Love, Wine, and Beauty of Tuscany and Umbria

TRAVEL FROM mid-April to mid-October

Umbria, Tuscany

  • 2 Nights Luxury Accommodations at Your Choice of Hotel in Southern Umbria
  • 3 Nights Luxury Accommodations at Your Choice of Hotel in Northern Umbria
  • 2 Nights Luxury Accommodations at Your Choice of Hotel in Val d’Orcia
  • 3 Nights Luxury Accommodations at Your Choice of Hotel in Siena
  • Private airport and train station transfers (where applicable)
  • Private transfers between destinations
  • Automatic rental car (where applicable)
  • Private wine tasting and sunset picnic in Umbrian Countryside
  • Private hot air balloon experience with Umbrian breakfast
  • Private cooking class in Val d’Orcia
  • Private e-biking experience in Crete Senesi
  • Private tour of Chianti (optional)
  • Private truffle hunting and pasta-making experience (optional)
  • Daily breakfast
Love, Wine, and Beauty of Tuscany and Umbria



Southern Umbria

Welcome to Italy! Your driver will be waiting at the arrival hall of Rome Fiumicino International Airport to take you through the Latium countryside to Umbria. Check in at your hotel of choice and use this first day to relax by the pool or explore the amenities of your selected property.


Wine Tasting

It’s time for a wine-tasting experience in the Umbrian countryside! Your driver will pick you up at the hotel (depending on the location of your selected property) and take you to our partner winery. Here, you will have the opportunity to learn more about the wine production cycle, embrace the aromas and the sights of the surrounding environment, and discover the richness of flavor of local wine varieties that will be served with local products.


Northern Umbria (Assisi or Perugia)

After breakfast, your driver will meet you at the hotel to take you to your next hotel of choice in Northern Umbria (Assisi or Perugia). Enjoy the ride through the countryside and, optionally, let us take care of lunch reservations on the way. Check-in at your hotel of choice and spend the afternoon at leisure.


Hot air balloon experience

Your day will start with a private drive through the North Umbrian countryside. Once you reach your destination, you will embark on a once-in-a-lifetime experience, a private hot air balloon ride over Umbria. Enjoy the sights of one of the most spectacular Italian landscapes, and once back on land let us pamper you with a lovely traditional breakfast.


Day at leisure or truffle hunting tour

You can spend the day at leisure or opt for a fun truffle-hunting experience in the Umbrian countryside. After meeting your driver, you will head to the countryside where you will be joined by the local truffle-hunting expert. Follow him and his dog through the forest as he shares the secrets of this ancient practice and keep your eyes open for the best truffles. Your daily “catch” will be the main ingredient in the pasta-making class that will follow the truffle hunting experience.


Val d’Orcia

Today, you will head to Val d’Orcia, the southernmost part of Tuscany. Here, beautiful landscapes and scattered traditional villages create a wonderful setting for a relaxing and memorable stay. Check into your hotel of choice and enjoy an afternoon at leisure.


Tuscan cooking class

The best way to immerse yourself in the Tuscan culture is by joining a cooking class. After meeting your driver, you will head to the Tuscan countryside where your culinary experience will start by picking the freshest ingredients with the help of a local chef. He will discuss the menu with you over a glass of local wine and you will all start preparing traditional local recipes. After all the dishes are completed, you will taste the fruits of your labor, family style, with lots of laughs, local stories, and, of course, some more local wine.



Your next destination will be Siena, and your driver will be ready to help with your luggage and transfer you to your next hotel. Once you complete the hotel check-in formalities, spend the day relaxing or exploring the picturesque area of the Crete Senesi, a wonderful part of Tuscany that needs no introduction.


E-biking through Tuscan fields

Today, you will meet your expert local guide at the starting point of a lovely e-biking tour through the Crete Senesi area. Enjoy the fresh breeze as you pass through the lush vineyards, fields, and beautiful villas. Follow the lead of your guide to discover the most romantic spots of the region surrounding Siena, and once finished let us help you book a lovely traditional Tuscan lunch.

DAY 10

San Gimignano and Chianti

Enjoy a day of relaxation in Siena or add another adventure to your itinerary. We suggest a tour of the Tuscan countryside, to be precise in Chianti, the world-famous wine region. Here, you will visit enchanting little towns such as San Gimignano, the Manhattan of Tuscany, and Greve in Chanti, the small village that works as a “gatekeeper” of the Chianti region. Since no Chianti tour is complete without wine, you will have the opportunity to visit our partner wineries for wine tasting accompanied by local products.

DAY 11

Departure day

After breakfast, embark on one last scenic drive through the Italian countryside on your way to the Florence International Airport for your flight back home.

