Italy Tours & Luxury Travel

Experience Italy’s timeless ruins, vibrant piazzas, and Mediterranean elegance.

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discover italy your way with private guided tours

Explore Italy where sun-drenched vineyards roll across Tuscan hillsides, Renaissance art graces centuries-old basilicas, and the scent of the sea drifts along the Amalfi Coast. From the grandeur of Rome and the canals of Venice to the elegance of Lake Como and the charm of Puglia, each region reveals its own distinct character.

With a Kensington Destination Expert, you’ll uncover Italy's most authentic experiences, curated with the ease and refinement that transform a beautiful trip into an exceptional one.

ACCOMODATIONS

Stay in handpicked masserie, boutique hotels, and luxury villas full of Italian charm.

PRIVATE GUIDED TOUR

Savor private vineyard visits, olive oil tastings, and countryside tours through iconic landscapes.

LOCAL INSIDER ACCESS

Private tastings, exclusive reservations, and behind-the-scenes access to the festivals, events, and experiences.

SEAMLESS TRAVEL

Enjoy tailored private transportation connecting beaches, towns, and countryside with ease.

PLAN YOUR STAY WITH KENSINGTON

Find Inspiration in Our Handpicked Tours and Book Your Luxury Escape Today

Rome & Amalfi Coast Discovery

Rome to Sorrento via Pompeii combining private touring with shared Capri excursions and coastal downtime

8 DAYS FROM$6,567per person

Rome & Amalfi Coast Discovery

Walk the Colosseum and Roman Forum privately, as your guide shares stories of the empire.
Join a small-group Vatican tour through Raphael Rooms and Michelangelo's Sistine Chapel.
Stop at Pompeii en route to Sorrento, then explore the town's center with a private guide.

8 DAYS FROM$6,567per person

Rome & Amalfi Coast Discovery

Walk the Colosseum and Roman Forum privately, as your guide shares stories of the empire.
Join a small-group Vatican tour through Raphael Rooms and Michelangelo's Sistine Chapel.
Stop at Pompeii en route to Sorrento, then explore the town's center with a private guide.

Best of Rome, Florence, and Venice

Experience Italy's must-see sights: the Colosseum, Michelangelo's David, and the Grand Canal

10 DAYS FROM$10,700per person

Best of Rome, Florence, and Venice

Hear ancient Rome's rivalries at the Colosseum and Forum on a privately guided tour.
Take in Florence's Duomo and Michelangelo's David with an expert private guide.
Savor Venice cicchetti on a bacari crawl, then glide the Grand Canal by private gondola.

10 DAYS FROM$10,700per person

Best of Rome, Florence, and Venice

Hear ancient Rome's rivalries at the Colosseum and Forum on a privately guided tour.
Take in Florence's Duomo and Michelangelo's David with an expert private guide.
Savor Venice cicchetti on a bacari crawl, then glide the Grand Canal by private gondola.

The Grand Tour of Italy

Italy's best, in one journey: from Roman ruins and Amalfi coastlines to Tuscan wines and gondola rides

12 DAYS FROM$15,040per person

The Grand Tour of Italy

Explore Rome's top sites, from the gladiators' Colosseum to Michelangelo's Sistine Chapel.
Journey along the Amalfi Coast to visit Positano, Amalfi, and Ravello.
Walk Florence's Renaissance streets and admire Michelangelo's "David" at the Accademia.

12 DAYS FROM$15,040per person

The Grand Tour of Italy

Explore Rome's top sites, from the gladiators' Colosseum to Michelangelo's Sistine Chapel.
Journey along the Amalfi Coast to visit Positano, Amalfi, and Ravello.
Walk Florence's Renaissance streets and admire Michelangelo's "David" at the Accademia.

Classic Rome: The Eternal City

Privately guided Rome in 5-days with iconic ruins, Vatican gems, and culinary insider access

5 DAYS FROM$3,840per person

Classic Rome: The Eternal City

Gain priority entry to the iconic Colosseum, hearing ancient tales from your expert guide.
Pursue your passions and explore Rome's best museums at your own pace with expert-curated tips.
Find serenity in the Vatican Gardens, then marvel at the Sistine Chapel with a private guide.

