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Crossing Sicily: A Hiking Adventure Across the Island
Date and group size

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Price is based on twin-share rooms. Choose how many members of your group would like to stay in single occupancy rooms during the trip.

Select your adventure protection

Redpoint travel protection
Weather shifts, flights cancel. Core and Premium include Redpoint travel protection to cover you when they do. Standard follows 57hours' booking policy. See full coverage
Every booking, whichever you pick
Cancel within 48h of booking 100% refund
Cancel 60+ days before departure (Any or no reason) 70% refund
Full coverage details
Basic Standard terms Most popular Core protection Recommended Premium protection
Cancel within 48h of booking
100% refund 100% refund 100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund 70% refund 75% refund
Cancel any time (Covered reason)
75% refund 100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p. Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p. Up to $100,000 p.p.
Basic Standard terms
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Rescue, evacuation, and medical coverage
Most popular Core protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
75% refund
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Recommended Premium protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
75% refund
Cancel any time (Covered reason)
100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Cancellation policy

The percentages in the table above are of the full trip price, not of what you’ve paid at the time of booking.

Cancellations made within 48 hours of booking receive a full refund on all plans, including booking fees and insurance. After the 48-hour window, your refund depends on your selected protection plan and when you cancel. Core and Premium plans extend your cancellation rights beyond the Standard policy:

  • With Core, a covered reason gets you 75% of your trip cost back — even the day before you go.
  • With Premium, a covered reason gets you 100% of your trip cost back — and any other reason gets you 75%, right up to the day you leave.
What counts as a covered reason
  • Sudden illness or injury — yours, a travel companion’s, or an immediate family member’s, confirmed by a doctor
  • Death of a traveler or an immediate family member
  • A natural disaster affecting your destination or your departure point
  • A government travel advisory against travel to your destination

Changing your mind isn’t a covered reason. Premium is the only plan that covers that. Documentation is required for all insurance claims.

Everything the travel insurance covers

Both plans include travel insurance through Redpoint Travel Protection. Core insures 75% of your trip cost; Premium insures 100%.

Maximum per person:

  • Trip cancellation — up to 100% of your trip cost
  • Cancel for any reason — up to 75% of your trip cost (Premium only)
  • Trip interruption — 150% of the trip cost limit
  • Trip delay — $200 a day, $1,000 max
  • Itinerary change — $250
  • Single occupancy supplement — up to 100% of trip cost
  • Missed connection — $1,000
  • Travel inconvenience — $250 each, $750 max
  • Pet return — $1,000 per pet
  • Baggage and personal effects — $2,500, max $300 an item
  • Baggage delay — $600, after 12 hours
  • Baggage delivery — $100 per trip
  • Emergency medical expenses — $100,000
  • Medical evacuation and repatriation — up to $1,000,000

These are maximums. What a claim actually pays depends on what you can document and on the policy’s exclusions — pre-existing conditions and undeclared activities among them. We’ll send the full policy wording with your confirmation.

Reserve deposit (30%) $0
Second Payment Amount: $0
Crossing Sicily: A Hiking Adventure Across the Island
Itinerary
Caltanissetta to Palermo (11 Days)
Date(s)
--
Number of travelers
1 Person
Cancel in the first 48h for free
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Travel and medical insurance available
Earn $0.00 Adventure credits
  • Join us on an 11-day hiking trip from Caltanissetta to Palermo, tracing Sicily’s historic paths through a landscape filled with stories. Begin in Caltanissetta's lively streets before venturing into the island’s rugged interior, where every day brings new encounters—whether it’s with ancient ruins, quaint villages, or breathtaking views. Feel the Mediterranean sun as we wander through rolling vineyards and fragrant fields, experiencing the authentic side of Sicily away from the crowds. Each stop offers a taste of local culture, with amazing meals and traditions that have stood the test of time. This is not just a hike, it’s an adventure that reveals the true spirit of Sicily!

    • We’ll meet in Caltanissetta and have a guided tour of the city center. Later on, we’ll have dinner and get ready for tomorrow.

