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Countryside, Castles, and Wine – OH MY! 7 or 9 Day Drool Worthy Tuscany Itinerary

Countryside, Castles, and Wine – OH MY!

7 or 9 Day Drool Worthy Tuscany Itinerary

Ready to make your friends want to smack you upside the head?  They’ll think that recent email you received from a Nigerian prince promising you riches wasn’t actually a scam and  allowed you to fund this drool worthy trip.  You could easily spend $5000+ on a one week inclusive trip to Tuscany with wine tours, cooking classes, riding vintage Vespa’s through the eye popping countryside, but this itinerary will show you how to sleep in ancient castles, sip and stroll your way thru vineyards, and gorge your soul on movie worthy scenery without breaking the bank.  In fact, the whole trip for flight from USA, hotel, and car was less than $1500 per person for 9 Days!! (food, drink, and souvenirs are not included as let’s face it, some of us can shop, eat and DRINK more than others…I’m not going to name names here 😀…Charles)

WHERE:   Tuscany Regions of Lucca, Pisa, Arezzo, Firenze, Siena, and parts of Umbria

tuscany map

You may have the universe if I may have Italy. – Giuseppe Verdi

WHY:   Jaw Dropping Views, Drool Worthy Castles, Startling Sunsets, Mouthwatering Vittles, and did I mention WINE!  Oh yes, and MORE WINE!  If these photos don’t convince you, nothing will.

WHEN TO GO:   We recommend trying to see Tuscany in the shoulder season to save some money and avoid it being overcrowded with tourists.  (March- May, September- November)

BUDGET:   This itinerary is targeted for mid-budget travelers who want to stay in luxurious, unique, and envy evoking accommodations without breaking the bank.  Hotels were chosen based on views, uniqueness, service, and parking.  Hotels averaged $150 a night in May, 2017 (subject to change)


  • AIRPORT:  We flew into Pisa but Florence or Bologna also would work, even Milan and Rome are not too far away.  Our Recommendation for finding the best flights  is Google Flights. We paid $587 from Dallas to Pisa using this tool.  Airport codes for searches (Pisa: (PSA), Florence (FCR), Bologna (BLQ), Milan (MXP), Rome (FCO).  To see how to get great deals on flight, See our article on our Top Tips to save money when traveling. 
  • INTERNAL TRANSPORTATION:  We recommend renting a car.  (it’s easy to drive in Italy and many of our recommendations would be very hard if not impossible to reach by public transport.  We were able to book an compact car via Hertz for 9 days for $186.00)   We tried to keep drive time between locales less than 2 hours, most around 1 hour.  It’s ideal if you can drive a standard (stick shift) as automatic cars are available in Europe but much more expensive.  We also recommend opting for the smallest car possible in Europe even if offered an upgrade as some roads are small and parking even smaller.

NOTES:   Florence is not included on this itinerary intentionally.   We tried to focus on smaller towns and areas that evoke “classic” Tuscany imagery.   Florence is fabulous and if you have the time would be an easy add on.


Day Location of Lodging Where to Stay  Price USD
1 Lucca, Tuscany Lucca in Azzurro Maison de Charme  $108.01
2 Mercatale Val Di Pesa, Tuscany Castello Di Gabbiano  $193.00
3-5 Cortona, Tuscany (-1 day Optional) Villa di Piazzano Residenza d’Epoca $488.46
6-7 Pienza, Tuscany Agriturismo Il Macchione $301.00
8 Orvieto, Umbria (Optional) Hotel La Badia di Orvieto  $130.08
9 San Gimignano, Tuscany Casanova di Pescille  $129.81
Average Cost Per Night $150.04


  • Where to Stay:  Lucca in Azzurro Maison de Charme
  • Drive Time From Pisa Airport:  29 minutes, 35.0 km
  • Where to Eat:  Da Giulio $$
    • Type of Food:  Traditional Italian
    • Why:  Great food where locals eat.  Fresh and authentic.  Cozy, Family Owned
    • Recommended Dishes:  Chicken and Rabbit
  • What to See
    • Visit Pisa for the Tower but stay here- not nearly as overrun with tourists.  Beautiful small wall towned, with interest shops, churches and narrow walkways.   If you have time visit the near by stunning gardens at Villa Reale di Marlia.
  • What to Buy
    • Cheese (special cheese rolled in hay, pepper, and herbs.)  Wine.  Gourmet Sauces.  Ask and they will vacuum pack your cheese to make it easy to bring back home.
  • Drive Time to Next Location  :  57 minutes, 90.4 km
Lucca Italy Lucca Italy
Lucca Italy WIne Lucca Italy WIne
Lucca Italy Art Lucca Italy Art