Love, Wine, and Beauty of Tuscany and Umbria luxury
Assisi - Love, Wine, and Beauty of Tuscany and Umbria luxury
Hot Air Balloon - Love, Wine, and Beauty of Tuscany and Umbria luxury
Truffle Hunting - Love, Wine, and Beauty of Tuscany and Umbria luxury
Val d Orcia - Love, Wine, and Beauty of Tuscany and Umbria luxury
Siena - Cooking Class - Love, Wine, and Beauty of Tuscany and Umbria luxury
Siena - Love, Wine, and Beauty of Tuscany and Umbria luxury
San Gimignano - Love, Wine, and Beauty of Tuscany and Umbria luxury

Discover the elegant Cala del Porto Resort in Punta Ala. This peaceful oasis harmoniously blends with the Tuscan coast, offering two distinct experiences of beauty. The resort consists of two establishments: Hotel Cala del Porto, perched on the hills above the harbor, and Cala Beach, right on the sandy shores. Guests can indulge in both, with access to two beaches, Alleluja and La Vela, for ultimate relaxation. Unwind in stylish rooms and suites, showcasing modern touches and stunning archipelago views from private balconies or terraces. Immerse yourself in sophisticated cuisine as you savor the flavors of land and sea at gourmet restaurants serving delectable dishes that combine the essence of Tuscan and Mediterranean traditions.

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Il Bottacio offers a tranquil retreat nestled in the lush Tuscan landscape. An esteemed Relais & Chateaux Maison since 1988, it is a bespoke sanctuary designed for art and nature aficionados seeking a personalized refuge. Eight exclusive rooms and elegant suites await to pamper you with unmatched relaxation. Antique and contemporary design pieces – with the signature of Carrara and Ferragamo – and high-quality materials create a warm yet luxurious environment. Il Bottacio’s serene essence thrives in its verdant garden, where guests can indulge in Nino Mosca’s culinary mastery of melding fresh seafood and local ingredients. Complete your experience with a rejuvenating treatment at the Otzium Wellness Spa and rediscover your inner peace.

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Located along Viareggio’s stunning seafront, the Sina Astor offers a front-row seat to the mesmerizing pristine beaches of the Versilia region. The recently renovated hotel boasts spacious, bright rooms and suites adorned with elegant fabrics and contemporary design, some featuring balconies or terraces. Indulge in seafood delicacies and fine wines at Ristorante La Conchiglia and enjoy panoramic sea views. Unwind at the Sunset Bar, sipping aperitifs while gazing through picture windows onto the sea and the vibrant promenade. The Sina Wellness Club, Viareggio’s premier wellness haven, showcases state-of-the-art amenities, including a modern fitness area, body and spiritual treatments, a heated indoor pool, and a chromotherapy whirlpool. Treat yourself to an unforgettable stay at Sina Astor.

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Castello di Casole is a 10th-century estate, spread across more than 4,000 acres of land. It is so deeply ingrained in the region’s history that guests can even find artifacts from the Etruscan farmers displayed at the property. The hotel features luxurious accommodations, an outdoor pool, a spa, and fitness center, and 2 restaurants. The rooms and suites are individually decorated, and guests can find a great variety of options, from classical to modern. All rooms share the same respect for the long history of the property and combine classic furnishing with all modern amenities, while the spacious bathrooms boast Carrara marble or mosaic flooring and antique mirrors.

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Savor the pleasures of slow living at Castelfalfi, located near San Gimignano in the heart of the Florentine countryside. Experience the beauty, unspoiled nature, traditions, and exquisite cuisine that define the Tuscan dolce vita. Toscana Resort Castelfalfi features a modern, CasaClima®-certified building alongside a historic tobacco warehouse, blending past and present seamlessly. Surrounded by majestic Tuscan hills, vineyards, olive groves, and woodlands, the resort offers an ever-changing landscape. What truly sets this resort apart is its warm, simple, and attentive hospitality.

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Nestled between Chianti vineyards, corn fields, and chestnut forests, Castel Monastero is a restored medieval hamlet dating back to the 10th century. The historic castle provides its guests with beautiful views of Tuscany, a pool, a wellness center, and two gourmet restaurants, where guests can have a gastronomic experience, tasting classic Tuscan dishes. The hotel also has a large wine cellar and a bar. The rooms and suites at Castel Monastero are decorated in a rustic style with stone and wood décor and feature great views of the Tuscan countryside. The property’s XIII century cellar features some of the finest wines of the region.

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Borgo San Felice is a magical oasis on a hill among olive groves and vineyards, a true luxury hotel in Tuscany’s wine district, where guests receive the warmest of welcomes and first-class service. Almost an entire village has been converted into this upscale property. The rooms and suites are concentrated either in one of the buildings in the heart of the village or scattered in the neighboring houses surrounding the square. Each one is unique since it inherits various characteristics of the original construction and mixes modern and classic styles. Relax in the Tuscan countryside in a modernized spacious suite with elegant décor or take a dip in the hotel’s pool, absorbing the panoramic views.

