Sicily/Malta Itinerary Input for Fall 2027 - Experience and suggestions?

Just a point to ponder: I’ve been to Malta, and I had a fine time and it has some fine qualities, but if I were choosing whether to stay 17 days on Sicily or split it with Malta, I’d choose Sicily only every time. And I have not even been there yet, just based on many trips to Italy and that one visit to Malta. If you have a strong desire to see Malta on this trip, of course just ignore me.

Re: Sicily - Can’t quibble too much as you’ve clearly thought through this itinerary and have plans all along the way. The pace is nice, and feels like there’s some built-in flexibility.

My only impulse is that Palermo gets some short shrift while you have like 4 whole days in Trapani. I haven’t been, but it feels like overkill. The town itself is small, and Erice is probably worth a day but you’re also up there in a snap from Trapani. A full day and two nights in Palermo is decent, but also means you’re not seeing Monreale. Personally, Palermo is one of my top underrated cities. I’d love to see it get another day here. I think you’d enjoy comparing its three big markets, they each have a different vibe.

Also, Villa Romana is one of the singular sights on the island and as Roman sights go one of the best anywhere. I feel like a lot of folks making plans on this forum are prepared to pass by it, but it’s absolutely worth the few hours detour.

We just got back a week ago from Sicily. I recommend you spend more time in Palermo and less in Trapani. In Palermo, we took the Streety market food tour for 3 hours and I highly recommend this. We ate at a Michelin rated restaurant called Palazzo Bracaforte which was excellent. Two appetizers, two entrees, one desert and a bottle of wine for under $150. We also stayed in Ortigia and took a boat tour of the coves and caves with swimming. From Trapani, another 8 hour boat tour to the Egadi Islands.

Thank you for this feedback. I was fluctuating between 3 and 4 days in Trapani. We are a group of 4 - 2 couples, who travel a good amount together. We are in our late 60's to mid-70's. We have enjoyed bigger cities but tend to like a slower pace of travel these days. The points about Palermo are well taken and I could easily add a day to Palermo doing a 3 Palermo, 3 Trapani, 1 Agrigento, 4 Ortigia. Is there a specific neighborhood or area you would recommend in Palermo that might be a little more self-contained for dinner and wandering in the evenings - I'm thinking of how we stayed in Trastevere when we were in Rome.

As far as Villa Romana - I'm wondering if we could do this as a detour on our way from Agrigento to Ortigia. Looking at Google Maps, it looks like we would add about an hour of driving time. We could get out mid morning, go to the villa for a couple of hours and arrive in Ortigia in the late afternoon. Otherwise it looks like 4.5 hours of driving from Palermo.

I love the recommendatins for the Streety food tour and the boat tour out of Ortigia. Both are definitely our type of activity.

Malta is on the list for a couple of reasons and important to the group. I'll let you know if we decide we should have just dedicated it to Sicily.

We stayed in Palermo for 2 nights in June, 2022 and it was wonderful, can't wait to go back. We drove rental cars to get to the city but dropped them off at the train station and took a taxi to our apartment, then walked everywhere else. We (5 adults) stayed on Via Gaetano Sgarlata, between Via Bari and Via Bandiera. It was a great location, walkable to so many sites but fairly quiet since it's on a side street. If you look on google maps you'll see an apartment (Ai Mori di Maqueda). It was 3 br, 2 ba. Wonderful hosts. I liked everything about the apartment. It's currently listed on booking.com with only 7 reviews but you'll also find it on AirBnB with many years of excellent reviews. That area may be a great place to base.
We also stayed in Ortigia for 2 nights at the beginning of that trip (couple, 60's). I loved Ortigia and would have considered staying longer but I'm not sure I would choose a self catering option there, because there are so many wonderful b&b type hotels and because eating out is a huge part of the experience there. If you are set on self-catering and can't find anything in Ortigia, staying in Siracusa and just walking into Ortigia is easy, and it might be easier for you to base in Siracusa for your day trips (getting a cab etc). We stayed in a B&B in Ortigia closer to the bridge and walked to the Archaeological park, ~2miles, very doable, although not the prettiest areas to walk through (safe, just boring.)

