Welcome to Timeless Wanderers – Our Travel Story Begins Here
Hello fellow wanderer,
We’re Gary and Sally—two Aussies who traded routine for the road, suburbia for slow travel, and a house full of “stuff” for a suitcase and a dream. If you’re receiving this, welcome to our very first email from Timeless Wanderers—our home for stories, savings, slow travel inspiration, and all the real-life magic that comes from living intentionally on the road.
Let’s start by introducing ourselves properly.
Who Are We?
We’re a couple in our early 60s, with decades of experience in hospitality and an even longer passion for travel. After raising a family, running a business, and doing the “normal” thing for most of our lives, we always had this dream quietly simmering in the background: to live in Europe, explore at our own pace, and one day call a little part of it home.
Well, we finally made it happen.
In 2022, we sold almost everything—our home, our cars, furniture, even most of our books and kitchen gadgets (yes, even the coffee machine!). We kept only the sentimental pieces and our sense of adventure. Since then, we’ve been traveling long-term across Europe, one experience-rich stop at a time.
Why Timeless Wanderers?
We believe travel isn’t just about ticking places off a list. It’s about how it makes you feel—the connection, the discovery, the slowing down. There’s something timeless about walking the cobbled streets of a Tuscan hill town, skiing through powdery Alpine snow, or sipping coffee in a quiet square where nothing seems rushed.
That’s what Timeless Wanderers is all about: travel that lingers with you long after the journey ends.
What We Write About
We’re not luxury travelers. We’re not budget backpackers either. We sit somewhere in the middle—slow, smart, and intentional travel, with a focus on three main areas:
1. Tuscany and Italian Living
Italy has captured our hearts in a big way—especially Tuscany. We’ve spent weeks in Florence, months in hilltop villages, and have fallen for places like Lucca, Arezzo, Pitigliano, and Pienza. We’ll be sharing our favorite spots, hidden gems, scenic routes, best eats, and real tips for traveling Tuscany without the tourist crowds.
2. Skiing in Europe
We’re avid skiers and have been hitting the European slopes for over 20 years. From the Austrian Alps to the Dolomites, and lesser-known ski towns like Nassfeld or Serfaus, we love exploring ski resorts that offer charm and value—especially for fellow Australians who dream of a white winter.
(Fact: Sally had her first ski trip in Lech Austria 25 years ago, because it was a favorite of Princess Diana!)
3. Saving Money Through Housesitting
Housesitting has been a game-changer for us. We’ve stayed in stunning homes across Europe, often for weeks at a time, without spending a cent on accommodation. It’s not just about saving money—it’s about living like locals, caring for pets, and becoming part of a community. We’ll be sharing tips, honest stories, and how you can get started too.
Our Current Chapter: Montenegro & A New Project
Right now, we’re writing to you from a sunny little coastal town in Montenegro, where we’ve just taken on a completely new challenge—renovating an apartment we’ve bought to list on Airbnb.
Why Montenegro? It’s still under-the-radar, incredibly beautiful, and affordable compared to many parts of Europe. Think sparkling Adriatic waters, dramatic mountains, medieval towns, and friendly locals. It’s also been a fantastic base for us to catch our breath, stay put for a while, and try something new.
We’ll be sharing the whole renovation journey with you—what it’s like buying property in the Balkans, the design choices we’re making, the budget (yep, we’re keeping it real), and eventually, a sneak peek before it goes live.
What You Can Expect From Us
We know your inbox is a busy place, so we promise not to spam you. Here’s what our emails will include going forward:
Honest travel stories from the road
Guides to our favorite towns, ski resorts, and off-the-path destinations
Budget travel tips and how we save through housesitting
Updates on our Airbnb journey and seasonal travel ideas
A peek behind the scenes of slow travel life
Whether you’re planning your own adventure, dreaming from your desk, or just love travel stories that feel like a conversation with old friends—we’re glad you’re here.
Want to Connect?