5 DAYS FROM$3,840per person

Classic Rome: The Eternal City

Gain priority entry to the iconic Colosseum, hearing ancient tales from your expert guide.
Pursue your passions and explore Rome's best museums at your own pace with expert-curated tips.
Find serenity in the Vatican Gardens, then marvel at the Sistine Chapel with a private guide.

The Flavors of Tuscany

Florence's Renaissance art meets Tuscany's best: vineyard tours, cheese tastings, and unforgettable dining

10 DAYS FROM$8,338per person

The Flavors of Tuscany

Trace Florence's Renaissance gems with an expert, ending with Michelangelo's famed "David".
Savor Montepulciano's farm-to-table bounty with Pecorino cheese, meats, and organic wines.
Cook Italian classics in a quaint village with a chef, savoring each dish with Tuscan wines.

10 DAYS FROM$8,338per person

The Flavors of Tuscany

Trace Florence's Renaissance gems with an expert, ending with Michelangelo's famed "David".
Savor Montepulciano's farm-to-table bounty with Pecorino cheese, meats, and organic wines.
Cook Italian classics in a quaint village with a chef, savoring each dish with Tuscan wines.

Sicily's Finest: Culture, Cuisine & Mt. Etna

Dive into Sicily's bold flavors, ancient temples, and dramatic volcanic terrain with curated ease

7 DAYS FROM$5,695per person

Sicily's Finest: Culture, Cuisine & Mt. Etna

Experience Palermo's rich history and taste local street food like arancine and crocchette.
Slow down at a countryside villa in Aragona, where Sicilian flavors and wellness meet.
Explore Agrigento's Valley of the Temples with a private guide revealing its secrets.

7 DAYS FROM$5,695per person

Sicily's Finest: Culture, Cuisine & Mt. Etna

Experience Palermo's rich history and taste local street food like arancine and crocchette.
Slow down at a countryside villa in Aragona, where Sicilian flavors and wellness meet.
Explore Agrigento's Valley of the Temples with a private guide revealing its secrets.

Rome & Florence Highlights: A Food & Wine Journey

Discover Rome and Florence's iconic monuments on private and shared tours with Tuscan food and wine

9 DAYS FROM$6,315per person

Rome & Florence Highlights: A Food & Wine Journey

From the Colosseum arena to Vatican masterpieces, take in Rome's must-sees on shared tours.
Taste Trastevere with a local food insider, pairing Roman classics with wine and dinner.
Walk Florence's Renaissance icons with a private guide, then join a Tuscan cooking class.

9 DAYS FROM$6,315per person

Rome & Florence Highlights: A Food & Wine Journey

From the Colosseum arena to Vatican masterpieces, take in Rome's must-sees on shared tours.
Taste Trastevere with a local food insider, pairing Roman classics with wine and dinner.
Walk Florence's Renaissance icons with a private guide, then join a Tuscan cooking class.

Italian Family Vacation: City Highlights

Gladiator training, pizza making, gondolas, and hands-on fun across Italy's iconic cities

10 DAYS FROM$5,770per person

Italian Family Vacation: City Highlights

Taste Rome one scoop at a time on a self-guided gelato crawl through lively neighborhoods.
Visit the Colosseum with an expert and train like a gladiator in replica armor.
Tour Florence with a local guide, and join a shared pizza-making class for hands-on family fun.

10 DAYS FROM$5,770per person

Italian Family Vacation: City Highlights

Taste Rome one scoop at a time on a self-guided gelato crawl through lively neighborhoods.
Visit the Colosseum with an expert and train like a gladiator in replica armor.
Tour Florence with a local guide, and join a shared pizza-making class for hands-on family fun.

Positano to Puglia: Italian Coasts Unveiled

Embark on a coast-to-coast journey from the cliffside allure of Amalfi to the sun-soaked Puglia

8 DAYS FROM$10,447per person

Positano to Puglia: Italian Coasts Unveiled

Check off your bucket list with guided exploration of coastal stunners: Amalfi and Ravello.
Ascend Mt. Vesuvius with a guide for a slope-side wine tasting and panoramic views of Naples.
Discover Puglia's olive oil heritage on a private tour of ancient groves and oil tastings.

