How Far in Advance Should You Book Summer Travel?

Planning a summer holiday often starts with one simple question: when should we actually book?  The answer depends on where you’re going, who you’re travelling with, and how specific your requirements are, but for most luxury family travel, the earlier you plan, the better the outcome.

For peak summer dates (late July to mid-August), booking 6–9 months in advance is ideal. The best hotels, room categories, and flight times are typically secured early, particularly for destinations like Greece, Italy, and popular Mediterranean resorts. Waiting too long often means compromising - whether that’s on room layout, availability, or price.

Families, in particular, benefit from booking early. Larger rooms, interconnecting options, and family suites are always limited and tend to sell out first. If you’re travelling with younger children or require specific setups, such as separate sleeping areas or villas, early planning is essential.

There’s also the added advantage of choice. Booking in advance allows you to select the most convenient flights, secure preferred dates, and plan your itinerary without pressure. It gives you time to think through the details, whether that’s transfers, room configurations, or adding a second destination to your trip. There are also loads of amazing deals in the winter months that can be taken advantage of. 

That said, not every trip needs to be booked far in advance. More flexible travellers—those open on destination, dates, or hotel, can sometimes find opportunities closer to departure. However, this approach rarely works well for high-demand summer travel, especially during school holidays.

Ultimately, booking early isn’t just about securing a holiday, it’s about securing the right holiday. The difference between a good trip and a seamless, well-planned one often comes down to timing.

At Kudo Lifestyle, we guide clients on when to book based on their specific plans, ensuring access to the best options before availability becomes limited.

Winter transforms the Dolomites into one of Europe’s top ski destinations. Snow-covered peaks, festive villages, and world-class slopes make it a completely different experience from summer.

This is the best time for:

• Skiing across the Sellaronda circuit

• Staying in cosy alpine hotels with spa facilities

• Snow activities like sledging and snowshoeing

• Christmas markets and festive trips in December

The ski infrastructure is excellent, and resorts like Val Gardena are particularly well set up for families and beginners.

Winter trips tend to feel more structured — ski school, lift schedules, and planned days on the slopes — but also more “classic holiday” in terms of routine.

Which Should You Choose?

If you want a relaxed, outdoorsy trip with flexibility and fewer crowds, summer is ideal. If you’re looking for a more traditional holiday with a clear focus — skiing, snow, and alpine atmosphere — winter is the better choice.

Both seasons work well for families, but in very different ways. Summer is easier with younger children and more flexible day-to-day, while winter is better suited to families with slightly older kids who can ski or take lessons.

The biggest difference isn’t just the weather — it’s the pace and structure of the trip.