I’m so excited to share and experience Portugal together! Since we both seem to have similar attitudes toward travel and discovery, I didn’t build this itinerary around monuments and must-see lists, as other trips predictably do. I crafted it for beauty, respect for tradition, unexpected discoveries, extraordinary food and wine, and the kind of slow, meaningful experiences we both crave and enjoy.

As you know, Portugal is one of my favorite countries and one of Europe's most unique treasures. The Portuguese are very warm and welcoming and deeply connected to their history and culture. 

Lisbon 🇵🇹 From a golden sunset sail on the Tagus River with wine in hand to a magical day in the fairy-tale castle of Sintra with our very own private guide—my dear friend António, who knows every hidden corner of this extraordinary UNESCO World Heritage site.

Aveiro 🚣 From charming canal-side accommodations to gliding through ancient waterways aboard a traditional painted Moliceiro boat, discover one of Portugal's most charming and unexpected cities, famous for its Art Nouveau architecture.

Porto 🍷 From painting traditional azulejo tiles using centuries-old techniques with Port wine in hand, to a private natural Green Wine tasting with the author of the definitive book on Portuguese wine, to an evening in a deconsecrated 19th-century chapel that has become one of Porto's most extraordinary atmospheric wine bars.

Setúbal 🐬 A working port town just south of Lisbon, unpolished and unpretentious—famous for its fresh fish market, its own invention (choco frito, fried cuttlefish), and the resident bottlenose dolphins of the Sado Estuary, one of only three resident dolphin communities in all of Europe.

All you need to do is relax and enjoy. I'll take care of the rest.❣️

Lisbon (Sept 22–26)
Portugal's capital and your starting point—a city of hills, trams, and river light. You'll arrive into Alfama, the oldest neighborhood in the city, staying right where the real Lisbon lives rather than the postcard version of it. A sunset river cruise on the Tagus and a day trip to Sintra's fairy-tale palaces set the tone early. I chose Lisbon to open the trip because it's the easiest place to land, settle in, and get your bearings with António as your guide from day one.

Aveiro (Sept 26–28)
Known as "the Venice of Portugal" for its canals and colorful moliceiro boats, Aveiro is a quieter, gentler stop between two bigger cities. A canal cruise and an afternoon at Costa Nova beach — famous for its candy-striped fishing houses — give you a breather and a completely different visual world before Porto. I chose it as a stopover precisely because it's small, walkable, and unlike anywhere else on the route.

Porto (Sept 28–Oct 1)
Portugal's second city, and the namesake of Port wine itself. A Douro river cruise, Port and Vinho Verde tastings, and a hands-on tile-painting workshop let you experience Porto's two defining traditions — wine and azulejos — directly rather than just observing them. I chose Porto because it has a completely different character from Lisbon: grittier, more vertical, built on the wine trade rather than empire.

Back to Lisbon (Oct 1–7)
You return to Lisbon as a home base for the trip's final stretch—first with António's place as your anchor for further discoveries, including a day trip to Setúbal, a working port town known for its fresh fish market, the invention of choco frito, and a completely different, unpolished side of the Lisbon area. I depart on the 5th, and from there, the city is yours—your first stretch of fully independent travel on this trip.

Departure
You fly home to Arizona on Oct 8, closing out a journey that moved from grand capital, to quiet canal town, to wine city, and back to Lisbon on your own terms.

🏫 All accommodations (apartments, BnBs, hotels, guest houses). All (except hotel stays in Lisbon between flights) with kitchen facilities, some with washing machines for laundry days. Most with views. Twin beds or 2 double beds. Other amenities.
🚕 Transfers and transportation (city trams, trains, metro, taxi/Uber, ferry)
🌅 Welcome to Portugal sunset river cruise with wine and snacks (Lisbon)
🏰 Day trip to Sintra castle with private guide
🛥️ Ferry across the Tagus River to Cacilhas, known for its seafood restaurants and views of Lisbon
⛵️ Canal boat ride in Aveiro (the 'Venice' of Portugal)
🚤 River cruise & Port Wine tasting (Porto)
💚 Green Wine tasting (Porto)
🙌🏽 Traditional hands-on tile painting workshop (Porto. Includes two original tiles made by us!)
🍇 Wine bar visit — Capela Incomum, a deconsecrated 19th-century chapel turned atmospheric wine bar (Porto)
🐬 Dolphin Bay boat excursion — Sado Estuary resident bottlenose dolphins (Setúbal)
🛫 Airfare to and from Lisbon for me (Zani), from Spain
✅ Additional FREE visits to important sights, and unique experiences
✅ Ample free time to rest or explore beyond what I curated

Your airfare from Arizona
Your solo accommodation in Lisbon, Oct 5–8
Meals, beverages, snacks, personal expenses, souvenirs (we each cover our own)
Tips, where applicable

It is highly recommended that you purchase comprehensive travel insurance before your departure. A good travel insurance policy generally covers:

• Trip cancellation or interruption due to illness, injury, or unforeseen circumstances

• Medical emergencies and hospitalization abroad

• Emergency medical evacuation and repatriation

• Lost, stolen, or damaged luggage and personal belongings

• Flight delays, cancellations, and missed connections

• Accidental death and dismemberment

• 24-hour emergency assistance and travel support

Travel insurance is an investment in peace of mind and is strongly advised for any international trip of this duration and cost.