As Italians, we're not particularly famous for planning our holidays far ahead of time. In fact, research consistently shows that many of us tend to book our trips at the last minute — and that's exactly what we see in our day-to-day experience as well.
For some travellers, booking early means enjoying the months ahead with complete peace of mind and the pleasant anticipation of a great holiday waiting just around the corner. For many others, however, thinking about all the components involved in organising an important trip can feel more like work than the preparation for something enjoyable. And so planning gets postponed until a few weeks — or even a few days — before departure.
If you have the possibility to plan your holidays well in advance, we genuinely encourage you to try a different approach and book your walking holiday several months ahead.
Why should you do it? In this article, we'll explain all the advantages. And we'll even tempt you with a discount available on trips booked between three and six months before departure.
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The most obvious advantage is also one of the most important: having more options.
Booking well in advance gives you access to a much wider range of destinations, departure dates and itineraries, including those that tend to fill up quickly.
Planning ahead allows you to compare different trips at your leisure, consider the level of difficulty, the season that suits you best and the type of landscape you'd like to explore, without being forced to adapt your plans to whatever availability remains.
This is especially important for highly sought-after itineraries or trips that rely on accommodation with limited capacity. Mountain holidays involving overnight stays in alpine huts are a perfect example: once beds are fully booked, there are often no alternative options nearby.
The same applies to islands, small villages and remote regions, where accommodation is limited and often reserved many months in advance, particularly during peak season.
We carefully select the standard accommodation for each of our trips based on comfort, character, hospitality, location and value for money.
Booking early gives us the best chance of securing availability in the properties we consider ideal for each specific itinerary: charming hotels, agriturismi, guesthouses and family-run establishments that play an important role in the overall quality of the experience.
For last-minute bookings, we may sometimes need to arrange alternative accommodation, which may not be quite as well suited to the route, may be less conveniently located or may involve additional costs. In some cases, extra transfers or minor itinerary adjustments may be necessary.
Booking ahead therefore means a greater likelihood of experiencing the trip exactly as it was originally designed.
Planning ahead can also help reduce travel costs.
If you're travelling by train, especially on long-distance routes, knowing your departure dates early often allows you to access more affordable fares and choose schedules that fit perfectly with your walking itinerary.
The same is true — even more so — for flights, particularly for travellers coming from overseas or covering long distances. Early booking not only helps reduce costs but often makes it easier to find convenient connections, fewer stopovers and more flexibility when planning additional nights before or after the trip.
If your itinerary includes an art city and you'd like to spend a few additional days exploring its cultural treasures, booking in advance gives you more time to evaluate your options and choose experiences that truly match your interests.
You might want to add guided tours, wine tastings, food experiences, museum visits, local workshops or extra nights in a destination you'd like to explore more deeply.
In addition, we'll have a better chance of securing tickets for experiences with limited availability, such as popular museums, guided tours or small-group tastings, helping you make the most of your holiday.
If you'd like assistance organising these additional days, remember that we're happy to help. We can suggest extensions, activities and practical solutions to enhance your trip without making it more complicated.
When you book your holiday early, you can relax and enjoy the months leading up to departure knowing that a wonderful experience is already waiting for you.
Having your trip confirmed means you can prepare gradually: choose your equipment, train if necessary, learn more about the places you'll visit and simply enjoy the anticipation — which is already part of the journey.
Trying to organise everything in the days immediately before departure can quickly become stressful — hardly the ideal way to begin a long-awaited holiday.
When travellers book early, they help us distribute our workload more evenly throughout the year and allow us to inform our suppliers well in advance, helping them organise their own operations more efficiently.
Better planning allows us to collaborate more effectively with accommodation providers, guides, transport services and all the local partners who contribute to making each trip special.
It also helps small businesses and local communities manage staffing, purchases and services more sustainably, benefiting the entire travel ecosystem.
Additionally, it allows us to balance cash flow during quieter periods of the year. While this may not directly affect your experience, it is another positive consequence of booking early and contributes to a healthier, more sustainable travel industry overall.
If you're worried about the possibility of having to cancel due to unforeseen circumstances, consider adding cancellation insurance when booking.
Depending on the policy conditions, this may allow you to recover travel expenses if you're unable to depart due to eligible unexpected events, including certain health-related circumstances affecting you or your family.
As always, we recommend carefully reviewing the policy terms, conditions, exclusions and coverage limits before purchasing.
To make booking ahead even more rewarding, our Early Booking discounts are available throughout the year on trips booked between three and six months before departure.
Simply enter the appropriate code during the online quotation process or provide it to our team by email.
EARLY3
Book at least 3 months before departure and receive a 3% discount.
EARLY4
Book at least 4 months before departure and receive a 4% discount.
EARLY5
Book at least 5 months before departure and receive a 5% discount.
EARLY6
Book at least 6 months before departure and receive a 6% discount.
The promotion is currently available year-round with no fixed end date and applies to all eligible trips that meet the conditions listed below.
Every trip benefits from early planning, but some itineraries make the advantages even more evident: routes with limited accommodation, highly sought-after destinations or longer journeys that require international flights and more complex travel arrangements.
The Alta Via di Fanes and Sennes is one of our most spectacular Dolomite adventures, designed for experienced walkers looking for a more challenging and remote mountain experience.
You will cross high-altitude plateaus, dramatic rock formations, alpine valleys and mountain huts scattered throughout the Fanes-Sennes-Braies Natural Park, one of the most beautiful areas of the Dolomites.
Because accommodation is limited to a small number of mountain refuges, early booking is particularly important. This is the perfect trip for travellers seeking a true alpine adventure and willing to work a little harder to reach extraordinary places.
This itinerary brings together some of Sicily's most fascinating highlights: the volcanic landscapes of the Aeolian Islands, the power of Mount Etna, charming seaside villages and the timeless elegance of Taormina.
Walking among the Aeolian Islands means exploring landscapes shaped by fire and sea, enjoying extraordinary coastal views and experiencing the unique rhythm of island life.
The best accommodation on the islands tends to fill up quickly, especially in spring, summer and early autumn. Booking ahead gives you more freedom when choosing dates, accommodation and transport arrangements.
This itinerary is designed for travellers who want to dedicate a longer holiday to Italy and experience several of its most iconic regions in a single trip.
From the vineyards and hilltop villages of the UNESCO-listed Langhe region to the dramatic coastal scenery of the Cinque Terre and the artistic treasures of Florence, it offers an extraordinary variety of landscapes and experiences.
Particularly appealing to long-haul travellers, this itinerary makes the most of an international flight by combining several destinations into one unforgettable journey. Booking early helps secure the best accommodation and often results in more favourable flight options.
A grand walking holiday through the very heart of Tuscany, designed for travellers who want to fully immerse themselves in some of Italy's most iconic landscapes.
The itinerary combines vineyards, cypress-lined roads, medieval villages, art cities and the rolling hills that have become synonymous with Tuscany around the world. Chianti offers wine country charm, while Val d'Orcia provides thermal towns, abbeys and unforgettable countryside scenery.
Like the previous itinerary, this trip is particularly attractive for international travellers seeking a longer Italian adventure. Booking early helps secure the most charming accommodation and makes it easier to add extra days in Florence, Siena or Rome.
Booking early doesn't mean giving up spontaneity. It simply means starting your journey with more choice, more time to prepare and the peace of mind that every detail has already been taken care of.
And, of course, with a wonderful holiday already waiting on the horizon.
Written by the SloWays Team
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Nominee Best Specialist Tour Operator 2025
Touroperating
S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486
