Traveling in October 2026 - Ideas - Last minute

A friend and I had a great time 2 years ago starting 2 nights in Trieste. Other stops we made were 4 nights in Padua with day trips to Treviso and Vicenza. Driving from Padua to Bolzano on the Great Dolomites Road ( https://goo.gl/maps/xgcsztYzs8w WOW!). 2 nights in Bolzano and then driving to Verona for 2 nights. Weather was beautiful, food fantastic, sights unbelievable.

We had more time than you do so we continued to Bologna, Turin, Barbaresco (Alba truffle festival and wine town visits) and took the Skyway Monte Bianco in Courmayeur.

I made a trip to Abruzzo last March and assume October would have same type weather. Remarkably scenic area. Great regional food, beautiful beaches.

I've been to Greece from late Sept to mid Oct several times and found it a great time to be there as the main tourist season is over, the weather is comfortable without the heat of summer and the Aegean still warm for a beach day.

You may want to concentrate larger islands like Naxos that is the largest of the Cyclades or Crete which is the largest of the Greek Islands.

There are several others such as Chios, Lesvos, Lemnos (Northern Aegean Islands) that have a nice Greek vibe and and still under the radar for most first time visitors.

Don't overlook the Peloponnese which has just as much to offer as any island if not more as it's a large area with a wealth of history, architecture, mountains, beaches, villages, etc. to consider.

All would have more than enough to meet your needs.

I wouldn't hesitate going to Greece mid-to late October.

The end of the peak tourist season in Greece starts around mid-October. During the second half of the month, the weather is generally nice enough for swimming. That said, while Paros and Crete work for that, Santorini isn't really a destination for swimming.

What people in Europe refer to as a "beach club" is more akin to international all-inclusive resorts offered by travel agencies. There's no point in looking for that in Greece, you’ll find everything you need, and much better without staying in that kind of place.

Crete is so huge that you'll find a bit of everything there. If you don't stay for at least a week you'll only see a tiny fraction of it (it doesn't even feel like an island).

The whitewashed houses are in the Cyclades island group (which includes Paros and Santorini).

You have nothing to worry about if you're allergic to fish in Greece, aside from octopus, fish is very pricey in restaurants. You'll have tons of food options, even if you don't eat meat either, and Greeks are bigger fans of grilled meat than Sicilians. :-)

Everything is open year-round in Greece, even on the smaller inhabited islands. Starting in mid-October, it's the beach facilities that begin to close down. Towns and villages go about their usual routines, just with fewer tourists.

The islands you mentioned all have airports with flights from Athens, you won't be able to get from one island to another except by ferry. Ferry connections are less frequent than in summer, but the main routes operate year-round to serve the islanders' needs.

Italy is great too, it’s a different country and a whole different world. Whether you go to Italy or Greece, it’s a deliberate choice based on what you’re looking for.

We're headed for Greece next week (will be away for 3 weeks, mostly Crete plus Rhodes, a couple days on Santorini, then flying home with a few days' stopover in Tbiisi, Georgia).

Late September into October is my favorite time of year to visit southern Europe. Last year we spent the same time period in Puglia; the previous year roughly the same time in Corsica; the year before that we did Malta + Istanbul. Loved each one of those trips, and felt like they were timed quite nicely.

The only hard part about it is we depart home feeling like it's late summer, when we come back it seems jarring to be immediately running the Halloween-Thanksgiving-Christmas in-your-face gauntlet...like we pressed the pause button on real life, then when we come home, everything is moving in super-fast-forward speed and we are not quite ready for it. YMMV.