Country Roads of Italy - Classic Group

Country Roads of Italy - Classic Group

Rome

The famous Spanish Steps at Piazza di Spagna, Rome, Italy

Days 1-2
The winding road of Sorrento located on the Amalfi Coast, Italy
Sorrento

The winding road of Sorrento located on the Amalfi Coast, Italy

Days 3-4
Idyllic Capri and its harbour landscape, Italy
Capri

Idyllic Capri and its harbour landscape, Italy

Day 4
View of Vesuvius from the forum in Pompeii, Italy
Pompeii

View of Vesuvius from the forum in Pompeii, Italy

Day 5
The rooftops of Assisi, Italy
Assisi

The rooftops of Assisi, Italy

Day 7
Florence

Florence, Italy

Day 9
Aerial view of famous medieval San Gimignano in the province of Siena, Italy
San Gimignano

Aerial view of famous medieval San Gimignano in the province of Siena, Italy

Day 10
Siena

The medieval town of Siena, Italy

Day 10
Pisa

Aerial view of Pisa and its famous Leaning Tower, Italy

Day 11
Facade and bell tower of the Cathedral of Lucca, Italy
Lucca

Facade and bell tower of the Cathedral of Lucca, Italy

Day 11
Cinque Terre

Village of Vernazza, Cinque Terre, Italy

Day 12
Venice

A gondola journey through the canals of Venice, Italy

Days 14-16

Map
8 Views
16 Days From

$6450

$6230

Country Roads of Italy - Classic Group

16 Days Starting in Rome, Italy and ending in Venice, Italy

Visiting: Rome, Vatican City, Sorrento, Capri, Pompeii, Todi, Assisi, Perugia, Cortona, Florence, Siena, San Gimignano, Lucca, Pisa, Cinque Terre, Parma, Modena, Venice

Tour operator:

Insight Vacations

Tour code:

E722N26

Guide Type:

Fully Guided

Physical rating:

Medium

Tour operated in:

English
From: $6450 $6230 (USD) Operator discount: -$220

NB: Prices correct on 03-Mar-2025 but subject to change.

Tour Overview

Embark on the "Country Roads of Italy - Classic Group" tour, a captivating journey through Italy and Vatican City, where history, culture, and gastronomy intertwine. Begin in Rome, exploring ancient treasures with a local expert, and savoring authentic Roman cuisine. Discover the breathtaking Isle of Capri, the medieval charm of Assisi, and the artistic heart of Florence. Delight in the culinary wonders of Parma and Modena, and experience the enchanting canals of Venice. This tour offers unique experiences, including a visit to a traditional glassblowing workshop and a cruise to the colorful island of Burano. Travel in luxury aboard a spacious, air-conditioned coach, and enjoy comfortable accommodations throughout. With guided tours, authentic dining, and cultural insights, this tour promises an unforgettable Italian adventure.

Highlights

  • Savor the ancient treasures of Rome, including the Circus Maximus and the Ancient Forum.

  • Admire the views of Mount Vesuvius from the cliffs of Sorrento.

  • Cruise to the Isle of Capri and explore its charming town and boutiques.

  • Discover the medieval architecture and cobbled streets of Assisi.

  • Explore the UNESCO World Heritage Site of Cinque Terre on the Italian Riviera.

  • Glide through the canals of Venice by gondola and visit St. Mark's Square.

  • Visit a traditional glassblowing workshop in Venice and witness the craft firsthand.

  • Taste the award-winning gelato in San Gimignano, known as the 'Medieval Manhattan' of Italy.

Places You'll See

St Peter's Basilica Over The Aelian Bridge, Rome, Italy

Sunset View Over Piazza Navona In Rome, Italy

Sorrento, Italy

View From Mount Solaro On The Island Of Capri, Italy

Pompeii, Italy

Picturesque Assisi. In The Province Of Perugia, Umbria, Italy

The Uffizi Gallery In Florence, Italy

Aerial View Of Ponte Vecchio Bridge, Florence, Italy

Siena, Italy

View Of Piazza Dell'anfiteatro Square, Lucca, Italy

Facade And Bell Tower Of The Cathedral Of Lucca, Italy

Pisa, Italy

Village Of Vernazza, Cinque Terre, Italy

jesserobertos

Gondolas In Venice, Italy

St Mark's Square, Venice, Italy

The Grand Canal With Rialto Bridge In Venice, Italy

Itinerary

Expand All

Day 1: Welcome To The Eternal City Of Rome

Location: Rome

Accommodation Name: Room 007 Select, Rome

Meals Included: Dinner

Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in before joining your Travel Director for a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. End the day getting to know your fellow travelers over Roman specialties during dinner at a local restaurant.