8 DAYS FROM$10,447per person

Positano to Puglia: Italian Coasts Unveiled

Check off your bucket list with guided exploration of coastal stunners: Amalfi and Ravello.
Ascend Mt. Vesuvius with a guide for a slope-side wine tasting and panoramic views of Naples.
Discover Puglia's olive oil heritage on a private tour of ancient groves and oil tastings.

Savoring Northern Italy: Barolo Wines & Bologna

Sip, savor, and slow down through Piedmont and Emilia-Romagna on a luxe food and wine journey

10 DAYS FROM$13,475per person

Savoring Northern Italy: Barolo Wines & Bologna

Walk Turin's Baroque streets with a private guide and taste the city's legendary giandujotto.
Uncork Barolo in its birthplace, and hunt for truffles through the Langhe with a local expert.
Sample handmade pasta, cured ham, and aged cheese on a guided Bologna food tour.

10 DAYS FROM$13,475per person

Savoring Northern Italy: Barolo Wines & Bologna

Walk Turin's Baroque streets with a private guide and taste the city's legendary giandujotto.
Uncork Barolo in its birthplace, and hunt for truffles through the Langhe with a local expert.
Sample handmade pasta, cured ham, and aged cheese on a guided Bologna food tour.

Venice, Milan & the Lakes of Northern Italy

From Venice's canals to a Lake Como sailing, a privately guided journey through Northern Italy's finest.

10 DAYS FROM$16,820per person

Venice, Milan & the Lakes of Northern Italy

Drift Venice by gondola, step inside a glassblowing studio, and pour a Spritz like a local.
Walk Verona's Roman amphitheater and taste Bardolino wines and olive oil along Lake Garda.
Uncover Milan's cathedral, La Scala, and da Vinci's Last Supper on a private guided tour.

10 DAYS FROM$16,820per person

Venice, Milan & the Lakes of Northern Italy

Drift Venice by gondola, step inside a glassblowing studio, and pour a Spritz like a local.
Walk Verona's Roman amphitheater and taste Bardolino wines and olive oil along Lake Garda.
Uncover Milan's cathedral, La Scala, and da Vinci's Last Supper on a private guided tour.

Italian & French Riviera Getaway

Discover scenic and cultural gems from the Cinque Terre to Nice, with market walks and private sunset cruises

10 DAYS FROM$13,752per person

Italian & French Riviera Getaway

Savor expertly crafted espresso in the heart of Milan's rich coffee culture.
Taste your way through Italy and France, indulging in a fusion of Mediterranean flavors.
Explore Cinque Terre's colorful villages with the expert insights of a private local guide.

10 DAYS FROM$13,752per person

Italian & French Riviera Getaway

Savor expertly crafted espresso in the heart of Milan's rich coffee culture.
Taste your way through Italy and France, indulging in a fusion of Mediterranean flavors.
Explore Cinque Terre's colorful villages with the expert insights of a private local guide.

The Essence of Puglia: Italy's Coastal Gem

A journey through Puglia's ancient caves, olive groves, white-washed Alberobello, and Adriatic lifestyle

10 DAYS FROM$10,323per person

The Essence of Puglia: Italy's Coastal Gem

Learn bread-making at a beloved Matera bakery, leaving with your own freshly baked creation.
Head underground to marvel at the stunning rock formations of the Castellana Caves.
Explore Alberobello's UNESCO-protected trulli homes, then savor a local lunch with wine.

10 DAYS FROM$10,323per person

The Essence of Puglia: Italy's Coastal Gem

Learn bread-making at a beloved Matera bakery, leaving with your own freshly baked creation.
Head underground to marvel at the stunning rock formations of the Castellana Caves.
Explore Alberobello's UNESCO-protected trulli homes, then savor a local lunch with wine.

