The Best of Southern Tuscany (Pienza, Montepulciano & Montalcino) and Cinque Terre (Vernazza, Corniglia, Manarola, Riomaggiore & Monterosso)

We are calling this the ‘Companion Experience’ as this is a parallel program to our Tuscany Photo Tour; however, this amazing holiday vacation is so good, you and the photographers will have a lively debate as to who is the ‘featured guest’ and who is the ‘companion’!

Group Size: 6

Group Leaders: Two Leaders: Certified Italian tour guide, Martina and  Magnum Excursions’ lead Susan Spinosa. Both have first hand knowledge of the area and will ensure the group has a lot of fun while also developing knowledge of the region.

Cost: $7,900, Single Supplement $750

Initial Deposit $2,500

If interested in Tuscany, but prefer not to join us in Cinque Terre, Tuscany only portion is $5,600. While this is certainly possible, we highly recommend the combined trip as Cinque Terre is amazing … and of course you want to learn to make Pesto like a real Italian.

Summary:

Discover two of Italy’s most famous destinations in one remarkable adventure.

• Tuscany – In Tuscany, you’ll explore the medieval charm of Lucca and see the iconic leaning tower of Pisa, while savoring the region’s famed wines and culinary delights.
• Cinque Terre – Following, you’ll experience the breathtaking coastal villages of Cinque Terre followed. This is the ideal journey to get to know Italy’s diverse landscapes and rich cultural heritage.

Where you’ll stay – Home Away From Home

Where you call home when you are away from home can make all the difference. That’s why we’ve used local experts to handpick accommodations that blend a mix of Italian hospitality, comfort and local character (you want to feel like you’re in Italy, not Idaho). We have made an effort to make each home base be located in a region that will allow convenient daily travel to the awesome sights and village we will be experiencing.

Getting around 

Arriving in Italy – We recommend arrival and departure flights into Florence International Airport, known as Amerigo Vespucci Airport (FLR). Our driver will collect you at this location and transfer you to our first home base in Pienza, Tuscany.

Dedicated Private Driver – Throughout your tour, travel seamlessly in the comfort of our dedicated vans, as you journey on daily excursions spanning small towns and off-the-beaten path adventures. While one group heads out for morning and afternoon landscape photography sessions, this parallel experience offers a rich and indulgent immersion into the heart of Southern Tuscany — ideal for travelers who want to savor the culture, flavors, and charm of the region at a relaxed pace.

Your days will unfold among the rolling hills and timeless hilltop towns of Pienza, Montepulciano, and Montalcino. Each morning begins unhurried, allowing you the freedom to enjoy a leisurely start before the day’s curated activities. From wine tastings at renowned local estates, to visits to family-run Pecorino cheese farms, and hand-crafted olive oil experiences, this journey blends authentic Tuscan flavors with cultural richness. There will also be opportunities to tour medieval villages, explore boutiques and artisan shops, visit historic churches, join an optional hands-on cooking class, or simply sit at a café soaking in the scenery.

Draft Agenda

• Day 1 (October 27th): Arrival in Val d’Orcia, no activity on this day as people might want to just settle down/unwind/relax. Optional walk-around before dinner for those who are interested!
• Day 2 (October 28th): After breakfast, visit Montalcino and wine-tasting in the countryside around lunch time. Optional visit to the sunset location later in the day together with the photographer’s group. 

• Day 3 (October 29th): After breakfast, visit Montepulciano and cooking class there around lunch time. Optional visit to the sunset location later in the day with the photographer’s group. 
• Day 4 (October 30th): After breakfast, visit Pienza and do a cheese-factory visit (and possibly tasting). Optional visit to the sunset location later in the day with the photographer’s group. 

• Day 5 (October 31th): After breakfast, transfer to Siena (1h) to do some walk-around and some shopping. Have lunch there. The photography group will also visit on that day, so it will be good that everyone will be together! We might do sunset in Siena, the plan will be to arrive there by lunchtime and spend the day walking around till sunset. The non-photographers will be free to head back sooner if they are done with the visit.

• Day 6 (November 1st): After breakfast, transfer to San Gimignano (1h40m) in time for lunch (all together). After lunch, the photographers will stick around till sunset, while the non-photographers will start heading back with a stop in Monteriggioni, another little historic town on the way.

• Day 7 (November 2nd): Transfer day to Cinque Terre. No activities on this day as it’s going to be a fairly long day for everyone; we might take a stop in Portovenere if the weather is good (all together) and then proceed to reach Manarola. As usual, optional outing with the photography group to check out the town’s most photogenic spot and most famous view. 
• Day 8 (November 3rd): After breakfast, they might do a pesto making class (upon availability!) which is something very typical to do in Cinque Terre as pesto comes from that area. Later in the day, boat ride to check out the villages from the sea, possibly with an aperitivo around sunset.
• Day 9 (November 4th): Exploring the Cinque Terre by train; today as we will move around the villages to check them out and walk around them, with lunch in Monterosso al Mare. Later in the day the group will join the photographers for the sunset or if you feel tired you can return back to the hotel to relax till dinner. 
• Day 10 (November 5th): Today will be the final day when we’ll drive back to Florence, so no activities planned for the day.

The two groups reunite midday from 11:00 AM–3:00 PM to share the magic of Tuscany and Cinque Terre together—often over lunches in charming villages and light touring—before separating again for afternoon activities. Evenings bring everyone back together from 7:00 PM onwards, just in time for memorable dinners featuring regional cuisine, local wines, and the warm atmosphere Tuscany is known for. On some days, the tour group and photo groups will be traveling together as we explore the small villages for beautiful sights.

Built with flexibility in mind, this companion program balances meaningful experiences with room for relaxation, shopping, and personal time, ensuring each guest enjoys Tuscany in their own perfect way.

PROGRAM HIGHLIGHTS FOR COMPANION PARTICIPANTS

• A balanced mix of culture, flavor, leisure, and discovery
• Authentic farm and artisan interactions (cheese, wine, olive oil)
• Time built-in for shopping, relaxation, and personal interests
• Daily reunion moments for shared meals and togetherness

Included in the trip:

• Transfers from arrival airport to our hotel and return
• All transfer transportation for the entire trip
• Rooming at a 3 star hotel for 9 nights
• Breakfast each morning
• Arrival and farewell celebration Dinner
• Assistance from 2 guides each day
• Activities including but not limited to:
  • wine tasting: with lunch included
  • cooking class in Tuscany
  • pecorino cheese factory trip (you will definitely want to bring several versions home!)
  • some admissions into historical sites (Duomo, Churches, Museums and any other)
  • pesto class in Cinque Terre
  • and afternoon boat ride along Cinque Terre
  • Arrival and farewell celebration Dinners

Not Included in the trip:

• Airfare to/from your home to Florence, Italy
• Lunches and dinners except as noted with the included activities
• Tips/Gratuities for guides and drivers

To book this trip and for more information, please contact Buddy Eleazer at buddy.eleazer@gmail.com