Portugal 

Portugal is a captivating blend of historic charm, dramatic coastline, and vibrant culture, where cobblestone streets, tiled façades, and fresh Atlantic seafood define everyday life. From the golden cliffs of the Algarve to the soulful sounds of Fado in Lisbon, it offers warm hospitality and rich traditions.

Day Highlights Overnight
Day 1 This is the travel day. Getting to the airport and taking an overnight flight to Lisbon. In flight
Day 2 Arriving in Lisbon, renting car and driving to Sintra area. Sintra
Day 3 Tour Pena Palace, Moorish Castle & Montserrat Palace & Gardens. Sintra
Day 4 Quinta de Regaleira and Gardens, Cabo da Roca, Praia da Ursa. Beach Sintra
Day 5 Leave Sintra, Visit town of Obidos, Arrive in Porto. Porto
Day 6 Sights of Porto. Porto
Day 7 Leave Porto, visit town of Amarante, arrive in Duoro. Duoro
Day 8 Santuário de Nossa, visit to a winery. Duoro
Day 9 Leave Duoro area, stop in the town of Evora, arrive in Lux (Lagos area in the Algarve region). Luz
Day 10 Hike along the Seven Hanging Valleys Trail, Lunch at by the sea, explore Lagos. Luz
Day 11 Visit the Benagil Cave, explore the town of Faro. Luz
Day 12 Beach day at Praia do Camilo Luz
Day 13 Drive back to Lisbon, Visit Praca do Comercio, Pink Street, and cocktails on terrace. Lisbon
Day 14 Sights of Lisbon. Tram ride. Dinner and Fado show. Lisbon
Day 15 Free day in Lisbon; Belem Castle, visit to Pastéis de Belém. Lisbon
Day 22 Taxi to the airport, flight home.

Portugal Itinerary Summary (2024)

  1. September 10: Departure from Toronto to Lisbon at 22:50. ​

  2. September 11:

    • Arrival in Lisbon at 11:10 AM. ​

    • Car rental. ​

    • Lunch in Cascais (recommendation: Yellow Street or Old Town). ​

    • Visit Boca do Inferno for scenic coastal views. ​

    • Check-in at Sintra hotel at 3:00 PM. ​

    • Explore Sintra and dinner in Sintra. ​

  3. September 12: Sintra sightseeing (recommend parking at Pena Palace and walking to Moorish Castle, 20 minutes). ​

  4. September 13:

    • Visit Quinta de Regaleira and Gardens (tickets needed). ​

    • Explore Cabo da Roca (free). ​

    • Visit Praia da Ursa Beach and Praia da Adraga. ​

    • Dinner at Moinho Dom Quixote (no reservations, arrive early for sunset at 7:40 PM). ​

  5. September 14:

    • Drive to Porto via Obidos (1 hour from Sintra). ​

    • Have Ginja drink in a chocolate cup, walk the streets, and explore the city wall. ​

    • Optional stop in Aveiro for a canal tour, walking, shopping, and lunch. ​

    • Arrive in Porto and check-in at Airbnb at 3 PM. ​

    • Porto sightseeing:

      • Liberade Square (start walking tour here). ​

      • Vitoria viewpoint (views of Old Town and river). ​

      • Igreja do Carmo-Capela (exterior tiles). ​

      • Clerigos Church and Tower (250 feet tall, tallest building in Porto). ​

      • Porto Cathedral (blue tile cloisters, great views). ​

      • Church of St. Francis (beautiful interior). ​

      • Ribeira neighborhood and square (river views, colorful buildings). ​

      • Sunset viewpoint in Vila Nova de Gaia (cross the bridge). ​

      • Porto Wine Cellars for wine tasting. ​

      • Terrace Lounge 360 (rooftop bar, no reservations). ​

    • Parking in Porto: Alfândega Car Park, €35 for 48-hour ticket. ​

  6. September 15: Porto activities:

    • Walk Santa Catarina Street (main shopping street). ​

    • Visit Majestic Café (historic café, top 10 most beautiful in the world). ​

    • 10:30 AM reservation at Livraria Lello (world’s most stunning bookshop, €8 entry fee, refunded with book purchase). ​

    • See art at Sao Bento Train Station. ​

    • Visit Batalha Square and 18th-century Batalha Palace. ​

    • Walk the riverfront. ​

    • Book a 6 Bridges Cruise (50 minutes, approx. ​ €15, book on Gaia side). ​

    • Visit Jardim do Morro (city views). ​

    • 9:30 PM dinner reservation at Rua Tapas e Music Bar. ​

  7. September 16: Finish Porto activities. ​ Drive to Douro Hotel at 5 PM. ​

  8. September 17: Douro sightseeing:

    • Visit Santuário de Nossa. ​

    • Winery visit (Quinta do Panascal). ​

    • Scenic drive between Peso de Regua and Pinhao (N222). ​

  9. September 18:

    • Checkout of Douro at 8 AM. ​

    • 4.5-hour drive to Evora. ​

    • Lunch in Evora and explore town and Roman ruins or visit Almendres Cromlech. ​

    • 2.5-hour drive to Luz. ​ Check-in at Airbnb at 4 PM. ​

    • Visit Sagres lighthouse (extreme western point of Europe). ​

  10. September 19:

    • 8 AM: Hike Seven Hanging Valleys Trail (3.5 km moderate trail along the coast, start at Praia do Marinha beach). ​