      Meals: Dinner
      Accommodation: 3-star hotels, converted farms, agrotourism B&Bs or charming family-run hotels

      Noto beautiful town Sicily
    • Today, we will explore the natural protected area of Montegarufi, which is very interesting for its mining and geological heritage, and climb up to Monte Mimiani. We’ll transfer to an agriturismo accommodation, where we’ll spend 2 nights, enjoying delicious food, local products, fantastic wine, and more.

      Meals: Breakfast, lunch, dinner
      Distance: 23 km (14.3 mi)
      Elevation: +600 m (1,969 ft), -700 m (2,297 ft)
      Duration: 10.5 hours spent outdoors
      Accommodation: Agrotourism B&B

      Caltanisetta view hiking
    • We will climb to the beautiful natural area of the Serre, on the slopes of Cozzo Pirtusiddu, from where we can see most of the peaks of Sicily, all the way from the Madonie down to the Sicani mountains. We will also walk on mixed terrains and explore the towns of Vallelunga Pratameno and Villalba. We transfer from Vallelunga Pratameno back to our accommodation.

      Meals: Breakfast, lunch, dinner
      Distance: 18 km (11.2 mi)
      Elevation: +600 m (1,969 ft), -700 m (2,297 ft)
      Duration: 10 hours spent outdoors
      Accommodation: Agrotourism B&B

      Sicily village
    • We’ll hike the Antica Traversata Siculà trail to the Gulfa caves, known for their prehistoric heritage, and continue toward Alia, where we’ll catch our first glimpse of the Madonie peaks. From there, we’ll descend into the valley and climb back up before reaching the enchanting village of Roccapalumba, where we’ll settle in for the night.

      Meals: Breakfast, lunch, dinner
      Distance: 21 km (13.0 mi)
      Elevation: +500 m (1,640 ft), -700 m (2,297 ft)
      Duration: 12 hours spent outdoors
      Accommodation: Hotel/Agrotourism B&B

      Madonie mountains
    • Most of the day, we are going to be walking on shepherd tracks that follow Medieval royal roads. We will walk across extensive pastures and climb up to the amazing fortress of Vicari.

      Meals: Breakfast, lunch, dinner
      Distance: 22 km (13.7 mi)
      Elevation: +600 m (1,969 ft), -600 m (1,969 ft)
      Duration: 10 hours spent outdoors
      Accommodation: Agrotourism B&B

      View of the countryside, fields and hills in the region of Vicari
    • We will walk  across the Bosco della Ficuzza natural protected area following trails in the woods.

      Meals: Breakfast, lunch, dinner
      Distance: 12 km (7.5 mi)
      Elevation: +400 m (1,312 ft), -300 m (984 ft)
      Duration: 9 hours spent outdoors
      Accommodation: Agrotourism B&B

    • From the entrance to the Bosco della Ficuzza natural protected area we will we’ll walk to Cefalà Diana with its impressive Arab baths and the ruins of its castle. We will then walk to Marineo.

      Meals: Breakfast, lunch, dinner
      Distance: 15 km (9.3 mi)
      Elevation: +400 m (1,312 ft), -600 m (1,969 ft)
      Duration: 9 hours spent outdoors
      Accommodation: 3-star hotels, converted farms, agrotourism B&Bs or charming family-run hotels

    • We will first visit an impressive canyon with natural waterfalls in Marineo. Then, we will follow quiet country roads (mixed terrains) along the Sconzano river and walk across Misilmeri.

      Meals: Breakfast, lunch, dinner
      Distance: 14 km (8.7 mi)
      Elevation: +200 m (656 ft), -500 m (1,640 ft)
      Duration: 8.5 hours spent outdoors
      Accommodation: Agrotourism B&B

      small alcantara gorge, sicily
    • From Misilmeri, we will explore the Arbëresh area following down the Scala dei Muli to enjoy beautiful views of Palermo’s gulf from above. Then, we’ll head on to Palermo city center.

      Meals: Breakfast, lunch, dinner
      Distance: 17 km (10.6 mi)
      Elevation: +800 m (2,625 ft), -600 m (1,969 ft)
      Duration: 8 hours spent outdoors
      Accommodation: 3-star hotels, converted farms, agrotourism B&Bs or charming family-run hotels

      Palermo from above
    • After breakfast, you have a day off to enjoy the city and do whatever we want to do. Eat, drink, walk, sightsee, mingle with the locals, drink too many cups of coffee—the choice is ours alone.

