Need help deciding between a few different places!

How long is your trip? That is a lot of traveling around to places quite far from each other.

At the named places 80% of local culture died already around 30-40 years ago.
Officially of course not.

Have you scoped out your transport for getting from place to place yet? Let us help you flesh out this itinerary and then see what else you could fit in.
May is early for swimming.

Huh these places are reasonably far apart & you're going to be spending 3 days transiting just inside Europe to get to these 3 different islands / countries. How many weeks EXCLUDING arrival and departure days? Skip Gran Canaria, it's off the coast of N Africa & quite a ways from the other destinations.

Have you actually looked at flights? Use Google flights, search on destinations & prices may help you figure out where to go in what order. Make it a multi-city flights, so you can fly in to one place & out of the other. Make sure you're not there over May 1st , Labor day, & the weekend before or after, many many people have the entire week off.

Personally, i would focus on the absolute musts you've already identified, May should be OK for swimming in Sicily, I've swam May 1st in the Amalfi Coast but it wasn't warm. Sicily seems like a winner, lots to do, lots of beaches, use Search bar at top for more ideas, a very cursory glance found these - https://community.ricksteves.com/travel-forum/italy/favorite-sicilian-beach-town. Agreed with valadelphia, May is early for swimming, it's not going to be WARM, so if that's a must, maybe skip something (Spain?) and add Greece.

Ischia, Gran Canaria, Crete, or Cyprus. - Well, since you've mentioned Montepulciano, (WHY? To drink wine? Sample hilltop town in Tuscany?) which you can access from Rome but pretty sure there's not a train all the way to this hilltop town... so you'd probably rent a car (somewhere?? Perhaps from FCO), drive there & back & then take train to Ischia on a LONG day. (Others may suggest someplace closer to it to rent a car.) Ischia is probably the least touristy place you've mentioned. Good luck! Get back to us as you book flights, will be interesting to see how you route it!

lagergren.9
Ischia will probably be the least touristy. Also the most relaxing. Don't know about the nightlife though.

As one of our other posters pointed out on a different thread recently, there's a conflict between "not too touristy" and "cool beach bars/nightlife".

I too wonder how long you have for this travel given the distances between the locations. I see you have Montepulciano as someplace that is already set in your plans but I see it as somewhat of an outlier. You could maybe do this:

Barcelona to Ibiza by ferry (? is there one) or flight
Ibiza to Sicily via flight
Sicily to Naples via flight, then ferry to Ischia

Have you researched any of the transportation between these locations?

Hi guys, thank you for all the helpful responses! We will be going for around 20 days. That definitely makes sense that having good nightlife and not having tourists kind of clash. We wanted to go to Montepulciano because we wanted somewhere in Italy wine country that was a little more laid back. It was hard to choose because there are so many little towns in wine country. I'm not sure if we will rent a car, but it seems like we might have to to go to Montepulciano. The reason we are thinking about gran canaria is because it would be warm enough to go in the water and lay out on the beach. I've looked at some flights, and it seems like Cyprus is kind of harder to get to.

You really have plenty for 20 days already if you consider getting to and from and day trips. How many days did you have lined up for each place?
Maybe start in Sicily or Tuscany, end in Barcelona with Ibiza toward the end. OR vice versa, if you had no interest in partying in Ibiza (May might be a bit early)--since your best bet for swimming is probable one of the islands, and Sicily probably the better bet. I have swam off southern Tuscany in late May, but it's iffy.

Get your nightlife in Spain, your history/rusticity in Italy. Scenery galore everywhere

There are some relatively cheap flights from Barcelona to Ibiza and Gran Canaria. Barcelona is one of my favorite cities so that is definitely a must. I guess what we are looking for is a wine-country destination and a beach destination where it will be warm enough to lay out on the beach and maybe go in the water. I think we will also for sure go to Sicily- maybe Palermo? 20 days isn't a ton of time so I'm wondering if 5 destinations will be too much.

Thank you valadelphia! That sounds like a really good plan and I appreciate your help! Do you think we should eliminate Crete & Cyprus then and just focus on Italy and Spain?

Your original post says "We are already set on going to Barcelona, Ibiza, Sicily, and Montepulciano" so most answers are taking it for granted that those will already be included. Since you could spend 20 days just in Sicily, I would work on the overall itinerary and then figure out where to fit in a beach. You could definitely do that in/near all the places on this initial list, provided we get a warm May (again, definitely toward the end).

Do you think we should eliminate Crete & Cyprus then and just focus on
Italy and Spain?
YES, absolutely!

Ischia has some nice beaches BUT it also has thermal spas. If you want some ideas on the spas, let me know.

Hi Linda, yes I would definitely be interested in ideas for thermal spas!

My time on Ischia was a day trip by high speed ferry from Sorrento in September 2012, so quite a while ago. but I do remember the day so well. Friend and I spent a very nice day at the Negombo thermal spa enjoying all of the various pools and having a nice glass of limoncello on the beach facing the spas.

