In each edition of Trending-Now, we spotlight fresh itineraries and emerging slow travel experiences. October to December, Dream-Else focuses on immersive three-day itineraries designed for the curious, the mindful, and the inspired - from countryside retreats to coastal cities alive with tradition. These journeys invite explorers and innovators to balance creativity with celebration, authenticity seekers to connect with Sicily’s traditions and communities, and premium travellers to enjoy cultural festivities in comfort and care - each experiencing Sicily at its most authentic.
As Sicily turns from golden autumn into the warmth of winter light, the island’s rhythm is marked by Saints’ Days, festive gatherings, and the sparkle of Christmas markets. Whether you are seeking creative escapes, meaningful connections with local life, or a seamless premium experience, Sicily in autumn and winter offers celebrations that inspire and endure.
A Refined Weekend at a Glance
A premium weekend break in Catania & Etna that pairs the Le Vie dei Tesori heritage openings in Catania and Bronte Pistachio Festival.
Dates: Weekend options Oct 11-12 or Oct 18-19
Where: Refined accommodation near Catania / Etna slopes (country hotel or seaside boutique).
Why It's a Special Event
Catania revealed: Le Vie dei Tesori’s timed entries to palazzi, monasteries, and terraces - short, level walks between signature spaces.
Customised for Premium Travellers
Gentle pacing: late starts, step-light routes (2-3 km/day), frequent café pauses, seating reserved at demos/tastings.
Immersive: curated guides for history, wine, and food; small-group or private hosting for a personalised experience.
Harvest focus: seasonal menus, winery/olive-oil add-ons, and Bronte’s pistachio specialities - authentic flavour with minimal effort.
What You will Discover
Explore Sicily the leisurely way, with immersive visits to mountain hilltop villages with highlight the Isnello Autumn Flavours Fair - Nov 8-9.
Dates: November 8-10
Where: Isnello and Hillltop Villages in northern Sicily, inside the Madonie Mountain Park.
Authenticity Seekers: In the Madonie’s high villages, this autumn trade queues for conversations - a farmhouse stay with simple cooking classes, an e-bike glide through chestnut woods with local products tastings, all curated with our trusted eco-partners.
Authentic Experience Designed For
Small groups (6-12) or couples comfortable with farmhouse stays.
Guests with moderate fitness for a guided e-bike ride (20-25 km, gentle climbs).
Eco-minded travellers who prefer short transfers, local guides, and hands-on experiences during harvest season.
What’s Happening
Team-Building and Co-Working in an inspirational setting directly on the slopes of the Mount Etna.
Dates: November 28-30
Corporate Experience: Through this immersive 3-day team-building retreat, combine co-working sessions with active challenges - guided lava hikes or cycling tours and celebrate together at the Feast of Saint Andrew.
Why It’s Unique
Culture as a catalyst: Your team are not just “seeing” Sicily - they are inside living rituals (Feast day lights, markets, local producers). Shared, emotive moments spark trust and story-sharing fast.
Who It’s For
- Teams seeking stronger connections. Combine co-working with active team-building in nature, encouraging collaboration and shared achievement.
- Corporate teams looking for a unique team-building retreat combining work, bonding, and Sicilian traditions.
What’s on in December
Feast-day lights on Dec 8 kick off the season, with Christmas markets running through to early January. Discover holiday programmes at Teatro Massimo, pop-up food/craft nights (Sanlorenzo Market), nativity displays in churches, and year-end concerts in the historic centre.
Dates: Dec 7-9 (timed around the Feast of the Immaculate Conception on December 8).
Your base
A luxury boutique hotel in central Palermo (steps from the historic core and theatres) - or, on request, a private coastal villa near Mondello for sea views with easy city access.
Why it resonates with Premium Travellers
Private transfers, timed entries, and concierge-held tables.
Expert-led access to Arab-Norman gems, theatre evenings, and curated Christmas markets.
Central luxury hotel (or discreet coastal villa) with space for spa/sea time away from the crowds.
Your Artistic Itinerary - Creative Weekend
Winter light on stone and citrus: market mornings in Ortigia, hands that make and mend, and a calm countryside farmhouse stay near Syracuse. where citrus gardens and kitchen tables braid into one story.
Dates: Dec 6-8, 2025 - with Sun, Dec 7 dedicated to the Radicepura Garden Festival
Where to stay
A restored authentic farmhouse in the countryside just outside Syracuse. Situated 15 min from Ortigia, with a relaxed day excursion to Giarre for the Garden Festival by car or train.
Where the artful meets the authentic
- Because people come first: the stallholder who knows the sea by scent, the grower who names each tree.
- Because you do, not only see: touch of flour, a path through citrus, gardens read like living texts.
- An Intimate, season-led, and lightly paced experience.
Itinerary theme - Team-Building Event
Shared rituals to strengthen teams: co-create by day (market challenges, micro-workshops in Ortigia) and bond by night amid Saint Lucia’s candlelit processions. The programme blends cultural immersion with purposeful moments.
Dates: December 12-14
Where: Syracuse, Sicily
What Your Team Will Experience
A 3-day cultural and team-building retreat in the historic city of Syracuse, blending co-working in inspiring heritage spaces with one of Sicily’s most cherished traditions: the Feast of Santa Lucia.
Why Join
- Unlike typical retreats, this experience immerses teams in a living Sicilian tradition that symbolises resilience, hope, and renewal.
- By combining cultural immersion, team workshops, and outdoor exploration, the retreat strengthens group connections while offering rare access to an authentic community festival.