  • Where to Stay:  Lucca in Azzurro Maison de Charme
  • Where to Eat:  Il Cavaliere $$$
    • Type of Food:  Tuscan
    • Why: Everything is great. On Castle grounds
    • Recommended Dishes: Everything
  • What to See/ Do
    • Just spending time roaming around the expansive grounds with 360 degree views of the Tuscan country side and vineyards was enough to convenience me not to leave.  The castle built in 1124 had a wonderful art opening when we stayed and offered free appetizers and wine.  If you stay at the Castle, they will allow you down stairs in the cellars for a tasting and take you around their vineyards for a private tour of all the various type of grapes they can grow.  Take a drive around the area to see the beautiful scenery and quaint towns.
  • What to Buy
    • Wine, wine and more wine- it will make you rethink Chianti!!  Try the Castello’s own vintages!   They also make their own olive oil.
  • Drive Time to Next Location  : 1 hr 23 m; 110.6 km

DAY 3-5: CORTONA, TUSCANY (Less one day optional)

  • Where to Stay:  Villa di Piazzano Residenza d’Epoca
    • Why: Beautiful restored villa with wonderful views, breakfast, and some of the best service I’ve ever experienced.   They have a great bar and even do local cheese tastings.  Easy Free Parking.
    • Book Hotel Here
    • Cost:  $162.82 per night
    • Other Cortona Hotel Options
  •  What to See/ Do
    • Cooking Class – One of my favorite all time experiences.  Chef Ryan Hanley brings you to his house teaches you about Tuscan culture over 7 hours while you cook a 12 course meal.  All ingredients are local, many from his garden.  Delight in cooking steaks in his fireplace, eating prosciutto cured by his neighbor, and being treated like a new family member by his wife and family.   Don’t miss this one!  Worth the splurge $100 per person
    • Wine Tour– you can spend big bucks taking a guided wine tour or you can venture out and do it yourself with a little homework.   We saved the $300 per person that these tours cost and did our own versions for less than $50 for both of us.   I did not want to visit a huge producer with no personality.  I wanted to visit a small producer who was passionate about wine and the wine making process.  Boy did with find the right place.  Meet Denis who owns and produces some amazing wines right outside Cortona at Leuta Vineyards.    You won’t just run into this vineyard.  You have to know it’s here and you won’t regret making an appointment.   Denis Zeni has traveled the globe studying wine, the process, and has implemented some really innovated ideas that are bound to impress you.  His life story is as amazing as his wine.
    • Castiglione del Lago– sadly missed by many Cortona visitors, this hillside village overlooking Lake Trasimeno is about 30 minutes outside of Cortona, and is well worth the visit.   It has a pentagon shaped castle (Fortress of the Lion) built in 1247 that has an amazing museum, the longest enclosed walkway I’ve ever seen and some jaw dropping views over the lake.  The little town is easily walkable, has great deals on sausage and olive wood goodies, and has some amazing little eateries.
    • Other activities:  Truffle hunting (in season Oct – Feb) if off season you can visit the Truffle store and museum. Stay at the “Under the Tuscan Sun” house, visiting the largest chocolate maker in Italy (Perguia).   Drive to Città di Castello
  • What to Buy
    • Italian Sausage, Wine, Carved Olive Wood
  • Drive Time to Next Location  : 53 minutes, 44.4km

DAY 6-7: PIENZA, TUSCANY (side trip Montepulciano)

