Feel good about booking your tour today. Enroll in AutoPay or pay in full when you book and if you change your mind, you have 60 days to receive a full refund of your payment.
Amble through ancient towns in the heart of Tuscany.
It doesn’t get much better than a Tuscan to-do list: Bike along cypress-lined city walls, take leisurely strolls through hilltop towns, and cap each meal off with a glass of Chianti. On this small group Adventure Tour in the heart of Italy, you’ll find yourself eager to say “check, check, and check” as you discover hidden corners of Tuscany (like Maremma!) where time seems to stand still.
Your tour package includes
- 10 nights in handpicked hotels
- 10 breakfasts
- 2 lunches
- 3 dinners with beer or wine
- 1 wine tasting
- Bike ride on Lucca’s ramparts
- Chianti wine tasting
- Siena’s Campo
- Piccolomini Library
- San Gimignano walk
An expert specializing in tours of this region is here to help.
Day-by-day itineraryPrint itinerary
We make it easy with down payments as low as $99, fee-free booking, and more
4.8 star rating
Overall rating 4.8 out of 5
5.0 star rating
Our tour guide Barbara was the BEST! She went over and above to make sure we had a great trip. She provided tons of wonderful information about the region and each stop along the tour. Our bus driver Luca was an expert at navigating the narrow and curvy country roads. The small group tour worked ...
4.0 star rating
Very enjoyable tour Barberra was great. My only feedback would be for you ach location provide written highlights and ideas for free time. Also I think more time in cities versus hikes but that is my preference. Time visits for when ships are open and get group to follow Italian eating timeframes...
5.0 star rating
Book now for this phenomenal tour. Hopefully you will have Barbara as your guide & Luca as your driver. I did meet several people returning home to America that said they have taken every Go Ahead Tour available all over the world, so I do not believe my experience was a fluke. Do be truthful a...
Hotels, flights & FAQHere's the nitty-gritty—where you’ll stay, how you’ll get there, and what to know about your destination before you go.
HotelsWe handpick every hotel to strike the balance of comfort, location, and local charm. Specific accommodations will vary based on your departure date, but these are frequently used hotels for this tour and we're confident you'll be satisfied.
This modern hotel is located in the historical center of Lucca. Guests enjoy a terrace, lounge bar and complimentary bikes. Nearby you’ll find the Luc...
This charming hotel is located near the city center of Siena. Guests enjoy a pool, restaurant, and bar and lounge. Nearby, you’ll find 18th-century ga...
This Tuscan style hotel is located on a wine estate in Montemarano of the Maremma region. Guests enjoy the outdoor pool, beautiful grounds, and restau...
This comfortable hotel is located in the heart of Pienza. Guests enjoy a bar, relaxation room, and free Wi-Fi. Nearby, you’ll find the Pienza Duomo, P...
This charming hotel is located near the Santa Maria Novella train station in Florence. Guests enjoy free Wi-Fi and a restaurant. Nearby, you’ll find t...
- Round-trip flight for your tour
- Airport transfers at your destination
- A great price locked in today
- 24/7 support from our dedicated service team
- Options for arriving early, staying longer, or requesting an upgrade
- Flexible rebooking options if your tour itinerary changes
- Find out more about flights