Wine & Bliss In Tuscany
SMALL GROUP TOURS
Destination: Italy • Duration: 8 days / 7 nights • Dates: Oct 3 - 10, 2026 • Destination: Italy • Duration: 8 days / 7 nights • Dates: Oct 3 - 10, 2026 • Destination: Italy • Duration: 8 days / 7 nights
Destination: Italy
Dates: Oct 3 - 10, 2026
Duration: 8 days / 7 nights
DAY 1
SATURDAY, OCT 3, 2026
Arrive Florence And Transfer To San Gimignano
Arrive Tuscany. You can fly into Florence or Pisa. Your driver will wait for you at the airport (or train station if you are arriving Florence by train) and enjoy the pleasant ride through the countryside to our hotel in San Gimignano. Upon arrival, settle in your room and relax. If time permits, you can relax at the hotel Spa facilities and indoor pools. In the later afternoon hours, meet your host in the lobby for a welcome drink and head out together to a nearby family-owned winery with a tradition of over 300 years. Here, enjoy a wonderful wine tasting – paired with the most amazing Tuscan dishes. It will be a fun beginning of our adventure discovering Tuscany, its wines, and flavors. Later, transfer back to our hotel.
DAY 2
SUNDAY, OCT 4, 2026
Siena / San Gimignano
In the later morning hours, it will be time to board our mini coach and enjoy the scenic drive to Siena where we’ll meet our licensed local guide at the gates and start our amazing tour of Siena’s UNESCO protected historical center. We’ll be walking through the cobbled stone streets, visiting the the squares and learn of the interesting history and life in Siena. After the tour, you’ll enjoy some free time to explore the town on own or to do some shopping, Then, we’ll gather again and head to a local taverna to enjoy a delicious lunch paired with amazing local wines. In the afternoon, we head back to San Gimignano and enjoy a walk around the town, exploring the picturesque streets and mighty towers. Free time to grab a gelato from one of the best gelaterie in the world, and / or sit down for drinks or coffee. Our driver will take us back to our hotel later on. If you wish to stay in town longer, it will be easy to get back to the hotel by taxi; it’s just a 10-minute drive. Enjoy your evening at leisure.
DAY 3
MONDAY, OCT 5, 2026
Montalcino - Pienza & Montepulciano
This morning we will head south to visit 3 amazing towns, taste local wines, and have an amazing time! First, we’ll head to Montalcino, a town known for its unique sort of wine, called Brunello. Enjoy a short walk in Montalcino, to see the town, before heading to a local winery to indulge in a wine tasting with a light lunch. Taste the amazing local Brunello wines. Then, head to Pienza, a picturesque Tuscan town known for pecorino cheese. Have some free time to explore on your own, taste pecorino or sit down for a coffee. Continue to Montepulciano, a town famous for its very special wine: Vino Nobile di Montepulciano. First, explore the town, and the amazing views, then we will sit at a local Enoteca, and enjoy an early dinner followed by wine tasting of amazing local wines and grappa. Return transfer to our hotel in San Gimignano in the evening.
DAY 4
Today we bid farewell to San Gimignano and this part of Tuscany while we head east to see and experience more of it! Enjoy the panoramic drive to Pisa. Upon arrival, meet our local licensed guide and enjoy a tour of Campo dei Miracoli. While here, also enjoy and have fun climbing the leaning tower. After the visit, some free time to buy a souvenir and to take some pictures before we head to Lucca, yet another amazing Tuscan town to discover. We will have lunch, cheese and wine tasting at a local restaurant.
In the afternoon hours check into our lovely hotel in Florence. Get settled, relax, and later we may meet and go out for dinner and drinks!
TUESDAY, OCT 6, 2026
San Gimignano - Pisa - Lucca - Florence
DAY 5
Enjoy a slow morning. Sleep in, or explore Florence on your own. In the afternoon, we’ll gather at the lobby to meet our local guide and enjoy a tour of Florence. Get to know all the main city areas while learning of its fascinating history, art, and renaissance. As part of this tour, we will also visit the Accademia Gallery, home to Michelangelo’s David. We will continue with this amazing tour of Florence from the rooftops! Our guide will take us to visit amazing rooftop bars where we’ll enjoy the views as well as some Aperitivo and some amazing Tuscan wines. It will be an evening to remember!
WEDNESDAY, OCT 7, 2026
Florence
DAY 6
THURSDAY, OCT 8, 2026
Florence
Today we’ll have so much fun in Florence! First, we’ll walk to the central market where we’ll meet our chef. We’ll watch him (and assist) picking and buying the ingredients for today’s lunch. Then, we’ll walk together to their nearby location where we’ll cook an amazing 3-course meal from scratch. Of course, we’ll sit down to enjoy the dishes we cookd with a glass of delicious local wine. This experience ends around 3 PM, so you have the whole afternoon to enjoy Florence on your own! If you’re up for a walk, join your host and head all the way up to Piazzale Michelangelo for amazing views of the town.
DAY 7
Today is the last day of this tour. The day is yours to explore Florence on your own! Walk along the river, explore the leather shops, sample some of the sweets from the bakeries, sit down for coffe and enjoy the atmosphere. A day at leisure in Florence is always a good idea!
