Top Italy Luxury Trips &amp; Packages In 2025/2026

Group Tour

Why we love them

Their travelers enjoy 24/7 travel expertise and dedicated service throughout the trips - everything is taken care of.

Lodging level

Premium - 4 star

Physical level

Easy

Trip pace

Balanced schedule

Themes

Cultural, Education / Learning

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$3,905

10 days From$3,175

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Sicily in Depth (Malta, Classic, 6 days)

By Insight Vacations

premier

4.6/5 Excellent

Group Tour

Why we love them

They really care about everyone's individual needs on each tour and they have an incredible attention to detail.

Lodging level

Premium - 4 star

Physical level

Moderate

Trip pace

Balanced schedule

Highlights

Palermo: Visit the spectacular 12th-century Palatine Chapel. Its sombre exterior gives away few clues to the riches inside. Step into a world where the walls glitter with 12th-century mosaics, the best of their kind in the world.
Agrigento: Admire magnificent Hellenistic remains in the Valley of the Temples, such as the massive Temple of Concord and clifftop Temple of Juno.
Piazza Armerina: Travel to the Villa Romana del Casale, a UNESCO site since 1997. The Villa is one of the most luxurious of its kind, showcasing it's rich and intricate mosaics which decorate almost every room.
Ragusa: During your walking tour with your Local Expert see the famous Baroque buildings and churches.
Modica: Experience Modica's celebrated hand-made chocolate.

Themes

Cultural, 50 Plus

What travelers are saying

"Got good overview of what history of sites seen."

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14 days From$5,325

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Tuscany Walking and Wine

premier

4.7/5 Excellent

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Visits

Pisa, Rome, San Gimignano, Siena, Tuscany

Highlights

Enjoy short walks in the classic rolling landscapes of southern Tuscany
Spend time in historic hill-top towns and cities of Florence and Siena
Enjoy wine tastings and delicious Tuscan cuisine

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"

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$2,854

8 days From$2,160

Health Safety +

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A Taste of Sicily - Palermo to Syracusa

premier

5/5 Excellent

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Physical level

Strenuous

Visits

Agrigento, Catania, Sicily, Syracuse

Highlights

Weeklong gastronomic journey across Sicily from Palermo to Syracusa
Visit a traditional Sicilian farmhouse to enjoy fresh produce and delicious flavours
Visit Sicily's most famous Classical remains in the Valley of the Temples

Themes

Cultural, Hiking & Walking

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"

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$3,112

8 days From$2,270

Health Safety +

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Annapurna Circuit Trek

premier

4.6/5 Excellent

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Physical level

Strenuous

Trip pace

Full schedule

Visits

Kathmandu, Pisa, Pokhara, Tibet

Highlights

11-day trek following the classic Annapurna Circuit
Enjoy spectacular views from the Thorong La Pass
Great value with all meals on trek included

Themes

Hiking & Walking, Trekking & Expeditions

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"

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$3,555

18 days From$2,770

Health Safety +

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Amalfi Coast Walking - Seafront Hotel Sole

premier

5/5 Excellent

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Visits

Amalfi Coast, Naples, Pompeii, Positano

Highlights

Off season hiking along Italy's gorgeous Amalfi coast, staying at a family-run seafront hotel
Indulge in delicious local wines and products made with the famous Amalfi lemons
Explore the off-season charms of Positano, Amalfi, Ravello, Pompeii and Herculaneum

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"

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$1,907

8 days From$1,550

Health Safety +

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A Taste of Italy - Walking in Puglia

premier

4.9/5 Excellent

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Visits

Alberobello , Altamura, Bar, Bari, Matera, Puglia

Highlights

Enjoy easy walks in Puglia's wild landscapes alongside tasty food and wine explorations
Discover Matera's ancient Sassi quarter and the conical trulli houses of the Itria Valley
Visits to baker and butcher, producers of cheese, olive oil and wine

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"

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$2,435

8 days From$1,820

Health Safety +

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Walking In Sicily

premier

4/5 Great

Small Group Tour

Why we love them

They travel to places beyond the typical tourist locations and offer exciting activities that bring the “wow factor” travelers want.

Lodging level

Premium - 4 star

Visits

Catania, Mount Etna, Sicily, Taormina

Highlights

Varied hikes among eastern Sicily's diverse landscapes based close to historic Taormina
Walk on the lava strewn slopes of Mount Etna and visit the Aeolian island of Lipari
Explore quaint inland towns and the quiet trails of the Pantalica Gorge

What travelers are saying

"Great trip covering highlights of Kerala. Fabulous tour leader and support team. The rides started easy and flat, and became progressively harder with increasingly longer hills as we headed into the mountains. The slow pace suited my ability. The spinning classes I did as preparation definitely paid off. The heat and humidity were challenging! Road conditions were better than expected. The bikes could have been in better condition- the mechanic was great in sorting out issues on the way. Most of the participants missed their various connecting flights arranged by Explore, including us! Arriving at 5am and having to be prepared to cycle at 8.30am wasn’t fun! Explore really need to consider this as I think it’s a regular occurrence!"