Italy Chill out Trips in 2025/2026

Accommodations

Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Create a customized Chill out tour to Italy

Work with a local expert to plan a seamless itinerary through Italy and Europe.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Recommended by

Italian Glory

4.8

(55 reviews )

No booking fees

Best price guaranteed

Great itinerary and tour director. Suggest: a slightly slower pace - limiting yourself to 1 optional experience/ day to avoid too/ long days -exhaustion, provide more suggestions for authentic food / restaurants on ‘free’ days.

Chill out Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Como, Ve

Milan, Rome, Lake Como, Como, Venice, Florence, Amalfi Coast & Campania

Duration13 days

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Rome & the Amalfi Coast

4.8

(89 reviews )

No booking fees

Best price guaranteed

Sorrento and the amafli coast amazing. Pizza and everything was on spec!! No issues..

Beach Chill out

Tour Type

Group Tour

Accommodation

Resort, Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, Amalfi Coast

Duration10 days

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Tuscan Escape

(4 reviews )

No booking fees

Best price guaranteed

Great trip overall. The day trip were great. I wish the hotel was near a town or close to restaurants, but overall very great trip

Chill out Local culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Lucca

Rome, Tuscany, Florence, Lucca, Montalcino

Duration7 days

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Ultimate Italy

(1 review )

No booking fees

Best price guaranteed

I met some amazing people and saw so many incredible sights in Italy! This trip exceeded my expectations!

Chill out Adventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Naples, Amalfi, Ca

Rome, Venice, Naples, Amalfi, Catania, Taormina, Syracuse, Cefalu, Florence, Palermo, Cinque Terre, Milan

Duration22 days

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Amalfi Coast Dream - Small-Group Tour

(1 review )

Trip customizable

Best price guaranteed

Received excellent service and suggestions for a tour we planned for our son and daughter when they toured the Amalfi Coast in August. Hotels were all in great locations close to the action and all excellent 4 or 5 star. Would definitely use or recommend the tour operator to friends or family.

Countryside and village visits

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Campania, Rome

Duration4 days

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Naples Express & Sorrento - Small-Group Tour

(1 review )

Trip customizable

Best price guaranteed

Pressed for time but eager to soak up the Amalfi Coast’s best? The Naples Express & Sorrento - Small-Group Tour is a 4-day sightseeing adventure perfect for families and travelers of all ages. Start in Rome and journey to Naples, where you’ll step back in time at the ruins of Pompeii. Set sail for a day trip to Capri’s idyllic shores, then relax in the charming town of Sorrento, with plenty of free time to explore at your own pace. The tour includes accommodation, transport, and guided sightseeing, ensuring comfort and ease throughout. The unique selling point? A thoughtfully curated itinerary that captures southern Italy’s must-see highlights in just four days—ideal for travelers who want a rich Italian experience without the rush.

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Lazio, Naples, Sorrento, Rome

Duration4 days

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Premium Rome to Venice

No booking fees

Best price guaranteed

Uncover the warmth and richness of Italian culture as you journey from Rome to Venice on an eight-day Premium adventure. Travel through the rustic heart of Tuscany as you seek out culinary delights and tucked-away treasures among the rolling countryside. Explore the wonders of Venice’s Piazza San Marco, Pisa’s Leaning Tower and Rome’s Colosseum – one of the Seven Wonders of the World – with an expert local leader. From ancient monuments and lively cities to sprawling vineyards and traditional Tuscan cuisine – this adventure will make memorable moments for both the Italian novice and maestro.

Chill out

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Chianti, Florence

Duration8 days

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Sicily & Aeolian Islands Discovery

Trip customizable

Best price guaranteed

Let Sicily and the Aeolian Islands cast their spell on you with the "Sicily & Aeolian Islands Discovery" tour. This nine-day chill out trip sails from Palermo to Taormina, unveiling a medley of sun-drenched beaches, archaeological treasures, and Mediterranean flavor. Set off from Milazzo to explore the enchanting islands of Lipari, Panarea, and Stromboli, each boasting its own blend of natural beauty and rich history. From the bustling streets of Palermo and Catania to the laid-back pace of island life, every day presents new vistas and culinary delights. This group tour is ideal for young adults, families, and seniors looking for an easy-paced escape that combines exploration with relaxation. Its unique selling point? The seamless transition from Sicily’s vibrant mainland to the enchanting Aeolian archipelago—offering a journey where every stop is a sensory celebration.

Chill out

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Palermo

Campania, Sicily, Lazio, Palermo, Catania, Lipari, Taormina

Duration9 days

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Amazing Amalfi Coast - Small-Group Tour

Trip customizable

Best price guaranteed

Discover the wonders of southern Italy on the "Amazing Amalfi Coast - Small-Group Tour." This five-day adventure, crafted for families, seniors, and curious travelers, departs from Rome and journeys through the Gulf of Naples, the historic ruins of Pompeii, and the vibrant Amalfi Coast & Campania region. Highlights include a ferry ride to the island of Capri—an enchanting jewel of the Mediterranean—and the cliffside charm of Positano’s colorful villas. The itinerary is thoughtfully designed to provide plenty of free time, encouraging personal discovery and relaxation along the coast’s breathtaking scenery. This countryside and village visits tour package stands out for its leisurely approach and expert balance of guided sightseeing and independent exploration—an ideal way to experience the Amalfi Coast’s legendary allure.

Countryside and village visits

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Campania, Positano, Rome

Duration5 days

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The Marco Polo

Trip customizable

Best price guaranteed

Experience Italy’s most iconic cities on 'The Marco Polo,' a 4-day guided art and architecture tour from Rome to Venice via Florence and Bologna. Witness Michelangelo’s David, stroll Florence’s cobbled alleys, and float along Venice’s dreamy canals. This easy-paced group tour welcomes families, seniors, and young adults, offering ample opportunities to explore monuments, churches, and charming shops. The standout feature is its immersive, whirlwind introduction to Italy’s artistic and architectural masterpieces, making it an ideal short escape for travelers eager to soak up the country’s timeless beauty.

Art and architecture Chill out

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Lazio

Duration4 days

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Combine your Italy Chill out Trips with Nearby Countries for an Unforgettable Trip

Explore Chill out Trips with itineraries going through multiple countries, including Italy

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Alternatively, explore other Top Activities in Italy: Cultural, religious and historic sites Tours, Art and architecture Tours or City sightseeing Tours.

Italy Chill Out Trips 2025/2026

See Italy tours departing in

Create a customized Chill out tour to Italy

10 Chill out Trips in Italy with 150 Reviews

10 Chill out Trips in Italy with 150 Reviews

Italian Glory

Rome & the Amalfi Coast

Tuscan Escape

Ultimate Italy

Amalfi Coast Dream - Small-Group Tour

Naples Express & Sorrento - Small-Group Tour

Premium Rome to Venice

Sicily & Aeolian Islands Discovery

Amazing Amalfi Coast - Small-Group Tour

The Marco Polo

Combine your Italy Chill out Trips with Nearby Countries for an Unforgettable Trip

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

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Italy Chill Out Trips 2025/2026

See Italy tours departing in

Create a customized Chill out tour to Italy

10 Chill out Trips in Italy with 150 Reviews

10 Chill out Trips in Italy with 150 Reviews