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Italy, Tuscan countryside, Val D'Orcia, UNESCO Natural area
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Wine & Bliss In Tuscany


Destination: Croatia • Duration: 13 days / 12 nights • Dates: April 13-20, 2024 • Destination: Italy • Duration: 8 days / 7 nights • Dates: April 13-20, 2024 • Destination: Italy • Duration: 8 days / 7 nights • Dates: April 13-20, 2024

Destination: Italy

Dates: April 13 - 20, 2024

Duration: 8 days / 7 nights

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 Terry 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.

Hotel: Villa San Paolo Hotel and Spa 4*

Arrive Florence And Transfer To 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. Then, we’ll enjoy discovering the beautiful cathedral and admire the fascinating marble work of the interior. 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.

Hotel: Villa San Paolo Hotel and Spa 4*

Siena / San Gimignano


SUNDAY, APRIL 14, 2024

View of the Cathedral of Siena, in Tuscany, Italy


Today is a day to enjoy the Tuscan countryside to the fullest!

First, early in the morning, an optional activity – just for the brave and adventurous, we will head to the outskirts of Siena and board our fabulous hot air balloon and fly above Tuscany! It will be an unforgettable experience! The Supplement per person: $650, and a minimum 6 guests is necessary to organize this experience.

If you stay at the hotel, enjoy yourself, relax, sleep in, go to the spa or take a walk in town.

In the late morning hours, our driver will take us to a beautiful location where we will enjoy a Tuscan cooking class and learn how to make fresh pasta from scratch! After the cooking is done, sit down to enjoy the the meal with a glass of local wine. It will be a fun and relaxing day. The evening is free for everyone to take some time to rest and relax.

Hotel: Villa San Paolo Hotel and Spa 4*


San Gimignano / Siena


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!

Hotel: Hotel Degli Orafi 4*


Siena - Pisa - Lucca - Florence


In the morning 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. Visit the central Market and taste some of the local specialties, before visiting the Accademia Gallery, home to Michelangelo’s David. After the tour, enjoy Florence on your own! Explore the town, walk along the river, or all the way up to Piazzale Michelangelo for amazing views of the town. Let’s meet in the evening for drinks and a fun time!

Hotels: Hotel Degli Orafi 4*



Hot air balloon above Tuscany with Vagabonda Travel


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 $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.

Hotel: Hotel Degli Orafi 4*

FRIDAY, APRIL 19, 2024



A driver will pick you up in the morning and transfer to the airport (or train station).


Departure Italy


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.

Hotel: Villa San Paolo Hotel and Spa 4*

MONDAY, APRIL 15, 2024

Montalcino - Pienza & Montepulciano

Ponte Vecchio - the Old Bridge over the Arno River in Florence, Italy


Price Per Person In

Double Occupancy Rooms


Single Supplement


Request To Book

Vagabonda Travel’s light purple decorative pattern.

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

Tour is hosted by our Vagabonda Travel host Terry Abromitis

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

Half day walking tour of Florence with an expert local guide, as per program with priority entrance to the Accademia Gallery Museum

Farewell dinner at a surprise Estate right outside of Florence, drinks included

All tours as per program performed with a modern, AC, mini-coach

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, entrance to Siena Cathedral and lunch with wine tasting at a local restaurant in Siena

Full day tour, with an expert local guide to Montalcino, Pienza and Montepulciano with Brunello wine tasting and lunch at a local winery in Montalcino, and dinner and wine tasting in Montepulciano

Tuscan cooking class with lunch and wine in the Tuscan countryside

Florence, Italy, view of the Brunelleschi Dome at Sunset

Visas, passport, and/or departure taxes


Any 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.

Not Included

Hot air ballon flight above Tuscany experience, per person: $650 /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



Tuscan Countryside, view of green hills, Italy
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Coscia-Mancuso Family On Their Trip To Italy

- 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

Vagabonda Travel Independent Trip Clients, Megan Gersch and Jerry Leever

- 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's trip to Italy - Vagabonda Travel

- 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!

Happy Clients

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