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
1 tasting
1 cooking class
12 sightseeing tours
Expert Tour Director & local guides
Private deluxe motor coach
Included highlights
Bike ride on Lucca’s ramparts
Chianti wine tasting
Siena’s Campo
Piccolomini Library
San Gimignano walk
Maremma farm visit
Via Cava hike
Tuscan cooking class
Cortona walk
Montalcino walk
Itinerary
Overnight Flight1 night
Day 1: Travel day
Board your overnight flight to Florence today.
Lucca2 nights
Day 2: Arrival in Florence & transfer to Lucca
Included meal: Welcome dinner
Welcome to Italy! Transfer to your hotel in Lucca. Then, meet your Tour Director and fellow travelers at tonight’s welcome dinner.
We 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.
Located near Lucca's historic city wall, the Celide Hotel & Spa is only a few steps away from the major historical monuments. Guests enjoy access to a charming, in-house with an à la carte menu that specializes fish-based...
Hotel NH Siena
This elegant hotel is located in La Fortezza neighborhood of Siena. Guests enjoy free Wi-Fi, a fitness room and a restaurant. Nearby, you'll find Piazza del Campo, Fortezza Medicea, and Siena Cathedral.
Villa Acquaviva
This Tuscan style hotel is located on a wine estate in Montemarano of the Maremma region. Guests enjoy the outdoor pool, beautiful grounds, and restaurant. Nearby you’ll find the famous thermal baths of Saturnia, a golf course,...
Hotel Corsignano
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, Palazzo Piccolomini, and Piazza Pio II.
Grand Hotel Adriatico
This charming hotel is located in Florence’s city center. Guests enjoy a restaurant, courtyard, and fitness center. Nearby, you’ll find the Uffizi Galleries, Piazza del Duomo, and Ponte Vecchio.
Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.
Add our airfare and you’ll get:
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
In order to enter Italy, U.S. and Canadian citizens need a valid passport with an expiration date extending at least six months beyond the date of reentry.
We recommend having at least one blank passport page for entry stamps.
Beginning in 2026, U.S. and Canadian passport holders must register for an ETIAS travel authorization in order to enter many European countries.
Passport holders from over 60 visa-exempt countries (including the U.S. and Canada) will need to apply for an ETIAS travel authorization in order to visit 30 European countries. That means that even if you’ve previously traveled to any of these European countries without a visa, starting in 2026, you’ll need to get ETIAS authorization to visit them again. If you’re traveling to multiple countries with this requirement, you only need to complete the form once. All Go Ahead travelers are responsible for obtaining their own ETIAS travel authorization before departure. For more details, please visit our Help Center.
If you are not a U.S. or Canadian citizen, you must contact your destination country’s consulate for your specific entry requirements.
You can see the most up-to-date entry requirements for the destination(s) you’ll visit on tour by going to goaheadtours.com/entry-requirements and searching the code ATT.
You will walk for at least 2.5 hours daily across uneven terrain, including unpaved paths and cobblestone streets, with some steep hills.
Travelers should be healthy enough to participate in all included walks without assistance. Adding optional excursions may increase the total amount of walking on your tour.
You should feel comfortable managing your own baggage at times.
Go Ahead Tours and the Tour Director who accompanies your group are unable to provide special, individual mobility assistance to travelers on tour. The responsibility of the Tour Director is to ensure the group as a whole enjoys a relaxing and informative journey, and he or she cannot be relied upon to provide ongoing, individualized assistance to any one traveler.
If you have any mobility concerns or physical restrictions, please contact our Customer Experience Team.
Depending on local weather conditions, seasons and trail closures, the activities and sequence of your included walks may change.
Chianti Region – 3 miles / 1 hour. A paved and gravel path that begins with a steep incline then continues on flat ground through vineyards and farms.
Monteriggioni – 3–4 miles / 1 hour. A gravel path with some rocky areas though the woods into the open countryside with wheat fields and farms.
San Gimignano – 2–2.5 miles / 1 hour. A gravel path up a small incline for views of the surrounding countryside and town.