As I said, it was just a day trip and predominantly a day at the spa as I did not explore Ischia other than my time at Negombo.

Attached is a general link to descriptions of the various thermal spas located on the island.

https://www.ischiainsider.com/en/e/thermal-baths-and-spas-on-ischia

There are some relatively cheap flights from Barcelona to Ibiza and Gran Canaria. Barcelona is one of my favorite cities so that is definitely a must. I guess what we are looking for is a wine-country destination and a beach destination where it will be warm enough to lay out on the beach and maybe go in the water. I think we will also for sure go to Sicily- maybe Palermo? 20 days isn't a ton of time so I'm wondering if 5 destinations will be too much.

Whew, so glad to see you're narrowing your choices down, perhaps just Spain & Italy for a 20-day trip on the ground? Which you can easily fill with sun and fun! So how about Barcelona, Ibiza (have you checked the water temperature? Might still be chilly!) & Sicily? Maybe you're aware, but Sicily is a quality wine producer, so you could skip the hassle & travel of getting to a Tuscan hill town, you should be able to find a nice vineyard to visit in Sicily! Here are some links, use the search bar above for more.

https://community.ricksteves.com/travel-forum/italy/wineries-in-sicily-46db6939-e602-4a04-a6ea-dd6ea2b51a28

https://www.ricksteves.com/travel-tips/travel-classes/monday-night-travel/italian-wine

We decided not to go to Ibiza anymore because it seems very overpriced. We also are more into bars than the clubs that are packed to the brim and play EDM music. We also eliminated Gran Canaria for sure. If anyone has recommendations on other places to go let me know!

Barcelona, Ibiza, Sicily, and Montepulciano, Ischia, Gran Canaria, Crete, or Cyprus? You might want to look on Google Maps to see where all these places are located.

Ibiza and Barcelona have beaches, and they're both very good for nightlife. Sicily not so much and Montepulciano is off the beaten path south of Siena, Italy.

You might want to do some more research and try to go to places that are closer together and where travel between cities are more efficient. And by the way, distances between the cities listed are quite long.

We changed it so we are only staying in Barcelona and Sicily. We are flying into Palermo and will spend a couple of nights there and in San Vito Lo Capo. Does anyone have any recommendations for things to do in Sicily or vineyards to visit there?

-not too touristy (we want to experience the local culture)

Wrong list to fit that criteria.

I didn’t see this post before, but here’s 2 cents worth now:

Sicily - down by the southern coast, be sure to make a visit to the Valley of the Temples, by Agrigento. It has lots of Greek temples (from when Sicily was part of ancient Greece), all in better shape than the temples in what’s now Greece. There’s also Segesta, with an amazing ancient temple and a theater, between Erice and Palermo. Much of the interior of Sicily is very rustic, but away from beaches.

Cyprus was on our agenda for January, but got canceled for another time. The northeastern part is controlled by Turkey. The southern part is Greek, with more places for entry.

Crete was a fantastic 3-week trip in 2019. Many places had beaches, as well as sights from the Minoan society, much older than ancient Greece. In particular, Kato Zakros (far southeast corner) had ruins and gorges for exploring, plus nice, black sand beaches and very few visitors/tourists.

Another potential big island in the Mediterranean is Sardinia, part of Italy but with its own culture. There are extremely Ritzy beach locales in the northeastern part, but much more reasonable places everywhere else. Historic Nuraghe throughout, that you won’t find anywhere else on Earth. More rustic than elsewhere, too, but beach after beach opportunities. We’re going next month!

Hi Cyn,

Thank you so much for the information! We have decided to avoid traveling to a lot of places and just spend 10 days in Barcelona and 9 days in Sicily. We are staying in Palermo most of the time, but we are going to San Vito Lo Capo for 2 days. The valley of the temples looks really interesting. Would you say it could be a good day trip? Also, have you been to any wineries in Sicily? Thanks!

Hey, it's great you've taken some advice along the way & aren't cramming in additional out of the way places (like Montepulciano) that are harder to reach without a specific need to go there! Two places with lots to do, have you booked your hotels / airbnb's? (I don't recall when you're traveling, but if it's sometime this year, I would work on reservations after booking flights - Multi-city would be the way to go, into Barcelona & out of Sicily, you can buy a cheaper ticket inside Europe.) Enjoy!! LOTS of threads on Sicily, day trips from Palermo, wine & the region around Palermo, use the search bar above. PS, Here's a great list of threads about Sicily, with info about smaller towns & getting around. https://community.ricksteves.com/travel-forum/italy/2-weeks-in-sicily

OP says they're going in May! Yikes! I do hope they've booked their flight and are at least looking at lodging.

I also agree with everyone that their shortened itinerary is far superior to the original plan.

From your list Crete is a good choice. It's a big island, and you can easily go to the parts that are not over-touristed and still have plenty of authentic culture. I'd focus on the west end of the island, has all the things you're looking for.

But your current itinerary sounds great of course.