Small Group Italy Tours & Private Adventures
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Welcome to the Story of Italy.

Luggage Packed. Secrets Waiting.
Small Group Italy Journeys Thoughtfully Curated by Now Journey


50+ Five-Star Reviews on TripAdvisor



Mark Story, Managing Director of Now Journey

A Note from Mark Story

Now Journey is personal by design.

Now Journey was created around a simple idea: the best travel experiences feel effortless, personal, and quietly unforgettable.

The kind of journeys where every detail has been thoughtfully handled for you — from distinctive hotels and remarkable Tour Captains to the pacing of each day itself — so you can simply settle in and experience the destination more deeply.

We travel in small groups by design, allowing room for spontaneity, connection, and the kinds of moments that rarely happen on larger tours.

Welcome to Now Journey — personally curated by Mark Story.

Is Now Journey Right for Me?

★ Italy's Best First Time Tour → Italy's Great Cities Tour | Is a Now Journey Tour Right for Me?

Italian-Inspiration. American-owned.
Small Group Journeys up to 16 Guests, or Go Private.

Italy Small Group Tours in 2026: High-End, Curated Experiences with Now Journey

Luxury Italy Small Group Tours 2026 — Travel Differently with Now Journey. Experience Italy the way discerning travelers prefer: in small groups of no more than 16 guests, led by expert Tour Captains and local guides. Now Journey's luxury Italy tours are curated for authenticity and ease — no big buses, no long lines, just beautifully crafted itineraries that include exclusive rooftop aperitivos, private after-hours visits, and seamless connections from Venice to Rome and beyond. Every Journey is designed to deliver the Italy you've dreamed of — intimate, personalized, and unforgettable.

Plan Your Tour to Italy and Beyond with Now Journey's Style of Travel to Match Your Preferences: Fully-Hosted, Private Now Journey or Self-Guided

Whether you prefer a fully hosted small group or a bespoke private journey, Now Journey crafts experiences that match your style. From start to finish, our travel planners handle the details — hotels, guides, transfers, and tickets — so you can simply enjoy. Discover the art of effortless travel with Now Journey.
Chat to Start Planning here.

The Modern Traveler with Now Journey

At Now Journey, travel isn't just about where you go — it's how you go. Our guests travel intentionally: to experience new rhythms, embrace local life, and discover meaning in every moment. From Venice's canals to Tuscany's vineyards, things may look or feel different from home — and that's where the beauty lies. Our travelers understand that true luxury is found in connection, gratitude, and the wonder of exploring the world together.

Compare our Favorite Small Group Tours of Italy.

There are places that stay with you not because you remember every detail, but because something inside you shifted while you were there. Italy has a way of doing that. Happiness comes easier here, in the rise of church bells over a quiet piazza, the first sip of a perfect espresso, or the way sunlight touches ancient stone and timeless art.

It is a country that feeds every sense. You linger over long lunches that become memories, wander through galleries filled with masterpieces, and drift into restful afternoons under cypress trees or beside bright blue seas. And when evening arrives, Italy rises to meet you, whether it is an open-air opera in Verona, a candlelit palazzo in Venice, or a warm and welcoming osteria in Naples.

Italy offers beauty, serenity, and nourishment for the spirit. And once you have felt it, you never forget it.

Signature Now Journey Experience
Venice • Florence • Tuscany • Rome • Amalfi Coast

Italy's Great Cities — The Original 12-Day

★ 12D: Venice, Florence, Tuscany & Rome

Our signature small group experience. Enjoy Italy's iconic trio with curated hotels, skip-the-line touring, Discovery Walks, and a Tour Captain hosting throughout.

From $9,979/person + Air
Bellagio • Lake Como • Venice • Florence • Tuscany • Rome • Amalfi Coast

Italy's Great Cities — Complete 14-Day

★ 14D: Boutique Hotels + Additional Inclusions

An expanded experience with elevated boutique hotels, expanded inclusions, and added comfort while maintaining true small group travel.