Ski Cortina: Queen of the Dolomites

Descend Cortina's legendary runs with private guides, alpine-chic lodging, and tailored services

9 DAYS FROM$10,184per person

Ski Cortina: Queen of the Dolomites

Stay 6 nights in Cortina with alpine-chic comforts and Superski pass access to 12 top resorts.
Snowmobile to iconic Dolomite peaks, snowshoe scenic trails, then retreat to an outdoor spa.
Savor Alpine flavors with on-slope lunches at cozy mountain huts and apres-ski in Cortina.

9 DAYS FROM$10,184per person

Ski Cortina: Queen of the Dolomites

Stay 6 nights in Cortina with alpine-chic comforts and Superski pass access to 12 top resorts.
Snowmobile to iconic Dolomite peaks, snowshoe scenic trails, then retreat to an outdoor spa.
Savor Alpine flavors with on-slope lunches at cozy mountain huts and apres-ski in Cortina.

The Best of Sardinia: From Countryside to Emerald Coast

Go off-road, set sail, and uncork Sardinia's best on a private coastal journey from Chia to Porto Cervo

9 DAYS FROM$9,608per person

The Best of Sardinia: From Countryside to Emerald Coast

Explore Chia's hidden coves by private jeep, swimming and unwinding at secluded beaches.
Journey off-road to a Bronze Age nuraghi village, then settle in for a coastal aperitivo at sea.
Island-hop the Emerald Coast by private yacht, swimming turquoise bays and lunching ashore.

9 DAYS FROM$9,608per person

The Best of Sardinia: From Countryside to Emerald Coast

Explore Chia's hidden coves by private jeep, swimming and unwinding at secluded beaches.
Journey off-road to a Bronze Age nuraghi village, then settle in for a coastal aperitivo at sea.
Island-hop the Emerald Coast by private yacht, swimming turquoise bays and lunching ashore.

Rome to Malta Luxury Escape

Roman wine tastings and curated dining followed by Malta's Blue Lagoon and Baroque sights

10 DAYS FROM$12,390per person

Rome to Malta Luxury Escape

Balance relaxed Rome exploration with a guided escape to the vineyards of Castelli Romani.
Visit Gozo's UNESCO-listed temples and coastal landmarks with a knowledgeable private guide.
Cruise Malta's shoreline by private yacht, stopping to swim in clear Mediterranean coves.

10 DAYS FROM$12,390per person

Rome to Malta Luxury Escape

Balance relaxed Rome exploration with a guided escape to the vineyards of Castelli Romani.
Visit Gozo's UNESCO-listed temples and coastal landmarks with a knowledgeable private guide.
Cruise Malta's shoreline by private yacht, stopping to swim in clear Mediterranean coves.

Ultimate Italy & La Dolce Vita Train Journey

Traverse Italy in style, from coast to coast, revealing iconic sights and dreamy scenes by luxury train

11 DAYS FROM$21,253per person

Ultimate Italy & La Dolce Vita Train Journey

Explore Milan's treasures, from The Last Supper to high-end shopping with a personal guide.
Stay in picture-perfect Cortona and uncover San Gimignano's gems with your private guide.
Discover Venice's historic wonders and relax on the scenic shores of Portofino's coastline.

11 DAYS FROM$21,253per person

Ultimate Italy & La Dolce Vita Train Journey

Explore Milan's treasures, from The Last Supper to high-end shopping with a personal guide.
Stay in picture-perfect Cortona and uncover San Gimignano's gems with your private guide.
Discover Venice's historic wonders and relax on the scenic shores of Portofino's coastline.

Rome & Amalfi Coast Exclusive Escape

Experience true Italian luxury with private sports cars, yachts, and special access to top landmarks

8 DAYS FROM$34,936per person

Rome & Amalfi Coast Exclusive Escape

Enjoy premier access to Rome's Colosseum and Forum with an expert archaeologist guide.
Self-drive the scenic Appian Way in a vintage Alfa Romeo, with a guide leading the way.
Enjoy a private Chef's Table on the Amalfi Coast, crafting a tasting menu behind-the-scenes.

8 DAYS FROM$34,936per person

Rome & Amalfi Coast Exclusive Escape

Enjoy premier access to Rome's Colosseum and Forum with an expert archaeologist guide.
Self-drive the scenic Appian Way in a vintage Alfa Romeo, with a guide leading the way.
Enjoy a private Chef's Table on the Amalfi Coast, crafting a tasting menu behind-the-scenes.

