Timeless Custom Itineraries
We can help you plan your dream European getaway
A personalised itinerary designed just for you
With over 20 years exploring Tuscany and more than 25 winters spent skiing across 50 resorts in Europe, we know what makes a trip truly special. We loved Tuscany so much that we made it our home, and we now live there full-time—while still chasing the snow in the Alps each winter.
Planning a holiday can be exciting, but deciding where to go, how long to stay, and how to fit everything in can quickly feel overwhelming—whether it’s wandering Tuscan villages, tasting local wines, or skiing the Alps.
That’s where we step in. We help you create a personalised itinerary based on your travel style, budget, and pace—whether that’s scenic drives through the countryside, a few days in hilltop towns, food and wine experiences, or a week of skiing and sightseeing.
Our goal is simple: to make your European holiday easier, smoother, and full of memories you’ll treasure long after you return home.
Gary & Sally email: info@timelesswanderers.com
Tuscany and Skiing Europe Travel Planning Itinerary Service
We offer a personalised Tuscany and Skiing Europe travel planning service designed for travellers who want a seamless, authentic holiday experience without the stress of research and logistics. Each itinerary is carefully crafted to match your travel style, interests, and pace, covering accommodations, transport, daily activities, dining recommendations, and local experiences. Rather than generic packages, you receive a thoughtfully planned journey that saves you hours of planning and ensures every day of your holiday flows effortlessly.
Important: fees cover research, itinerary creation, and logistics planning only. All flights, accommodations, transport, and activities are booked directly by the client.
Easy
1 to 4 Days
Tuscany
Perfect for short Tuscany escapes or add-on trips. Includes a personalised itinerary with must-see highlights, ideal base locations, transport flow between towns, and curated dining and sightseeing recommendations for a smooth, stress-free visit.
$179
Discover
7 Days
Tuscany
Perfect for first-time visitors or those with limited time, this itinerary focuses on the highlights of . It includes a well-balanced mix of iconic cities, countryside experiences, and leisure time. Ideal for travellers who want a beautifully planned week without feeling rushed.
$279
Signature
10 days
Tuscany
A deeper exploration of Tuscany, allowing time to experience both famous destinations and lesser-known gems. This itinerary offers a slower pace, more immersive experiences, and additional flexibility for wine regions, villages, and cultural stops.
$389
Premier
14 Days
Tuscany
Designed for travellers who want to truly live Tuscany, this itinerary offers a relaxed pace with in-depth exploration of multiple regions. It allows for extended stays, day trips, countryside drives, and memorable local experiences without rushing from place to place.
$479
Discover
7 Days
Skiing in Europe
Perfect for a full-week ski holiday. This package delivers a detailed day-by-day itinerary, resort comparisons, skill-level slope planning, lesson timing suggestions, rest days, and après-ski ideas for a balanced and enjoyable trip.
$279
Signature
10 Days
Skiing in Europe
Designed for longer stays and deeper mountain exploration. Includes advanced itinerary planning, multiple ski area options, pacing for endurance, progression planning, dining recommendations, and off-snow experiences.
$389
Premier
14 plus Days
Skiing in Europe
A fully curated ski journey for dedicated skiers or extended winter getaways. Features comprehensive planning across multiple resorts or regions, long-stay pacing, flexible activity options, and contingency planning for weather and rest days.
$479
Please note: This fee covers planning and research only. You book all travel directly to maintain full control and flexibility.
If you have any questions please reach out to us by email info@timelesswanderers.com
FAQ Section – Clear & Trust-Building
Q.What’s the difference between a travel agent and a travel planner?
A. A travel agent mainly books flights, hotels, and packages. And usually has no experience in travelling to the places you are travelling to. We as travel planner focuses on creating a personalised itinerary – designing your daily plans, experiences, and travel flow to match your style, interests, and goals.
Q. What does the itinerary planning fee include?
A. Your planning fee covers destination research, accommodation recommendations, transport planning, daily schedules, timing logistics, and curated experiences tailored to your preferences.
Q. Do you book flights, hotels, or activities?
A. No. Timeless Wanderers provides expert planning and recommendations only. All bookings are made directly by you, giving you complete control and transparency.
Q. Why should I pay for an itinerary instead of planning myself?
A. Planning a multi-day Tuscany trip can take dozens of hours. My service saves you time, avoids costly mistakes, and ensures your itinerary flows smoothly—so you experience Tuscany with confidence and ease.
Q. Can the itinerary be customised?
A. Absolutely. Every itinerary is fully personalised based on your interests, travel pace, budget preferences, and travel style.
Q. Is this suitable for couples, families, or solo travellers?
A. Yes. Each itinerary is tailored specifically to who is travelling, including families with children or multi-generational trips.
Q. What format will I receive my itinerary in?
A. You’ll receive a clear, easy-to-follow digital itinerary that you can view, download, and access while travelling.