From the Iberian Peninsula to southern Italy, this 13-day odyssey takes in the culture, history, and cuisine of two distinct European locales. Discover Porto's flavorful food scene, go wine tasting in the Douro Valley, and get lost in the labyrinth of Lisbon's Old Town. Then it's off to Sicily for a week of ancient ruins, sun-soaked cities, and turquoise seas as you hop between Palermo, Agrigento, and Catania.


  • Immerse yourself in Porto's vibrant culinary scene with a walking food tour
  • Discover the fantastical hilltop palaces of Sintra
  • Hear live fado music in Lisbon's atmospheric Bairro Alto
  • Go hiking & wine tasting on the slopes of Mount Etna
  • Stroll through the exquisite Greek ruins of Agrigento

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Porto, Afternoon Food Tour Porto
Day 2 Tour Historic Porto, Join a Portuguese Cooking Class Porto
Day 3 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 4 Transfer to Lisbon via Coimbra Lisbon
Day 5 Get to Know Lisbon with a Local, Evening of Fado Lisbon
Day 6 Day Trip to Sintra, Cascais & Estoril Lisbon
Day 7 Fly to Sicily,  Explore Palermo Palermo
Day 8 Day Trip to Cefalù & Sicily's Best Beaches Palermo
Day 9 Transfer to Agrigento, Discover the Valley of the Temples Agrigento
Day 10 Transfer to Catania via Villa Romana del Casale Catania
Day 11 Mount Etna Half-Day Tour & Wine Experience Catania
Day 12 Day Trip to Syracuse, Ortigia & Noto Catania
Day 13 Depart Catania  

Detailed Itinerary

Day 1: Arrive in Porto, Afternoon Food Tour

Porto's stunning setting along the Douro River
Welcome to Porto! Upon arrival, you'll be met at the airport by your driver and transferred to your hotel in the city center. Spend the rest of the afternoon settling in, or head out to learn more about Porto and its cuisine with a walking tour of the historic downtown. Guided by a local expert guide, this small-group excursion offers a first-hand look at the culinary renaissance that the city is experiencing, including the rebirth of specialty food shops and new restaurants that are adopting old methods.

You'll take part in several distinct tasting locations that harken back to an era of simple, quality products and recipes created by people who love what they do. Learn about these family-owned businesses and why they are an integral part of what makes gastronomy in Porto so unique. Furthermore, you'll witness the revival of Portuguese cuisine while you explore local restaurants, cafés, and stores offering the best of Porto.

Day 2: Tour Historic Porto, Join a Portuguese Cooking Class

Colorful houses in Porto's Ribeira neighborhood
Explore more of Porto today with a private tour, learning about the city's history, heroes, and battles as you make your way through the trendiest and most cultural areas of town. Start in the UNESCO-listed city center to admire renowned monuments and sites, including the São Bento Railway Station, Clerigos Tower, Church of St. Francis, Lello Bookshop, Sta. Catarina Street, Majestic Café, and Bolhão Market. After visiting Porto Cathedral, you'll finish the tour along the banks of the Douro River for views over the city from the Miradouro da Vitória.
After lunch, the rest of the day is free to explore. A good place to start is the Ribeira neighborhood, which sits alongside the river and is one of the oldest parts of the city. Famed for its narrow and colorfully-tiled dockside houses, as well as its views of the iconic double-decked Dom Luís Bridge, this UNESCO-listed area is a must-see. You could also join a private cooking class for an introduction to the flavors of Portuguese cuisine. After preparing dishes made from locally-grown products, you'll sit down and enjoy a memorable meal paired with dynamic wines and spirits.

Day 3: Day Trip to the Douro Valley, Wine Tasting & River Cruise

Vineyards overlooking the Douro River
Today your private driver will be waiting to whisk you into the mountains and valleys of the famous Douro Valley wine region, where you'll visit traditional wineries accompanied by your expert guide. After a wine tasting, you'll enjoy a traditional lunch at one of the valley's famous quintas (estates). 

After lunch, it's time to hop aboard a riverboat for an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks. At the end of the day, your guide will return you to Porto, where you can spend the evening at leisure in the city's lively Ribeira area.