We’d love to hear from you! Hit reply and introduce yourself—tell us where you’re from, what kind of travel you love, or what you’d like to read more about. Or follow our updates here:
Instagram: @timelesswanderers
Pinterest: Timeless Wanderers Travel
Blog: www.timelesswanderers.com (launching soon)
Thank You for Joining Us
This email is just the beginning. Our travel life isn’t glamorous every day. Sometimes it’s full of magic—sunsets in Tuscany, skiing through untouched snow, waking up in a stone cottage with mountain views. Other days, it’s WiFi issues, missed trains, or carrying groceries uphill. But every step of it feels worth it.
We’ve learned that travel doesn’t have to be fast to be fulfilling. You don’t need to see it all—you just need to feel where you are. That’s what we hope to bring to your inbox and your screen with Timeless Wanderers.
Until next time—stay curious, wander slowly, and thank you for letting us be part of your journey.
Warm wishes,
Gary & Sally
Timeless Wanderers
Tuscany Perfect 7 DAY ITINERARY
A seven-day tour of Tuscany is best, it allows you plenty of time to explore the region more deeply.
DAY 1 FLORENCE
MORNING
Uffizi Gallery – link Book tickets in advanace
Piazza del Duomo – Climb to the top of the dome or bell tower for the stunning views.
AFTERNOON
Ponte Vecchio
Palazzo Pitti and Bobocci Garden
EVENING
Piazzale Michelangelo – enjoy a panoramic view of Florence sunset.
Roof top bar
Dinner : Savor Tuscan cuisine at a local trattoria
Stay in Florence for 2 nights
WHERE TO STAY IN FLORENCE
Florence city centre is quite compact and very easy to get around. So you can stay much any where within 10-15 minutes walking distance from the Duomo it will be OK.
HERE ARE SOME SUGGESTIONS
(one of the most popular low-budget options)
B&B Le Stanza del Duomo (we always seem to stay here the location is great and the staff are always fantastic)
DAY 2 FLORENCE
MORNING
Accademia Gallery: Visit to see “ David Michelangelos”
Santa Croce Basillica: the burial place of famous Italians like Michelanglo and Galileo.
AFTERNOON
Beholi Gardens Wander theough these historic gardens and enjoy the peace and serienty.
Oltrarno District: Discover artisan workshop and the beautiful Santo Spirito Basilka.
EVENING
Dinner: Enjoy dinner in the Oltrano district, known for its authentic restaurants.
BEST TIME TO VISIT FLORENCE
Florence is a year-round destination no matter the weather or season! Peak season is usually the warmer months of July and August. The average temperature in July and August is 31oC(88oF). It’s slightly cooler in June and September, but these months are also hectic.
Winters can be chilly with an average high of 11oC(25oF) but there are many great museums offering shelter from the adverse weather.
We much prefer to go in the shoulder seasons which offers the most pleasant weather for experiencing the city. It’s a great time to visit, less crowds and usually lower prices on accommodation.
DAY 3
MORNING
Travel to Siena: Drive or take a train to Siena (about 1.5 hour from Florence)
Piazza del Campo: Visit the heart of Siena.
AFTERNOON
Siena Cathedral: Explore the Gothic Catherdral
Travel to San Gimignano (45 minutes from Siena)
EVENING
San Gimignamo: Stroll the Charming streets, enjoy local Gelato from Gelato Dondoli.
Dinner: Enjoy a meal at a local Trattoria stay in SAN GIMIGNAMO
.
Where to stay in San Gimignano
MORMORIA – Tuscan Estate offering wine tasting, scenic views of San Gimignano. Beautiful locations right in the middle of the vineyard
Hotel Leon Bianco – Great location right in the middle of the historic centre, with stunning countryside views. Modern amenities and peaceful surroundings.
Hotel L’Antico Pozzo – Set in the heart of San Gimignano on central via San Mattee spacious and beautiful rooms come and have breakfast In the Courtyard this really is a gem in San Gimignano.
Beautiful apartment in the city center
Casa Vesta – Situated in the center of San Gimignano. Spacious 2-bedroom apartment with all the modern amenities also has its private entrance.
DAY 4 CHIANTI WINE REGION
MORNING
Drive to Chianti: Explore the stunning Chianti countryside.
Greve in Chianti: Visit this enchanting town and its main square.
