Italy and Greece Itinerary

Greece › Itinerary for Italy & Greece
By Santorini Dave

Planning a Trip to Italy and Greece

For a first trip with two weeks, I’d visit Florence, Rome, Athens, and Santorini. Take the high-speed train within Italy and fly between the two countries. With 7 to 10 days, pick one country and stick to it.

• Two weeks: Four bases work well. Don’t try to fit Venice, the Amalfi Coast, and several Greek islands into the same trip. Two weeks is the minimum to visit both countries, and even then it will feel rushed.
• Three weeks: Add Venice and Naxos or Paros, or give Crete five or more nights.
• Best months: June and September for sightseeing and island time. September has warmer seas. July and August are hotter and busier; May and October are good for sightseeing, with less reliable beach weather.
• Flights: Arrive in one country and leave from the other. If possible, don’t waste time backtracking.

Two Weeks in Italy and Greece

This route is 14 days and 13 nights, including arrival and departure days. Long-haul flights may add travel days. Reverse order is fine.

1. Florence – 3 nights: Two full days for the city’s art, churches, and wandering. Take the high-speed train to Rome, about 1½ hours.
2. Rome – 4 nights: Three full days for ancient Rome, the Vatican, and neighborhoods. Fly to Athens.
3. Athens – 2 nights: A short visit for the Acropolis, Acropolis Museum, and historic center. Fly to Santorini to save time.
4. Santorini – 4 nights: Caldera views, villages, wineries, and a boat tour. Fly home via Athens, or fly directly to a European hub if it you can make it work.

Want more beach time? Replace Florence with 3 nights on Naxos or Paros, between Athens and Santorini. Choose Naxos for sandy beaches, villages, and local food; Santorini is the choice for caldera views.

Arrival and transfer days aren’t full sightseeing days. Book popular sights ahead, especially the Uffizi, Colosseum, Vatican Museums, and Acropolis.

Three Weeks or More in Italy and Greece

For 21 days and 20 nights: Venice (3 nights), Florence (3), Rome (4), Athens (2), Naxos or Paros (4), and Santorini (4). Travel south through Italy by train, fly Rome–Athens, then continue to the islands. Venice–Florence takes roughly 2¼ hours by high-speed train.

For Crete, replace the final two islands with Santorini (3 nights) and Crete (5). Use the seasonal Santorini–Heraklion ferry and concentrate on one part of Crete.

With four weeks, add an agriturismo stay in Tuscany or Umbria, Naples and the Amalfi Coast, or Matera. In Greece, consider Milos or Nafplio. Pick an addition that fits your route rather than trying to see everything.

Map of Greece and Italy with Key Ferry Ports

Getting Between Italy and Greece

For most travelers, flying is best. Rome–Athens operates year-round and takes about 2 hours. Direct flights from Italy to islands such as Santorini, Mykonos, and Crete are mostly seasonal; operating months and days vary. Don’t assume a route runs daily or throughout May–October. Search Google Flights for your dates. Outside the summer season, plan around connections through Athens.

Ferries make sense for western Greece or a trip with your own vehicle. Italy’s departure ports include Venice, Ancona, Bari, and Brindisi. Main Greek arrival ports are Igoumenitsa and Patras, with additional services to Corfu and Kefalonia depending on the route and season. Crossings take many hours, sometimes overnight.

There are no direct ferries from Italy to Athens, Santorini, Mykonos, or Crete. Don’t treat an Adriatic ferry as a shortcut to the Cyclades. For Greek island hopping, check the actual sailings before fixing hotel dates, especially outside summer. Leave at least a night between your last ferry and a separately booked flight home.

One Week in Greece

For most first-time visitors, I’d choose Athens and one island.

• Athens and Santorini: 3 nights in Athens, 4 in Santorini. Fly between them.
• Beaches and views: 4 nights in Naxos or Paros, 3 in Santorini. Check flights via Athens and the ferry between the islands before choosing the order.
• Nightlife and views: 3 nights in Mykonos, 4 in Santorini. Best when seasonal international flights and the inter-island ferry fit your dates.
• Crete and Santorini: 4 nights in Crete, 3 in Santorini. Use Heraklion for the ferry connection. Flying into Chania adds a substantial drive across Crete; four nights is enough for one region, not the whole island.

One Week in Italy

For most first-time visitors, I’d choose Rome and Florence.

• Art and history: 4 nights in Rome, 3 in Florence. To include Venice, make it Rome (3), Florence (2), Venice (2). That’s a fast trip, so you’ll need to skip the Tuscan day trips.
• Northern Italy: 2 nights in Venice, 2 in Milan, 3 on Lake Como. Fly into Venice and out of Milan.
• Rome and the coast: 4 nights in Rome, 3 on the Amalfi Coast. Travel via Naples; flying home from Naples saves backtracking.

See Also

• Where to Go in Greece
• Complete Greece Travel Guide