• Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
1-440-804-5062
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
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Your Dates Here!
Day One 
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​Welcome to Lake Como. Join us in the garden of the hotel as we welcome you with a glass of local wine to toast each other. Afterwards we will have a orientation walk of the beautiful town of Varenna and have a stop at Villa Monastero and its botanic gardens- home to thousands of rare species of plants. Join us for a short walk to our first dinner together near the shores of lake Como.

Welcome drink/ Tour of the Botanical Gardens at Villa Monastero and the town of Varenna/ Dinner/Overnight Lake Como-Varenna.

Day Two
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​We will spend the day on the lake as we travel across to the town Lenno and visit Villa Balbianello built in 1787 and a tour of its breathtaking gardens and partake in the lake views. We continue our tour of the lake as we boat to the famous town of Bellagio where you can have lunch in any one of the cafes the town has on offer. Then you can take your time to wander the streets of Bellagio. We will return to Varenna in the afternoon where dinner will be on your own with plenty of recommendations from us.

Breakfast/ Ferry to Lenno and Villa Balbianello/ Ferry to The Town of Bellagio/ Overnight Lake Como-Varenna.
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Day Three 
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We are off in the morning to Cinque Terre by train. Cinque Terre, or five lands is made up of five villages that line the rugged coast located in a national park preserved as a UNESCO World Heritage Site. Our destination is the lovely town of Monterosso. After checking in we will have a walk down to the shore where you can put your feet in and soak up the exquisite scenery.  In the afternoon we will ride the train to together to Vernazza for our tour of this small beautiful town. If you want you can walk back the 2+ hours to Monterosso along the Cinque Terre National Park trail or take the train back. Either way join us for dinner back in Monterosso. Afterwards we will join the evening passeggiata  as we stroll just like the Italians do! 

Monterosso/Breakfast/Train to Cinque Terre/ Walk/ dinner together/ UNESCO World Heritage Site/ Overnight Monterosso.
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Day Four
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We are off to Riomaggiore and the national park of Cinque terre.  Be sure to pack some walking shoes as we will use the train and our own feet to navigate to this town.  We will take our time and to sit and feel the beauty of this area. The afternoon is yours to do what ever you want, take the train back up and stop at other towns along the line or grab and umbrella down at the beach and chill the rest of the afternoon. 

Dinner on  your own with plenty of recommendations from us.
Monterosse/Breakfast/Train to Cinque Terre/ Walk/ UNESCO World Heritage Site/ Overnight Monterosse.

Day Five 

We leave early for Florence, where we will be picked up by our driver and head for Tuscany and the heart of Chianti. Here we will have a stop to  a small quaint town known for its wine and food. We will take our time and you may have lunch on your own. Then it is off to the heart of Tuscany where we  will be staying at a beautiful working farm.  We will tour their wine making facilities and have dinner together featuring a traditional Tuscan meal.
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​Breakfast-Train and van transportation-Chianti & Greve/Wine tasting/ Dinner together/ UNESCO World Heritage Site. Overnight outside of San Gimignano

Day Six 
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Our day will be spent climbing the medieval towers of San Gimignano and enjoying this spectacular village. Lunch at any one of the cafes before continuing your visit at any one of the museums in town. In the evening we are back at our Fattoria where you can enjoy the pool or take a walk along the country road to see the spectacular views. Either way join us a little before dinner as we have a cooking lesson not to be missed. Dinner together in the converted farm house.
Breakfast/ UNESCO World Heritage Site of San Gimignano/ Dinner together/ Overnight San Gimignano
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Day Seven 
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​We are back in Florence this morning to catch our fast train to Rome and then onto Napoli. Here we will be whisked by our driver to the ruins of Pompeii for our tour. In 79 A.D the explosion of Mount Vesuvius caused the destruction of the town. Called one of the best preserved ancients sites in the world, we will take our time to visit the ruins and absorb all that the site has to offer. Afterwards we will take our drive along the Amalfi coast and then settle into our hotel near the scenic village of Sorrento. Join us as we have a toast of prosecco (Italian Champagne) before dinner on your own with recommendations from us. Breakfast/ Transportation to Pompeii/ Tour of Pompeii/ Amalfi Coast Drive/Overnight Sorrento

Day Eight
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​Today we are off to Positano and the Amalfi coast. We will grab a local bus that will zoom us around the spectacular roads that lead us to this magnificent village. Take your time and lounge on the beach or shop in town. Many places to sit seaside and have a bite to eat. Then we will return to Sorrento and ready ourselves for  our farewell dinner together. Breakfast/ Visit to Positano/ Farewell dinner together/Overnight Sorrento.UNESCO World Heritage Site-Amalfi Coast.
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Day Nine
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Take your time lounging on the balcony of our hotel with views of the Gulf of Naples and Mt. Vesuvius in the background, before taking off to catch your flight from Naples to get back to the states.

What you get with this tour-

  • Lake Como and the Exquisite Town of Varenna
  • Villa Balbianello  Tour
  • The Town of Bellagio
  • Boat Rides on Lake Como
  • The Villages of Cinque Terre
  • Hiking & Train ride in National Park of Cinque Terre
  • The Village of Greve in Chianti
  • Cooking lesson- Tuscany
  • San Gimignano
  • Tuscan Village & Winery of San Donato 
  • Stay at a working Tuscan farm and winery
  • The Ruins of Pompeii
  • Sorrento and the Amalfi Coast
  • Four UNESCO World Heritage Sites
  • Cheese and prosciutto taste testing
  • Special wine tastings
  • Visit to local markets
  • Prosecco Sampling
  • Olive Oil & Olive tasting
  • Meetings with the locals
  • Eight full Breakfasts
  • Five multi-course dinners (including wines)
  • Experienced tour leaders
  • Comfortable transportation
  • High Speed Train Travel
  • Carefully selected hotels in great locations
  • Careful Attention paid to the pace of the trip, so you get the most impact!
Cost per person-$ TBD 

Book your flights into Milano and out of Naples (or Rome)

Transportation to  our starting hotel and transfer from our last hotel is not included in price. We will be on hand to arrange these segments as you wish.
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Contact

The Olive Odysseys 
46 Shopping Plaza
​Drive # 107
Chagrin Falls, Ohio
​44022 U.S.A
Phone: ​1-440-804-5062
​
[email protected]
Copyright 2025-2026 All Right Reserved

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A member of the
​American Society of Travel Advisors
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy