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Essence of Romantic Italy

Feel the romance on this Italian escape that combines sunset strolls through the Tuscan hillside, cooking classes in Florence, wine tastings set amongst some of the oldest and most-prized vines in the region, visits to charming medieval towns including Siena and San Gimignano, and meandering picturesque villages like Pienza with its breathtaking views. The romantic vibes continue along the pebble-beach shores of Positano as you enjoy time in the sun on the Amalfi Coast. Take a boat ride to the island of Capri, and indulge in gelato as you wander the colorful, winding streets.

Trip Type: Cosmopolitan


Essence of Romantic Italy
Essence of Romantic Italy
Essence of Romantic Italy
Essence of Romantic Italy

Day By Day

Day 1 – Arrive in Rome and Drive to Palazzetto

Arrive at the Rome Airport and collect your rental vehicle for your self-drive to Palazzetto.  Please allow at least three hours for the 145 mile drive, longer in case of traffic along the way.

Starting Accommodation: Relais Borgo Santo Pietro

Day 2 – Food Experience and Florence Walking Tour

In the morning, attend an amazing Tuscan Cooking Class. As a first step, you will go shopping with the chef at the central market near Santa Croce Square. You will meet the butchers, the bakers, and the farmers selling vegetables from their own fields. You will learn how to select the highest quality ingredients and taste local foods and wines. After grocery shopping you will have a coffee break in one of the Ancient Cafes of Florence. Then you will reach a beautiful kitchen in a Florentine palace and you will start putting your hands on the ingredients to create your own meal, under the expert supervision of the Chef. The cooking class will end with a lunch (bruschetta, fresh home-made pasta, and a main course) paired with a selection of Tuscan wines.

This afternoon, you will be taken on a private walking Tour, with a local English speaking professional guide focused on the 'Italian Genius in Florence' (about 3 hours). The guide will meet you at the designated location, and take you for a tour through the historical center to admire the city landmarks, avoiding the most crowded places. You will admire the highlights of Italian renaissance art and be fascinated with the stories of the important figures and dynasties of Florentine history who boosted its splendor. The itinerary will feature Ponte Vecchio bridge, Piazza della Signoria with the Palazzo Vecchio, Via Tornabuoni and Palazzo Strozzi, Piazza della Repubblica. You will see the beautiful recently restored church of Santa Maria Novella, the Church of San Lorenzo with the Medici Chapels and, of course, the gorgeous Santa Maria del Fiore Cathedral, with the Giotto bell Tower. Last but not least, you will visit the Accademia Gallery and have the chance to stand face to face with Michelangelo's David. Return to your accommodation in Palazzetto at your leisure.

Starting Accommodation: Relais Borgo Santo Pietro
Meals: Breakfast, Lunch

Day 3 – Super Tuscan Wines, Bolgheri Wine Estate

Today will be dedicated to the Northern part of Maremma, around the little village of Bolgheri, that from almost total obscurity in a wine-sense became ultra-fashionable over the past 30 years with the rise of the Sassicaia and other Supertuscans phenomenon.

Visit one of the pioneer wine makers of the area, Le Macchiole to recognize the enormous potential for quality of this soil and its unique position. The top wines to be tasted: Paleo Rosso (Toscana IGT, their flagship wine), Scrio (Toscana IGT) and the Bolgheri Rosso (ex-Macchiole - Bolgheri DOC). A light lunch with cold cuts and cheese is included, then head to L'Ornellaia Wine Estate, which is approximately 10 minutes drive. The winery was founded in 1981, in a beautiful, unspoiled part of Tuscany. From the outset, the mission was to produce outstanding wines. Since then passion and dedication, coupled with a unique territory and an extraordinary microclimate, have brought the winery's prestigious labels great success and recognition as one of the most important wineries in the world. They offer a truly outstanding Tour & Tasting program, with the tasting of 3 superb wines included.

Starting Accommodation: Relais Borgo Santo Pietro
Meals: Breakfast, Lunch

Day 4 – Palazzetto, Tuscany at Leisure

Perhaps with your time at leisure, visit the famous San Galgano Abbey, located just five minutes drive from Palazzetto. It was built in the early 13th century and is a Cistercian abbey which lies in the municipality of Chiusdino. The place is rich in history and is reminiscent of the medieval times during which it was built. The place is shrouded in mystery and is one of the greatest places to visit when traveling around Tuscany. Currently the abbey has no roof and presents a clear view of the sky above, but its walls have stood for centuries. The monasteries, cloisters and churches at this place are a thing of beauty and serenity. The sword of Galgano is framed in stone and can be viewed by visiting Montesiepi Rotunda.

Starting Accommodation: Relais Borgo Santo Pietro
Meals: Breakfast

Day 5 – Val d'Orcia Excursion

Today, enjoy a full day excursion to Val D’Orcia. The Val d’Orcia extends from the hills south of Siena to Monte Amiata. It is characterized by gentle, carefully cultivated hills occasionally broken by gullies and by picturesque towns and villages such as Pienza, Radicofani, Montepulciano and Montalcino (the Brunello di Montalcino is counted among the most prestigious of Italian wines). It is a landscape which has become familiar through its depiction in works of art from the Renaissance painting to the modern photograph. You will first visit a famous estate located near Montepulciano in the very heart of Tuscany, in an area known as the 'Crete senesi'. Your visit starts with the vineyards, Vinsantaia and Barricaia, and ends with a wine lover’s four-course gourmet lunch, paired with 4 top wines.

Afterwards, head to the beautiful wine estates in Montalcino (from Montepulciano 25 miles – 45 minute drive), the zone for Brunello production. Start with a guided tour of the vineyard. You have the chance to expand your understanding of the production process and to enjoy the selection of wines available for tasting (3 wines and snack included).

Starting Accommodation: Belmond Castello Di Casole
Meals: Breakfast, Lunch

Day 6 – San Gimignano and Siena

San Gimignano is a small walled medieval hill town in the province of Siena, known as the Town of Fine Towers, it is famous for its medieval architecture, unique in the preservation of about a dozen of its towers, which, with its hilltop setting and encircling walls form a 'medieval skyline'. Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino contain frescos, including cycles dating from the 14th and 15th centuries. The 'Historic Centre of San Gimignano', is a UNESCO World Heritage site. The town is known for its white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape, grown on the sandstone hillsides of the area.

San Gimignano to Siena is a 25-30 mile drive, taking less than an hour. Siena is a beautiful town of medieval origin, characterized by the orange-brown color of its land and buildings. In the Piazza del Duomo, admire the Cathedral, with its coating of white-black marble that dominates the entire plaza. Your guide will cover the city’s and people in a fascinating itinerary that alternates popular districts and rich noble palaces, fountains, towers, arches and artisan workshop, up to the Piazza del Campo (the shell-shaped square where the medieval districts compete for the famous Palio, in an unbridled and breathtaking horserace).

Starting Accommodation: Belmond Castello Di Casole
Meals: Breakfast

Day 7 – Val D'Orcia and Pienza at Leisure

A suggested excursion for your day at leisure is to drive to Val D’Orcia. The Val d’Orcia extends from the hills south of Siena to Monte Amiata. It is characterized by gentle, carefully cultivated hills occasionally broken by gullies and by picturesque towns and villages such as Pienza, Radicofani, Montepulciano and Montalcino. It is a landscape which has become familiar through its depiction in works of art from the Renaissance painting to the modern photograph. In the afternoon, perhaps then discover the beautiful village of Pienza. The historic center of Pienza in south-east Tuscany is listed as a UNESCO world heritage site and situated in the Val d'Orcia which is also listed by UNESCO as a World Cultural Landscape. Pienza enjoys a strategic position standing high atop a hill, dominating all the Orcia Valley with extraordinary views.

Starting Accommodation: Belmond Castello Di Casole
Meals: Breakfast

Day 8 – Drive Casole d'Elsa to Naples

Please allow 5 hours drive time for today's drive of 310 miles, longer to allow for traffic and stops along the way. 

You will return your rental car and be transferred to your Positano accommodation by private van.

Starting Accommodation: Hotel Il San Pietro Di Positano
Meals: Breakfast

Day 9 – Capri Boat Tour

Today is a full day excursion to Capri island by private boat with captain. Note, you will need to make your own way to and from the harbor today, a short distance from your hotel.

Located in in the gulf of Naples, Capri has always been loved by intellectuals, artists and writers. After a nice 30 minutes cruise, you will reach the beautiful island and tour around it on your private boat. You will visit several of the grottoes and stunning rock formations that dot the coastline, including the famed 'Blue Grotto', the former pleasure pool of the Roman Emperor Tiberius (be aware that entrance in the Grotta Azzurra is not always possible because of weather conditions, and limited access is regulated by local authorities; extra charge applies).

You will have time for a swim in one of the island's many inlets before reaching the island's port at Marina Grande, where you will be dropped off for a few hours of exploration at your own leisure. Your captain will provide you with maps of the island, as well as information about the 'must-see' stops to be visited. You can then have a nice ice cream or coffee at the famous Piazzetta and time off for shopping and relaxing before heading back by boat to the coast. You will be back in the afternoon to enjoy a lovely evening at leisure.

Starting Accommodation: Hotel Il San Pietro Di Positano
Meals: Breakfast

Day 10 – Positano at Leisure

Free day to enjoy Positano or visit the picturesque villages along the Amalfi Coast. You can visit Amalfi by public transportation (1 hour bus ride), with its lively alleyways, its lemon trees and gorgeous Cathedral. Stroll amongst the lively and colorful streets and visit the local shops. If you want to enjoy lunch in Amalfi, there are a number of high quality local restaurants.

Starting Accommodation: Hotel Il San Pietro Di Positano
Meals: Breakfast

Day 11 – Positano at Leisure

Today will be at your own leisure, to relax and enjoy the enchanting atmosphere of the lovely village of Positano. The urban structure of Positano is made of terraces, of small narrow and winding streets and of homes climbing the hillside. Typical are the many 'steps' from the city center that come down to the beach. The main beaches of Positano are the Spiaggia Grande and Fornillo, both reachable on foot. Laze in the sun, do some shopping in Positano's colorful boutiques, and enjoy a Delizia al Limone!

Starting Accommodation: Hotel Il San Pietro Di Positano
Meals: Breakfast

Day 12 – Sorrento Half Day Tour

A private car with a local English speaking driver will pick you up from your hotel and take you along the coast to Sorrento where you will enjoy the enchanting atmosphere of this lovely village at your own pace. Sorrento has been a favorite resort since Romans times, and it became an elite tourist resort in the eighteenth century, its hotels welcomed such luminaries as Ibsen, Wagner and Nietzsche. The high position above the sea and the consequent absence of a true sea promenade create its extremely original nature. Linked to the enchanting beauty of the place is the tradition whereby the name of Sorrento originates from the mythical mermaids whose soft singing tempted Ulysses and his crew in the Odyssey. After discovering the magic of Sorrento, you will be returned to Positano. Half day excursion, allow four hours.

Starting Accommodation: Hotel Il San Pietro Di Positano
Meals: Breakfast

Day 13 – High Speed Train Naples to Rome and Trastevere Food Walking Tour

Ahead of your rail journey, you will be transferred from your accommodation in Positano to Naples Railway Station by private vehicle.

Travel by high speed train from Naples to Rome. It takes an average of 1 hour 44 minutes to travel from Naples Centrale Station to Rome Termini Station by train, over a distance of around 117 miles (189 kilometers).

This afternoon, enjoy a unique Rome Walking Group Food Tour, to discover Trastevere, a Roman neighborhood, away from most tourist areas. Enjoy Roman life and Roman culture... and of course the food!

An English-speaking guide will take you off the beaten path to experience the real flavors of Rome in the vibrant neighborhood of Trastevere. Not just another food enthusiast, this is the only Roman food tour led by a real food-guide. Your guide will share insider tips on Italian cuisine and introduce you to local food specialties, immersing you in Rome’s rich culinary traditions. In between each delicious tasting, you'll get an insider’s view of the history, culture, and architecture that define the Eternal City. You’ll finish at a special venue with a wine tasting and fresh pasta prepared by a chef.

Starting Accommodation: Singer Palace Hotel, Rome
Meals: Breakfast

Day 14 – Depart Rome

Please be in the hotel lobby 10 minutes prior to pick-up time to ensure adequate time to load luggage. Ahead of your flight, you will be transferred by private vehicle from your Rome accommodation to Rome Airport for check in.

Meals: Breakfast


Package Level: Superior

Please note all prices listed are approximations and subject to current rate of exchange adjustments. Each itinerary can be fully customized to your interests and needs.

Twin Share
1/1/2022 - 12/31/2022$22,900

Terms and Conditions

Prices are per person, twin/double share in USD. All highlighted savings are reflected in the price. Price does not include airfare unless otherwise stated. Travel may be limited to certain days of the week. Hotels and tours remain subject to availability. Cancellation penalties and other booking or alteration restrictions may exist. Please note blackout dates may apply to Christmas, New Year and local special event periods. Pricing may increase over Holiday and special event periods and may not be reflected in price grid. Prices indicated remain subject to change without notice. Prices are not guaranteed until full payment is received and processed. CST #2012413-20 See our full Terms and Conditions: www.swaindestinations.com/terms



13 Nights


From $22,900 Per Person


Palazzetto; Casole d'Elsa; Positano; Rome


  • 8 Days Rental Car
  • 4 Nights Palazzetto (Tuscany)
  • Florence Walking Tour & Cooking Class
  • Bolgheri Wine Estate Tours with Light Lunch
  • 3 Nights Casole d’Elsa countryside
  • Winery Visits Val D’Orcia
  • Guided Tour of Siena
  • Private Transfer Naples to Positano
  • 5 Nights Positano
  • Boat Excursion to Capri
  • Half Day Trip to Sorrento
  • Private Transfer to Naples Railway Station
  • High Speed Train Naples to Rome
  • Private Transfer from Rome Railway Station
  • 1 Night Rome
  • Trastevere Food Walking Tour
  • Private Transfer to Rome Airport
  • Meals: 14 Breakfasts, 3 Lunches
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