From $12,579/person + Air
Venice • Florence • Rome

Italy's Great Cities — 10-Day

★ The Classic Italy Tour in a True Small Group from Venice to Rome.

Begin in Venice with 2 days and nights, then to Florence, birthplace of the renaissance, check out Tuscany for 2 days, and finalé in Rome for 3 days.

From $8,579/person + Air
Asolo • Lake Garda • Verona • Bologna

Northern Italy Bella Tour —

★ 9D: Asolo, Vicenza, Verona, Lake Garda & Bologna

A relaxed northern escape blending vineyard towns, lakeside charm, and elegant cities. Explore classic piazzas, savor northern cuisine, and enjoy the peaceful shores of Lake Garda.

From $7,579/person + Air
Tuscany Villa

Tuscany: Treasures of Tuscany Tour

★ 9D: Florence + Countryside Villa Stay

Experience Renaissance Florence and the rolling hills of Tuscany while staying in a private villa. Quiet hilltowns, vineyard landscapes, and slow, authentic Tuscan living await.

From $6,929/person + Air
Amalfi Coast

Amalfi Coast Adventure

★ 9D: Capri & the Amalfi Coast — Positano • Ravello • Amalfi • Sorrento

Colorful cliffside towns, shimmering sea views, and the charm of Capri. This journey centers on scenery, coastal culture, and unhurried days by the water.

From $11,379/person + Air
Puglia & Basilicata

Puglia Tour

★ 8D: Polignano • Matera • Lecce • Otranto

Italy's sun-soaked southeastern heel: whitewashed towns, cliffside beaches, ancient cave streets, and the warm character of southern Italy.

From $7,879/person + Air
Northern Italy

Italian Lakes & Cinque Terre

★ 10D: Lakes Orta, Maggiore & Como + Cinque Terre

A dream for those who love waterfront beauty. Mountain-framed lakes, elegant promenades, and the pastel cliffside villages of Cinque Terre.

From $9,579/person + Air
Taormina, Sicily

Sicily

★ 8D: La Dolce Vita Sicily

An island-hopping escape rich in history, sea views, and coastal relaxation. Explore atmospheric Sicily and the turquoise warmth of Sardinia.

From $8,879/person + Air

The Now Journey Difference

Some places change you quietly.

Not all at once — but in the hush of evening canals, the glow of ancient stone, and the feeling that the world has opened just a little wider.

A New Story Beyond the Journey

WHITE-
GLOVE:
KILGORE

Original Series Development
by Mark Story

Cinematic storytelling, hospitality sensibility, and a deep belief that place should be felt — not just visited.

Now Journey + White-Glove: Kilgore

Beyond travel, a new story is being created.

White-Glove: Kilgore is an original cinematic series rooted in mystery, atmosphere, hospitality, and the emotional pull of place.

Created by Mark Story through Tufty Agency, the project reflects the same instinct behind Now Journey — crafting experiences people continue thinking about long after they end.

Enter the Story More & Support the Story

Guest Stories from the Journey.

itinerary was meticulously crafted

"The itinerary was meticulously crafted, with every detail seamlessly planned and executed, ensuring that our journey was not only smooth but also filled with unforgettable experiences."
— Mikki on the Bella Northern Italy Adventure

Australia Tour

"From the moment we embarked on our journey to the final farewell, the quality of service was unmatched, with every need anticipated and every expectation exceeded."
— Australia Adventurers

Italy Tour

"The itinerary was flawless, with every detail perfectly planned and executed." — Italian Lakes Adventure


Read TripAdvisor Reviews from guests who have experienced traveling with Now Journey.

Reviews from Now Journey guests on TripAdvisor highlight exceptional service, well-organized itineraries, and memorable experiences. Guests praise the knowledgeable guides, comfortable accommodations, and personalized touches. Travelers consistently rate Now Journey as a top choice for unforgettable trips.