Day 2: Rome With A Local

Location: Vatican City, Rome

Accommodation Name: Room 007 Select, Rome

Meals Included: Breakfast

Today is devoted to The Eternal City. Join a Local Expert to discover the modern-day city and how people lived in Ancient Rome. See St. Peter's Basilica in the Vatican City. Then cross the Tiber river to see the Circus Maximus and learn about the history, the construction and the legends of the iconic Colosseum on a guided visit. Imagine the roar of the spectators as you enter the arena and stroll around picturing the gladiators and their adoring fans.

Day 3: Sorrento

Location: Sorrento

Accommodation Name: Majestic Palace Hotel, Sorrento

Meals Included: Breakfast

Venture south leaving the region of Lazio for Campania. Drink in the views of the Bay of Naples and the distinctive outline of Mount Vesuvius as you reach the resort town of Sorrento.

Day 4: Capri, The Isle Of Dreams

Location: Capri, Sorrento

Accommodation Name: Majestic Palace Hotel, Sorrento

Meals Included: Breakfast

Meet your Local Expert and cross the Bay of Naples to reach the beautiful Isle of Capri, a rock rising sheer from the Mediterranean! For 2,000 years, Capri has beckoned visitors from Tiberius Caesar to Gracie Fields. Arriving at the Marina Grande by boat, ascend to Capri town. Explore the narrow alleyways, browse in exclusive boutiques and wonder at the views over the Tyrrhenian Sea. Descend to the port by funicular railway and return to Sorrento, where you are at leisure for the rest of the day.

Day 5: Pompeii And Todi

Location: Pompeii, Todi

Accommodation Name: Fonte Cesia, Todi

Meals Included: Breakfast, Dinner

Journey to the ancient Roman city of Pompeii and explore this extraordinary site with your Local Expert. Travel into the heart of Italy to enjoy free time in Todi, located on a hilltop pedestal overlooking a vineyard-covered plain. Savor the distinctly medieval ambiance during your orientation and admire the Piazza del Popolo where locals take their evening 'passeggiata'. Take in the flavors of the region and enjoy dinner at a local restaurant with a glass of Orvieto Classico wine - a magical culinary experience!

Day 6: Todi

Location: Todi

Accommodation Name: Fonte Cesia, Todi

Meals Included: Breakfast

Immerse yourself in the enchanting medieval town of Todi, where you can wander through picturesque streets, marvel at historic architecture, and enjoy stunning views of the surrounding Umbrian countryside.

Day 7: Assisi And On To Perugia Relaxed Start

Location: Assisi, Perugia

Accommodation Name: Sangallo Palace Hotel, Perugia

Meals Included: Breakfast

In Assisi, see St. Clare’s Church and the cathedral. Continue to walk down the Via San Francesco and visit the huge Basilica of St. Francis with a Local Expert. Journey to beautiful Perugia, the jewel of Umbria. Your guided walking exploration begins in the main street of Perugia's Old Town. See the Collegio del Cambio, the splendid Priors' Palace, the Cathedral and the finely sculptured Great Fountain in the magnificent main square. In the evening there is the option to discover the edible treasures of a traditional Umbrian kitchen, accompanied with wines of the region.

Day 8: Perugia, The Jewel Of Umbria Relaxed Start

Location: Perugia, Cortona

Accommodation Name: Sangallo Palace Hotel, Perugia

Meals Included: Breakfast

Time to explore more about this gem of a town. Join a MAKE TRAVEL MATTER® Experience as you visit an artisanal workshop and meet Marta, a recipient of a TreadRight Foundation grant. Learn how Marta and her weavers are preserving the ancient craft of loom-weaving. With the rest of your day at leisure, perhaps visit Cortona, one of the oldest hill towns in Tuscany. On this Optional Experience, journey to a recently unearthed Etruscan Temple before a guided exploration through the town's historic center with views of Lake Trasimeno and the Val di Chiana.

