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A Grand Italian Trip: Venice, Florence, Gradara, San Marino & San Leo

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A beautifully balanced 9-day Italian adventure that weaves together culture, countryside, and unforgettable cities.

Duration
9 days
Group Type
Private
Season
Spring/Autumn
ABOUT THIS TRIP
Overview

Embark on a 9-day Italian journey through Venice, Florence, Urbino, Gradara, and the Montefeltro region, where iconic cities, rolling landscapes, and medieval villages come together in perfect harmony.

From wandering the canals of Venice and the Renaissance streets of Florence to exploring the historic charm of Urbino, Gradara, San Marino, and San Leo, this thoughtfully paced itinerary blends cultural treasures with hands-on experiences -wine tastings, local cheese and cashmere farms, and authentic Italian traditions- creating an unforgettable journey through Italy’s art, history, and countryside.

ITINERARY
Day to Day

Days 1-2: Discover Venice’s most iconic landmarks by land and water, from Rialto to St. Mark’s, complete with a gondola ride and insider guidance.

Days 3-5: Experience Florence and Tuscany through medieval towns, Renaissance masterpieces, and world-class wine and cuisine.

Day 6: Arrive in Gradara with a guided visit to its iconic medieval castle.

 

Day 7: Discover the Republic of San Marino and enjoy a scenic wine tasting overlooking the Adriatic.

Day 8: Visit the fortress of San Leo and explore unique rural traditions.

Day 9: Check out and depart for your return home

ITINERARY
Day to Day

Days 1-2: Discover Venice’s most iconic landmarks by land and water, from Rialto to St. Mark’s, complete with a gondola ride and insider guidance.

Days 3-5: Experience Florence and Tuscany through medieval towns, Renaissance masterpieces, and world-class wine and cuisine.

Day 6: Arrive in Gradara with a guided visit to its iconic medieval castle.

 

Day 7: Discover the Republic of San Marino and enjoy a scenic wine tasting overlooking the Adriatic.

Day 8: Visit the fortress of San Leo and explore unique rural traditions.

Day 9: Check out and depart for your return home

This itinerary can be further customized according to your wishes & preferences

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IN DETAIL
Day to Day
DAYS 1-2 : VENICE

Once you arrive in Venice, enjoy a free day to wander at your own pace; explore hidden alleys, canals, and local cafés as you settle into the city.

On day 2, begin your guided journey in the lively Rialto district, home to the iconic Ponte di Rialto, the first bridge built over the Grand Canal. Follow your local guide through the atmospheric “sestieri,” Venice’s historic neighborhoods, until you reach the magnificent Piazza San Marco. There, a traditional gondola awaits you. Glide through the Venetian canals as your gondolier navigates the waterways using a unique dialect shared only among gondoliers.

After some free time to enjoy the square or nearby shops, rejoin your guide for an in-depth visit to the Doge’s Palace. Explore grand halls decorated by masters such as Tintoretto, Tiziano, and Veronese, then continue to St. Mark’s Basilica, the famed Golden Cathedral, where shimmering mosaics and priceless treasures showcase the artistry of centuries of Venetian craftsmen.

DAYS 3-5 : FLORENCE

On Day 3, take the train from Venice to Florence and enjoy a free afternoon discovering the city at your own pace, from Renaissance piazzas to artisan shops along its historic streets. \

On Day 4, embark on a private tour of Siena and San Gimignano, starting with a scenic drive through the Tuscan hills to the medieval “town of towers,” a UNESCO World Heritage Site. Explore San Gimignano’s charming streets and panoramic viewpoints before continuing to a beautifully restored former convent, now a premier wine estate, where you’ll savor a gourmet lunch paired with local wines. In the afternoon, travel onward to Siena to explore its rich architectural heritage and landmarks independently, from the magnificent cathedral to the iconic Piazza del Campo.

