Charm of San Marino & Italy Tour: Pompeii Ruins, Leaning Tower of Pisa & Capri Island

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Total Trip:

10 Days
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Countries Visited:

Italy, San Marino
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Places Visited:

Rome, Assisi, Siena, Florence, Pisa, Padua, Venice, San Marino, Naples, Pompeii, Sorrento, Capri
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Departure Dates:

Dates are flexible and customizable for private departures.
A vacation in Italy is not just a getaway, but a journey into antique splendor, historic opulence, and how the modern world can fit like a puzzle piece into the past. Your 10-day San Marino and Italy tour to Pompeii ruins, Leaning Tower of Pisa, and Capri Island is an exploration of Italy showing you the ineffable charm of medieval towns and the mesmeric shimmer of ancient Roman ruins. You will find Renaissance statues decorating a public square and opulent palaces lining the central streets of

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Day 1

Beginning a Roman Holiday

Rome is a city immortalized in its history and endlessly gripping. The Colosseum continues to stand tall overlooking the ruins of the Roman Forum. Elements of the imperial past, from stonework to inspiring works of art now fill museums and large piazzas. Churches fill the skyline with elegant domes and bell towers, none more empowering than St. Peter’s Basilica in Vatican City.

You arrive at the airport to find your private transfer waiting. When you enter the city, there is an unmistakable aroma of orange. Palm trees sporadically line the cobbled avenues. The scent of fresh gelato spills out of Gelateria Fatamorgana, filling Piazza degli Zingari with the aroma of creative flavors, such as almost milk and ginger. The large concrete dome of the Pantheon, the largest of its kind, hides behind the romantic facades surrounding antique buildings.

What's Included:

included

Transfer

included

Accommodation

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Day 2

Golden Umbria to Green Tuscany

In the morning, Rome’s vibrant energy returns to the streets filled with the aroma of fresh espresso. The shops along Via del Corso open their opulent doors to the city. Your private transfer meets you at your hotel and leads you out of Rome, venturing to the golden hills of Umbria. Located on the hillside across the valley from Puglia is the quaint town of Assisi, home of St. Francis. The cathedral stands atop the mountain with a pristine white façade resembling a white pearl topping a golden crown. The cobblestone streets intertwine winding up the hillside around medieval buildings.

St. Francis Basilica stands underneath the protection of Rocca Maggiore, a picturesque castle located on the mountain summit. The impressive basilica was erected in the 13th century after Francis was canonized, creating one of the most visited Christian pilgrimage destinations in the world. The lower church was erected with late Romanesque vaulting and houses the tomb of St. Francis. The upper church has a more Gothic design with soaring vertical lines. The combination of the church’s grand ambiance balances the quaint atmosphere of the city, where the aroma of olive oil wafts from the doorframes.

What's Included:

included

Transfer

included

Tour

included

Accommodation

included

Breakfast

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Day 3

Bridge to the Renaissance

Florence is a city that embodies the Italian Renaissance in its very essence, exuding artistry from the open piazzas to the glamorous museums. The Ponte Vecchio connects the outer ring of the city to the historic center along the pathway constructed by the Romans, creating the Old Bridge.

After breakfast, your guide leads you on a walking tour of the open-air museum that is Florence. The Piazza della Signoria dates back to the 14th century as the center of Florentine power. However, Roman and Etruscan remains hint at a more historic origin. Neptune’s Fountain graces the side of Palazzo Vecchio. The fountain was commissioned in the 15th century. Neptune stands tall overlooking the square in marble opulence. Smaller river gods grace the fountain basin modeled in bronze. Marble seahorses emerge from the water. The pristine fountain points to the grandeur of the Loggia dei Lanzi, an outdoor sculpture gallery lining the piazza’s southern border. Renaissance artistry is all around you, emerging from every corner of the city.

What's Included:

included

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included

Accommodation

included

Breakfast

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Day 4

Finding Miracles

The morning casts a light over the marble façade of San Lorenzo Church, the final resting place of Galileo Galilee. Charming cafes serve frothy cappuccinos, and Pasitcceria Cosi fills Piazza della Repubblica with the aroma of freshly baked bomboloni, an Italian donut often filled with chocolate. After breakfast, your guide meets you at your hotel leading you away from the Renaissance city.

Pisa remains home to one of Italy’s most coveted universities. In the late 10th and 11th centuries Pisa’s navy rivaled its northern neighbor of Genoa’s power and even surpassed it. Today, the city is famous for the Square of Miracles where you find the iconic image of the Leaning Tower of Pisa. Construction of the tower began in the 12th century using marble. The edifice now stands more than 183 feet tall containing 294 steps. Thin columns encompass each tier of the tower. The feeling of standing in front of the tower, an image you have seen depicted in movies, postcards, and magazines brings an almost overwhelming joy to the piazza. The tower is larger than you imagined and its skewed axis shows more prevalently in person than any image could capture.