Maremma Villages – 5.5 miles / 4.5 hours. A long gravel pathway on flat ground from Sovana to Pitigliano.
Cortona – 1–2 miles / 1 hour. An easy, downhill walk from St. Margaret’s Church through the town.
Montepulciano – 1.5–2 hours / 1 hour. A paved road through the Tuscan countryside with a few inclines and declines.
Montalcino – 4 miles / 2–2.5 hours. A walk through the countryside on a mostly flat gravel path, with one steep downhill portion.
Round-trip flights booked through Go Ahead Tours arrive in and depart from Florence. When you first arrive, a representative from Go Ahead Tours will meet you at the airport. Please remain in the arrivals lounge, as the representative may be escorting fellow travelers to the bus at the time of your arrival.
Transfers to and from the airport at the beginning and end of the tour are included for travelers who purchased their flights through Go Ahead Tours. Travelers who booked their own flights are responsible for securing their own airport transfers.
All other included transportation on this tour is by private motor coach.
Please note that our travelers are limited to one checked bag and one carry-on bag per person due to storage limitations on motor coaches and other transfers, which may include train connections or flights.
Contact your airline(s) for baggage size and weight restrictions for your flights, which may include on-tour flights in addition to your round-trip flights to and from tour. Please note that your included on-tour flights may have more restrictive baggage limits.
Some airlines may impose additional charges if you choose to check any baggage or exceed baggage size and weight restrictions. Be advised that you are responsible for any baggage fees incurred on all flights.
Make sure you label your baggage and keep valuables, medication, and documents in your carry-on bag.
We recommend packing lightweight, loose-fitting clothing that can be easily layered to accommodate varying temperatures, as well as a light jacket or rainwear.
Light hiking boots or sturdy sneakers are recommended for the cobbled stones and uneven terrain.
You may want to consider packing a collapsible walking stick for more challenging walks.
Pack a travel water bottle to stay hydrated on hotter, sunnier days.
You may want to pack dressier attire if you plan to visit a high-end restaurant or attend a special performance.
It is preferable not to visit churches or other religious sites with bare legs and shoulders (and entrance may be denied on this basis)
At least 60 days prior to departure, check with your doctor or healthcare provider for the latest updates and entry requirements, or visit the Center for Disease Control and Prevention website at cdc.gov.
If you have medication that you take daily, be sure you have enough for each day of the tour as well as any possible delays encountered.
If you have dietary restrictions and/or food allergies please notify Go Ahead Tours at least 30 days prior to your departure by logging in to your account and updating your traveler info. To update this information closer to your departure date, please call our Customer Experience Team.
You can see the most up-to-date entry requirements for the destination(s) you’ll visit on tour by going to goaheadtours.com/entry-requirements and searching the code ATT.
Tuscany is world-famous for its wine, oil, sauces, and pasta. Menus favor subtle, lighter pastas and desserts made with nuts, fruit, and honey. Try a dish featuring the region’s Chianina beef, perhaps the most prized breed of cattle in all of Italy. For wine, popular Tuscan reds include Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano, which are primarily made from the Sangiovese grape. Well-known white wines are also made around the San Gimignano region.
For more authentic meals, try local trattorias, small restaurants set away from the main piazzas. A typical Italian meal includes wines and the occasional beer, followed by a few sips of after-dinner drinks like grappa or limoncello.
Italy operates on the European standard 220-240 volts and uses Types C, F, or L plugs with two or three small, round pins.
We recommend packing a universal adapter, as well as a voltage converter if you plan on using your own hairdryer or other device without a built-in converter.
The strength of the air conditioning in European hotels is often not as strong or as cool as what you might be used to in the U.S. or Canada. When air conditioning is available, it is usually regulated seasonally and controlled centrally by the hotel.
Your hotel may provide hairdryers, irons and other small appliances. However, these amenities cannot be guaranteed.
Wi-Fi is available in most hotels, though some charges may apply.
There is no Wi-Fi on any of the motor coaches.
