How does a tailor-made Tuscany trip work?

Share your dates, group size and interests using the form. One of our Tuscany travel experts will get in touch, design a day-by-day itinerary around you, and refine it with you until it is just right.

Is there a cost to get an itinerary?

No. Requesting a tailored itinerary is free and there is no obligation to book.

How far ahead should I plan my Tuscany trip?

The earlier the better, especially for peak season, but we can also help with shorter-notice trips. Tell us your dates and we will check what is possible.

Can you include flights, hotels and activities?

Yes. We can arrange stays, transport, guides and experiences, and advise on flights. Tell us what you would like us to handle.

Can I change the itinerary after I receive it?

Of course. Your itinerary is a starting point. We will adjust the pace, places and activities until you are happy.

Tuscany Tours & Trips

Dreaming of Tuscany? Tell us when you want to travel, who is coming and what you enjoy, and our travel experts will design a tailor-made itinerary for you. Hotels, transport, guides and experiences are all taken care of.

When?Travellers

Why book with TossnTrips

✓ Itineraries designed by Tuscany experts
✓ Free quote, no obligation
✓ 24/7 support while you travel

1Tell us your plans

Share your dates, group and interests in a couple of minutes.

2We design it for you

A travel expert builds a day-by-day itinerary around your trip.

3Travel with confidence

Hotels, transport and guides arranged, with support throughout.

Photos from Tuscany

Overcast day in Tuscan hills featuring cypress trees and traditional stone house. — Photo by Mehmet Turgut Kirkgoz

Panoramic view of Volterra's historic architecture and scenic landscape under a clear sky. — Photo by Maria Doina Mareggini

A panoramic view of the historic town of Pienza, Tuscany, with Renaissance architecture. — Photo by Giuseppe Di Maria

From above picturesque view of ancient town with brick buildings and green trees located on hill in sunny day in countryside — Photo by Andrea Piacquadio

Breathtaking view of rolling hills and cypress trees in Tuscany, Italy, under a clear blue sky. — Photo by YIYANG LIU

Panoramic view of vibrant green hills and bridge in Tuscany, Italy. — Photo by Duc Tinh Ngo

Capture the serene landscape of Tuscany's rolling hills in spring, featuring lush greenery. — Photo by Duc Tinh Ngo

Breathtaking aerial view of the rolling hills in Tuscany, Italy, during sunset. — Photo by Paul Scheelen

Scenic view of rolling hills and cypress trees in Tuscany, Italy during sunrise. — Photo by Duc Tinh Ngo

Sunlit Italian landscape featuring lush greenery and rustic villas among rolling hills. — Photo by Helena Jankovičová Kováčová

Itineraries Places Travel styles Who it's for By length FAQ Contact experts

Why travel to Tuscany?

Tuscany offers something for every kind of traveller, from well-known highlights such as Florence and Siena to quieter places worth discovering. A tailored itinerary lets you choose the mix that suits you.

Our team plans every detail around your dates, pace and interests, and is available 24/7 while you travel.

Popular Tuscany itineraries

Use these as inspiration. Every trip is tailor-made, so we will adjust the route, pace and hotels to suit you.

7 days

Tuscany Highlights

A well-paced week covering the best known sights, with time to explore at your own speed.

FlorenceSienaPisa

10 days

Best of Tuscany

A fuller journey that adds more places and a few local experiences along the way.

FlorenceSienaPisaSan GimignanoChianti

5 days

Florence & Siena Short Break

A shorter trip focused on Florence and Siena, ideal if you have limited time.

FlorenceSiena

12 days

Pisa to San Gimignano Journey

A longer route linking Pisa and San Gimignano, with room for off-the-beaten-path stops.

PisaSan GimignanoChiantiLucca

Most popular places in Tuscany

Florence

Siena

Pisa

San Gimignano

Chianti

Lucca

See Tuscany your way

Pick what you enjoy and we will build the trip around it.

Tuscany trips for every type of group

Tuscany itineraries by length

Tuscany trip FAQs

Contact our Tuscany travel experts

Our team has planned trips to Tuscany and knows the places worth your time. Tell us what you have in mind and we will send you a tailored itinerary, free of charge.

✓ Personal itinerary built around you
✓ Free quote, no obligation to book
✓ Support 24/7, before and during your trip

Get your tailored itinerary

Free, no obligation. Tell us a little about your trip and we will design it around you.

Where would you like to go?When are you travelling?

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What are you interested in?

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