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The Best of La Dolce Vita

Venice, Florence & Rome Cultural Walking Tour

7 DaysStarting at $6,695
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Overview

Join us in these three must-see cities…to see them like most families never get the chance! In one perfectly timed week, you'll discover the best of Italy without feeling like you're in a rush. Our local guides know how to get you a ride in the best gondolas, find the creamiest gelato and pull strings to get kid-friendly access to Michelangelo's David and the Sistine Chapel. Near Florence, you'll live and play like a Tuscan famiglia at a countryside hotel with a swimming pool, easy access to walking paths, and a treasure hunt in Siena. We bring sprawling Rome down to size from the Trevi Fountain to the Colosseum. Best of all, you'll meet pizza-makers, art experts and gladiator trainers who all give Italy a happy personal spin for your family. 

Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure

Itinerary Highlights

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• Explore Venice on a privately guided walk to Piazza San Marco, the Bridge of Sighs, the Rialto Bridge and — of course — a gondola ride on the narrow canals.

• Zip by high-speed train to Florence where the city's amazing history comes to life on a walk from the red clay dome of the Duomo to the covered Ponte Vecchio across the Arno.

• Skip the line at the Academy Gallery to see Michelangelo's David.

• Visit the walled hill town of San Gimignano to see its medieval towers at sunset and meet the best gelato maker in the world (and taste his gelato for ourselves).

• Walk through the Tuscan countryside to visit with a family of shepherds who make their own cheese and treat us to a generous tasting at the farm.

• Train to Rome, where a guided walk leads to the Trevi Fountain, the Spanish Steps, the Colosseum and the Roman Forum.

• Join your guide for a special visit to awesome St. Peter's Basilica and the Sistine Chapel to see Michelangelo's ceilings.

• Learn to toss your own pizza or make your own pasta from scratch with a local Roman friend

 

Download Full Daily Itinerary

Map

  • Starting Point:

    Venice – 2:00 pm – Lobby of Hotel Saturnia

  • Ending Point:

    Rome – 12:00 pm – Lobby of Rome Times Hotel
Itinerary Map

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Walking Level

  • Daily Mileage Options: 2-7 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Venice, Florence, and Rome; as well as well-maintained countryside trails, vineyard, olive groves and shepherds’ paths of compressed dirt and stone, and even sections of the famed Camino de Santiago de Compostela. Generally, the walks in Venice, Florence and Rome are level, and the paths through the Chianti countryside are gently rolling with some elevation gain and loss.
To See Mileage Daily, Download Full Itinerary

Dates & Prices

The earlier you book, the more options you’ll have and the lower your price. Secure your spot with a deposit of just $500 per person at the time of reservation. Plus, you can always change your mind — there’s no fee to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Hotels

We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

Rome Times Hotel

A perfect example of modern Italian design, this sleek hotel is just a few minutes’ walk from Trevi Fountain and the Spanish Steps. The spacious, bright rooms offer extra-plush beds, elegant bathrooms, and double soundproof windows.

Hotel Saturnia

This historic 4-star hotel is just a three-minute walk from Piazza San Marco, about as perfectly located as you can be in Venice! Parts of it date back to the 14th century, and the same family has owned it for over 100 years.

Ca’ Sagredo Hotel

Ca’ Sagredo Hotel is a private palazzo, a noble residence, a museum, and a stunning luxury hotel. Perfectly-sited alongside the Grand Canal, enjoy the classic Venetian styling and warm Italian hospitality during your upscale stay.

Villa Le Barone

This historic home dates to the 16th century, and your hosts are a count and countess. Its rooms have wood-beamed ceilings and antiques. The property boasts lovely gardens, a new saltwater infinity pool, and a terrace for sunning and Chianti sipping.

Borgo Di Vescine

This charming inn is built within the dwellings of a 13th-century Etruscan village in the heart of the Chianti region. Each room is one of the original houses, updated with modern amenities. From the pool, you’ll have stunning views of the Tuscan hills.