What's Included:

included

Transfer

included

Tour

included

Accommodation

included

Breakfast

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Day 5

Labyrinthine Excursion

The sunrise over Venice brings to light the curvaceous domes atop St. Mark’s Cathedral. Gondolas wade in the canal moored to the cobblestone walkways. Every street feels more like a promenade than a sidewalk, leading over walkways and underneath elevated passageways. Your guide meets you at the hotel to lead you on a morning tour of the City of Bridges, taking you into St. Mark’s Square and onto the Bridge of Sighs. The latter bridge was famous for its romantic interpretation, as given by Lord Byron, of a prisoner’s last glance at their beloved city.

From the outside, the iron wrought gates frame the windows in the pearled color arching over the Rio di Palazzo. The bridge was erected in the 17th century to connect the interrogation rooms of the Doge’s Palace with the new prison. Your private tour leads you through the new prisons, and also to the Bridge of Sighs where you can look out on the beauty of Venice through the sliver of light. Look down upon the stone bridge from where you viewed the Bridge of Sighs earlier, standing in front of the Grand Canal and out to the horizon.

What's Included:

included

Tour

included

Accommodation

included

Breakfast

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Day 6

The Smallest Voices

The quiet wisp of gondoliers pushing their oars against the water creates an elegant morning sound. After breakfast, you traverse the Grand Canal, leaving behind the grace of the Venetian Republic and finding the fifth smallest country in the world inside the borders of San Marino. The micronation is the oldest surviving sovereign state in the world, and its republic dates back to the 4th century AD. The entire country is 24 square miles.

On the ridge of Mount Titano stands three fortresses, Guaita, Cesta, and Montale. Each fortress has a panoramic view stretching from the Apennines to the coastal plain and even reaching as far as the Dalmatian Coast. A paved path links the fortresses, beginning with Rocca Guaita, the oldest fortress, dating back to the 13th century. The forceful rockface adds to the luster of the countryside. The trees paint the surrounding landscape emerald, interrupted by the red roofs of the medieval buildings. The country of San Marino may be small, but its majesty speaks wonders.

What's Included:

included

Transfer

included

Accommodation

included

Breakfast

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Day 7

The Depths of Rome

The Tiber River shines in the morning light against the background of the Castle Sant’Angelo. You leave your hotel following your guide through the Eternal City. You step beyond the iconic images of Rome and into Castel Sant’Angelo overlooking the banks of the Tiber River. The grounds were converted into a papal fortress in the 6th century, but the castle was originally a mausoleum for Emperor Hadrian constructed in the 2nd century AD. The imposing exterior informs the eclectic interior, housing the Museo Nazionale di Castel Sant’Angelo.

The museum contains an eclectic array of paintings, sculptures, and military memorabilia dating back centuries, including weapons used by soldiers once positioned to protect the castle. The fortress had a secret 13th century passageway leading to the Vatican to protect the popes in times of crisis. The upper floors are decorated with lavish Renaissance style. When you reach St. Peter’s Square, the opulent décor of the piazza, crowned by the basilica, personifies the radiance of style and history around Rome.

What's Included:

included

Tour

included

Accommodation

included

Breakfast

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Day 8

Sun Route to Preservation

The sunshine casts a light over the vast landscape outside of Rome. After breakfast, your guide escorts you from the Eternal City once more, taking you southbound to the regal city of Naples, located on the Bay of Naples. After a tour of what many refer to as the capital of Southern Italy, you begin to wind around the arching bay to arrive at the mesmeric ancient city of Pompeii.

Enter Pompeii to find the open Forum with a backdrop of Mount Vesuvius in the distance casting an ominous ambiance to the historically preserved grounds. The excavations around Pompeii continue, showcasing the vastness of the cityscape and the immensity of its tragic conclusion. The streets were cast in large, raised stones and bordered by raised buildings to allow the waters to filter out of the city when it rained.

When you reach the House of Menander, you find the fresh-looking accommodations of a wealthy merchant. Pillars flank the entrance and lead to the atrium with an intact wooden roof. Your guide points to the decoration of the interior rooms where paintings depict scenes from Homer’s Iliad, including the undeniable image of the Trojan Horse. The air is scented with lemon from the gorgeous lemon trees around the bay. The modernity of cameras and cell phones juxtapose the lavish history all around you with the outline of Mount Vesuvius ever-present in the background.

