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Winding roads, medieval villages, and stunning vistas – Tuscany is as breathtaking as anything you’ve ever seen, and Things I wander will spend nine glorious days there in during a Central Italy trip in 2023. Our journey will take us deep into the heart of Florence where priceless art, hidden churches, and secret bakeries abound, as well as through romantic hamlets and signature landscapes of rural Tuscany as we trace the ancient roads of one of Italy’s most storied destinations. Our photos will be incredible – our memories will be even better.
| Trip Dates | Cost | Includes | Min. Group Size | Max. Group Size | Activity Level |
| To be announced | TBA | All lodging, meals, ground transport & activities | 6 | 10 | Moderately high - extensive walking, stairs, steep inclines, uneven surfaces |
*Please note – Significant walking, uneven streets, stairs, hiking on unpaved terrain, sometimes very steep inclines.
*Minimum Age for This Trip: 18 years old
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Itineraries
Saturday - Day 1
Arrive in Florence
We will coordinate itineraries and have a personal driver picking up members of our group as they arrive and shuttling them to a historic hotel in downtown Florence. Our lodging is in a beautiful small inn that has exquisite period decorations and is within short walking distance of the heart of the city. While you wait for others to arrive, lounge in the lovely common areas of the hotel, have a drink in the inn’s quaint bar, or wander through a bit of Florence, one of Italy’s most breathtaking cultural centers.
We will have a late dinner on this evening at a nearby cafe to get to know each other a little and talk about our upcoming days.
Sunday - Day 2
Under the Tuscan Sun
We will be up early this day to board our van for Tuscany. Along the way to our villa, we will stop at two extraordinary medieval villages, Volterra – the legendary home of Twilight’s vampires, and San Gimignano, a charming, ancient town filled with stone towers and artists. We will spend a few hours exploring both, and later that afternoon, we will arrive at our private villa situated in the heart of Southern Tuscany. Settle in, take a swim in our pool, and explore our historic home. We will head to a nearby village for dinner and a little twilight wandering before tucking ourselves in for the night.
Monday - Day 3
Red Roofs and Red Wines
After breakfast, our driver will pick us up for a short drive to the city of Cortona, a medieval city perched atop a hill that is renowned as one of Italy’s most beautiful. Next stop will be Chiusi, a tiny village that is more than 1500 years old and has one of Tuscany’s oldest cathedrals. We will visit a winery in the area as well.
For dinner, we will have an Italian chef coming to our villa to give us a cooking and wine pairing lesson, helping us to create our own feast!
Tuesday - Day 4
The Estrucian Trail
Early risers can join Cynthya for a jaunt out of the villa at sunrise to catch the sun’s first rays glinting across the rolling Tuscan landscape. After breakfast, we will drive to the southern border of Tuscany to see several story-book beautiful villages perched on the top of tall hills – the key to their survival during Italy’s tumultuous past. We will also visit Terme Saturnia – an area of cascading hot springs – for a dip in water that legend says has healing powers.
Dinner and socializing will be at a family-owned trattoria in a village near the villa.
Wednesday - Day 5
Classic Tuscany
Today we will wander the towns of Montepulciano and Pienza, and we will drive through the UNESCO-World-Heritage-designated countryside of Val d’Orcia looking for perfect Tuscan landscapes. If we are lucky, we will find sunflowers blooming, and we will definitely find painting-worthy slopes dotted by Tuscany’s signature cypress trees.
We will have a leisurely dinner in a nearby village and look for a nice spot to shoot the sunset from.
The pace on this day will be a relaxing one to restore our energy for the vibrant streets of Florence.
Thursday - Day 6
A Very Cool Day
After breakfast, we will bid farewell to our villa and board our van for the ride back to Florence.
Once we are checked in, we will set off on foot through the streets of Florence, which is dominated by a spectacular duomo (cathedral) and rich Renaissance history. From the colorful gelato stands to the priceless statues that stand throughout the city, we will wander through a photographer’s treasure trove of carved facades, gilded walls, and colorful shops until we arrive at a sidewalk cafe for lunch.
After lunch, we will make our way to one of Florence’s best secrets – a colorful neighborhood filled with artisans, winding alleys, and a spectacular church that tourists rarely find. From this charming part of town we will walk to a beautiful nearby piazza for a drink and a snack.
Dinner will be at a trattoria near our hotel known for its historic interior and artful dishes.
Friday - Day 7
Florence, uncovered
After breakfast, we will have some leisure time to explore shops where outstanding values on leather goods, gourmet foods, art, and more can be found.
We will meet up for a light lunch, and then embark on a gourmet walking tour of Florence, sampling its marvelous flavors and hearing from a local guide what makes Tuscan food so uniquely wonderful.
Dinner will be in one of Florence’s famous trattorias, where we will put all of our newfound foodie knowledge to work on a fine meal.
And then there is something very special in store today – a celebration in Florence that is both legendary and a photographers dream, and the entire schedule has been built around us being in Florence for it. It is the Festa Della Rificolona – the paper lantern festival – when thousands of paper lanterns are carried through the streets to celebrate the birthday of the Virgin Mary. It is an absolutely breathtaking sight, and we are going to be there for it. It is going to be amazing!
On this evening, night owls are welcomed to join Cynthya on a tour of some of Florence’s nightlife spots. If we are up late enough (ahem, 2 a.m.) then we will go in search of one of Florence’s secret bakeries — wholesale bakers that will surreptitiously serve pastries out of their side door if you discreetly knock on it.
Saturday - Day 8
The Art of Florence
After breakfast, we will meet up with our guide for the morning who will bring us to the Duomo and the Uffizi, one filled with masterpieces and the other one a masterpiece itself. Our guide will give us interesting insights, and she will also get us past the line waiting to get in!
Lunch will be at a sidewalk trattoria, then we will stroll to two iconic market where vendors have been peddling everything from oils and spices to silk and leather for at least 500 years. Besides being magnificently colorful, the markets also offer the best wares in Florence, and we will leave plenty of time in the afternoon schedule for shopping and exploring.
On this evening, we will watch the sun setting over the city of Florence from the city’s best vantage point – a plaza high on a hill overlooking the city. A crowd gathers here every evening to watch the spectacular show as well as to gawk at one of the city’s David statue replicas that sits at the center of the square. When the sun is down, we will toast Florence over a late dinner and then check out a local cocktail bar.
Day 9
Departures
Our shuttle driver will begin transporting people to the airport according to their flight times.
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