    • Visit Boneca Beach Restaurant/Bar and nearby caves. ​

    • 5 PM: Explore Lagos old town/downtown. ​

    • Dinner at Don Sebastiao. ​

  11. September 20:

  12. September 21:

    • Visit Praia do Camilo and Praia Dona Ana (kayaking available). ​

    • Explore Ponta da Piedade (coves and caves). ​

    • 5 PM: Explore Lagos old town/downtown. ​

    • Dinner at Don Sebastiao. ​

  13. September 22:

    • Drive to Lisbon. ​ Check-in to apartment after 3 PM. ​

    • Visit Praca do Comercio, Pink Street, and Terraço Chill-Out Limão. ​

  14. September 23:

    • Ride Tram 28. ​

    • Visit Castle of São Jorge, Miradouro da Graça, and Miradouro de Santa Luzia. ​

    • Dinner at Lumi Rooftop Restaurant (no reservation). ​

    • 7:30 PM reservation at Antikuario Café (send request via ​

Day 1 - Overnight flight to Lisbon.

Day 2 - Arrive In Lisbon, Portugal

  • Car rental at the airport. ​

  • Lunch in Cascais on either Yellow Street or Old Town, wonder through old town Cascais.

  • Visit Boca do Inferno for scenic coastal views. ​

  • Check-in at Sintra hotel at 3:00 PM. ​

  • Explore Sintra and dinner in Sintra. ​

Day 3- Sintra‍ ‍

A day to explore Cefalu. Don’t miss these sights:

  1. Cefalù Cathedral (Duomo di Cefalù): A magnificent Norman cathedral with twin towers and stunning Byzantine mosaics. Don’t miss the rooftop of Cathedral for stunning views of the town and the sea and inside the chapel.

  2. La Rocca: A steep hike leads to panoramic views and ancient ruins, including the Temple of Diana.

  3. Old Town (Centro Storico): Wander through medieval lanes, charming piazzas, and lively markets filled with local flavor.

  4. Bastione di Capo Marchiafava is a historic coastal bastion located at the edge of Cefalù’s old town, built as part of the town’s defensive walls. Today, it’s a scenic viewpoint perched above the sea, offering panoramic views of the Tyrrhenian coastline and the rugged cliffs below—an ideal spot to watch the sunset or take photos of Cefalù’s stunning seaside landscape.

  5. Lavatoio Medievale: A beautifully preserved medieval washhouse carved into rock and fed by natural springs.

  6. Lungomare Beach: A golden stretch of sand perfect for swimming and sunset strolls along the promenade. This beach also has a touch of Hollywood fame—it appeared as “the beach” in The White Lotus Season 2. While the series’ hotel scenes were filmed in Taormina, there’s no beach directly by the hotel, so this picturesque shoreline in Cefalù served as its stand-in.

  7. Museo Mandralisca: A small but fascinating museum featuring art, archaeology, and the famous Portrait of an Unknown Man by Antonello da Messina.

  8. Watch the spectacular sunset by Largo Eroi del Mare by the pier of the Old Town.

Food tip🍦 - there is wonderful bakery/gelateria by the front of Duomo di Cefalu called Duomo Serio 1952. Have a traditional Sicilian break there which consists of a brioche and granita before exploring the Duomo. In the evening enjoy a gelato, and let me know if they still have a gelato called ‘Greta’.

Cefalu, Sicily harbour at night.
Cefalu duomo
Cefalu, Sicily balconies

Day 6- Lipari

Take the train from Cefalu to Milazzo, a port town where you can board the hydrofoil to the island of Lipari. Depending on where you are staying in Cefalu you could walk to the train station or take a taxi. Once reaching Milazzo, there is public bus that will take you to the port.

Lipari is the largest and liveliest of the Aeolian Islands, located off the northern coast of Sicily in the Tyrrhenian Sea. It’s known for its volcanic landscapes, charming old town, and role as the hub for exploring the surrounding islands. We stayed at the beautiful hotel Hotel Villa Enrica - Aeolian Charme boasting panoramic views of Lipari town. We quickly found out though that while the town appears to be close to the hotel, it’s quiet a walk uphill. Shortly after arriving we opted for renting scouters to get around for the next few days.

In the evening we went into Lipari town. Lipari town is the lively heart of the Aeolian Islands—small, sun-washed, and effortlessly charming. It rises straight from the sea with pastel houses, a busy little port, and a dramatic hilltop Castello di Lipari watching over everything like an old guardian.

Day 7 - Lipari

The morning was spent exploring some of Lipari’s beaches. The evening was spent admiring the Tyrrhenian Sea sunset views by visiting the Tenuta di Castellaro winery at sunset. Reservations are required.