Day 4: Transfer to Lisbon via Coimbra

Coimbra's Largo da Portagem Square

Today, after breakfast and check-out, you'll meet your driver for the transfer south to Lisbon. About halfway through the trip, stop to spend some time exploring Coimbra. This medieval capital of Portugal wears its weighty importance in Portuguese history with dignity and pride, witnessed by its multicolored collage of buildings that span nearly a millennium. The historic core cascades down a hillside to create a lovely setting along the east bank of the Rio Mondego.

Upon arrival, you'll meet with a local guide for a private tour of the city. The 13th-century University of Coimbra remains the star attraction, with a tremendous amount of history and knowledge accumulated within its walls. A must-see is the Baroque library, home to an incredible collection of over 200,000 books stored in carved and gilded bookshelves. The Chapel of Saint Michael next door is also worth the visit, and make sure to take a stroll through the atmospheric medieval streets of the historic center before getting back on the road and continuing to Lisbon.

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Day 5: Get to Know Lisbon with a Local, Evening of Fado

A statue of King Joseph I at Lisbon's central Praça do Comercio
First things first, you’ll get your bearings on a privately guided tour of the city’s most happening neighborhoods as you hop on board an iconic tram and head into Bairro Alto. Continue onto Chiado and discover a cultural enclave where the great writers and philosophers of the 20th century used to gather to hone their ideas. Next up is the picture-perfect neighborhood of Alfama. Here, you’ll get a feel for traditional Lisbon with its narrow cobblestoned streets and the stunning 12th-century Sé de Lisboa Cathedral.

After spending some time getting to know Lisbon, your private guide will give you recommendations for lunch or dinner and you will have the rest of the day to explore one of Europe's coolest cities at your own pace. In the evening, you’ll head back into the Bairro Alto and enjoy a night at one of the city’s best fado restaurants, where good food, the perfect setting, and the melancholic tones of traditional fado music come together for a truly authentic night out.

Day 6: Day Trip to Sintra, Cascais & Estoril

Sintra's hilltop setting near Lisbon
Sintra's hilltop setting near Lisbon

After breakfast, your private driver will pick you up to start today's adventure in Sintra. Located just half an hour east of the city, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces. 

After touring the palace you'll have a break for lunch, at which point you can also stroll through the historic village of Sintra and do some shopping and/or sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss locales in this area include the dramatic coastal cliffs of the Cabo de Roca, the wide and inviting Guincho Beach (a popular surf spot), and the glamorous towns of Cascais and Estoril.  After the tour, a private transfer will take you back to your hotel in Lisbon.

Day 7: Fly to Sicily, Explore Palermo

A colorful sunset over Palermo
It's time to bid Portugal farewell as you make your way to the Lisbon airport this morning to catch your flight to Palermo, where a private driver will be waiting to transfer you to your hotel. Get settled, then meet your guide for a private half-day tour of the Sicilian capital.
Quattro Canti (officially known as Piazza Vigliena), Palazzo Reale, the 12th-century Duomo (the Palermo Cathedral), and Marina Square are some examples of architectural masterpieces you'll come across. You'll also visit Capo Market, a great spot to pick up some lunch or a typical snack like panelle (chickpea fritters) and cazzilli (pan-fried potato croquettes).

Day 8: Day Trip to Cefalù & Sicily's Best Beaches

Take a day trip to the beautiful seaside town of Cefalù
Start your morning with a scenic one-hour train ride along the coast to Cefalù, a historic port town. You can start a self-guided tour in the city center at the Lavatoio Medievale, a 16th-century washhouse that utilizes running water from the River Cefalino in its stone basins. Nearby is the Porta Pescara, a gate to Cefalù Beach featuring great views of the coast. Perhaps take a walk to the old harbor and stroll the seaside promenade; the city's Lungomare Beach is also a popular destination. 

You should definitely visit the 17th-century Bastione di Capo Marchiafava, one of many old defensive fortresses located along the coast. The view from the top of the Bastione is a real treat. Nearby you'll find the Norman-Arabic Duomo Basilica Cattedrale (Cefalù Cathedral) which dates to the 12th century. And if there's time, climb the Rocca, the promontory above the city. A steep staircase winds through city walls before emerging onto a rocky outcrop with stunning views of the city and ocean. Stop at a beachside bar for an aperitivo before catching the train back to Palermo.

