Explore Tuscany Tour: Ancient Towns, Coastlines, Snorkeling & Trekking

A 8 day trip to Italy 
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Step off the beaten path on your custom-tailored luxury vacation for a view of the unparalleled charms of Tuscany. From undulating open valleys to treasured shores, experience an unforgettable journey through the uncharted and overlooked splendors of Elba, Florence, and the surrounding beauty of Tuscany. The Mediterranean sun spreads over the rugged and lush niches of the Island of Elba. Emerald hills and cypress trees expand across the lengths of the horizon. Museums display breathtaking artwork. Ancient villages display remnants of their heritage along cobbled lanes and antique walls.

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General Information

view of a beautiful beach and water in Italy
Detailed Itinerary

Places Visited 

Elba, Portoferraio, Volterra, Marciana Marina, Marciana, Alta, Rio Marina, Porto Azzurrro, Capoliveri, Florence, Capo Sant’Andrea, Piombino

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Seemingly Known

Culture is the root of all things in Tuscany, emanating from the cobblestone streets and cast across the landscape in vineyards and cypress trees. The emerald hillsides are as much a part of people’s lives as the traditional prosciutto made from boar as well as the unparalleled frescoes decorating secluded churches in medieval villages. When you arrive at Florence International Airport, your private transfer greets you and welcomes you to Italy. Soon you settle into your luxurious accommodation in the heart of Florence’s historic center, where the truth in the cultural base of Tuscany comes to life.

The scent of fresh pastries blends with the savory aroma of simmering sauces. Olive groves grow outside of the city, and the Arno River separates the city center from Oltrarno, connected by a series of bridges; including the Ponte Vecchio, the Old Bridge, lined with goldsmiths and jewelers. Florence has a tangible energy and remains one of the most visited cities in the world. And yet it can maintain pockets of uncharted beauty, alongside the breathtaking art of Michelangelo and Botticelli. The narrow streets of the Oltrarno intertwine sophisticated artisan shops, woodwork and ceramics, and the distinctive traditional flavors of Tuscany. Settling into Florence is emblematic of the surrounding region, filled with endless beauty any way you turn your head.

What’s Included: transfer, accommodation

Day 2: En Route to the Waters

The emerald colors of Tuscany glisten in the morning light. The grass has a fresh layer of dew blanketing the hills, and the scenic trees complement the distant villages in the countryside. At breakfast, the aroma of fresh espresso becomes inescapable, practically overtaking every café in the city, coupled with the fresh scent of sweet brioches. Your private transfer meets you after breakfast, eager to escort you from Florence to the charming, enchanting hillside city of Volterra, surrounded by preserved medieval ramparts. Consider learning more about your experienced Tuscany travel agents, who strive to provide you with the most memorable and delightful touring experiences. The town is built on an Etruscan settlement that once claimed as many as 25,000 people at its height of power.

The cream-colored stonework rises out of the encompassing greenery, topped with red tiled roofing. The cobbled streets wind through the buildings and lead through the history of the town inside its large walls, which in some places stand more than 36 feet tall. The Cattedrale di Santa Maria Assunta stands behind the Palazzo del Pópolo. The church stands enlarged with a Pisan design in the 13th century, which has created the focus of the city’s skyline. The interior of the church holds a spectacle of artistry, from paintings by Tito to a Romanesque sculpture carved of notable wood. After your exploration of the Volterra, your private transfer leads you the remainder of the way to Piombino, where you board the ferry to the Island of Elba.

What’s Included: breakfast, transfer, guided tour, accommodation

Day 3: Inside the Pearl of the Mediterranean

The Island of Elba is often referred to as the “Pearl of the Mediterranean,” surrounded by waters shimmering between three shades of blue. Rugged hills and cliffs give way to lush grasses and towering trees. Limestone fortresses stand overlooking the water. Legends of this mystical island have been whispered since Jason and Argonauts, in their search for the Golden Fleece. In the morning, you find a gentle, cool breeze blowing in from the coast. The aroma of the sea blends with the earthy scents of the island. After breakfast, your private transfer takes you to the main port city of Portoferraio, which means Iron Port. Napoleon helped set up the infrastructure of the entire island in the 19th century.

Old Town has a network of narrow streets and hidden alleys winding near the old harbor, leading to a set of 16th-century fortresses flanking the cityscape. Explore the sights, from the Piazza Cavour to the Salinata di Napoleone. At the top of the hill is Villa Dei Mulini, Napoleon’s home during his exile on the island. The villa is now a museum preserving its former elegance when the emperor resided inside the walls. The canary yellow exterior houses lavish furnishings and a splendid library. Gold leafed posts support marble tabletops.

High ceilings dangle graceful chandeliers. Italianate gardens blossom against the azure sea in the background, providing an unparalleled view. The luxuriousness of the villa contrasts the idea of Napoleon’s “imprisonment” on Elba, and instead shows a paradise. When the sun begins to set behind the Mediterranean, you will board a boat for a spectacular cruise along the coastline, showcasing the golden color of the landscape and the simple pleasures of sipping a cool drink in the coastal breeze.