What's Included:

included

Transfer

included

Tour

included

Accommodation

included

Breakfast

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Day 9

Cruising the Tyrrhenian Sea

In the morning, the view out to the Bay of Naples is clear and colorful, filled with creamy cliffs, azure waters, and the lingering presence of Mount Vesuvius in the distance. After breakfast, you step aboard a ferry and venture to the famed isle of Capri, favored by Roman emperors and classic Hollywood stars. The wind brushes off the water and passes through your hair before you arrive at the 200-foot cliffs lining the coastline of the Tyrrhenian Sea. The colorful homes along Marina Grande recall the heritage that the town started as a humble fishermen’s village.

After you explore the island, you step aboard a small rowboat with a guide who leads you to the extraordinary Blue Grotto. The water floods the cave when the tide comes in. An opening to the sea brings in a sliver of light that reflects an ethereal blue glow in the darkness of the grotto. The cool air and the scent of the sea surround you. The natural marvel of the Blue Grotto has charmed visitors since the days of the Romans, who believed the cave was home to sea nymphs.

What's Included:

included

Transfer

included

Tour

included

Accommodation

included

Breakfast

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Day 10

End of an Escapade

In the morning, the Vatican Gardens shine an unimaginable green, offering a rare glimpse into the surreal ambiance of the manicured landscape, filled with hidden grottoes and box hedges. You can traverse the squares in the early light, lingering around the quiet trickle of the Trevi Fountain. The aroma of espresso filters out of the corner café. The tranquil morning contrasts the fast-paced and energetic city that will soon return to the streets.

Soon, your private transfer will meet you at the hotel and escort you to the Fiumicino Airport but you could always extend your stay in Italy, savoring the historic marvels woven into the everyday lives of the locals. One of our Italy travel companies would be happy to help you add a trip extension!

What's Included:

included

Transfer

included

Breakfast

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Trip Highlights

  • Traverse the cobblestone streets and stunning marbled cathedrals in the medieval towns offering glimpses into the preserved beauty of the past
  • Stroll along the historic streets of Pompeii to see the remnants of the past frozen in time
  • Discover the Renaissance splendor of Florence cast in the architecture open to the streets, from Ghiberti’s Gates of Paradise to the Elegant Loggia 
  • Witness the elegant design and architectural ingenuity of the Leaning Tower of Pisa
  • Experience the stunning Renaissance masterpiece inside Cappella degli Scrovegni, known as the Sistine Chapel of Padua
  • Explore the majesty of San Marino, one of the smallest countries in the world
  • Revel in the romantic stories incorporated into the mythology of the Bridge of Sighs in Venice
  • Savor the unique aquatic glow of the Blue Grotto on the island of Capri
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Detailed Description

Italy embraces its aura of romance and history, exuding classic tales of beachside vacations and gondola rides across the Grand Canal. The rugged rotunda of the Colosseum fills a picturesque image of antiquity, and Michelangelo’s David embodies ingenuity and perfected artistry. Your custom tailored San Marino and Italy Tour to Pompeii ruins, Leaning Tower of Pisa, and Capri Island takes you on a guided exploration of the country’s beloved cities and treasured sites, showcasing opulent antiquity in the realm of modern luxuries.

Your Italy vacation begins with you arrival in Rome, where you private transfer is waiting at the Rome Fiumicino International Airport. Once inside the city center, you find the past standing with powerful stature around the streets. The following day, your guide leads you out of the city and into the Umbrian countryside to the hilltop town of Assisi, where the Basilica of St. Francis of Assisi stands overlooking the valley. In Siena, you find the beauty of the medieval Tuscan city encompassing the hillside before settling in Florence.

In Florence, your guide leads you on a fabulous walking tour of the city, taking you along the cobbled streets, showing you the radiance of Giotto’s belfry and the Piazza della Signoria. You will also venture into the Museum of the Academy to view Michelangelo’s David. You leave the Renaissance city behind for the once naval powerhouse of Pisa to visit the Piazza dei Miracoli, home to the Leaning Tower of Pisa. Continue to Padua for a tour of the city’s treasured cathedrals before arriving Venice.

Discover Venice on a guided morning walking tour. The afternoon is at your leisure to visit the many iconic sites and artistic islands around the Grand Canal, including Murano. On your journey back to Rome, you stop in the oldest independent principality in the world, San Marino. Follow your guide through the stunning sites of the Eternal City, from the Trevi Fountain to St Peter’s Basilica.

The following day, you travel along the Sun Route taking you on a vibrant tour of Naples before you explore the uniquely preserved ruins of Pompeii. Wake up on the seaside in Sorrento and enjoy the ferry ride to the enchanting Island of Capri. Enjoy a half-day exploration of the land and sea, taking in the Blue Grotto before returning to Rome for the evening. On your final day in Italy, your private transfer meets you at the hotel after breakfast, escorting you to the Fiumicino Airport for your flight home.

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Starting Price

$2745 per person (excluding international flights)

This trip is customizable for your private travel.
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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.

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