The best of Sicily Tour
Experience Sicily by Travelling Across the Island
10-day small-group journey • up to 10 guests • depth over rushing
This small-group journey is designed for travellers who want to experience Sicily in depth, combining the iconic highlights with places and moments most travellers don’t reach. Over 10 days, we travel across the island in a loop staying in a series of carefully chosen locations — from the east to the north-east, into the interior, and down to the south and south-east. Each stop offers a different perspective, from historic towns and archaeological sites to quieter corners shaped by local life. Nature and food are part of the journey throughout — from local markets and regional dishes to moments like a long lunch in a family-run agriturismo in San Angelo Muxaro, set among olive trees in the Sicilian interior. One full day is dedicated to the Aeolian Islands, adding a different dimension to the journey, shaped by volcanic landscapes and a slower island rhythm.
Continue your Journey across Sicily
For those travelling in autumn, this journey can continue into Western Sicily — a part of the island that feels different. The structure remains similar, but the setting shifts: smaller towns, quieter coastal landscapes, and experiences that feel more remote and less visited. Some guests choose to combine both journeys to experience Sicily more fully, without compressing it into a single itinerary. If this is something you’re considering, mention it in the waitlist form below.
Dates for 2027
3 - 12 May & 27 Sept - 7 Oct
The Best Of Sicily Tour Itinerary
DAY 1 ⎯ Catania · Taormina · Milazzo
Pick up in Catania. Visit of Taormina town and its Greek theatre. Transfer to Milazzo for welcome dinner.
DAY 2 ⎯ Eolian islands (Lipari + Vulcano)
Full day trip by ferry to Vulcano and Lipari, with a choice of crater walk or coastal time, then transfer to Cefalù.
DAY 3 ⎯ Cefalù · Monreale · Palermo
Guided walk of Cefalù and free time. Visit of Monreale Cathedral, then arrival in Palermo.
DAY 4 ⎯ Palermo
Walking tour of Palermo including street food market, cathedral visit. Free time in the afternoon and evening.
DAY 5 ⎯ San Angelo Muxaro · Valley of the Temples
Off-the-beaten-path village experience with local tastings and lunch in an agriturismo. Guided visit of the Valley of the Temples.
DAY 6 ⎯ Piazza Armerina · Ragusa Ibla
Visit of the Roman Villa mosaics, then transfer to Ragusa Ibla with town exploration.
DAY 7 ⎯ Ispica · Scicli
Walk through the Ispica canyon and caves, followed by Scicli visit and a local herbs experience.
DAY 8 ⎯ Noto · Syracuse
Visit of baroque Noto and the Neapolis archaeological park in Syracuse.
DAY 9 ⎯ Ortigia
Guided walk of Ortigia with local food experiences and farewell dinner.
DAY 10 ⎯ Departure
After breakfast transfer to Catania airport or train station.
👉 Full itinerary details are shared once you join the waitlist.
Pricing Information
€4,740 per person in private room. €4,270 per person when sharing a twin or double room.
What's included
✔ 9 nights in carefully selected 4★ hotels with continental breakfast
✔ 5 dinners dinners and 4 lunches featuring local cuisine
✔ Local tastings and food experiences throughout the journey
✔ Guided walks in Sicily’s most iconic towns and hidden villages
✔ Guided visits to key archaeological sites and cultural landmarks
✔ Aeolian Islands day trip (Vulcano & Lipari, including ferry)
✔ Walking experience in the Ispica canyon and caves
✔ Sensorial herbs experience in Scicli
✔ All entrance fees to included sites
✔ Private driver and transport throughout the journey
✔ Transfer to Catania airport or train station on departure
✔ English-speaking tour leaders throughout the tour
👉 Full details are shared after joining the waitlist.
What's excluded
❌ Flights to from Catania Airport.
❌ City Tax (paid locally)
❌ Travel Insurance for Italy.
❌ Tips for Tour Leaders and Driver.
❌ Anything not listed under “What’s included”
Before and during the journey
🌿 Two group Zoom calls to help you prepare (flights, logistics, what to expect).
🌿 A private group to connect with other travellers before departure.
🌿 A dedicated WhatsApp group for updates and easy communication throughout the trip.
👉 You’ll feel supported both before and throughout the journey!
Is this Journey right for you?