Day 5 features a private walking tour of Florence’s highlights, beginning at Piazza della Signoria with its grand palaces and sculptures, including a replica of Michelangelo’s David. Wander medieval streets once traversed by legends like Dante, Michelangelo, and Leonardo da Vinci, pass the Ponte Vecchio, admire the bustling Piazza della Repubblica, and marvel at the Florence Cathedral (Duomo) with its tricolored marble façade and Brunelleschi’s engineering genius. The tour concludes with a visit to Michelangelo’s original David, a 17-foot masterpiece, while your guide provides rich insights into Florence’s art, history, and architecture throughout the experience.

DAY 6 : GRADARA

Settle into your elegant historic hotel in the heart of Gradara, then explore the village’s famous castle; the legendary backdrop of Paolo and Francesca’s love story as told by Dante.

Enjoy free time to wander the cobbled streets and dine in one of the village’s romantic restaurants.

DAY 7 : SAN MARINO

Spend the morning exploring San Marino’s medieval towers, narrow lanes, and centuries-old independence.

Continue to a boutique winery on Monte San Bartolo, where vineyards drop toward the sea.

Taste local wines in one of the region’s most panoramic spots before returning to Gradara for the night.

DAY 8 : SAN LEO

Walk through the dramatic fortress of San Leo, once home to the mysterious alchemist Count Cagliostro. Then, choose from one of the following rural experiences:

  • Formaggio di Fossa (cheese) Experience: Travel to Talamello or Sogliano al Rubicone to see cheese aged in underground pits and enjoy a tasting lunch of regional specialties.
  • Cashmere Goat Farm: Learn about cashmere production from goat to yarn, including hand-combing, spinning, and a sheepdog demonstration.
  • Goat Cheese Farm: Explore artisanal goat cheesemaking from pasture to plate, ending with a guided tasting paired with local bread, honey, and wine.

These optional activities can be combined or selected individually based on interest and timing, offering a hands-on taste of Montefeltro’s rural heritage.

DAY 9 : DEPARTURE

After breakfast, say goodbye to Gradara and the scenic Montefeltro countryside.

On departure day, your driver will transfer you to the airport in plenty of time for your flight.

We hope your Italian journey was full of unforgettable moments, and we look forward to welcoming you back soon!

ACCOMMODATION
Our preferred hotels
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images/galleries/aqua-palace-hotel/aqua-palace-hotel-1.jpg Aqua Palace Hotel

Indulge in the magic of Venice's canals and the allure of its historic charm by choosing Aqua Palace Hotel for a truly enchanting and immersive Venetian experience.

images/galleries/Brunelleschi_Hotel/Brunelleschi-Hotel-9.jpg Brunelleschi Hotel

Discover the epitome of luxurious comfort and historical charm at Brunelleschi Hotel, where every moment becomes a timeless and unforgettable experience.

images/galleries/Ca-Pisani-Hotel/ca-pisani-hotel-1.jpg Ca' Pisani Hotel

Experience Venetian elegance and charm at its finest by staying at Ca' Pisani Hotel, where timeless luxury and impeccable service await to make your Venice visit truly unforgettable.

images/galleries/charming-house-DD724/charming-house-DD724-1.jpg Charming House DD724

Indulge in a truly enchanting Venetian escape at Charming House DD724, for the perfect blend of luxury and personalized service!

images/galleries/Gallery-art-hotel-florence/gallery-hotel-art-intro.jpg Gallery Hotel Art

Where Art and Luxury Converge: Discover the Splendor at Gallery Hotel Art

images/galleries/Glance-hotel/Glance-hotel-4.jpg Glance Hotel

Elevate your stay in Florence to unparalleled heights at Glance Hotel, where captivating design, modern luxury, and a prime location converge for an unforgettable experience.

images/galleries/Hotel-Ai-Cavalieri-di-Venezia/Hotel-Ai-Cavalieri-di-Venezia-15.jpg Hotel Ai Cavalieri di Venezia

Experience the timeless charm of Venice from the elegant and centrally located Hotel Ai Cavalieri di Venezia, where luxury, comfort, and the city's enchanting ambiance await.

