Yes, it's very possible to cover Italy and Greece in a single trip as they're close to each other. There are also many transportation options between the two countries.
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Brindisi is probably the Italian port most commonly associated with taking a ferry to Greece and has the most options. Frequent ferries leave Brindisi for Corfu, Kefalonia, Igoumenitsa, and Patras. It's possible to get between Brindisi and Corfu (the closest Greek port) in as little as six and a half hours.
The ideal number of days to spend in Greece depends on your travel preferences, interests, and the specific destinations you wish to visit. To explore multiple regions and get a taste of different aspects of Greece, a recommended duration would be around 7 to 10 days.
Looking for a connection with the closest Greek island from Italy? The Ionian island of Corfu is just 8 hours from the port of Brindisi! In 2023, you will be able to travel by ferry to the Greek islands of Corfu and Kefalonia from Italy.
Italy has more (easily accessible) history, a richer range of cuisine, better cooking and food tours, and more sightseeing opportunities. Greece has better beaches, a more relaxing atmosphere (especially on the islands), and cheaper food and hotels.
Italy's best travel months are May, June, September, and October. They're also the busiest and most expensive time to visit (with the north remaining just as busy throughout midsummer). Crowds aside, these months combine the convenience of peak season with pleasant weather.
The best time to visit Greece is outside the busy summer peaks, during spring (April to June) and early fall (September and October). Temperatures are warm but not stifling, and you'll find that destinations are open but still relatively quiet.
Santorini is best known as a romantic island with one-of-a-kind views, whereas Mykonos is more about sandy beaches and spirited partying. Depending on the vibe you seek, both islands suit holidays à deux. Solo travellers and groups of friends will also find both appealing, though Mykonos offers more in terms of edge.