What’s Included

  • Meals: All breakfasts and five dinners.
  • Hotels: Award-winning boutique properties, thoughtfully selected for their exceptional location, design, history, and regional character.
  • Tour Leader(s): Expert guides who are your well-connected local friends and provide you access to people and places you wouldn’t find on your own.
  • Supplemental Experts: Additional regional guides and specialists on select tours.
  • Transportation: All land transportation as listed in the daily itinerary, including fares for trains, ferries, and other modes of travel.
  • Privileged Access Events: One-of-a-kind access to remarkable people, places, and experiences arranged just for you, as noted in the daily itinerary.
  • Admissions & Entry Fees: Entry to tastings, historic sites, and other scheduled activities listed in the daily itinerary.
  • Baggage Transfers: Upon arrival, we whisk you and your bags directly to your room—no waiting, no tipping.
  • Gratuities: All gratuities at hotels, restaurants, and for baggage handling.
  • Dedicated Guest Services Coordinator: Your pre-trip concierge and tour expert, available to answer questions and ensure you’re fully ready to get the most out of your tour.
  • Equipment: Premium gear and expert guides for kayaking, rafting, glacial hiking, and snorkeling as outlined in the daily itinerary on select tours.
  • Perfect Pairings Dinner: A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.
Not Included: Tour Leader gratuities, travel to and from your trip’s start and end points, and any meals or activities taken independently.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, "Classic Journeys provides unbeatable access to experiences around the globe." Here’s what that access means for you.

  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it’s closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including rainforest lodges, 16th century villas, and award-winning properties that show up on World’s Best and Gold lists.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.

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FAQs

Why is Classic Journeys the best tour company for Venice, Florence & Rome tours?
Classic Journeys delivers the most genuine and cinematic walking tour of Italy’s iconic cities—Venice, Florence, and Rome. You’ll explore with expert local guides (who will become your well-connected friends) and experience places and moments—from private gondola rides to hands-on pasta-making—that other travelers only dream about. Small groups, privileged access to legendary sites, authentic meetings wiht locals, and award-winning boutique hotels let you see, taste, and feel Italy at eye level, every step of the way.
Which sites does this Classic Journeys itinerary include?
This handcrafted itinerary is a masterclass in Italian highlights: strolling to Venice’s St. Mark’s Basilica, the Doge’s Palace, and gliding through the canals by gondola. In Florence, gaze up at the Duomo’s terracotta dome, skip the line for Michelangelo’s David at the Accademia, and linger amidst masterpieces at the Uffizi. Rome sweeps you from the Colosseum (with special arena access) and the Roman Forum to timed entry at the Vatican Museums and Sistine Chapel—all curated with immersive experiences led by passionate local experts.
Do you secure skip-the-line/timed entry for popular sites?
Yes, every Classic Journeys guest enjoys timed or skip-the-line entry to legendary sites—no waiting at the Vatican, Uffizi, Accademia, or Colosseum. In each city, you’re led by expert local guides whose insider access and storytelling unlock hidden layers of history and culture, so your journey is seamless, enlightening, and truly unforgettable.
When is the best time to visit Venice, Florence and Rome?
The best time to visit Italy is in the Spring (April–June) and autumn (September–October), which are ideal for exploring Italy’s great cities. You’ll enjoy mild days, blooming gardens, and shaded piazzas, plus lighter crowds—all perfectly suited to Classic Journeys’ leisurely walking pace and exclusive encounters. We also have a special year-end trip to welcome the new year in style. Traveling with a small group means more room—and more magic—in museums, markets, and neighborhood trattorias.
How active is this cultural walking tour and is it suitable for families and mixed abilities?
You’ll walk two to seven miles daily, ambling over Venetian bridges, through Florence’s piazzas, and Rome’s cobbled lanes. The pace is relaxed, and routes are thoughtfully chosen for all abilities—families, kids, and mixed groups—so everyone can savor Italy’s beauty without missing a thing. Expect level city strolls mixed with gentle country trails for memorable nature walks together with an expert local guide leading the way.
Are culinary and wine experiences included?
Deliciously yes. You’ll dine like (and with) locals when you sip Chianti at a family-run Tuscan winery, try your hand at pizza or pasta-making in Rome, and wander lively markets. Dining is as local and authentic as it gets—gelato tastings, chef-led dinners, and meals with artisanal food makers are all woven into your journey. You’ll also enjoy Perfect Pairings Dinner: A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.
How many travelers are in each small group on your Venice–Florence–Rome tour?
Classic Journeys groups are truly small—usually fewer than 10 travelers and no more than 18. You’ll share incredible experiences in Italy with your travel companions, so every moment feels personal, friendly, and flexible. This cozy size allows special access and genuine camaraderie with fellow travelers and guides.