Villa Balbianello on Lake Como, Italy

Romantic Destinations of Italy and Spain Itinerary

Ratings of Zicasso's Service
Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited

Italy, Spain

Places Visited

Florence, Tuscany, Chianti, Siena...

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Suggested Duration

14 Days

Walk hand in hand through the best of Italy and Spain on a handcrafted getaway designed just for two. Exquisite destinations set the scene, from historic cities to artisanal towns to Mediterranean villages of color and cobbles. Celebrations revolve around new experiences such as tapas hopping, Chianti vineyards, and driving a vintage Fiat 500. There’s also plenty of space and time for romance to thrive in Florence, Cinque Terre, Lake Como, Madrid, and Seville.

Customizable Itinerary

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Trip Highlights

  • Walk hand in hand through the cobbled villages of Cinque Terre, Italy’s most romantic coastal destination
  • Feel the amorous energy of Seville, a passionate city in Andalusia
  • Explore the beauty of Tuscany, from Florentine piazzas to Chianti vineyards and the wonder of Siena
  • Discover remarkable art and architecture, like Da Vinci’s The Last Supper in Milan, Moorish Cordoba, and Roman Segovia
  • Madrid provides an enchanting capital city experience with something new on every corner in a laid-back atmosphere
  • Enjoy leisurely time along the water in Bellagio, a glamorous village on Italy’s Lake Como
  • Indulge in romantic dining experiences including a candlelit dinner, tapas hopping, a Tuscan farmhouse visit, and afternoon coffee at old-world cafes
  • Drive a vintage Fiat 500 through the hills, walk along the Cinque Terre coastline, and experience an authentic flamenco performance

Detailed Description

Romance thrives easily in Italy and Spain. Watch the sunset from a village as the light clings to Mediterranean cliffs. Hop between tapas bars in Seville’s lively old quarter. Laze an afternoon away at a waterside Lake Como café or a Tuscan vineyard or a Moorish alcazar. There will also be candlelit dinners and many other classical scenes, but when the destinations are so exquisite, you don’t always need something extra special. Just toast to two and walk hand in hand through places that seem to come from a dream.

This handcrafted tour will take you to the most romantic destinations in Italy and Spain. These two countries are dotted with unique experiences, so there’s always a memorable way to go out exploring. The first stop will be Florence, a city of the Renaissance and a gateway to the rest of Tuscany. Next, you will travel to Vernazza, a quiet village on the Cinque Terre, perched just above the Mediterranean. Then, visit Bellagio and a lakeside hotel on Lake Como, where there is a possibility for adventure, but the experience mostly concerns romantic downtime. Those three stops in Italy will include a few treats as you travel between them, such as a visit to Da Vinci’s The Last Supper in Milan and 12th-century Pisa.

Fly from Milan to Madrid and the Spanish capital will be the next place you walk hand in hand with your loved one. Stop to try chocolate and churros, sip wines on the Plaza Mayor, find yourself at an Egyptian temple, and spend most of day ten in nearby Segovia. Then, take the train to Seville, a city with much passion and amorous energy. You’ll sense it on the streets of the old quarter, feel it during a flamenco performance, and taste it while you go tapas hopping. Whether it’s a languid morning or a full day of exploring, the experience for two will always be authentic.

Starting Price

$5,900 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

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

4.9 stars based on 8495 reviews.

Italy Tour Review: Cinque Terre, Positano, 15-Day Trip

The trip was very well planned by Zicasso's travel company and all of the stops and pick-up points, cars, trains, boats, etc., were there and reliable. We had a fantastic time.

Reviewed By Jeffrey C.

Italy Trip Review: Amalfi Coast, Capri, Naples, Rome, Pompeii,...

I am writing to express my immense gratitude to the entire team at Zicasso’s travel partner for curating the most spectacular trip to Italy for my family. From start to finish, the level of service was beyond impeccable and truly set a new standard for what we consider luxury travel.

The planning process was an absolute pleasure. Communication was one of their greatest strengths; our contact was consistently available and responses to our questions were nearly instantaneous. This travel company made us feel like we were their only clients. They took the time to understand the different ages and interests within our family, and built a bespoke itinerary that perfectly balanced history, leisure, and unique local experiences.

This was genuine white-glove service in every sense of the word. From the moment we landed, every detail was flawlessly executed. Private drivers were waiting for us, guides were engaging and knowledgeable, and our accommodations were magnificent. We never once had to worry about a single logistic, allowing us to be fully present and enjoy our time together.

If you are looking for a travel partner that offers unparalleled personalized service and flawless execution for a trip to Italy, look no further. Thank you for giving our family memories we will cherish forever.

Reviewed By Christopher L.

Italy Travel Review: Rome, Ravello, Amalfi Coast, Positano,...

My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.

After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.

From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.

The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.

The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.

We are very happy with our experience with this travel company and would not hesitate to recommend it!

Reviewed By Anne F.

Italy Family Trip Review: Venice, Florence, Rome, Naples,...

Our trip was a family one, two grandparents over 70, two parents and one adult son, one teenage girl, and one younger girl, 12. Three of us had been to Italy while the others had not. We wanted as complete a trip as we could in 14 days, so we included all the traditional places, Venice, Florence, Rome, and Naples/Pompeii. We spent three days in each and one day in Ferrara. While it was a lot for 14 days, we did not feel rushed.

What I like about Zicasso is they give you options to pick the best fit for your trip—we worked with two other agencies before we picked Zicasso’s travel partner. This travel partner took the time to understand our needs: three hotel rooms, all different in sizes, and tours and timing. Very important was the degree of coordination before the trip with the travel agent; she was available and knowledgeable, and took the time to adjust our needs. One of the best things about this travel partner was they used a van for all the travel, except from Rome to Naples. This was a much better option than the train for seven people and baggage.

During the trip, we were met on time by every driver and every guide. The hotels were excellent and the whole trip went well. When we had a delay on the train, the driver knew it and adjusted our pick-up.

Reviewed By Fred S.

Italy Tour Review: Wine Tour, Cooking Classes, Local Cuisine,...

Zicasso’s travel company was wonderful in planning our trip on short notice and in line with our requests and preferences. Their suggestions of what to do and where to stay were perfect. And when we accidentally got off on the wrong island, the travel company quickly got us new ferry tickets to get to the right place. It was all seamless.

Reviewed By Sherry G.

Italy Honeymoon Review: Rome, Sorrento, Cooking Class, Private...

This trip was the greatest week of our lives! Everything planned was better than I could have imagined. The private drivers being coordinated behind the scenes made the trip so easy and removed all the stress of trying to navigate a new country. Every driver and our tour guide was so nice and I feel like we made friends with all of them.

My favorite part of the trip was definitely the cooking classes and that every tour was private and intimate for my wife and I. The connections Zicasso’s travel agent hooked us up with made the trip the most memorable experience. Our travel agent and the travel company took special care of all the tiny details of the trip; our hotel knew it was my birthday and had a special surprise for me! I’m beyond thankful for the perfect honeymoon they provided my wife and I.

Reviewed By Branson S.

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