Italy’s Icons & Insider Access

Enjoy expert-led VIP experiences, keyholder status, and five-star luxury in Italy's iconic cities

10 DAYS FROM$51,351per person

Italy’s Icons & Insider Access

Enjoy exclusive access to the Vatican Museums, lighting the Sistine Chapel candles at dawn.
See Michelangelo's David privately and gain special palace access for a unique wine tasting.
Dine privately at a Ponte Vecchio jeweler's, with access to an ancient jewelry collection.

10 DAYS FROM$51,351per person

Italy’s Icons & Insider Access

Enjoy exclusive access to the Vatican Museums, lighting the Sistine Chapel candles at dawn.
See Michelangelo's David privately and gain special palace access for a unique wine tasting.
Dine privately at a Ponte Vecchio jeweler's, with access to an ancient jewelry collection.

La Dolce Sardinia: Unwind in Style

Unwind at curated luxury stays, taste local wines, and sail the breathtaking waters of the Emerald Coast

9 DAYS FROM$15,610per person

La Dolce Sardinia: Unwind in Style

Make traditional Sardinian ravioli at a local winery, then taste four regional wines at lunch.
Slow down at a luxury resort, restore at the spa, and dine at a Michelin-starred restaurant.
Journey by jeep through Supramonte highlands and nuraghi ruins, ending with a winery tasting.

9 DAYS FROM$15,610per person

La Dolce Sardinia: Unwind in Style

Make traditional Sardinian ravioli at a local winery, then taste four regional wines at lunch.
Slow down at a luxury resort, restore at the spa, and dine at a Michelin-starred restaurant.
Journey by jeep through Supramonte highlands and nuraghi ruins, ending with a winery tasting.

Let us plan your perfect trip

Want to build an itinerary from scratch?

All our itineraries are starting points, created to inspire and always customized for our clients. If you already have ideas, let us know your interests and preferences so we can craft an itinerary just for you.

Let us plan your perfect trip

“I have had great experiences working with Kensington. Jenny planned a great trip and worked to meet all my requests. The drivers and guides were also great. This was my third trip with Kensington and not my last!”

– customer

“Thank you so much! Everything was fantastic. We want to go back again and again and see all the rest of Italy. Everyone was great and we could not have enjoyed our stays as much if you had not planned everything for us so perfectly!”

– Marybeth Durkin

“It was so easy to work with Kensington Tours...the experience was consistent, timely, and allowed us to have an amazing trip! The personalized experience was perfect and we are looking at doing another trip with Kensington in the near future.”

– Emese Nicholson

“This is our second time using Kensington. And again, it was a flawless, unforgettable and, at risk of being overly dramatic, life-affirming experience. Thanks to Courtney and the team for once again exceeding our expectations. ”

– Bob O.

“Coordinated trip options and transfers, wonderful hotel choices even when we had to opt for ‘different’ city. Great pre and post communication w advisor. Suggested side trips ( fiord speed boat cruise) campy but very fun”

– Debra

“From top to bottom all staff are knowledgeable with excellent customer service. Ownership looks out for you even when you are not with them through direct contact at all times ”

– Mitch

“Their attention to detail and the knowledge of the their home. My wife and I made a trip to Bali. Our guides Ardita and Pande were so amazing. On time, with the need to make anything possible for you! Thanks”

– G. Perentis

“What a trip of a lifetime. Gonzalo was an amazing guide. He was kind,caring, and very informative. Hosea is the best driver in Cusco. We appreciated the attention to detail and always having someone keeping us informed on what was going on next. ”

– sarah lake

Exclusive Perks When you Book with Kensington

Personalized Journeys, just for you

Every itinerary is designed to match your interests and pace.

Exclusive Skip-the-Line Access

Enjoy priority entry to the world’s most iconic sights.

Hidden Gems & Insider Experiences

Discover places and moments only locals know or experience.

24/7 Support

Travel with peace of mind knowing Kensington experts are just a call away throughout your journey.