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, and finally to Cinque Terre and Portofino on the Italian Riviera.

Download the free brochure

  • Limited to 22 guests.
  • From $4,495 per person, based on double occupancy.
  • Single supplement $799.

August 21-28, 2022

May 21-28, 2023

Day 1: Arrive in Bolsena, Italy

  • You’ll start the journey at Lake Bolsena, a favorite vacation spot for Romans.
  • You’ll take a stroll along the lake and through the narrow streets of Bolsena on your way to the welcome dinner – an authentic Italian meal.
  • Hotel Holiday 4*
  • Meals included: Welcome dinner

Day 2: Orvieto to Siena

  • 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. 
  • After your visit to Orvieto, you’ll take a drive through the Tuscan countryside where you’ll have lunch in a typical picturesque village on the way to Siena.
  • Hotel Garden 4* or Four Points by Sheraton Siena 4*
  • Meals included: Breakfast and dinner

Day 3: Siena

  • In the morning you’ll do a walking tour through the streets of Siena paying particular attention to the Piazza del Campo where local contrade (neighborhood groups) race horses each year.
  • The afternoon is open for shopping, exploring Siena or just being lazy by the pool.
  • Hotel Garden 4* or Four Points by Sheraton Siena 4*
  • Meals included: Breakfast

Day 4: Florence

  • In the morning, you’ll visit a Tuscan winery and arrive into Florence around lunchtime.
  • After lunch, you’ll take a walk to the best overlook of 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. There’ll also be time to walk around Boboli Gardens, not far from the Ponte Vecchio.
  • For dinner, you’ll enjoy authentic Florentine Style Steak and authentic Gelato – from where gelato originated.
  • AC Hotel by Marriott Firenze 4* or Grand Hotel Baglioni 4*
  • Meals included: Breakfast, lunch, and dinner

Day 5: Florence 

  • In the morning you’ll visit 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) before lunch in the center of town. 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.
  • AC Hotel by Marriott Firenze 4* or Grand Hotel Baglioni 4*
  • Meals included: Breakfast and lunch

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.
  • Hotel Laurin 4* or Best Western Hotel Regina Elena 4*
  • Meals included: Breakfast and lunch

Day 7: Portofino

  • In the morning, you’ll head to Portofino, which is just two miles away from the hotel. You’ll enjoy a drink at the Piazzetta and explore the town.
    After, you’ll jump on the ferry that will take us to the remote village of San Fruttuoso.
  • Enjoy lunch before touring the famous abbey. If you’re a snorkeler and adventurous, you’ll have the opportunity to stay behind and see Christ of the Abyss, a dramatic bronze statue of Jesus submerged 15 meters under the Mediterranean Sea.
  • Take the ferry back at your leisure; there’s one every hour until 4PM.
  • In the evening, you’ll enjoy your farewell dinner at legendary Ristorante Antonio.
  • Hotel Laurin 4* or Best Western Hotel Regina Elena 4*
  • Meals included: Breakfast and lunch

Day 8: Portofino 

  •  After a leisurely breakfast, start your journey home.


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 Classic Tour:


  • Welcome package with luggage tags.
  • A 15-minute concierge call to prepare you for your journey.
  • Smaller groups with a maximum of 22 guests.
  • Rudy Maxa’s expert team lead by his Tour Director will make your trip carefree. In addition to the team traveling with you, local tour guides with extensive knowledge will show you around at select destinations. 
  • Choose excursions included in the program or enjoy the freedom to explore on your own.
  • Optional airport arrival meet and greet with transportation to the first host hotel (additional fee required).
  • Handpicked hotels inspected and approved by Rudy Maxa’s Team.
  • Breakfast daily, and meals included per program.
  • Luggage Butler Service available for an additional fee.
  • Transportation between destinations per the itinerary.