AFTERNOON
Castellina in Chianti: another pictureque town
Radeta in Chianti: A charming village ideal for a relaxed afternoon.
EVENING
Dinner enjoy a rustic meal at an Agriturismo (farm stay) sampling local food and wine.
Wine Tasting at Renowned Wineries
Chianti is synonymous with exceptional wine, and visiting a winery is a must. Some of the top wineries include:
- Castello di Brolio: One of the oldest wineries in Italy, this castle estate offers wine tastings, guided tours, and stunning views.
- Antinori nel Chianti Classico: A modern architectural masterpiece that blends contemporary design with a deep-rooted winemaking heritage.
- Castello di Ama: Known for producing elegant wines and housing an impressive collection of contemporary art installations.
- Fontodi: An organic winery specializing in high-quality Chianti Classico and the famous Flaccianello wine.
Where to Stay in Chianti
Chianti offers a variety of accommodations, from luxurious wine estates to charming countryside agriturismos.
Luxury Stays
- Castello di Spaltenna (Gaiole in Chianti): A stunning medieval castle-turned-hotel offering luxury suites, a spa, and fine dining.
- Villa Bordoni (Greve in Chianti): A boutique hotel with elegant rooms, a renowned restaurant, and a tranquil setting among the vineyards.
- Belmond Castello di Casole: A lavish retreat featuring historic charm, top-tier service, and breathtaking views.
Boutique Hotels & Farm Stays
- Fattoria Poggiarelli (Radda in Chianti): A charming farmhouse offering wine tastings and scenic countryside views.
- Il Borgo di Vescine (Radda in Chianti): A medieval hamlet converted into a boutique hotel with traditional Tuscan décor.
- Agriturismo Podere Campriano (Greve in Chianti): A family-run organic farm offering comfortable rooms and winemaking experiences.
DAY 5 PISA AND LUCCA
MORNING
Travel to Pisa
Piazza dei Miracoli – Visit the leaning tower
Make sure to climb the tower
AFTERNOON
Travel to Lucca – (30 minute from Pisa)
Lucca is a charming walled city.
Lucca Walls – Walk or bike along the walls.
Histrorical centre: Explore luccas narrow streets enjoy the atmosphere of Piazza dell Anfiteatro.
EVENING
Dine in Lucca at a local Trattoria, enjoy the city’s relaxed ambience.
Stay in Lucca you like us, may not want to leave this gem of a town.
WHERE TO STAY
San Lucca Palace Hotel An old palace just inside the walls provides lots of old-world charm.
Palacio Rocchi, BNB. A luxurious Four stay guesthouse in the heart of Lucca Historic Centre. Expect an extravagant room with grand furniture.*Find out more via link attached.*
Grand Universe La Residenza, Lucca.
A historic hotel with true luxury. Consider this contemporarily. Chic Style Hotel. It’s ideal for travellers seeking modern comfort and historical charm.
We have stayed here many times for a night or two. Beautifully decorated small hotel and conveniently located in the center of Lucca. The hotel is modern and immaculately clean. The staff have always been friendly and helpful. One of our favourites.
Family run, this quiet house offers good sized comfortable rooms and a highly rated breakfast. Also has a private terrace for guests to enjoy.
B&B Anfiteatro
Located right next to Piazza dell’ Anfiteatro, this bed and breakfast offers comfortable rooms with spectacular views of the historic square. Its perfect for those wanting to be in the heart of the old town.
DAY 6 VAL D’ORCIA
MORNING
Drive to Val d Orcia: Breath taking hills, landscape, romantic farms, picturesque cypruss avenues.
Pienza – Explore this beautiful town, (sample the pecorino cheese)
AFTERNOON
Montepulciano: Visit the hilltop town famous for its Vino Nobile wine or tour a winery enjoy a tasting.
Bagno Vignoni: Stop by this charming village with it’s unique thermal baths in the main town.
EVENING
Dinner: Enjoy a meal at your Agriturismo Farm Stay
Where to Stay in Val d’Orcia
Luxury Retreats
- Rosewood Castiglion del Bosco (Montalcino) – A luxurious resort set in a historic estate, offering vineyard tours, fine dining, and a world-class spa.