Please contact your mobile service provider for information on roaming charges.
Italy is one hour ahead of Greenwich Mean Time (GMT) and six hours ahead of Eastern Time (ET).
When it’s noon in New York, it’s 6pm on tour.
You will use the euro on this tour.
Better rates of exchange are usually available overseas, although it’s worth ordering some currency from your local bank to use when you first arrive.
We strongly advise that you take debit/bank cards and credit cards, which can be used to withdraw cash at local banks as needed.
You can use most debit/credit cards at ATMs on the international networks Cirrus and Plus, but make sure to check with your home bank about withdrawal fees.
Inform your bank and credit card company of your travel plans so that they won’t confuse your international purchases for fraudulent charges.
International banks and businesses primarily accept debit and credit cards that work with the EMV chip system. If you do not already have at least one debit or credit card with a chip in it, we strongly recommend requesting one from your bank prior to your tour.
At the conclusion of your tour, it is customary to offer your Tour Director and driver a gratuity in local currency. Please keep current exchange rates in mind.
We recommend tipping the equivalent of $10USD to $12USD per person per day for your Tour Director and the equivalent of $4USD per person per day for your driver.
If applicable, we also recommend the equivalent of $2USD per local guide.
Tips can only be paid in cash.
If you are traveling to multiple countries with different currencies and the same Tour Director, ask them what currency they prefer for their tip.
The cost of porterage is included in your tour price, and it is not necessary to tip baggage handlers.
Most optional excursions will be available for purchase while you are on tour.
Your Tour Director will only accept cash (in USD only), Visa or MasterCard as payment for optional excursions.
Please be advised that if you pay for an excursion by credit card while on tour, it may take up to three months for your card to be charged.
Some optional excursions may only be purchased in advance. See page four of your tour itinerary for more information.
Beautiful tour through the countryside of Tuscany. The tour exceeded our expectations! We had 11 people in our group which was the perfect size. Wide range of experiences from cooking class, staying at an agritursmo, riding bikes around the village of Lucca and ending our...
Lovely Tuscany
5 out of 5 stars
5th-time traveler Ann, traveled in Oct 2024
I returned home from the Go Ahead tour of Tuscany last week- and fortunately I have probably hundreds of photos of lovely places and beautiful scenery to make sure I have many memories down the road. I enjoyed the trip immensely. We were fortunate to have great weather for our...
EF Go Ahead
Thank you for sharing your experience on our Tuscany tour! It sounds like it was a wonderful journey filled with beautiful scenery,...
Fantastic tour
5 out of 5 stars
1st-time traveler Jane, traveled in Oct 2024
This tour covers so many towns in Tuscany. The group size is small so you get to know everyone on it and makes it easier to cover so much area. The tour guide Barbara was very friendly and informative about the whole area. This tour was a great experience. So happy I did it.
Go Ahead Tours
Hi Jane,
Thank you for sharing your experience! It’s wonderful to hear how much you enjoyed exploring Tuscany and that the small group size...
Great Tour that exceeded our expectations
5 out of 5 stars
2nd-time traveler Barry, traveled in Sep 2024
This is the 2nd GoAhead tour my wife and I have taken and like the first one, it exceeded our expectations. Mary, our tour guide, was very knowledgeable, caring, and accommodating, and just an absolute sweetheart. The overall tour was great and it was made even more enjoyable by...
EF Go Ahead
Thank you so much for sharing your experience with us! We are thrilled to hear that your second Go Ahead tour exceeded your expectations,...
Positive on Tuscany
5 out of 5 stars
2nd-time traveler Paul, traveled in May 2024
This is an exceptional tour. The sites selected, the hotels ( except the one on Siena), were comfortable and inviting. The Siena hotel had some issues. The tour guide, Barbara, was outstanding. She made the trip more enjoyable by her knowledge, attitude, and support. I fully...
EF Go Ahead Tours
It's fantastic to hear that you found the tour of Tuscany wonderful! We regret to hear about the issues with the hotel in Siena. Your...
