Our 2 Week Mediterranean Tour Highlights:
Day 3: Day trip to Sintra & Cascais
Day 6: Day trip to the Douro Valley
Day 12: Vatican & City Squares
Day 13: Day Trip to the Amalfi Coast – Positano, Amalfi, Ravello
Day 1 – Arrival in Lisbon
You’ll land in Lisbon today, where your driver is waiting to take you straight to your hotel. No need to rush — the first day is just about settling in. Later, your guide will lead you through Alfama, the city’s oldest quarter. The lanes twist and turn, tiled walls catch the fading light, and you’ll likely hear the sound of Fado spilling from little taverns. It’s a gentle first taste of Portugal.
Day 2 – The Heart of Lisbon
Lisbon feels like a city built for walking. This morning, head to Belém to see the riverside tower and the grand Jerónimos Monastery. Both are reminders of Portugal’s seafaring past. Between visits to these iconic landmarks, your guide will ensure you find time to stop for a local favorite – a pastel de nata straight from the oven.
Later, hop on the classic yellow tram that winds through the old neighborhoods. It’s a fun way to see the city without climbing too many hills. In the afternoon, take time to explore Chiado’s cafés and bookshops before finishing with a glass of vinho verde in one of the lively squares downtown.
Day 3 – Sintra & the Seaside
A short drive takes you to Sintra, and you’ll quickly see why poets and kings loved this place. The colorful turrets of Pena Palace look straight out of a storybook, while the gardens of Quinta da Regaleira hide grottoes and secret stairways.
In the afternoon, your driver will take you down to Cascais. It’s a chic seaside town where locals stroll the promenade and fishing boats bob in the harbor. Have a lazy seafood lunch by the water before heading back to Lisbon in the evening.
Day 4 – Lisbon to Porto with a Stop in Coimbra
Today, you’ll travel north with your private guide, with your first stop in Coimbra, a riverside town with one of the oldest universities in Europe. The Baroque library is the highlight — a hushed, golden hall filled with centuries of knowledge.
Arrive in Porto by late afternoon. Your hotel will be right by the river, so you can step outside and immediately feel the energy of the Ribeira. Cobbled streets, painted houses, and cafés with outdoor tables make it easy to fall in love with the city at first sight.
Day 5 – Exploring Porto
Start the day in Ribeira, wandering through narrow streets that suddenly open to views of the Dom Luís Bridge arching over the river. Don’t miss Livraria Lello, a bookshop so ornate it feels like stepping onto a movie set.
In the afternoon, cross to Vila Nova de Gaia, where the port wine lodges sit. You’ll sample a few styles, learn the difference between ruby and tawny, and maybe pick a favorite. As evening sets in, the riverfront comes alive with music and lights, making it the perfect place for dinner.
Day 6 – A Douro Valley Escape
Today is all about the Douro Valley. Terraced vineyards tumble down to the river, and the pace of life seems to slow with every turn of the road. Visit a family-run winery, meet the people who keep traditions alive, and taste wines alongside fresh bread, olive oil, and local cheeses.
Later, take a short river cruise in one of the old wooden boats. The landscape is timeless — steep hills, small villages, and rows of vines as far as the eye can see. By evening, you’ll be back in Porto, with the valley’s calm still in your mind.
Day 7 – From Portugal to Tuscany
This morning you’ll fly from Porto to Rome, where your driver is waiting. From there, your driver-guide will take you north into Tuscany, rolling past olive groves and cypress-lined lanes until you reach Florence.
Settle into your hotel and enjoy your first Tuscan dinner nearby. A glass of Chianti, a plate of handmade pasta, and you’ll feel right at home.
Day 8 – Renaissance Florence
Florence is a feast for the senses. Start at the cathedral, its red-tiled dome towering over the city. Inside, the frescoed ceiling seems to stretch to the heavens. A short walk brings you to the Uffizi, filled with works by Botticelli, Raphael, and Caravaggio.
In the afternoon, visit the Accademia to stand before Michelangelo’s David — it’s more powerful in person than any picture can capture. End the day with a stroll across Ponte Vecchio, where jewelry shops line the bridge and the Arno glimmers below at sunset.
Day 9 – Wine & Villages in Chianti
Leave Florence behind for a day in the countryside. The Chianti hills are dotted with stone villages, vineyards, and olive groves. Stop in Greve to wander the market square before heading to a local winery for lunch and trying local samples.
In the afternoon, you’ll visit the hilltop town of Castellina. Climb the old Rocca fortress tower for panoramic views over the Chianti hills. Your guide will then lead you through the quaint streets before finishing in the medieval vaulted passageway that looks out over the surrounding countryside.
Day 10 – Florence to Rome via Siena
Your first stop on day 10 is Siena, a medieval town where time seems to stand still. The Piazza del Campo is famous for its horse race, but even without the spectacle, it’s one of Italy’s great public squares. Visit the cathedral, with its striking striped marble, before continuing to Rome.
You’ll arrive in Rome in the afternoon and have some time to check in and unwind at your accommodation. When you are ready, your guide will lead you through Piazza Navona and Campo de’ Fiori, two of Rome’s most beautiful squares.
Day 11 – Ancient Rome
Visit some of Rome’s most historical sites on your 11th day. Start with a guided tour of the Colosseum and imagine the roar of the crowd when the amphitheatre was at the height of its glory. Next, you’ll explore the Roman Forum, where temples and arches still stand in silent witness to centuries gone by.
Climb Palatine Hill for sweeping views, and then end the afternoon with a quiet walk through the Orange Garden on Aventine Hill, where you’ll see the famous St. Peter’s “keyhole view”.
Day 12 – The Vatican & City Squares
This morning, your guide will take you across the river into Vatican City, the world’s smallest country, but home to some of the greatest treasures on earth. Inside the Vatican Museums, it feels like every hallway leads to another masterpiece — from ancient sculptures to Renaissance frescoes. Eventually, the path brings you to the Sistine Chapel. Even if you’ve seen it in photos a hundred times, nothing compares to standing beneath Michelangelo’s ceiling. Afterwards, step into the breathtaking St. Peter’s Basilica. Admire the soaring dome and masterpieces by Bernini, Michelangelo, and generations of artists.
Back in central Rome, follow the trail of fountains and piazzas. Toss a coin into the Trevi Fountain, climb the Spanish Steps, and end at the Pantheon, where sunlight streams through the open dome. Dinner tonight is best enjoyed in Trastevere, a lively neighborhood filled with trattorias and candlelit corners.
Day 13 – A Day on the Amalfi Coast
An early start takes you south to the Amalfi Coast. The drive itself is unforgettable, winding along cliffs that drop into the sea. First stop is Positano, where pastel houses cling to the hillside. Stroll the beach or browse the little boutiques.
Continue to Amalfi, with its striking cathedral and bustling piazza. Then head to Ravello, perched high above the coast. The gardens at Villa Cimbrone are famous for their views — the kind you’ll remember long after you’ve left. By evening, you’ll be back in Rome, tired but full of memories.
Day 14 – Farewell Rome
Enjoy a relaxed breakfast before your driver takes you to the airport. You’ll leave with the flavors of Portugal, the art of Florence, the drama of Rome, and the romance of the Amalfi Coast all packed into two wonderful weeks together.