  • Where to Stay:  Agriturismo Il Macchione
    • Why: Family run historic restored villa with suite/ full apartment type rooms with views  that will make your jaw drop.  Great Breakfast, service and honor bar.  Full kitchens in room.  This is the quintessential idea of what a Tuscan villa should be with views over the Val D’Orcia.  Easy Free Parking.  Only a few rooms that many guests return to each year, so book early.
    • Book Hotel Here
    • Cost:  $150.50 per night
    • Other Pienza Hotel Options
  •  What to See/ Do
    • Drive Val D’Orcia:  This is the classic Tuscan picture that you’ve seen in magazine.  This valley is truly breathtaking.  Pack a picnic, jump in your car, and get lost exploring the hills and small villages.
    • Market Days:  Many towns and villages still have market days, where locals come to buy fresh food and other goods.   Try being a local for the day and seeing how and what they buy.  You’ll get the best deals on vittles for your picnic basket and have fun trying to negotiate the price in Italian.
    • Cheese Tastings in Pienza:  This town is famous for cheese.  Stop by and do a full cheese and wine tasting.
    • Montepulciano.  You can’t miss this charming town with the famous wine.   Explore the cellars built deep under the town in the mountain.   Every corner has some interesting find here.  Scenes from the Twlight movie “New Moon” were filmed here.    Try Wine tasting at  Cantina Ercolani, Cantina Fattoria della Talosa and Icario
    • No trip would be complete with out bath time.  Try the Thermal Springs in Bagno Vignoni
    • Hidden Gem:  Monteverdi Tuscany, Castiglioncello del Trinoro.   This place is amazing and you won’t find it in a guide book.  The secret little town looks like it’s a place that famous stars would vacation where no one would ever bother them. Sitting on a hilltop, the whole town is basically one hotel with restaurant/ bar.  Wander around, have a glass of Champagne, enjoy the view, and see the Etruscan ruins.
    • We accidently ran into this charming villa that presses it’s own Olive Oil which you can taste, drop by Chiarentana
    • Other Activities:  Ride bikes or Vintage Vespas through countryside.  Book early.  We missed it by not booking ahead.
  • What to Buy
    • Pecorino Cheese and of course, WINE!  Ask and they will vacuum pack your cheese to make it easy to bring back home.
  • Drive Time to Next Location  : 1hr, 16 min, 78.4 km



  • Where to Stay:  Hotel La Badia di Orvieto
    • Why: Restored 6th Century Abbey has charm in spades.  Leave time to wander the property and see the historic church and grounds.  Beautiful views of Orvieto up on the hill.  Easy Free Parking and great breakfast.  Restaurant on site.
    • Book Hotel Here
    • Cost:  $130.08
    • Other Orvieto Hotel Options
  •  What to See/ Do
    • The quaint town of Orvieto still on a volcanic tuff.  Don’t miss the Cathedral, famous St. Patrick’s well going down 496 steps and Etruscan ruins.  Rick Steves has a good guide
    • Orvieto Cathedral- Jaw dropping Cathedral gives Siena a run for it’s money.  We loved the layered white and black stone and sketch worthy mosaics.
    • Civita di Bagroregio– Get ready for your jaw to drop to the floor with this little gem!   About 41 minute drive fro Orvieto, this Etruscan founded town sits on a volcanic plateau sitting over a river.  The location itself looks like something made for movie sets.   Get ready to do a little walking as there are no cars allowed in town and it’s a bit of hike getting there but SO worth it.   You’ll thank me later!
  •  Drive Time to Next Location  : 2 hr, 4 min; 167.7 km



  • Where to Stay:  Casanova di Pescille
    • Why: Family restored villa/ farm overlooking the many towers of San Gimignano.  They also produce their own wine offered in honor bar, have drool worthy restaurant, and the views are non-stop.
    • Book Hotel Here
    • Cost:  $129.81
    • Other San Gimignano Hotel Options
  • Where to Eat: Zafferano by Casanova di Pescille $$
    • Type of Food: Italian, Mediterranean
    • Why: Everything is great and made by family, much is grown on the family farm. On grounds & even offer cooking classes.
    • Recommended Dishes: Everything
  • What to See/ Do
    • After a leisurely breakfast and walk about the grounds at our beautiful hotel in Orvieto, we headed to Siena 1 h 34 min (123.1 km)
    • Siena, the gem of Tuscany, is a site to behold.  Get tickets to the cathedral when you first arrive to get tickets as you buy tickets for a specific time that is available and you don’t want to miss out getting a slot
    • San Gimignano:  A world heritage walled city famed for it’s unforgettable skyline with 12 towers.
    • After 9 action packed days, we spent some time at the beautiful hotel, opened a bottle of wine and were in bliss just watching San Gimignano in the distance.
  •  Drive Time to Airport (Pisa):  1 hr, 17 min, 75km
Siena Plaza

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7 or 9 Day Tuscany Itinerary

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