What’s Included: breakfast, guided tour, accommodation

Day 4: More than Unique

Tuscany is not specially known for its islands, but after your time on Elba you will equate Tuscany with the Renaissance, hilltop towns, and unforgettable island life. After breakfast, your transfer meets you at your hotel and takes you to the unspoiled nature of Cap Sant’Andrea. The closer you come to the coastline, the more narrow and windy the road becomes. Chestnut trees cascade down the hillside, highlighting the mixture of mountains and sea. The water shimmers turquoise, and you can see the powerful summit of the island’s tallest mountain, Monte Capanne, standing 3,343 feet above sea level. The bay is crystal clear, offering you a view down to the seafloor.

South of the bay, you find impervious cliffs maintaining a stronghold over the island’s past trading. You can dip your toes into the water, letting the refreshing cool temperature lap over your toes. Step out into the bay and enjoy time snorkeling along the shoreline. The calm current moves your body in a swaying motion. The rocks and mosses under the water are visible, along with sporadic fish swimming; you spot a seahorse now and again in the soft coral. With the clarity of the seawater, you can even see the remains of a shipwreck off the right tip of the island, submerged more than 30 feet below the water’s surface. It is clearly a vision of Elba you have never seen before and a version of Tuscany you could have never imagined.

What’s Included: breakfast, guided tour, accommodation

Day 5: Active Elba

In the morning, the rich and slightly bitter aroma of espresso blends with the sweet seaside scent. Today you choose to explore the island by sea once more, taking you on the water to discover the hidden wonders of the northwest coast. When you climb into the kayak, you have a relaxed ease. The current is soft against the beach, and the water is cool on your skin. When you move forward, you can feel droplets of the ocean dripping from your paddle. Your guide leads you through the water’s path alongside the coastline, taking in the Tuscan Archipelago.

Your view of the island is spectacular, showcasing the various shades of green and gray emanating from the cliffs, mountains, and flora. Cascading rocks open to tiny beaches only reachable by water, including the small bay of Caletta. When you pull your kayak up for a break, the gravelly beach is soft underneath your feet. The lighthouse of Punta Polveraia remains a sensational spot on the island, where the sunlight reflects off the water and illuminates the untouched reaches of the island in every direction. From the height of the lighthouse, you can see the whole Isle of Corsica in the distance on a clear day.

What’s Included: breakfast, guided tour, accommodation

Day 6: Taking in the Sights

After breakfast, the island is yours to discover at your leisure, trekking through the miles of walkways that inhabit nature, history, art, and adventure. The town of Marciana Alta stands at an altitude of 1,230 feet above sea level and remains one of the oldest towns on the island. The Pisan Fortress encompasses the majority of the town, once protecting the citizens from pirate attacks. The narrow stone streets twist around the city and beneath stone arches; petite balconies, decorated with bright flower boxes, open up to a spectacular coastal view. A funicular carries individuals to the summit of Monte Capanne, for an unadulterated panorama of the coastline and the Mediterranean Sea.

The island’s most important pilgrimage site of Santuario della Madonna del Monte is situated in the hills beyond the village. The historic church possesses a single stone that legend claims held an image of Mary, painted by a divine hand. 16th-century frescoes decorated the walls behind the high altar and were discovered in the mid 1990s. A fresh water spring pours from the outside wall and dates back to the 17th century. Whether hiking through the mountainside or along the shores of Elba, you are sure to find splendor.

What’s Included: breakfast, transfer, guided tour, accommodation

Day 7: Returning to Renaissance Streets

The towns across Elba have designated days for their weekly markets, where fishermen sell their fresh catch, and the succulent aroma of fresh produce from local Tuscany fills the villages. After breakfast, your private transfer takes you to the harbor at Portoferraio, where you meet your ferry back to mainland Italy. The remainder of the day is yours to revel in Tuscany, whether strolling around the artistic streets of Florence or indulging in the beckoning tranquility of medieval villages around the hillsides. For a unique view of the city, you can visit the Stibbert Museum, situated on the Florentine hillsides overlooking the city.

The Stibbert Museum displays the collection of a 19th-century English-Italian gentleman named Frederick Stibbert and is spread across two large villas. Inside the villas is an assortment of European, Japanese, and Islamic armor. The antiques are arranged in a way that makes the entire collection look ready to march out of the galleries, including the poised, promenading horses. The light glistens off of the metal ornaments standing in front of Renaissance frescoes decorating the walls. Much of the European armor comes from the 16th century and ranges from Italy, Germany, and France.

What’s Included: breakfast, transfer, accommodation

Day 8: Back on Track

In the morning, the image of the city returns, surrounded by a sea of lush hills and valleys instead of the Mediterranean. The city’s charm remains, whether emanating from the priceless artwork inside the Accademia or the delicious aromas of creamy gelato drifting out of a celebrated gelateria. You sip on your morning espresso and watch the city life return to the streets. The coastline feels far away, replaced by rolling hills and villas. After breakfast, your private transfer meets you at the hotel, ready to escort you to Florence International Airport. Soon your flight will carry you away from the medieval towns of Tuscany and the clear turquoise waters around Elba, but the memories of your discovery of the uncharted beauties of Tuscany will remain.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.