This journey suits travellers who enjoy being active and exploring a destination by moving through it, rather than staying in one place. You’ll feel comfortable on this journey if you:
✔ Enjoy moderate daily walking (around 2–4 hours), sometimes on uneven terrain such as cobblestones, paths, and archaeological sites
✔Are generally fit and comfortable being on your feet for several hours across the day
✔ Are happy changing base and experiencing different parts of the region,
✔ Enjoy being part of a small group, while still having space to do your own thing within a shared rhythm
Most of our guests are women travelling solo, or come with a friend or partner, and are aged 45–70.
Join the Waitlist
❣️ If this journey feels aligned, you can join the waitlist to access full details and early booking.
→ Places are limited to 10 guests.
🔹 Early-booking benefits are reserved for those on the waitlist.
This journey can also be combined with the West Sicily Tour for a more in-depth experience of the island.
👉 You’ll receive the full itinerary, booking details, and early-booking benefits before bookings open. Joining the waitlist gives you the option to review everything first and decide if it’s right for you.
THE MOST FREQUENTLY ASKED QUESTIONS
Bookings are typically confirmed around 6 months before departure. Because we work with small hotels and trusted local partners, early planning is essential. These journeys are best suited to travellers who are comfortable planning 9–12 months ahead.
Joining the waitlist does not commit you to the journey.It gives you early access to full details, pricing, and the best level of support while you consider whether it’s the right fit. Guests who join during the early-bird window also receive additional benefits, including early-bird bonuses and savings on the deposit. You can still join later, but those who plan early usually benefit most.
This is an active journey with daily walking of around 1–3 hours. You’ll walk on a mix of cobblestone streets, steps, and natural paths. A good level of mobility and comfort on varied terrain is important. There is one longer walk (Vulcano crater), which is optional.
Yes! The majority of our guests, about 80% travel solo.You’ll be part of a small group of like-minded travellers, and private rooms are always available.
All core activities are part of the shared experience of the journey. For longer walks an optional activity is offered. Each day also includes free time, from a couple of hours to free evenings for dinner.
No! Flights are not included.
Guidance on flights, timing, and travel planning is provided during the preparation phase, including the group Zoom calls before the journey.
Not sure yet?
If you have a quick question before taking the next step and joining the waitlist, you can reach out below.
Testimonials
Here are extracts from some of testimonials we received from our lovely guests. If you want, you can read the full testimonials or watch the live testimonials (short videos of 1-4 minutes).
...The experience of this tour will be one I will never forget, nor the wonderful women I met! I believe the tour was good value for money. I never expected to see so much in 10 days!...
Catherine P. | Hamilton, BERMUDA
....the Best of Sicily Tour was a perfectly planned trip. It hit all the highlights, as well as those out of the way places and local people that you will never find in guidebooks or online. I highly recommend it. Very reasonably priced and good value for money. For sure I’ll be back. ....
VIVIEN T. | New York, USA
....My trip to Sicily with Rocky Travel was by far the best trip I’ve been on as a solo traveler! This trip did not disappoint. I recommend for anyone who likes a small intimate group of like minded people to seek out Michela at Rocky Travel and plan your trip to Sicily! ....
Lucy C. | Virginia Beach, USA
....This was my first tour, and I wondered if I'd like it. I'm now a big fan of small group tours with hand-picked like-minded travellers. I'll be looking out for more!...
Marion H., | Adelaide, AUSTRALIA
....The tour takes you on a wonderful journey through Sicily. And the whole experience has been incredible. I give this tour a ten out of ten. I highly recommend it to anyone, any lady who wants to experience the flavours of Sicily and amazing sights. ....
Kathy M., | Tweed Heads, AUSTRALIA
...I thoroughly enjoyed my trip to Sicily. Travelling with Rocky Travel was so easy and well-organized. Michela always ensured we had enough time to see everything while bonding with other women travelling in the group. The accommodations were well chosen and often located where walking into town during our free time was easy. ....
MARIE-JOSÉe V. | Toronto, CANADA
Read All Guests Testimonials from the Best of Sicily Tour from 2019-2025.
Images from our Best of Sicily Tour
Considering this journey?
→If this feels like the right way for you to experience Sicily, you’re in the right place!
I personally read and reply to every message. Places are limited to 10 guests.
Check all other Mediterranean Tours and our Italy Small Group Tours For Over 50.
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