Tuscany has been part of our lives for more than 20 years. What started as regular visits soon became a passion, and eventually, we fell in love with the region so much that we made it our home.
Living here has given us the chance to experience Tuscany beyond the guidebooks.
We’ve explored its medieval hilltop towns, quiet country roads, local markets, vineyards, and family-run trattorias, discovering the places and experiences that make every visit unique.
Planning a holiday to Tuscany should be exciting, but with so many beautiful towns, wineries, and attractions to choose from, it can be difficult to know where to start or how to make the most of your time.
That’s where we come in.
We create personalised Tuscany itineraries built around your interests, travel style, budget, and the kind of holiday you want to experience.
Whether you’re planning your first visit or returning to discover more of this incredible region, we’ll help you build an itinerary that fits you perfectly.
From scenic drives through the Val d’Orcia and wine tasting in Chianti to exploring historic cities, discovering hidden villages, or simply enjoying the slower pace of Italian life, we’ll help you experience the Tuscany we’ve come to know and love.
Our goal is simple: to take the stress out of planning so you can relax, travel with confidence, and enjoy an unforgettable Tuscany holiday filled with memories you’ll treasure for years to come.
Gary & Sally email: info@timelesswanderers.com
Easy
Up 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
Up to 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
Up to 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
Up to 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
Please download as a PDF or print the questionnaire, fill out and return for us to start your dream holiday. Email the completed questionnaire back to us at info@timelesswanderers.com
Tuscany Questionnaire
Important: fees cover research, itinerary creation, and logistics planning only. All flights, accommodations, transport, and activities are booked directly by the client.
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.
