Splendors of the Italian Coastline: Elba Island & Cinque Terre Tour

The town and port of Portoferraio on Elba Island, Italy

What to expect on this itinerary

Enjoy the splendor of the Italian coastline, from the majestic Riviera to the wonder of the island of Elba during your custom tailored tour that offers you the luxury of the Mediterranean. Crystalline waters lap at the pebbled beaches shaded by bright umbrellas. The scent of fresh grilled prawns blends with the sea breeze as fortresses cling to the cliffs, resolute in their protection the shorelines. From Roman roots to the Grandeur of the Genoese Republic, you will discover the pleasures of the Mediterranean through the villages, culture, and the gorgeous scenery.

Countries Visited

Italy

Places Visited

Pisa, Levanto, Monterosso, Portoferraio

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Levanto – Arrive at Pisa Airport and Transfer to Stunning Seaside Levanto

Pisa was once a maritime power that fought for power along Italy’s Mediterranean seaboard. Most famous for its Leaning Tower, the city of Pisa thrived under the spoils of its naval supremacy as it built structures rich in religious affiliation and artistic interpretation. Your flight will land at Galileo Galilei International Airport in Pisa, and you will meet your private transfer and embark on the brief journey from the airport to the charming seaside town of Levanto, located at the north end of the Italian Riviera.

Before leaving Pisa, you will have an introductory tour of the city which will highlight the grandeur of its past and the beauty of its architecture, including the Piazza dei Miracoli and beyond. The Leaning Tower of Pisa rises to a height of 186 feet, with its crown reaching the top of the Cathedral of Santa Maria Assunta. The Cathedral was erected in the 11th-century but consecrated 50 years after the foundation was laid. Marble rows of pillars layer the façade and create a motif that encircles the structure. Frescoes decorate the interior, along with an oval dome that allows for light to spill into the nave.

After your time exploring the city, your private transfer will escort you to Levanto, the first town north of Cinque Terre, separated from the five towns by the coastal mountains. The Mediterranean Sea shines indigo against the beaches of the town, and the waves splash against the boulders of the mountains that move out from the coastline. Surfers catch waves up to 12 feet tall in the distance, and you will reach your gorgeous villa-style accommodation that offers a view of pastel colored homes and the shimmering waters of the coastline.

What's Included:

Accommodation
Transfer
Day 2

Levanto – Explore the Trails and Historical Churches of Cinque Terre

Day 3

Levanto – Relax on the Shores and in the Culture of Cinque Terre

Day 4

Levanto – Visit Abbey San Fruttuoso and the Luxuries of the Gulf of Poets

Day 5

Portoferraio – Fly from Pisa to the Island of Elba at Portoferraio

Day 6

Portoferraio – Indulge in a Food and Wine Tour of Elba Island

Day 7

Portoferraio – Relax in the Towns and the Beaches of Elba at your Leisure

Day 8

Portoferraio – Depart for Home

Trip Highlights

  • Visit the secluded shores of the hidden Abbey San Fruttuoso to both bask in the sun and view the stunning historical architecture
  • Wander along the trails that connect the five towns of Cinque Terre to indulge in the sensational views and the charming provincial churches
  • Explore the pure culture of the small fishing villages and narrow cobbled streets of towns along the Gulf of Poets
  • Indulge in the flavors of Cinque Terre with a private cooking class based on the distinctive culinary traditions of the Italian coastline
  • Witness the exceptional architecture of the Republic of Pisa with an introductory tour, including climbing to the top of the Leaning Tower of Pisa
  • Enjoy the unique properties of the wines produced on the historical and gorgeous island of Elba during a private wine and food tour
  • Visit the opulent villa in which Napoleon lived during his exile on Elba
  • Discover the breathtaking castles, fortresses, mountains, and villages during your time on Elba
  • Relish the sunlight and warm sandy beaches set against the refreshing waters of the Mediterranean Sea

Detailed Description

The Italian coastline captivates visitors and locals alike with the combination of pristine shoreline, dramatic mountains, and beautiful waters. Your 8-day tour along the Mediterranean shores will take you to the Italian Riviera and Elba Island to weave history, countryside, and cuisine into an impressive embodiment of Italian culture. Your luxurious adventure will begin with your arrival at Galileo Galilei Airport in Pisa. Your private transfer will meet you at baggage claim and lead you on an excursion through Pisa’s history to introduce you to the charm of a city often overshadowed by the fame of the iconic Leaning Tower. You will continue to the seaside town of Levanto where you find the gorgeous villa-style hotel awaiting your arrival.

The next day, you will take the quick train ride from Levanto to Monterosso al Mare, one of the five towns of Cinque Terre. Various trails connect the five towns, including a pathway leading to the churches and sanctuaries constructed along the hillside. Visit the historical structures and the charming towns as you make your way across the trail. Relax the next day as you enjoy the beachside culture of Cinque Terre and the Italian Riviera, and then venture north of Levanto to the small towns known for their focaccia or bask in the sun on the narrow stretch of shoreline at Riomaggiore. In the afternoon, you will meet your private cooking instructor for a lesson in the cuisine of Monterosso.

Move on the next day with a private boat ride to the Abbey of San Fruttuoso, located on a secluded beach reachable only by sea or walking trail. After you visit the Abbey, you will make your way to the town of Tellaro, and see the villages on the Gulf of Poets that lead to Portofino. The next day,  your private transfer will escort you to the airport in Pisa for your flight to the island of Elba in the town of Portoferraio. Take your time to acquaint yourself with the rich history, the vibrant culture, and the seaside charms of the islands largest city before you visit a villa that once belonged to Napoleon Bonaparte.

The grandeur of the island is yours to explore the next day with a wine and food tour. Appreciate the past as you taste the evolution of the island’s cuisine and sample the unique properties of the wines produced by the local vineyards. The next day, you will discover the enchanting villages found along the shores and inland at your preferred pace. Wander around the shops of Porto Azzurro and linger as you travel through Rio Marina to reach the camouflaged Pisan stronghold of Volterraio Castle. Conclude as your private transfer will meet you at your hotel lobby and take you to Elba’s island airport for your flight home.

Starting Price

$3,600 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.

4.9

Verified Traveler Reviews

Based on 6218 reviews

Maria S.
Italy Trip Review: Ciociaria, 2-Week Trip

Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.

Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.

I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.

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Andrew A.
Italy Family Vacation Review: Rome, Florence, Mount Vesuvius, Wine Tasting, 10 Days

This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.

From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.

What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.

We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.

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Michael E.
Italy Vacation Review: Venice, Florence, Rome, Sorrento, Murano, Burano, Pisa, Vatican, Colosseum, Pompeii, Capri, Private Tours, Cooking Class, 10 Nights

I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.

Trip Planning:

As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.

Transportation and travel between locations:

Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.

One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.

Venice:

Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.

The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.

Florence:

As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.

While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.

Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.

Day trip to Pisa:

The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.

The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.

Rome:

Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.

Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.

The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.

The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.

The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.

The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.

Sorrento:

We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.

During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.

Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.

On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.

Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.

Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.

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Susan F.
Italy Anniversary Trip Review: Rome, Orvieto, Siena, Montepulciano, Chianti, Florence, Bologna, Venice, Wine Tasting, Food Tour, 2 Weeks

Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.

All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.

Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.

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Mary J.
Italy Tour Review: 11 Nights

We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.

Excellent tour guides, drivers, and transportation were provided!

The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!

My husband and I saw and enjoyed what we needed to see and experience!

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Tracy S.
Italy Trip Review: Bike Tour, 5 Nights

It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.

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Customizable Itinerary

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

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