Day 9: Florence And Monteriggioni

Location: Florence

Accommodation Name: Relais Certosa, Florence, Borgo di Cortefreda

Meals Included: Breakfast, Dinner

Journey past Lake Trasimeno to Renaissance Florence. On arrival you will walk with a Local Expert to see the marble-clad cathedral, bell tower and Gates of Paradise on the baptistery. Enjoy time at leisure to explore Piazza della Signoria, still the political heart of Florence and an open-air gallery of Renaissance masterpieces. Spend time gazing at the fountains and sculptures along the front of the Palazzo Vecchio. Wander the area around Santa Croce Basilica, famous for the quality of its luxury goods of gold and leather. Journey through the rolling, cypress-clad hills and vineyards of Tuscany and enjoy a delicious exploration of Tuscany's red wines, discovering their robust flavors and absorbing history before arriving at your elegant hotel.

Day 10: Siena And San Gimignano Relaxed Start

Location: Siena, San Gimignano

Accommodation Name: Relais Certosa, Florence, Borgo di Cortefreda

Meals Included: Breakfast

This morning, explore Siena with Insight Choice. Choose to visit the medieval Basilica of St. Catherine or alternatively, sample panforte, a traditional Tuscan dessert. Continue to the hilltop town of San Gimignano strikingly visible from every angle, its towers dominate the skyline and give it the nickname the Medieval Manhattan of Tuscany. Enjoy tasting the award-winning frozen delights of master gelato maker, Sergio Dondoli, whose great inventions include innovative and mouth-watering flavor combinations. Journey through the rolling, cypress-clad hills and vineyards of Tuscany as you return to your hotel.

Day 11: On To Lucca Relaxed Start

Location: Lucca, Pisa

Accommodation Name: Villa La Principessa, Lucca

Meals Included: Breakfast, Dinner

Travel to Lucca to view the churches, squares and palaces, perfectly preserved within encircling medieval ramparts. Pause a while and taste the lavish loaves of buccellato, Lucca's sweet raisin anise bread, said to be a favorite of the ancient Roman army. Later, you could take the opportunity to explore Pisa.

Day 12: Exploring The Cinque Terre

Location: Cinque Terre

Accommodation Name: Villa La Principessa, Lucca

Meals Included: Breakfast

Get ready to explore the Cinque Terre, or five villages, which for years were only accessible by foot. This UNESCO World Heritage site is one of Italy's most beautiful landscapes. Join a Local Expert in one of the picturesque fishing villages, before cruising along the rugged coastline (weather permitting). There is plenty of time to explore the old medieval quarter and popular sandy beach before returning to your hotel in Lucca.

Day 13: On To Parma

Location: Parma

Accommodation Name: Starhotels Du Parc, Parma

Meals Included: Breakfast

Journey to the beautiful university town of Parma, world-famous for its local ham and cheese. Meet one of the locals, Paolo. Learn about the process of making Parmigiano-Reggiano as Signor Paolo shares with you his passions for Italian food, especially excellent quality Parmesan cheese. Taste samples of the famous Parmigiano-Reggiano, accompanied by a glass of wine.

Day 14: Modena And On To Venice

Location: Modena, Venice

Accommodation Name: Hilton Molino Stucky, Venice

Meals Included: Breakfast

Visit one of Modena's top producers of authentic, traditional, artisan balsamic vinegar and take a master class to understand what makes this vinegar as expensive as top-rated wines. Continue on through the Soave vineyards past Padua to Venice, Queen of the Adriatic. To the tune of accompanying musicians, you will be serenaded through the atmospheric canals as you glide by gondola past water-lapped doorways and rococo palaces.

Day 15: The Magic Of La Serenissima

Location: Venice

Accommodation Name: Hilton Molino Stucky, Venice

Meals Included: Breakfast, Dinner

Join a MAKE TRAVEL MATTER® Experience during a visit to a traditional glassblowing workshop, where you can see how beautiful handcrafted glass is made by expert glassblowers, safeguarding traditional skills. Visit St. Mark’s Square where the city’s former wealth and power is evidenced by the riches of St. Mark’s Basilica and admire the Doge's Palace with its adjoining Bridge of Sighs. In the evening, cruise the islands of the Venetian Lagoon to arrive at Burano, famous for its candy colored houses. Sit down to a sumptuous dinner with wine, sampling the local specialties.

Day 16: Arrivederci Venice

Location: Venice

Meals Included: Breakfast

Your departure transfer arrives at Venice Marco Polo airport.

What's Included

  • Local Expert Guides

    Guided tours and local expert insights are provided at various locations including Siena, Rome, Assisi, Perugia, Florence, and more.

  • Hotel and Restaurant Tips

    All hotel and restaurant tips are included.

  • Taxes and Porterage

    All taxes and porterage charges at hotels are included.

  • Luggage Handling

    Luggage is handled and delivered to your hotel door.