Day 8 - Lipari

Throughout Lipari town you’ll see many tour operators offering boat cruises to the surrounding islands. One of those island is Stromboli. Stromboli is called the ‘lighthouse of the Mediterranean’. It one of the most dramatic and unforgettable islands in the Aeolian chain—a tiny, conical volcano rising straight out of the Tyrrhenian Sea. It’s famous for its persistent volcanic activity, its black‑sand beaches, and its two charming villages that feel wonderfully remote. Its eruptions are typically small but frequent bursts of glowing lava—known as Strombolian activity—that shoot from vents inside the summit crater.

Travel Tip: Before you travel to Stromoli, I highly recommend watching the 1950’s movie called ‘Stromboli’, as it’s set on the real island of Stromboli. It’s a post‑war drama about a displaced woman who marries an Italian fisherman to escape a refugee camp, only to find herself trapped in a harsh, isolated life on the volcanic island of Stromboli. It blends personal crisis with the raw power of the island’s active volcano. It’s directed by Roberto Rossellini and stars Ingrid Bergman. The 2 later later marry in real life.

Lipari, Sicily
Lipari, Stromboli, Sicily

Day 9- Taormina

Reverse course from getting to Lipari. Take the hydrofoil back to Milazzo, at Milazzo port take the bus or taxi back to the train station. At the train station or on the mobile app purchase tickets to Messina. Once you arrive at Messina, you’ll need to change trains and purchase a ticket for Taormina. Once you arrive at Taormina-Giardini train station you’ll need to get up the mountain to the centre of town. Taormina has reliable public transportation from the Taormina‑Giardini train station to the town center. The main option is the Interbus service, which runs frequently and takes about 10–15 minutes to reach Taormina’s bus terminal.

Taormina is a hilltop town on Sicily’s east coast. It has dramatic views with the most notable being Mt Etna, the highest active volcano in Europe and stunning views of the Ionian sea. It’s a stunning town, known as the dolce vita of Sicily and the main filming locations of the show, White Lotus season 2. Taormina is steeply built and is known for it’s many staircases, so take not of this while figuring out where to stay.

We stayed in a beautiful Airbnb set about 360 steps above Corso Umberto, giving us a peaceful perch over the heart of Taormina. From the terrace, we had sweeping views of Mount Etna and the Bay of Giardini‑Naxos, and during our stay we were lucky enough to watch Etna’s lava glowing in the distance — an unforgettable sight right from our apartment.

This day was spent exploring the streets of Taormina and a visit to Villa Communale, a lush and nicely keep outdoor garden with sweeping sea views.

Travel Tip: If you looking to go to the beach the was shown in White Lotus Season 2, the one that is ‘part of the hotel’ in the show, it is not located in Taormina. The beach from the show is actually located in Cefalu.

Day 10 - Taormina

Morning - Visit the Greek Theatre of Taormina. The Greek Theatre in Taormina is one of those places that feels almost unreal when you’re standing in it. Carved into the hillside in the 3rd century BC, it perfectly frames Mount Etna on one side and the Ionian Sea on the other—arguably the most dramatic theatre backdrop in the world.

What makes it special isn’t just its age or beauty, but that it’s still alive. The theatre hosts concerts, opera, and film festivals, just as it did in ancient times, with acoustics so good you can hear a whisper from the stage. As the sun sets and Etna smolders in the distance, it’s hard not to feel like Taormina’s entire history—Greek, Roman, and Sicilian—has gathered in one breathtaking spot.

Afternoon - Beach time, take the cable car down to the Isola Bella and the beach. Isola Bella is Taormina’s little slice of magic—a tiny island that feels half wild, half dream. It’s connected to the mainland by a thin strip of pebbled beach that disappears when the tide comes in, so it sometimes looks like it’s floating in the Ionian Sea.

Once the private retreat of an eccentric English aristocrat, it’s now a protected nature reserve, covered in Mediterranean plants and surrounded by shockingly clear turquoise water. Whether you’re swimming, snorkeling, or just staring at it from above, Isola Bella has that quiet, cinematic beauty that makes you slow down and think, yes… this is why people fall in love with Sicily.

Day 11 - Taormina

A visit to a couple of towns near Taormina:

  1. Savoca. Most people know Savoca because The Godfather was filmed here — you can still sit at Bar Vitelli, unchanged and dripping with old-world charm. But even without the movie lore, the town feels timeless: medieval churches, crumbling palazzi, and a peaceful, almost sacred stillness once the day-trippers leave. It’s the kind of place where life moves slowly, bells echo, and you feel like Sicily is whispering its secrets rather than shouting them.

  2. Castelmola is a charming, medieval hilltop village located just above Taormina. Renowned as one of Italy's most beautiful villages ("I Borghi più belli d'Italia"), it offers breathtaking panoramic views of Mount Etna, the Ionian Sea, and the coastline. 

This itinerary is currently in progress (Feb/2026), stay tuned for updates.

Taormina, Sicily, Staircases
Taormina, Sicily, Teatro Greco, Ionian Sea
Taormina, Sicily, Mount Etna

Day 12 - Catania

This itinerary is currently in progress (Feb/2026), stay tuned for updates.