      Meals: Breakfast
      Accommodation: 3-star hotels, converted farms, agrotourism B&Bs or charming family-run hotels

    • Our trip comes to an end! If you’d wish to extend your stay, please contact us so we can make further arrangements.

      Meals: Breakfast

    • Please note that there can be last minute changes due to unforeseen circumstances such as extreme weather, earthquakes, volcano eruptions, pandemics, and events of similar nature.

    • Included:

        • A certified hiking guide with extensive knowledge of the area
        • 10 or 11-day hiking adventure across Sicily
        • Accommodation for 9 or 10 nights in 3-star hotels, converted farms, agrotourism B&Bs, and charming family-run hotels (double occupancy)
        • All meals as in the itinerary — breakfasts, lunches, dinners (from dinner on Day 1 through breakfast on the last day)
        • Luggage transfer from accommodation to accommodation
        • Transfer as needed during the tour
        • Guide’s expenses
        • Support person with a car for any emergency during the hiking days
        • City/tourist taxes

      Add-ons:

        • Single occupancy room (available to add at checkout)

      Not included:

        • Flights to Italy
        • Train or private transfers to the meeting point on Day 1
        • Water and extra drinks
        • Anything not mentioned in the “Included” section above
        • Insurance — recommended, available to add at checkout
        • Guide gratuities — optional
    • This Sicily hiking trip is suitable for generally fit hikers with previous multi-day trekking experience, prepared for full days of 6–10 hours on the trail. The key factor to consider is the number of consecutive trekking days and the daily elevation gains and losses, which can be demanding even when the terrain itself is not technically difficult. Arriving in good physical shape—used to walks of similar distance and height gain—will greatly enhance your enjoyment of the journey.

      There are two itineraries available, check them out to see day-by-day distances.

      Most of the route follows easy trails, gravel roads, and occasional asphalt, but the daily distances and elevation changes make the trek a solid challenge. The longest day covers 26.4 km (16.4 mi), with up to 1,078 m (3,537 ft) of elevation gain. Check out the itinerary for a full day-by-day breakdown of distances and elevation changes.

      You’ll only need to carry a small daypack, as your main luggage will be transferred for you each day. And if at any point you need to rest or skip a section, your guides are there to support you and ensure you can rejoin the group safely.

    • Here’s a list of the equipment you need to bring:

        • Day pack large enough to carry all the items listed (around a 25-40L bag)
        • Hiking poles — optional
        • Water bottle or hydration bladder (2L capacity)
        • Comfortable hiking clothes
        • Spare clothes for layering
        • Waterproof rain jacket
        • Sunhat
        • Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
        • Headlamp or flashlight
        • Sunglasses
        • Camera — optional (but recommended)
        • Sturdy walking shoes or boots

      Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

      Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!

    • Your guides will provide accommodation at the most characteristic and comfortable locations in the area, within a 30-minute drive from the end of the walk. The accommodation level will be inevitably varied (3-star hotels, converted farms, agrotourism B&Bs, and charming family-run hotels), depending on what is available in the area.

    • Group sizes and pricing

        • For this hiking trip in Sicily, the usual client-to-guide ratio is 10:1.
        • It takes a minimum of 6 people for this tour to operate. The maximum group size is set at 10 participants.

      Hiking in Sicily can be arranged for larger groups. Contact us to make arrangements.

      Min. age requirements

        • If you are older than 18, you’re good to go.
        • Minors younger than 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.

      If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

    • The starting point of your Sicily hiking trip is either Caltanissetta or Palermo, depending on the itinerary you choose.

        • To get to Caltanissetta (11-day trip), most people fly into Catania Airport (CTA). From there, you can take a train to Caltanissetta or arrange a private transfer with your guides for an added fee. Alternatively, you can choose to fly into Palermo Airport. However, in that case, booking a private transfer with your guide is mandatory. If you would like to arrange a private transfer, contact us.
        • To get to Palermo (10-day trip), most people fly into Palermo Airport (PMO). From there, you can take public transport or a shuttle to Palermo—it will take you 30-40 minutes.
    • We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

      Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

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