If you decide to keep Malta, I'd recommend flying rather than taking the ferry. It's a short, 35-40 minute flight from Catania, for under 50 euros each. A ferry is more expensive, takes longer, and most important, is subject to cancellation in bad weather -- like what's been happening all over Greece lately, at the same time you'll be traveling next fall.

Thank you. I will definitely check out that apartment. Based on input and further research I've adjusted the itinerary. I will continue to refine it so any further suggestions and recommendations are fun.
Palermo 3 nights - focus Palermo
Transition to Trapani - stop at Segesta
Trapani 3 nights: Options Egaedi Islands, Salt Pans and Marsala, Trapani and Erice
Transition to Agrgento:
Agrgento 1 night - afternoon/evening Valley of the Temples, stay at nearby argri-estate, late dinner at estate
Transion to Otigia - consider stop at Villa Romana of Casale on way
Ortigia: 4 nights: Options - explorre Ortigia/Siracusa, Full day inland Baroque Loop, Boat tour of sea caves, Noto valley - e-bikes and farm/vineyard
Transition to Malta -
Gozo: 5 nights at Farm villa with pool within wealking distance to Zaghra: Layed back - exploration of Gozo, 1 longer guide/driver day of mainland.

Lovely plan. A few thoughts from someone who plans Sicily trips:

• With no car, the long legs (Trapani → Agrigento, Agrigento → Ragusa) are where a private driver pays off. Buses are slow on those routes, and a driver can stop at Selinunte or a Marsala winery on the way.
• Late September is harvest time: Etna's north slope (Randazzo, Passopisciaro) has small estates that do lunch with the tasting. An e-bike vineyard ride there is a good half day.
• Near Agrigento, look at wine estates around Menfi or Sambuca di Sicilia for your farm stay.
• Ortigia: stay toward the southern tip or the Lungomare for quiet nights.

Happy to suggest specific estates by message.

Thank you Zoli. Based on input here and further research, I'm getting a better idea of the specifics and understanding of the island. If you have specific recommendations for estates, wineries or other local gems, they would be welcome. You mentioned the Etna vineyards. That seemed a little intimidating to coordinate so I was leaning toward the Val di Noto but would love to hear more on this choice. We like locally owned, immersive over bigger more formal. If you notice anything or have recommendations for the revised itinerary, also welcome!

Days 1 -3 (3 nights): Palermo touring the city neighborhoods, sights and markets with a possible excursion to Monreale.
Days 4-6 (3 nights) Transition to Trapani with a detour at Segesta on the way. Spend time exploring Trapani and Erice. Day trips to the islands either through a water excursion or to rent e-bikes and explore. And another day to the salt pans and Marsala.

Day 7 (1 Night): Agrigento overnight. We are now looking at Villa Athena for ease of accomodations and access to the Valley of Temples, but were thinking a local cooking class might work, then check in to do afternoon/evening at the Temples and return to eat at the Villa.

Days 8-11 (4 Nights): Ortigia: We will explore Oritgia/Siracusa, take an inland daytrip visiting Noto in the morning and Scicli for lunch and the afternoon. We were thinking of visitiong Romana del Tellaro on this day rather than trying to fit in Villa Roman de Castillo. Another day option is Val de Noto - renting e-bikes to explore the villages with lunch at a local farm or vineyard. Fuedo Maccari and Zisola Asienda were recommended elsewhere. Other options on this route would be a visit to the village of Marzimemi or Reserva Vendicari. Also on the table for consideration is a boat excursion to the sea caves.

Days 12-16 (5 nights): Malta: I am currently looking at 3 options for a 5 night base that includes Birgu (or Valletta), Xaghra Gozo, or Mellieha. They all have pros and cons. Gozo could make for difficult travel days to and from as well as excursion days being more challenging, but it is very appealing, Birgu would be the easiest for transition and and full country access and it would be charming in it's own right. Mellieha would be nice for an inbetween in terms of logistics but it isn't as appealing to us culturally and in terms of local accommodation options.

Thank you all.