Italy, Greece
& Türkiye

An eighteen-day voyage through the ancient heart of the Mediterranean, from the canals of Venice to the cliffs of Santorini.

Map of Italy and surrounding countries showing travel routes: a blue cruise route along the Italian coast with ports in Catania, Messina, and Naples; a red air route from Venice to Rome; and an orange train route from Florence to Venice and Rome.

Duration

18 Days

Countries

4 Nations*

Destinations

7 Cities

*Fun fact, the Vatican is the smallest nation in the world, covering just 109 acres.

— THE JOURNEY —

Where ancient worlds meet the open sea

This trip was built around three generations, including kids, parents, grandparents, aunts, and uncles. Eighteen days across Italy, Greece, and Türkiye, cities on land, islands by sea. We've taken this route ourselves and built this itinerary around what actually made it unforgettable. We handle all the research, so you avoid the overwhelm of planning.

This itinerary weaves together the greatest treasures of southern Europe and the eastern Mediterranean. It is an experience that begins in the unforgettable canals of Venice and builds, city by city, toward the infinite blue of the Aegean Sea.

You'll walk the corridors of the Vatican, stand before Michelangelo's David in Florence, drift through the whitewashed villages of Santorini, and wander the ancient ruins of Ephesus, all on a single, seamlessly orchestrated journey. From timed entry at the Vatican to private transfers from your Rome hotel to the port, every detail is carefully crafted to align with your group. In the same way we approach all of our trips, nothing is left to figure out on the ground.

Your Destinations

ITALY

Venice

View of a canal in Venice, Italy, with colorful historic buildings lining the water, boats docked along the edge, and a lamppost illuminating the scene at dusk.

Venice rewards people who slow down. Venice can be overwhelmed with day tourists from cruises and trains, which can ruin your experience. By spending several nights in the city, you can skip the crowds in St. Mark's Square at peak times and explore the neighborhoods most tourists don't bother with, then you can visit the major attractions when they are least busy and enjoy them even more.

  • Doge's Palace

  • St. Mark's Basilica

  • Murano & Burano

  • Jewish Ghetto of Venice

  • San Marco Museum

Florence

Aerial view of Florence, Italy, featuring the Florence Cathedral's bell tower with detailed marble design and the cityscape with terracotta rooftops and rolling hills in the background.

ITALY

The cradle of the Renaissance, Florence is a city that transforms the way you see art forever. The city is very walkable, and you can see unique architecture like the Baptistery or sit in a piazza and enjoy the sculptures. From Michelangelo's David to Brunelleschi's soaring dome, every corner reveals a new masterpiece of human creativity.

  • Accademia Gallery — Michelangelo's David

  • Brunelleschi's Dome (all 463 steps)

  • Florence Baptistery & Santa Reparata

  • Opera del Duomo Museum

Rome

Close-up view of the Arch of Constantine in Rome, Italy, with detailed sculptures and carved reliefs, set against a blue sky with scattered clouds and surrounded by green trees.

ITALY

A day trip to Rome doesn’t even begin to touch the surface of all of the history, architecture, and art. But, when planned right, you can fit most of the major sites in five days and still have time to experience the culture by wandering through piazzas filled with markets or enjoying a cappuccino and fresh-baked pastry. With 2,000 years of history, there are plenty of sites you may have seen in photos, but they are even more magnificent in person and are even better when shared with family or friends.

  • Colosseum, Roman Forum & Palatine Hill

  • Vatican Museums & Sistine Chapel tour

  • St. Peter's Basilica

  • Pantheon

MEDITERRANEAN CRUISE

View of the Aegean Sea from Santorini, Greece, with blue-domed churches, white buildings, and boats on the water.

Most cruise passengers spend their port days boarding buses and wandering in the same tourist cluster. The beautiful ports of the Mediterranean deserve better, and we help you avoid feeling like you’re in line at an amusement park. Although you can’t avoid the crowds entirely due to the size of the islands, we pre-book private guides and skip-the-line access to ensure the time ashore is spent experiencing the culture.

  • Santorini — private chauffeur for 5 hours

  • Ephesus, Türkiye — skip-the-line private tour

  • Mykonos — full day ashore wandering

  • Naples/Capri — Pompeii guided tour

  • Scenic days at sea

Practical Information

Everything you need to know before you go and while on your trip.

Flights

International flights arrive in Venice and return via Rome. Domestic transfers to airports are coordinated in advance for your entire group.

High-Speed Rail

City-to-city transfers within Italy (Venice → Florence → Rome) are on the Frecciarossa high-speed network, fast, comfortable, and scenic.

Accommodations

To maximize your time, we strategically identify lodging that aligns with your style and itinerary and avoids the wasted time and energy of being off the beaten path, unless that is what you want.

The Cruise

Your cruise departs Civitavecchia (Rome's port) on Day 11. Private ground transport from your hotel is arranged, so you can enjoy your last latte in Rome, and just show up.

Activities

When travelling to Italy, pre-booking all major attractions is a must to ensure entry. We will secure tickets and guides, so you spend your time experiencing, not waiting.

Local Tips

Before your trip, we'll share important details about your destination, including local etiquette and any local tourist taxes that must be paid in local currency.

This itinerary works beautifully for multi-family groups and multigenerational trips. With enough variety that everyone finds something that's theirs, and enough structure that no one has to figure anything out alone. If this sounds like your kind of trip, let's talk.

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