Under the Tuscan Sun: An Italian Escape
May 15-23, 2027
$4250 per person
Under The Tuscan Sun: An Italian Escape
Escape to the golden hills of southern Tuscany for a week you’ll never forget!
Under the Tuscan Sun: An Italian Escape, is a hosted small-group journey for 12 travelers. This trip is ideal for friends, couples, and food and wine lovers who want to experience the real Tuscany without the stress of planning it.
We’ll spend seven nights in a private villa with a pool. We will indulge in several dinners prepared for us by a private chef.
You can also look forward to a truffle hunt and a long castle lunch, a Brunello tasting at the source, e-bike rides through sleepy villages, a hands-on cooking class in Montepulciano, and wandering the hilltop streets of Cortona and San Gimignano.
Between the adventures, there’s plenty of time for pool days, slow breakfasts, and wine with your favorite people. You’ll feel relaxed, spoiled, and completely taken care of, with a camera roll full of memories and stories you’ll tell for years!
Traveling with Great Circle Travel means every detail is arranged for you, from the private Mercedes Sprinter transportation to the carefully chosen experiences. Your on tour hostess will be with you all week, so all you have to do is show up and savor every minute!
What Makes This Trip Different
Trusted Local Experts
We’ve teamed up with the best of Tuscany, including a private villa chef, welcoming family wineries, and passionate guides who know every hidden corner. You get the real Italy, from people who love sharing it!Thoughtfully Curated Experience
From the private villa and your own Sprinter vans to the truffle hunt and the cooking class, every detail has been designed with care. Each day flows easily, so you never have to wonder what’s next.Your Great Circle Travel Hostess
Your on tour hostess from Great Circle Travel is with you all week. She handles the details, answers every question, and shares in the fun right alongside you. She has spent much time in this area and knows it intimately.Relaxed Travel Without the Stress
We want you fully present. Private transportation, train travel, breakfast, and wine at the villa are all taken care of, so you can focus on the golden hills, the great food, and the people you love.
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Welcome to the Villa
Fly into Rome or Florence, then hop on the train to Arezzo. Your driver meets you there and takes you to the villa. Settle in, pour a glass of wine, and let your private chef welcome you with dinner!
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A castle lunch and truffle hunt
Head into the Tuscan woods to hunt for truffles, then settle in for a long Tuscan lunch at a castle. Bring your camera!
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Brunello country and Pienza
Visit a Brunello winery for a tasting experience and a Tuscan lunch. Explore the hilltop town of Montalcino, then drive to Pienza to wander its Renaissance streets.
Dinner is on your own in Pienza.
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E-bikes, village lunch, and pool time
Ride e-bikes from the villa to the surrounding villages, with lunch in one of them. Spend the afternoon at the villa and the pool.
**Optional: Vintage Fiat 500 Convoy through the region. Manual drive only.
Your private chef cooks dinner at the villa tonight!
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A cooking class in Montepulciano
Roll up your sleeves for a hands-on Tuscan cooking class. Then spend the afternoon and evening exploring Montepulciano, and be sure to peek into the famous wine cellar.
Dinner is on your own in town.
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Lunch and wine at a family estate: San Gimignano
Enjoy a Tuscan lunch and wine experience at a working family estate. Then head to San Gimignano, the town of medieval towers, for the afternoon, evening, and dinner on your own.
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Cortona and a final chef dinner
Spend the whole day in Cortona with a guided tour of the town. Lunch is on your own, so wander and pick a favorite spot.
Back at the villa, your private chef cooks one last dinner for the group!
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Arrivederci, Toscana
Your driver takes you to Arezzo, and then you ride the train to Rome airport (FCO). Rest up with a night at an airport hotel.
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Fly home with a phone full of photos and a heart full of Tuscany!
General
Itinerary
Final itinerary subject to minor adjustments.
Pricing & Inclusions
✔️ What’s Included
7 nights at private Tuscan Villa with pool
1 night in 4 star airport hotel near FCO
Arrival night welcome dinner prepared by private chef
Private transportation from train station to villa
Continental breakfast in the villa
Snacks and wine in the villa
Private transportation with Mercedes Sprinter vans throughout the trip
Experienced and passionate local guides and winery hosts
Instructions and assistance with logistics
Tourist tax where applicable
1 planned experience each day, as noted in itinerary
Farewell dinner prepared by private chef
Private transportation to the train station
2 meals per day provided as noted in the itinerary
Your very own Great Circle Travel Director
🚫 What’s Not Included
International airfare
Arrival airport transfers
Everything not mentioned in the included services
1 meal per day
Optional Fiat 500 Experience
Travel insurance - Travel insurance with emergency medical and evacuation coverage is strongly recommended.
Payment Schedule
Non-refundable deposit of $250 is required to secure your reservation
A second payment of $2000 is due January 14, 2027
The final payment of $2000 is due March 14, 2027
Cancellation Policy
Non-refundable deposit of $250
After March 14, 2027, all payments become non-refundable
Important Trip Information
Activity level
This trip is relaxed but active. Expect walking on cobblestones and hills in hilltop towns, plus an e-bike ride through the countryside. Please tell us ahead of time about any mobility concerns so we can plan for you.
Weather and flexibility
Mid-May is a lovely time in Tuscany, but weather can change. Experiences may be adjusted by season, weather, or availability, and your hostess will make sure the day stays wonderful.
Passports and entry requirements
You’ll need a passport valid for 6 months beyond our travel dates. Entry rules change, so please check current requirements for your country before you go.
Travel protection
We highly recommend travel protection to cover trip changes, illness, and the unexpected.
Join us in Tuscany
May 15-23, 2026
$4250 per person
FAQs
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Yes, though this particular trip is designed for double occupancy. Talk to your GCT Travel Director for more information. We will let you know about a single occupancy supplement that will change your per person cost.
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There is space for 12 travelers.
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Flying into Florence (FLR,) Rome (FCO,) and Milan (MSP) are the easiest.
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While not required, travel insurance is strongly recommended.
We highly encourage travelers to purchase coverage that includes:
Trip cancellation/interruption
Emergency medical coverage
Emergency evacuation coverage
Protecting your investment and your health while traveling internationally is important.
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Don’t worry - we will send plenty of packing tips and a detailed packing list closer to the trip so that you’ll know exactly what to bring (and what to leave at home.)
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Contact your GCT Travel Director,