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Set on a hill overlooking Val d’Orcia, a Unesco World Heritage site, Castello Di Velona is a restored 11th-century fortress. With breathtaking views and elegant common areas, the hotel also features a Tuscan restaurant and a spa center. Enjoy beautiful views of the rustic Tuscan vineyards from the spacious and bright rooms, luxuriously furnished and uniquely decorated with antique furniture and embroidered fabrics, featuring a log fire and a marble bathroom. Pamper yourself with a rejuvenating treatment at the OLISPA and let the thermal waters of Val d’Orchia regenerate your senses. Complete your experience with a culinary journey through the Tuscan flavors and aromas at the on-site gourmet restaurants. Discover an Italian oasis of relaxation at Castello di Velona Resort Thermal Spa.

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Grand Hotel Continental, a 5* boutique hotel in the historical center of Siena, awaits you just a few steps away from Piazza del Campo and the Duomo di Siena. This glorious 16th-century building was a preferred destination for young aristocrats and intellectuals. After a meticulous restoration, it continued its hospitality tradition as the top-notch hotel we know and love today. The splendor of the interior spaces is embellished with invaluable antiques and terracotta floors, making it a refined and luxurious place to stay to discover the treasures of Siena. Each of the 51 rooms and suites is a masterpiece inspired by the nobility of the Renaissance. Discover elegance, art, and fascinating history at the tables of the Sapordivino gourmet restaurant, the Lounge Bar, and the exclusive Wine Cellar, promising a culinary journey of the senses.

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An enchanting retreat awaits in the heart of Montepulciano's history. Originally a 16th-century noble residence, it was reborn as a charming relais thanks to Andrea and Angela. Influenced by African lodges, the villa underwent careful restoration while maintaining its original décor, resulting in a tranquil escape through the centuries of history. The retreat boasts an infinity pool and a Jacuzzi set among ancient olive trees. Immerse yourself in a kaleidoscope of colors and scents in the diverse gardens, which include a Tuscan Garden, and an Italian garden with a travertine fountain. Cicolina's rustic restaurant serves delectable seasonal dishes inspired by Tuscan recipes created with locally sourced ingredients.

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Let yourself experience authentic Italian hospitality in the beating heart of Sienna inside the Porta San Marco. With its prime location, Hotel Athena offers easy access to the main attractions. Within minutes, you can reach the Campo, the Duomo, and the Baptistery while enjoying a magnificent panoramic view of the serene landscape in a perfect atmosphere to relax and unwind. Cozy and charming, the design brings out the luxury of the architecture, blending modern comforts with a traditional feel. After a day of exploring the city and its surroundings, find the perfect spot on the beautiful panoramic terrace of the hotel. Sip an aperitif or savor a mouthwatering dinner by candlelight in the gastronomic excellence of Mangia restaurant, matching the delightful flavors of the local cuisine to the enchanting view.

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Palazzo Petrvs, a new addition to Italian hospitality, opened its doors this summer. Nestled in the Orvieto old town center, this charming boutique hotel exudes extraordinary beauty through its unique design that combines the retro palette of the 60’s with contemporary industrial elements. Dark green striped couches underneath minimalistic metal lights create an intimate atmosphere, while large arched windows let in natural light that warms the wooden details forming an earthly palette, ideal for a calm and relaxing experience. The Restaurant-Bistro awaits you to savor unique flavors that make the most of the local organic production. Experience Umbria in style with a stay at Palazzo Petrus.

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Born in the 16th century by the Piedivalle family, Palazzo Seneca in Norcia retains its historical allure. Noteworthy for the wooden choir of St. Benedict's Basilica and the Abbey of St. Eutizio, it showcases a magnificent 16th-century stone fireplace adorned with the family crest. The first hotel in Norcia underwent extensive restoration after the 1997 earthquake, reopening in 2008 as a seismic-safe monument. The hotel seamlessly blends simplicity, elegance, and comfort, offering rooms with carved wooden details and Simmons mattresses. The Vespasia Restaurant, awarded with a Michelin star in 2014, offers gastronomic excellence in an exquisite 16th-century setting. With impeccable service and a unique atmosphere, Palazzo Seneca promises a memorable experience.

