking architecture, impressive bridges, and renowned port wine.
Stroll through the ancient Ribeira district, a UNESCO World Heritage site, where narrow streets and historic arches tell the story of centuries past. Visit the 12th-century cathedral and step inside the stunning São Francisco Church, famous for its intricate gold-adorned interior.
Across the river in Vila Nova de Gaia, the city’s famous port wine lodges—Taylor’s, Cockburn’s, Croft, and Sandeman—offer guided tours and tastings, providing insight into one of Portugal’s most treasured traditions. Enjoy a glass of port at a riverside restaurant or explore the local shops along the waterfront.
With its mix of historic charm and modern vibrancy, Porto is a city full of character and discoveries at every turn.
Our hotel in Porto is 4-star. There are no upgrades.
Madeira: A Portuguese Island Paradise
Rising from the deep blue Atlantic, Madeira is a stunning sub-tropical island known for its dramatic landscapes, world-renowned wines, and warm hospitality. This Portuguese gem offers a perfect mix of natural beauty and cultural charm.
In the capital city of Funchal, stroll through pedestrian-only streets lined with colonial architecture, lively cafés, and boutique shops. Beyond the city, explore the island’s famous levadas—historic irrigation channels now scenic walking trails—leading to breathtaking views.
A visit to Porto Moniz is a must, where volcanic rock pools invite you to swim in clear ocean waters with waves crashing nearby. Enjoy fresh seafood, including the island’s legendary tiger shrimp—so large that just a few make a meal.
Your stay on Madeira includes a luxurious 4-star oceanfront resort, complete with gourmet dining and stunning coastal views—a perfect retreat after days of exploration.
Join Deb and Dan on this immersive journey through Portugal and Madeira—a refreshing escape to a place where authentic beauty and rich experiences await.
Our hotel in Madeira is a 4-star property. ALL rooms included in package are superior. They are partial or full sea-view rooms. Upgrade to a Suite is possible. Suites are full sea view and much larger. Cost for Suite upgrade is $141 per person per night. On request basis, no guarantee of availability. You must email us and we will submit your request and advise of outcome.