Exploring Portugal’s Most Romantic Enclaves: Trip for All-Aged Couples

What to expect on this itinerary
During this 10-day journey, you will witness some of the most iconic aspects of Portugal. Portugal is an amazing travel destination that is often overshadowed by some of the larger European countries, but this unique country has something to please everyone and usually always has its guests leaving enamored. Escape to Madeira Island for three days, indulge in a dinner cruise, and spend the night at a 13th-century castle.
Customizable Itinerary
Porto – Indulge in a River Cruise
Upon your arrival to Porto, you will be met by your private driver, who will transfer you to your luxurious accommodations in the heart of the city. After checking in and having ample time to settle in, you will embark on a romantic dinner cruise on the Douro River. This river tour will prove to be an amazing way to witness the picturesque city from a unique perspective, and during your cruise, you can dine on some of Portugal’s freshest fare. After admiring the gorgeous views as you sail, you will be returned to your luxurious accommodation.
What's Included:
Viana do Castelo – Tales of Lore
Braga – Private Horseback Ride
Guarda – Visit the Jewish Quarter
Guarda – Reconnect with Nature
Obidos – Sleep in a Castle
Obidos – Learn How to Make Ginjinha
Funchal – Escape to Madeira Island
Funchal – Taste the Flavors of Funchal
Funchal – Departure
Trip Highlights
- Escape to magical Madeira Island for three days of exploring tropical gardens, farmers’ markets, and delighting in picnics
- Indulge in a dinner cruise in Porto that will have you gliding along the calm waters of the Douro River
- Venture on a horseback riding tour among the beautiful backdrop of Braga’s scenery
- Marvel at Viana do Castelo, where you can hear tales of the town’s fascinating folklore
- Escape to the alluring Estrela Mountains, where you can admire the spectacular views that will surround you on every side
- Peruse the historical wonders of Guarda’s Jewish Quarter before discovering the beauty of Guarda’s castle and cathedral
- Spend the night in a 13th-century castle that has been converted into a stunning bed and breakfast
Detailed Description
When it is time for you and your significant other to escape, Portugal provides the perfect destination. From its charming villages that are full of cobblestone streets and medieval architecture to its numerous castles, Portugal presents a wonderland that boasts boundless beauty and boundless marvels to explore. This luxurious, 10-day journey will provide you with some of the most exclusive experiences that this country has to offer.
Your journey will begin in Porto, where you will begin with a dinner cruise, sightseeing the city from a unique perspective as you glide along the Douro. Day two will find you venturing to Viana do Castelo, which is a lovely enclave that is imbued with charm and history. While here, you will listen to fascinating tales of folklore. Later in the evening, you will be provided with the incredible opportunity to craft your own to keepsake.
You will transfer to Braga on day three, and upon your arrival, you will witness the Bom Jesus before embarking on a private, horseback ride. Two unforgettable days in Guarda will be waiting, which is where you will indulge in an escape to the Estrela Mountains. This getaway will give you the chance to reconnect with nature among majestic, mountain scenery. While here, you will enjoy perusing the historical gems that can be found in the Jewish Quarter before become exploring the city’s castle and cathedral.
Obidos will be next on your agenda, and here, you will indulge in a private tour of the city’s highlights. Your accommodation in Obidos will be what was once a royal castle but is now a high-end bed and breakfast. During your second day in Obidos, you will enjoy its many outdoor offerings as you begin the morning by embarking on a stand-up paddleboarding adventure at Obidos Lagoon. Following your SUP session, you can spend the afternoon strolling and sunbathing on the beach before partaking in your exciting evening event. This evening you will indulge in a class that will be taught by a local master on how to craft the famous cherry liqueur known as Ginjinha.
The final leg of your getaway will find you flying to Madeira Island for a three-day adventure. The following day will have you exploring two tropical gardens. Following your foray into the blossoming world of the botanical gardens, you will be led on a gourmet food tour excursion. During your tour, your culinary guide will introduce you to the flavors of the city.
Throughout your vacation, you will stay in luxurious accommodations and have every detail of your journey taken care of, including all private transfers to and from each destination. Nearly everything about this itinerary is customizable, so you can adjust nearly anything and everything to better suit your moods and interests once you are in Portugal.
Starting Price
$2,600 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.