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3 Nights Dubrovnik Extension

Dubrovnik, the Pearl of the Adriatic, or Kings Landing as it is known to Game of Thrones aficionados, is one of the must-see destinations in Croatia. Extend your trip with a 3-night stay in this magnificent walled city. Surrounded by scenict medieval City Walls, this former capital of the mighty sea-faring Republic of Ragusa will fill your days and nights with a myriad of landmarks, aristocratic palaces, majestic Baroque churches, fortresses, contemporary wine bars, top-notch restaurants, and, of course, plenty of opportunities to soak up the sun and relax by the azure Adriatic Sea. Visit Ston for a memorable oyster-tasting experience, taste the wines of Peljesac, or hop over to Montenegro for a day and explore the stunning landscape and history of Kotor Bay.

3 Nights Paris Extension

Continue your European adventure with a memorable 3-day extension in Paris. The "City of Lights," is a timeless destination with its iconic landmarks like the Eiffel Tower, Louvre Museum, and Notre Dame Cathedral, and an abundance of art, history, and culture. You can stroll along the charming streets and canals by the Seine, savor delectable French cuisine in cozy bistros, and indulge in world-class shopping on the Champs-Élysées. In three days, you'll immerse yourself in the essence of Paris, from its rich heritage to its contemporary allure, making it a must-visit destination for an unforgettable getaway.

3 Nights Athens Extension

Get a taste of history, culture and cuisine when you head off to Athens, the birthplace of democracy. Spend three nights at one of our top luxury hotels, with magnificent views of the Acropolis. Enjoy a full- day tour of the historical highlights around the city, including the Acropolis, the Acropolis Museum, the ancient Agora, the neoclassical buildings of Plaka, the changing of the guards at the Parliament building, Lycabettus Hill, and more. Your three nights/four-day extension includes roundtrip airfare from Cairo to Athens, private transfers, hotel accommodations, private tours, and local assistance.

Christine & Robert  - Travelive Reviews

Christine & Robert, USA

I wanted to let you know that our trip to Italy was just fantastic!

Everything about the time we spent on the Amalfi Coast was just perfect. The hotel was wonderful and every single person we came in contact with (drivers, tour guides, etc.) was just amazing!

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Jennifer & Josh  - Travelive Reviews

Jennifer & Josh, USA

What an amazing time we had in Italy!

We can’t thank you enough for all the help we got from you and the whole Travelive support team. Everything went so smoothly, and we had so much fun. Be assured next time we travel to the region we’ll reach out to work with you again! Italy was too beautiful not to go back!

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Christine M. - Travelive Reviews

Christine M, USA

Wanted to give you some feedback on our Path of the Gods adventure today. It was excellent!

Francesco, our guide, was awesome! He truly made our day extra special. We had a wonderful lunch with him at the end and really enjoyed talking with him. The food at the restaurant and the views of Positano were both fantastic! We were so glad we included that in our trip! We had fun sampling the limoncello yesterday and we also signed up for a pizza-making class last night. It was at Tirabuscio in Sorrento. We had so much fun and met a great group of people. Would definitely recommend it to anyone that wants to learn how to make Neapolitan pizza.

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Angie, Jason, Daria - Travelive Reviews

Angie, Jason, Daria, USA

Just want to thank you both for a job well done!! Loved every minute of our trip.

Deborah, Jason proposed to Daria at the Belmond Grand Timeo as per your suggestion!! PERFECT!! Thank you again for giving me the trip of a lifetime with my family. The memories are endless!!.

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Danielle - Travelive Reviews

Danielle, USA

This is the 2nd time I have used Travelive. I truly cannot say enough about how fabulous you all are!!!!

The trip was planned perfectly, and we didn't have to worry about anything. Each one of you was so professional and readily available. Simply surpassed our expectations! You made our trip to Italy and France that much more special. The drivers were amazing, and the tour guides were spectacular! Even the way the divers got us through customs they were true gentlemen and so patient with my parents! You made my family have the trip of a lifetime. THANK YOU SO VERY MUCH!!!

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Bernard  - Travelive Reviews

Bernard, USA

Grazie Mille! Everything has been like clockwork. Your colleagues on this side have been so wonderful to be with.

Sonia our guide at the Vatican & today at the Borghese Gallery was outstanding. Her knowledge of art/artists/paintings & and sculptures was beyond expectation. She was a walking art history presentation. The properties are beautiful. We really loved the Donna Camilla Savelli in Trastevere. A delightful and undervalued gem in Rome!

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Laurence & Lauren  - Travelive Reviews

Laurence & Lauren, USA

Hello! We had such an amazing trip. I can't begin to thank you enough for making our vacation so memorable and special.

It was beyond what we expected, and we are truly grateful for everything you did to help us! Already plotting in my head our next European excursion!!! It was perfect! Coordinating all those plans for us along the way (car service, hotel reservations, excursions, etc.) was the best part of the journey. Everything was perfectly seamless and easy. It was amazing!!

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Love, Wine, and Beauty of Tuscany and Umbria

TRAVEL FROM mid-April to mid-October

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