Start by Lake Bolsena, then to the village of Orvieto perched on a rock cliff. Next, the heart of Tuscany with a visit to Siena and Florence. Then west to quaint towns of Lucca, Pisa with its Leaning Tower, and finally to Cinque Terre and Portofino on the Italian Riviera.

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  • Limited to 18 guests.
  • Prices start at $4,795 per person and are based on double occupancy. There is a single supplement of $999.
  • There are no tours available at this time. To be informed when new tours become available, please use the contact form below.

There are no tours available at this time. To be informed when new tours become available, please contact us.

Day 1: Arrive in Rome, Italy

  • From Rome’s airport, you’ll be driven to Lake Bolsena, a favorite spot for Romans to vacation. There you’ll enjoy a welcome dinner with your new traveling companions at the Gio Ristocantina, where meats, fish, and pasta are served family style.  
  • Meal highlights: Dinner at Gio Ristocantina
  • Overnight at Hotel Holiday 4*

Day 2: Orvieto to Sienna

  • An early breakfast allows time to head to the mountain village of Orvieto—you may know the white wine from that region. The Duomo di Orvieto, built during the 13th century, is not much from the outside, but wait until you see the interior! Visit the network of caves that speaks of the city’s Etruscan roots. Explore a small museum underground that explains what history is known of the Etruscans. 
  • Lunch is in Cortona, en route to Sienna, at Ristorante La Logetta, a lovely restaurant with al fresco dining, or inside in its stone-walled dining room. In Sienna, the Hotel Garden is your home for two nights and you’ll enjoy dinner at the Salefino Wine & Cuisine restaurant near the hotel. 
  • Hotel Garden 4*
  • Meal highlights: Lunch at Ristorante La Logetta, Dinner at Salefino Wine & Cuisine.

Day 3: Sienna

  • Stroll Sienna in the morning, paying particular attention to the Piazza del Campo where local contrade (neighborhood groups) race horses each year.  Journey deep into Tuscan wine country with lunch at Castello Banfi and dinner at Ostorio le Logge near the Piazza del Camp.
  • Hotel Garden 4*
  • Meal highlights: Lunch at Castello Banfi, Dinner at Ostorio le Logge.

Day 4: Florence

  • In the morning, visit nearby Florence, Tuscany’s capital and home to the Duomo with its architecturally radical dome designed by Brunelleschi.  And, of course, there’s the Galleria dell’Accademia where Michelangelo’s sculpture, “David,” is the centerpiece (don’t miss Botticelli’s “The Birth of Venus and da Vinci’s “Annunciation,” as well).  There’ll be time for wandering (Vivoli for gelato, Ferragamo for shoes and clothing) with lunch at Rivoire.  Rudy’s favorite library, designed by Leonardo da Vinci, is tucked near the Duomo and is often missed by visitors; you won’t miss it.
  • Meal highlights: Lunch at Rivoire, Dinner at Il Latini
  • Sina Villa Medici 5* or Palazzo Magnani Feroni 5*.

Day 5: Florence to Lucca

  • Overlook Florence (a certain Instagram snap!) and pay a visit to an 11th-century church, the Abbazia di San Minato al Monte, with equally spectacular views. They’ll also be time to walk around Boboli Gardens, not far from the Ponte Vecchio.  After lunch, head to Pisa to see the tower that is still leaning—since 1372.  Check into a lovely, countryside hotel, the Bagni di Pisa in San Giuliano Terme, and head to the village of Lucca, known for its Renaissance walls and broad, cobblestone streets. It’s also the hometown of Puccini, and you may enjoy a stroll through the streets once walked by the great opera composer himself followed by a concert performance of some of the works of Puccini and Verdi in the San Giovanni church before dinner at Ristorante Giglio.
  • Meal highlights: Dinner at Ristorante Giglio
  • Bagni di Pisa 5*

Day 6: Cinque Terre and Santa Margherita Ligure

  • In the morning, your next destination is the gaily colorful villages of Cinque Terre.  Hike or take the short train to visit the five, steeply sloped towns overlooking the water or enjoy exploring. You’ll end the day at Santa Margherita Ligure, a neighboring town to the very fashionable Portofino.
  • Excelsior Palace Hotel 5* or Hotel Laurin 4*

Day 7: Portofino

  • Spend the day by the pool, take a hike to Abbazia di San Fruttuoso, or take a boat ride to Portofino with a visit to Castello Brown and the lovely church of St. Giorgio. You can also enjoy a leisurely ride on the water and visit the other picturesque towns in the area.
  • Excelsior Palace Hotel 5* or Hotel Laurin 4*

Day 8: Portofino 

  • End your Italian journey with a farewell lunch in the picture-postcard harbor of Portofino.


When you let The Original Savvy Traveler arrange your trip through Europe, you are guaranteed peace of mind. Rudy Maxa’s team provides personal service and assistance from booking all the way through your journey.

What’s included in your Luxury Tour:


  • Welcome package with luggage tags, tour information, and a personal gift from Rudy Maxa.
  • An exclusive experience with a small group (maximum of 20 guests.)
  • Rudy Maxa’s expert team lead by his Group Director will make your trip seamless, and magical. In addition to the team traveling with you, known and approved local guides with extensive knowledge will be show guests around.
  • The freedom to choose between multiple excursions and programs.
  • All tours, admissions, and entertainment.
  • Airport arrival meet and greet with transportation to the first host hotel.
  • Upscale, handpicked hotels inspected and approved by Rudy Maxa’s team.
  • All meals, including an upscale restaurant every night approved by Rudy Maxa’s team.
  • Luggage Butler Service: leave your bags in your hotel room in the morning and find them waiting in your room at your next hotel.
  • Transportation between cities in smaller luxury vehicles, high speed trains, or by air.
  • All gratuities.
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