Explore Tuscany and Cinque Terre

Tuscany – Cinque Terre

Explore Tuscany & Cinque Terre

Welcome to Italy


The Explore Tuscany & Cinque Terre tour is the ultimate introduction to Italy’s seductive scenery. From the rolling green hills of Tuscany to the steep hillsides with colorful houses in Cinque Terre, many artists have been inspired in these locations. Together, they create the ideal inspiration for your Italian getaway.

Consult with your Destination Specialist. We will ensure that the highlights of your trip are booked in advance so you won’t miss out on the fun! Plenty of leisure will be built in so you can take the time to explore on your own, and at your own pace. Let the journey guide you.

Read more about why we love the Explore Tuscany & Cinque Terre.

Make it Yours

  • Accommodation Italy offers a wide range of accommodation styles including boutique hotels, charming B&B’s, and luxurious castle hotels. Juniper Tours will select where you stay based on your preferences.
  • Transportation – All of the dots will be connected based on your preferences and budget.  Airport transfers, car rentals, train passes, even private chauffeurs!
  • Day tours and entrance tickets – pre-scheduled tours and experiences for a seamless and enriching travel experience!
Screen Shot 2021 06 07 at 11.19.48 AM

Explore Tuscany & Cinque Terre Daily Itinerary

Day 1: Arrival in Florence and transfer to Siena

Welcome to Tuscany! As you arrive in Italy, a private driver will pick you up and take you to your accommodations in Siena. Spend the rest of the day unwinding from your trip.

Overnight in Siena

Day 2: Siena

After breakfast, enjoy a walking tour through one of the best illustrations of Medieval towns in Italy. Later in the day, learn how to make a typical Tuscan meal in a private palace dating back to the 11th century. Complete your cooking session with an elegant meal and wine.

Overnight in Siena

Day 3: Day tour to Pienza, Montalcino and Montepulciano

Continue your exploration of Tuscany with a private driver taking you through Val d’Orcia, one of the most beautiful areas in Tuscany. Visit the towns of Montalcino, Montepulciano, and Pienza tasting the Tuscan flavors of wine and cheese along the way.

Overnight in Siena

Day 4: Siena to Florence

Today you will be heading to Florence. Along the way, make a stop in San Gimignano which holds one of the jewels in medieval architecture. It is called the Manhattan of Tuscany due to the skyline with many towers visible as you head into town. Stroll along the ancient cobble streets and visit the local vineyard. Enjoy wine and olive oil tasting before continuing on to Florence.

Overnight in Florence

Day 5: Walking tour of Florence

Today, delight in a guided tour through the city of Florence. See the Duomo, Giotto’s Bell Tower, the Baptistery, Piazza della Signoria, and Piazza Santa Croce just to name a few. The tour also included a visit to Uffizi Museum, one of the most admired and visited museums in the world with art collections ranging from the 13th and 18th centuries. Spend the rest of the day at your leisure.

Overnight in Florence

Day 6: Chianti with wine tasting and lunch

Known all over the world for it’s gentle rolling hills and vineyards, Tuscany will enchant you as you roam through the Chiantigiana countryside. Tour local vineyards as you taste wines of the region and enjoy lunch before heading to the village of Greve in Chianti. Greve is the heart of the Chianti Region and filled with local delicacies to satisfy anyone’s palate.

Overnight in Florence

Day 7: Florence to Monterosso with stopover in Lucca

Today you will continue on to Monterosso. On the way, you will experience a walking tour of Lucca, an ancient city with Roman origins. Known as the city of a hundred churches, the city is located with fortified walls built to protect during the Middle Ages. Enjoy lunch before continuing on to Monterosso where you will spend the evening relaxing at your leisure.

Overnight in Monterosso

Day 8: Full day of Cinque terre tour

After breakfast, you will start your discovery of Cinque Terre, a string of 5 villages clinging to the cliffs overlooking a stunning blue sea and immersed in a luscious vegetation. They offer stunning scenery that has attracted visitors from all over the world. 

Overnight in Monterosso

Day 9: Tigullio gulf

Continuing your journey, you will meet with a guide in Rapallo. Enjoy a public boat ride to San Fruttuoso to visit the San Fruttuoso Abbey. Then head to Portofino by public boat while savoring the breathtaking views from the sea. Enjoy lunch before heading to Santa Margherita Ligure, the most glamorous town of Tigullio. As you stroll along the promenade, admire the Castello di Santa Margherita Ligure where building started in 1550. At the end of the day, return to your hotel where you will spend the rest of the evening relaxing before your trip home. 

Overnight in Monterosso

Day 10: Departure home

As you draw in the last impressions of Cinque Terre’s splendor, a private driver will pick you up and take you to the airport Departure Hall in Florence where you can catch your return flight home.

Get Ready to Travel!

Your Explore Tuscany & Cinque Terre at a glance:

Explore Tuscany & Cinque Terre Highlights:

Selected activities based on your interests

Why We Love this Tour

Your Explore Tuscany & Cinque Terre offers a great introduction to Italy’s history, wine and romantic seasides. It offers the freedom and flexibility of a chauffeur experience with a price point closer to a group guided tour. You and your loved ones can encounter the best of Tuscany and Cinque Terre! 

We love this itinerary because it allows you to see the highlights of Italy’s ancient history and inspired romance as a first time visitor. If coming back, it offers a chance to explore new experiences or relive the best of what was seen before. By staying in stunning Tuscany before heading down to the charming Cinque Terre, you’ll have a plethora of sightseeing and touring opportunities. 

Why We Love Tuscany

The gentle hills of Tuscany filled with the region’s famous vineyards and castles are the picturesque setting provided as you enjoy the delectable wines of the land. You will experience a romantic blend of culture and history invigorated by the tastes of the region.

Why We Love Cinque Terre

The famed sea cliffs of the Cinque Terre make this a perfect introduction to Italy’s gorgeous coastline. From the steep slopes to the beautiful blue waters, Cinque Terre is loaded with incredible views. Being the birthplace of Limoncello, the many tastes of authentic Italy can be found here. Exploring through diving, hiking, car or by boat will surely exhilarate the senses.

Nights can be added or reduced, your route can be changed to your preference. Tours and activity options can be selected based on your interests and purpose of travel. 

Your Destination Specialist knows Tuscany and Cinque Terre and will take the time to learn what’s important to you. Your itinerary will be designed just for you to make the most of your time and experience while in Tuscany and Cinque Terre.  

Speak with our Travel Experts

Ready to Schedule your FREE Travel Consultation? 

Screen Shot 2020 09 10 at 5.08.57 PM

We’ll send you our free full color travel guide.
Just fill in the form below