  • Insight Flourish

    Occasional local specialties representing the destination are provided by the Travel Director.

  • Wi-Fi

    Complimentary coach and hotel Wi-Fi (where available) is included.

  • Airport Transfers

    Transfers are available at scheduled times if arrival and/or departure flights are as per the itinerary start and end dates.

  • Luxury Coach

    Travel in Insight’s luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom.

  • Hand Sanitizer

    Hand sanitizer is freely available on board the coach.

  • Unique Experiences

    Exclusive experiences such as a private visit to the Basilica of Saint Praxedes, a visit to a traditional glassblowing workshop in Venice, and a cruise to Burano for dinner are included.

What's Not Included

  • Optional Experiences

    Optional experiences such as visiting Cortona are not included and may require additional payment.

  • Flights

    International and domestic flights to and from the tour start and end locations are not included.

  • Travel Insurance

    Travel insurance is not included and is recommended to be purchased separately.

  • Personal Expenses

    Personal expenses such as souvenirs, additional meals, and beverages are not included.

  • Additional Transfers

    Transfers outside the scheduled times or for flights not matching the itinerary start and end dates are not included.

Mode of Transport

Travel in style with Insight’s luxurious, air-conditioned, 40-seat coach offering double the standard legroom and an onboard washroom. Enjoy complimentary coach and hotel Wi-Fi, and scheduled airport transfers if flights align with the itinerary.

Accommodation

Experience comfort and elegance at various accommodations including Room 007 Select in Rome, Majestic Palace Hotel in Sorrento, Fonte Cesia in Todi, Sangallo Palace Hotel in Perugia, Relais Certosa in Florence, Villa La Principessa in Lucca, Starhotels Du Parc in Parma, and Hilton Molino Stucky in Venice.

Dining Summary

  • 5 Dinner (D)
  • 15 Breakfast (B)

Additional Included Highlights

  • Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
  • Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.
  • We carry your bags for you and promptly deliver them to your hotel door.
  • From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
  • Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
  • If your arrival and/or departure flights are as per the itinerary start and end dates, then transfers are available at scheduled times. If your flights are outside these times, or you have booked additional nights accommodation with Insight Vacations, you may purchase transfers or make your own way from/to the airport.

Insight Experiences

  • Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.

Well-being

  • Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.
  • Hand sanitizer is freely available on board for you to use throughout the day.

Summary

  • Visit a glassblowing workshop in Venice.
  • Travel by hydrofoil to the Isle of Capri and ride in an open-top taxi • Explore Cinque Terre by boat • Glide along the Venice canals in a gondola.
  • Visit Papal Gardens and Castel Gandolfo • Positano • Basilica of Saint Francis in Assisi • San Gimignano.
  • Welcome Dinner in Rome • Highlight Dinner in Todi • Celebration Dinner on Burano island in Venice. Taste Chianti wine in Radda • Gelato in San Gimignano • Buccellato in Lucca • Balsamic vinegar in Modena • Parmigiano Reggiano in Parma.

Check out our Q&As

  • What unique experiences are included in the Country Roads of Italy tour?

    The tour includes exclusive experiences such as a private visit to the Basilica of Saint Praxedes in Rome, a visit to a traditional glassblowing workshop in Venice, and a cruise to Burano for dinner. Additionally, you will meet Marta in Perugia, who preserves the ancient craft of loom weaving, and learn about the process of making Parmigiano-Reggiano cheese in Parma.

  • What kind of dining experiences can I expect on this tour?

    The tour offers a variety of authentic dining experiences, including savoring dinner at a Roman restaurant in Rome, learning about and tasting quality vino rosso in Radda in Chianti, sampling Buccellato in Lucca, enjoying gelato in San Gimignano, and tasting Parmigiano-Reggiano cheese in Parma. You will also have a dinner with wine on the island of Burano.

  • How does the tour support sustainable practices?

    The tour includes MAKE TRAVEL MATTER® Experiences, such as visiting an artisanal workshop in Perugia where Marta and her weavers preserve the ancient craft of loom weaving, and a traditional glassblowing workshop in Venice, supporting the survival of this craft. These experiences contribute to the protection of cultural heritage and support UN Sustainable Development Goals.

  • What are some of the highlights of the tour in terms of sightseeing?

    The tour includes visits to iconic sites such as the Colosseum and St. Peter's Basilica in Rome, the Isle of Capri, the ancient city of Pompeii, the Basilica of St. Francis in Assisi, the marble-clad cathedral in Florence, and the canals of Venice. You will also explore the medieval town of San Gimignano, the Cinque Terre, and the charming city of Lucca.