Day 9: Transfer to Agrigento, Discover the Valley of the Temples

Temple of Concordia
The incredibly preserved Temple of Concordia in Agrigento

After breakfast, a private transfer will take you south to Agrigento. Upon arrival, you'll have the rest of the day to explore the city and its popular UNESCO-listed archaeological site, the Valley of the Temples. Meet with your guide to walk through the well-preserved Greek temples and the ancient city of Akragas with the option to spend time at the popular archaeological museum.

Along the way, you'll stop to marvel at the temples of Hera, Concordia, and Herakles as your expert guide reveals historical insight that brings the ruins to life. You'll also learn how these ridge-top temples once served as beacons for homecoming sailors. After the tour, the rest of the day is free for you to explore at your leisure.

Day 10: Transfer to Catania via Villa Romana del Casale

Catania's Piazza Duomo
In the morning, your private driver will pick you up to take you east to Catania, located on the beautiful Ionian Sea. On your way, you'll stop for a private tour of the UNESCO-listed Villa Romana del Casale. Discover some of the world's best-preserved and varied Roman mosaics as you explore the grounds of this ancient Roman villa. Incredibly luxurious and built on a vast scale, Villa Romana del Casale was probably made for a member of ancient Rome’s elite.

After the visit, continue to Catania to get checked into your hotel then head out for a guided stroll. See the city through the eyes of a local as your knowledgeable guide shares fascinating stories and introduces you to historic landmarks, many dating back as far as the 8th century BCE. Discover highlights like the Piazza Duomo, Pescheria, Castello Ursino, Piazza San Francesco, Via Teatro Greco, Piazza Dante, and the Piazza San Placido. As evening falls, you can uncover the secrets of Italian family recipes with a private cooking class in a local home—complete with dinner and a selection of local wines. 

Day 11: Mount Etna Half-Day Tour & Wine Experience

WIldflowers on the slopes of Mount Etna
After breakfast, your guide will pick you up from your hotel to start today's adventure to Mount Etna, Sicily's iconic active volcano. Start with a hike accompanied by an expert naturalist guide. Along the route, you'll discover craters, ancient lava flows, and breathtaking landscapes. You'll even have the chance to head underground and explore a lava cave with helmets and torches.

After scaling Mount Etna, discover the famous wine of the region, notable for its distinct characteristics bestowed by the fertile, mineral-rich soils surrounding the volcano. Taste a selection of local wines, and enjoy a typical Sicilian lunch made with local products.

Day 12: Day Trip to Syracuse, Ortigia & Noto

Explore Ortigia's spectacular waterfront
Uncover some of Sicily's greatest treasures on a fantastic full-day tour with an expert guide. After being picked up from your accommodation in Catania, you'll start today's excursion at the magnificent Neapolis in Syracuse. This UNESCO World Heritage Site and famous archaeological park houses impressive ruins and a magnificent Greek theater. Continue to the lovely peninsula of Ortigia, where you'll wander through the ruins of the Temple of Apollo and enjoy a gentle stroll to reach the spectacular white cathedral of Saint Mary of the Immaculate Conception.
After a visit to the Fountain of Arethusa, a legendary freshwater spring, you'll have some free time to have lunch before heading to Noto, where you can explore this jewel of Sicilian Baroque design. Admire the extraordinary architecture of this "open-air museum" and its many palaces, churches, and stairways. After an exhilarating day, sit back and relax as you are taken back to your hotel in Catania.

Day 13: Depart Catania

Mount Etna overlooking Catania's city streets
After a final leisurely morning in Catania, it's time to say your goodbyes to Sicily and transfer to the airport for your departing flight. Safe travels! 

More Great 13-Day Portugal & Italy Itineraries

Looking for more inspiration for your trip to Portugal & Italy? Check out these other great 13-day Portugal and Italy itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.  


Map of Highlights of Portugal & Sicily: Porto, Lisbon, Palermo, Agrigento & Catania  - 13 Days
Map of Highlights of Portugal & Sicily: Porto, Lisbon, Palermo, Agrigento & Catania - 13 Days