images/galleries/Hotel-Ai-Reali/Hotel-Ai-Reali-1.jpg Hotel Ai Reali di Venezia

Indulge in the ultimate Venetian luxury and immerse yourself in the rich history of Venice at Hotel Ai Reali di Venezia!

images/galleries/Hotel-Bucintoro/Hotel-Bucintoro-2.jpg Hotel Bucintoro

Experience the enchanting beauty of Venice from the comfort of Hotel Bucintoro, where timeless elegance and breathtaking views await your stay.

images/galleries/Calimala-hotel/hotel-calimala-1.jpg Hotel Calimala

Indulge in the essence of timeless elegance and exceptional hospitality at Hotel Calimala, where every moment is a refined blend of luxury and comfort, creating an enchanting stay in the heart of Florence.

images/galleries/Hotel-Cerretani-Firenze/Hotel-Cerretani-Firenze-1.jpg Hotel Cerretani Firenze - MGallery Collection

Indulge in the timeless charm of Florence while experiencing impeccable luxury at its finest by staying at Hotel Cerretani Firenze!

images/galleries/Hotel-Continentale/Hotel-Continentale-10.jpg Hotel Continentale

Indulge in the timeless allure of Florence's rich history and captivating beauty at Hotel Continentale, where luxury and sophistication await to elevate your stay to unforgettable heights.

images/galleries/Hotel-Heureka/Hotel-Heureka-5.jpg Hotel Heureka

Experience the epitome of Venetian charm and luxury at Hotel Heureka, where every moment is a masterpiece waiting to be discovered.

images/galleries/Hotel-lungarno/hotel-lungarno-1.jpg Hotel Lungarno

Elevate your Florence experience to new heights of elegance and sophistication by choosing to stay at Hotel Lungarno, where art, culture, and unparalleled views of the Arno River come together in perfect harmony.

images/galleries/Hotel-moresco/hotel-moresco-1.jpg Hotel Moresco

Indulge in the timeless charm of Venice and elevate your experience at Hotel Moresco, with luxury, elegance, and authentic Venetian hospitality.

images/galleries/Hotel-Palazzo-Stern/hotel-palazzo-stern-9.jpg Hotel Palazzo Stern

Experience the enchanting allure of Venice from the exquisite Hotel Palazzo Stern, where timeless elegance meets unparalleled canal-side charm.

images/galleries/Hotel-Spadai/Hotel-Spadai-14.jpg Hotel Spadai

Indulge in the epitome of luxury and hospitality at Hotel Spadai, where every moment is a captivating blend of comfort and elegance.

images/galleries/Palazzo-Castri-1874/Palazzo-Castri-1874-1.jpg Palazzo Castri 1874

Discover true luxury and timeless elegance at Palazzo Castri 1874 - an exquisite haven where every moment is a masterpiece.

images/galleries/Palazzo-Veneziano/palazzo-veneziano-1.jpg Palazzo Veneziano

For an unforgettable Venetian experience, choose to stay at Palazzo Veneziano and immerse yourself in the timeless elegance of Venice's canalside luxury.

images/galleries/San-Firenze-Suites-Spa/San-Firenze-Suites-Spa-4.jpg San Firenze Suites & Spa

Experience the epitome of luxury and relaxation at San Firenze Suites & Spa for an unforgettable stay in the heart of Florence's historic charm.

images/galleries/The-Moon-Hotel-and-Spa/Moon-Boutique-1.jpg The Moon Boutique Hotel and Spa

Indulge in an unforgettable retreat of luxury and relaxation at The Moon Boutique Hotel and Spa, where every moment is a celestial escape waiting to be experienced.

These are our top accommodation options for this trip. We only feature particular hand-picked hotels, which our team has carefully inspected. These hotels have received great feedback from our previous guests.

WHAT TO EXPECT
Inclusions & Exclusions
Inclusions
  • Boutique 4-5* accommodation
  • All private tours with excellent licensed guides, as described in the itinerary
  • All private transfers with professional drivers and luxury vehicles
  • All domestic flights/trains/ferries
  • All taxes and VAT
Exclusions
  • Personal travel insurance
  • International Flights
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