Poderuccio Dining Table

"The restaurant selection was a culinary dream, with each meal surpassing the last."
— Keith & Marla on the Amalfi Coast and Italy's Great Cities Tour



Read TripAdvisor Reviews from guests who have experienced traveling with Now Journey.

Pascal

"Our Tour Captain's expertise turned a great trip into an unforgettable adventure."
— Italy's Great Cities Guests

Italy Tour

"Traveling with such a well-curated itinerary elevated the entire experience."
— Georgia Brown on Private Adventure

Facebook® Travel Community

Join our online Facebook® travel community and start the conversation about Italy's Great Cities: Join in with managing director Mark Story here.

Italy Tour

"Our small group experience made the journey intimate and personalized."
— Italy Private Adventures

Rome Tour

"From start to finish, the quality of service was unmatched."
— Teresa on Italy's Great Cities Tour

Small Group Italy Tours

"Each day brought new discoveries and unforgettable moments, all thanks to the meticulous planning and local insights that were clearly woven into every aspect of the itinerary."
— Misti on Italian Private Villa

Italy Tours

"Traveling in a small, exclusive group made the entire experience feel incredibly intimate and personalized, allowing us to truly connect with each destination in a meaningful way."
— Leah on Italy's Great Cities

Start Your Journey!

1. Chat to discuss your trip with a Now Journey Trip Planner:

Click to discuss the Journey

2. Or Click Here to have us Email you more details.

3. Or Call or Text us today: +1 (720) 464-3248

4. Get a no obligation Trip Proposal for Italy here:
[ PLAN YOUR ITALY ADVENTURE ]
Get your No Obligation Trip Proposal

 

Travel Deeper

Italy is not something to rush.

It is something to enter slowly — through conversation, flavor, beauty, and the quiet confidence of a journey thoughtfully led.

Welcome to Now Journey.

Avoiding the traditional large tour model was where we began and we didn't stop there.
Creating an enhanced Journey for the Modern Traveler became our passion and is our guiding principle.

Prefer to avoid the big tour operator's large buses, long lines and touristic restaurants?
Yes, that's our preference, too. With Now Journey's approach you'll feel special,
set apart from the touristic mobs, and you will want to travel again and again as a Modern Traveler.

 
 

Book with Risk-Free Assurance.

Book your Now Journey with assurance with just a $700 per person deposit.*

If you need to cancel more than 90 days prior to departure, you will receive a full refund, less the transferable deposit and any unrecoverable costs. Some itineraries require non-refundable on-tour air at time of booking or may have a different deposit amount required.  

 

Amazing Journeys for Your Consideration

Select Adventures from Small Group Itineraries to Private Villa Experiences

Many of our small group adventures feature once-in-a-lifetime departures with our Now Journey Tour Captains and other notable personalities. Look for these specially-noted departures and expand your Journey.

Your Now Journey Tour Captain

The Perfect Balance of Personality and Service

Now Journey conducts thorough auditions each year to find just the right type of person to become a Now Journey Tour Captain.
The 'cream of the crop' is our objective with each Now Journey Tour Captain. We know an over-bearing personality can ruin a
Journey, and that's why we work so hard to find the right people. Are you interested in auditioning?

Check out our Now Journey Careers.  

Our Team of Trip Planners

Over 50 Years of Combined Trip Planning Experience

Now Journey's team of experienced trip planners combine 50+ years of professional trip planning experience coupled with an unsurpassed commitment to delivering outstanding personal service. Discover how Now Journey is different on your next vacation.

Let us hand-craft your next Journey.  

Welcome Modern Traveler.

We invite you to peruse our trip offerings and discover your next Journey.

We believe you will fall in love with the team at Journey once you've experienced our approach to travel and adventure. So, consider this your invitation to explore the world with us. We're here to help, answer questions and then lead you to new discoveries, tastes and perspectives. Welcome Modern Traveler!