Or, at a supplement of $690 - enjoy an exciting hot air balloon tour over the Tuscan hills! Departure from the hotel will be early in the morning, and we’ll transfer to the outskirts of the city to meet our expert hot air balloon pilot for a short safety briefing. Then we will board our basket, and silently fly above the most beautiful area of Tuscany, up on the height of 900 to 3.000 feet for approximately 1 hour. During the flight our expert guide will be also telling us about this exceptional area. At the end of your flight, the hot air balloon staff will welcome us back with a glass of local red Chianti, then we will head back to our hotel. The duration of this tour is up to 5 hours. Minimum of 6 guests is necessary to organize this tour.
Or, at a supplement of $180 per person – enjoy a morning tour of the Uffizi Gallery and the interior of the Duomo with a licensed local guide. The duration of this tour is up to 4 hours, Minimum of 4 guests is necessary to organize this tour.
In the afternoon hours, we’ll gather one last time, and head just a bit out of Florence to visit another amazing estate, where we will have fun tasting some of the amazing dishes such as Bistecca Fiorentina and other specialties in a fusion of traditional and modern fine dining. Of course, we will also taste their amazing wines of the house.
FRIDAY, OCT 9 2026
Florence
DAY 8
A driver will pick you up in the morning and transfer to the airport (or train station).
SATURDAY, OCT 10 2026
Departure Italy
What's Included
Accommodation at listed hotel with breakfast daily, based on double occupancy rooms, with the option for single use at a supplement
Arrival transfer from Florence airport or Florence train station to the hotel in San Gimignano organized according to your individual arrival time
Departure transfer from hotel in Florence, to Florence airport or train station organized according to your individual arrival time
Lunch with wine tasting at a local restaurant in Siena
Half day walking tour of Florence with an expert local guide, as per program with priority entrance to the Accademia Gallery Museum
Rooftop Sunset tour of Florence with aperitivo and wine tasting
Market tour and cooking class with lunch in Florence
Farewell dinner at a surprise Estate right outside of Florence, drinks included
All tours as per program performed with a modern, AC, mini-coach
The tour is hosted by a professional Vagabonda tour director
Welcome dinner and wine tasting at a local family-owned winery in San Gimignano
Full day tour of Siena and San Gimignano as per program with an expert local guide in Siena
Full day tour to Montalcino, Pienza and Montepulciano with Brunello wine tasting and lunch at a local winery in Montalcino, and dinner and wine tasting in Montepulciano.
Full day tour to Pisa and Lucca as per program with lunch, cheese and wine tasting. Expert local guide for the tour of Campo dei Miracoli and entrance to the leaning tower
Visas, visa waivers, passport, and/or departure taxes
Airfare: international and local
Meals, drinks and other items not listed above
Expenses of personal nature, including tips to guides and drivers, telephone calls, table drinks, internet, laundry, etc.
Travel insurance – highly recommended! Check out World Nomads.
Single room supplement
Not Included
Hot air ballon flight above Tuscany experience, per person: $690 /Minimum of 6 guests is necessary to organize this experience/
Florence tour: Duomo and Uffizi Gallery, per person: $180 / Minimum of 4 guests is necessary to organize this tour
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Optional
Happy Clients
- The Coscia-Mancuso Family, White Plains, NY
We cannot thank Vagabonda Travel enough for custom-designing our family trip to Italy. Memories to last a lifetime. Every detail of our trip was perfectly curated and exceptional. We would have never been able to plan this adventure on our own. Communication with the staff is excellent and we felt secure knowing we had contact number while we were traveling. Cannot wait to book our next trip with you soon!
Trip of a lifetime.
Happy Clients
- Megan and Jerry, Los Angeles, California
We have never used a travel service before, and Vagabonda absolutely blew us away! From their hotel bookings, to the day-by-day itinerary, to hidden gems we definitely would have never found on our own, we can't thank their team enough! Highly recommend for anyone who wants an authentic experience in Europe!
BEST TRIP EVER! We'll remember this for the rest of our lives!
Happy Clients
- Pete and Paula, Lindenhurst, New York
When my husband and I started planning our 30th Anniversary trip to Italy we had no idea where to even begin. That’s when I stumbled across Alida’s TikTok videos. I absolutely LOVED her content. To be honest, at first I was skeptical about planning a trip like this off of someone I saw in a TikTok video, but after meeting with her we knew we picked the right travel agency. Our 17-day trip was absolutely incredible. Alida and Vagabonda Travel made our lifetime dream of touring Italy one we will never forget!
Happy 30th Anniversary to Us! A TRIP OF A LIFETIME!
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Vagabonda's European small group tours are led by our professional hosts. We're dedicated to making sure that every moment of your trip counts. We believe in taking it slow and connecting with locals as we uncover amazing experiences in unforgettable destinations. Travel should be more than just a vacation - it should be an experience that touches your heart and deepens your relationship with the world.
Pricing
Price Per Person In
Double Occupancy Rooms
$1160
Single Room Supplement