  • What kind of transportation is provided during the tour?

    The tour provides travel in a luxurious, air-conditioned, 40-seat coach with double the standard legroom and an onboard washroom. Complimentary coach and hotel Wi-Fi are available, and scheduled airport transfers are provided if flights align with the itinerary.

  • Can I join the tour once it has departed?

    We regret that no refunds can be made for absences from a tour, including experiences such as missed meals or sightseeing.

  • How long has the tour company been trading?

    Since 1978.

  • What Ethical Travel credentials does the tour company have?

    Insight Vacations is a founding member of the TreadRight Foundation, a joint initiative created by the brands within The Travel Corporation (TTC) almost 15 years ago to ensure our impact through tourism is positive. Our ethos to #MakeTravelMatter guides our decision-making at every level of our business.

  • Will the accommodation included meet local health and safety regulations?

    Yes

  • Do you operate a “single share” option and how does it work?

    You have two options as a solo traveller. Either choose to be matched with a same sex partner for a room share - at no extra cost. Or choose a room of your own with a reduced or even free private room upgrade on select tours.

  • What policies are in place for Covid-19?

    Please contact us for latest COVID-19 policies

Reviews of this operator

Peggy Lindenborn  

Country Roads of Southern Italy and Sicily

02-Nov-2021

Country Roads of Southern Italy and Sicily is a delightful trip and our travel guides and driver, Enzo, Chris and Greg were amazing and made the trip very memorable. We saw so many places and had great experiences along the way! Thanks to them for such a wonderful vacation.!

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Trusted Customer  

Best of Spain & Portugal

11-Jan-2023

Great itinerary, good pace, tour director was friendly and very knowledgeable and organised. Bus was very spacious and driver was great. Yes would recommend insight to friends and families

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Jacqueline Thornberry  

Scenic Iceland and the Northern Lights

31-Oct-2021

The number is our group was small which meant we got to know each other. Our tour guide, Laura Spiers, was excellent as was our driver. The food was good, and of course everything we saw in Iceland was beautiful and educational.

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Kathryn Ronca  

Enchanting Canyonlands

08-Nov-2021

The trip was fantastic. Everything was well planned and exceeded my expectations. All insight personal were courteous helpful and professional Ann Manual and Kevin were a topnotch team There was attention to every detail and at all times felt safe and always a personal touch to the trip. The motor coach was clean and roomy and there was multiple wipe downs during the day All hotels were top notch and all staff at the hotels and restaurants were helpful and courteous I would recommend this trip as it gave you a fantastic view of the natural wonders of the the West.

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Patrick Ong  

Italian Intermezzo

12-Jan-2023

This trip is absolutely amazing! Worth every Penny! Our Tour guide did not Disappoint.

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Friday - Saturday

Apr 10, 2026 - Apr 25, 2026
$6475 $6255 (USD)

Operator discount: -$220 (USD)

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Apr 24, 2026 - May 09, 2026
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Operator discount: -$220 (USD)

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May 01, 2026 - May 16, 2026
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Operator discount: -$220 (USD)

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Operator discount: -$220 (USD)

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Operator discount: -$220 (USD)

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Jun 05, 2026 - Jun 20, 2026
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Operator discount: -$220 (USD)

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Operator discount: -$220 (USD)

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Operator discount: -$220 (USD)

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Aug 28, 2026 - Sep 12, 2026
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Operator discount: -$220 (USD)

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Sep 04, 2026 - Sep 19, 2026
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Operator discount: -$220 (USD)

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Sep 11, 2026 - Sep 26, 2026
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Operator discount: -$220 (USD)

Friday - Saturday

Sep 18, 2026 - Oct 03, 2026
$6725 $6505 (USD)

Operator discount: -$220 (USD)

Friday - Saturday

Oct 02, 2026 - Oct 17, 2026
$6575 $6355 (USD)

Operator discount: -$220 (USD)

Prices last published on 03-Mar-2025

Book with Confidence

  • Low Deposit

    Insight Vacations requires a minimum deposit of 350 USD per person or the full booking value, whichever is less, with the final balance not due until 90 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of insight vacations charges.

    Up to 91 days before tour starts: Forfeit 100% of deposit.

    At 90 days before tour starts: Forfeit 50% of booking price.

    At 29 days before tour starts: Forfeit 80% of booking price.

    At 1 days before tour starts: Forfeit 100% of booking price.

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