Florence, Chianti, Siena and the coast, planned around the way you like to travel.
Tuscany is where our story starts: our founder was born here, and our trip designers live and work in central Italy. A private trip lets you move between Renaissance Florence, the hill towns and the vineyards without timetables or tour buses.
Every itinerary below is a starting point. Swap a city day for a cooking class, add a night in the countryside, or join Tuscany to Rome, Umbria or the Cinque Terre. You travel with private drivers and hand-picked hotels, and our team is on WhatsApp around the clock once you land.
Private and fully custom. Use one as it is, or as the starting point for your own trip.
8 days · Florence, Chianti, Siena, Volterra
Moderate 40 to 50 km days through Chianti, San Gimignano and Volterra to the coast.
8 days · Florence, Pisa, Siena
Florence Highlights Tour, Wine Tasting and Cooking Class in Tuscany, Boat Tour Of Cinque Terre.
11 days · Maremma, Bolgheri, Cinque Terre
Giglio Island, Saturnia’s thermal baths, Bolgheri wines and a private boat day in the Cinque Terre.
12 days · Amalfi Coast, Rome, Florence, Venice
Capri by boat, Pompeii, the Vatican, a Tuscan countryside day and a private boat in the Venice lagoon.
13 days · Rome, Venice, Tuscany
Culinary Highlights of Rome, Venice – A Taste of the Lagoon, Barolo Wine Tasting.
Full day
Super Tuscan Wine Tour, Medieval Village Lunch & Authentic Cooking Experience.
Guided time with the Renaissance highlights, then free evenings in the city.
Hill towns of towers and stone, linked on our cycling days.
Coastal Tuscany: wine estates, thermal baths at Saturnia and Giglio Island.
An easy day trip from Florence on our 8-day Florence and Cinque Terre itinerary.
In their own words, from trips we planned.
“He customized our vacation to fit all of my requests. … The drivers and guides he used were knowledgeable, friendly and accommodating for any changes we made on the tour. The hotels he booked were all centrally located and close to wonderful restaurants and sites.”
John and Tiffany
“Every day was well planned using experienced drivers and local guides. … I was so happy not to drive and everything was beautifully arranged and curated daily by David. I would highly recommend this group.”
Jeff and Suzan, southern Italy
Trip stories from our travellers: A first trip to Rome, Siena, Florence and Venice · Wine, cooking and cycling in Siena, Assisi and Rome
Green hills, mild days and wildflowers. A favourite time for cycling and countryside stays.
Long, hot days. Plan early starts, pool time and the coast; Florence is at its busiest.
Grape harvest season, warm light and quieter roads: ideal for wine and food trips.
Quiet museums and cosy trattorias; some countryside hotels close for the season.
Something else on your mind? A member of the team replies personally.
Our Tuscany itineraries run from single-day food and wine experiences to the 8-day E-Bike Holiday and the 11-day Tuscan Coastal Escape. Tell us what you want to see and we will suggest a length that does not feel rushed.
Yes. Every trip is private, so we can join Tuscany to Rome, Umbria, the Cinque Terre or Venice. Our 12-Day Best of Italy already pairs the Tuscan countryside with Rome, Florence, Venice and the Amalfi Coast.
No. Our trips use private drivers and transfers, so you can enjoy wine tastings and village stops without driving or parking.
Yes. Our E-Bike Holiday rides from Florence through Chianti, Siena, San Gimignano and Volterra to the coast, with moderate daily distances.
Tell us your dates and what you love. Your trip designer will reply with ideas and a first proposal.
12-Day Best of Italy