Verified Traveler Reviews
Based on 400 reviews
The travel agent from Zicasso's tour company planned for my family of four the most spectacular and luxurious two-week trip around Portugal. We traveled to and enjoyed the highlights of Lisbon, the romantic architecture in Sintra, the incredible history of Évora, the beautiful coastline of the Algarve, the laid-back atmosphere and gorgeous scenery of Madeira, the beautiful, historical, bustling city of Porto, and the stunning scenery of the Douro Valley.
The travel agent's suggestions and bookings were all perfectly aligned with what we envisioned and the accommodations booked were all beautifully appointed and family-oriented – five-star hotels that catered to the entire family, with indoor pools and kids greeted with backpacks and toys at the door, and nightly treats on pillows.
The tour guides booked were all very knowledgeable and kind. They were patient with my two- and four-year-olds, and taught us all so many new, amazing things.
Every day was a highlight, but I would say my girls really enjoyed the tile painting as well as the pastel de nata-making workshops.
My husband and I really enjoyed Évora and Sintra, and truly seeing the beauty and history of it all.
We absolutely fell in love with Portugal, the culture, and the food. My only regret is not having more time so we could’ve seen the Azores as well and stayed even longer.
We so look forward to this travel agent planning us another perfect vacation in the near future!
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My wife and I have been lucky enough to travel to many places around the world, but our April 2025 journey organized by Zicasso's tour company was easily one of the best. Our agent and her team thought of every detail. All we had to do was show up and enjoy these two beautiful countries!
We went to Four cities: Lisbon, Porto, San Sebastián, and Barcelona. The itineraries were thoughtfully planned to give us great experiences without wearing us out too much. And the guides in each city were fun, knowledgeable, and engaging. The transportation was always easy and on time, and the hotels were top-notch.
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Our Zicasso travel agent curated a private tour for the six of us, including the perfect mix of historical, gastronomical, wine, and cultural experiences.
We stayed in Lisbon, Évora, the Dao Valley, the Douro Valley, and Porto. We traveled in a comfortable Mercedes van and, to break up our trips, we stopped at amazing sites along the way as we traveled from city to city.
Some of our favorite things were a private sunset sail in Lisbon, a fado dinner, the Évora Cathedral, a cork trek and wine tasting in Alentejo, the monastery at Batalha, wine tastings in Santar (Dao Valley), a boat ride on the Douro, wine tastings and hiking in the Douro Valley, the Bom Jesus shrine in Braga, the Port tasting and dinner in Porto, and multiple pastry tastings along the way.
Our guides were fantastic. They were attentive, on time, and very knowledgeable about the history and culture of each place we visited.
There were very few issues on our 17-day tour, which was literally one of the smoothest and best-curated trips we have ever had. We will use our travel company and agent again as we intend to go back to Porto and the Douro Valley.
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Overall, our itinerary, meals, excursions, drivers, and tour guides in Portugal were top-notch. Our first two hotel accommodations in Porto and the Douro Valley did not meet our expectations. The first one was extremely small and poorly lit; the second one was very isolated and difficult to get around. After that, the hotels improved substantially.
All communication with our Zicasso travel agent was done by text or phone.
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We recently returned from two fabulous weeks in Portugal. This was the first time we had used an agency to help plan, book, and manage a trip. We could not be more pleased and I highly doubt we will ever go back to handling all of that ourselves.
Zicasso’s travel specialist and his team (most notably our guide) were incredible. The travel specialist listened to our hopes for this trip (as well as what we like to do when traveling) and put together an awesome itinerary. Our main stops were Lisbon, the Algarve, Porto, and the Douro Valley.
Major highlights included four-hour walking and food tours in Lisbon and Porto (the first of which was the day we arrived from the United States. I didn’t think we could do it, but it was the best way to start our trip), the tile museum and tile workshop, a boat ride through the cave formations in the Algarve, a wonderful farm-to-table lunch and wine pairing under a 2,000-year-old olive tree in the Algarve, and an 18-mile e-bike ride in the mountains of the Douro (I definitely didn’t think we could do it).
The sites, the food, the hotels! We did so many things and had so many unforgettable experiences, but in the end, it was the kindness and generosity of all the people we met that will stay with us.
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This was a fantastic trip to Porto, Lisbon, and the surrounding areas, tailored to our needs and interests. We had an extensive walking tour of Lisbon, vineyards, and historic sites with our tour guide. Zicasso's travel agent provided personalized service consistent with a good small company. There was a rail strike while we were there and they handled it.
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