- Adler Spa Resort Thermae (Bagno Vignoni) – Perfect for those seeking relaxation, this spa retreat boasts thermal baths, wellness treatments, and stunning surroundings.
- Castello di Velona (Montalcino) – A historic castle-turned-hotel with panoramic views, an on-site vineyard, and an indulgent spa experience.
Boutique & Mid-Range Stays
- La Bandita Townhouse (Pienza) – A stylish boutique hotel blending contemporary elegance with historic charm in the heart of Pienza.
- Relais Il Chiostro di Pienza – A former monastery offering stunning views and a peaceful atmosphere.
- Dimora del Poggio (San Quirico d’Orcia) – A classic Tuscan farmhouse surrounded by rolling fields and cypress-lined paths.
Budget-Friendly & Agriturismos
- Agriturismo La Fonte (Pienza) – A charming, affordable farmhouse stay where guests can experience local farming traditions and enjoy home-cooked meals.
- Podere Spedalone (Pienza) – A rustic agriturismo with warm hospitality, farm-to-table dining, and stunning countryside views.
Le Ragnaie (Montalcino) – A vineyard agriturismo offering cozy accommodations and organic wine tasting
DAY 7 MONTALCINO AND CORTONA
MORNING
Montalcino: Visit this town known for Brunello di Montalcino wine.
AFTERNOON
Travel to Cortona – a scenic drive to this charming hilltop town. Made famous by the book and movie Under the Tuscan Sun
EVENING
Dinner: Enjoy a final meal in Cortona enjoying the flavors of this region.
Stay in Cortona
WHERE TO STAY
Cortona is small and very much on the map for tourists, so don’t be surprised if you can’t find cheap accommodation if staying here. Of course, being a tourist destination means it has lots of options, many of which are very nice, so you have a good selection to choose from.
Below are some places in town that we would recommend:
Villa Di Piazzano is just at the bottom of the hill that Cortona sits atop. Villa di Piazzano is a fantastic 5-star hotel set inside a noble villa with manicured gardens and grounds.
Monesary Di Cortona Hotel and Spa
This Boutique Hotel – kids free hotel is located in an ancient Monastery and boasts a beautiful garden.
Hotel San Michelle is located inside one of the oldest buildings in Cortona, the ancient Baldelli Palace, located right in town.
Stylish apartments in the center of town are attractive and very comfortable, you will be tempted to settle in for a very long time.
In the delightful full historic center, a very comfortable apartment and has every comfort you need.
This seven-day itinerary offers a balanced mix of charming towns, breathtaking scenery, Romantic farms, and Medieval villages to conjure up a perfect vacation.
Bonus Tip
Best Time of Year for Wine Travel in Tuscany
April to June: Spring bloom, warm days, perfect for vineyard walks.
September to October: Our favorite time to visit, it’s harvest season, grape stomping festivals, golden vineyard views.
July–August: Hot, crowded, but good if you’re combining with beach trips.
November–March: Quiet season, ideal for truffle hunting and wine cellars, but less vineyard activity.
How to Book Winery Visits
Most top wineries require reservations, often booked via their websites. Many now offer curated tasting experiences, cellar tours, cooking classes, and even picnic packages in the vines.
Or, if you prefer a guided experience, platforms like Viator and Get Your Guide offer full-day wine tours from Florence, Siena, or Lucca with transport included.
Best Time to Visit
Winter (December to February)
Our best time to visit Tuscany is winter as it is quieter, with few tourists and all the festive decorations. While entrance tickets for museums and monuments are the same price all year round,
Hotels and car rentals are much cheaper than the warmer months.
Summer (June to August)
Summer brings very warm weather and a busy tourist season. If summer is the only time you can come to Tuscany, don’t despair. While its not the ideal time to visit, it’s not as if every town, beach, or vineyard is permanently packed. You can always find that hidden gem. If visiting in summer, you just need to plan ahead, making reservations in advance and visiting places at the right time.
Autumn (September to November)
September has great weather, lower prices, and fewer crowds. But don’t worry everything is still in full swing, before things die down and everyone closes up for winter.
Spring (March to May)
Spring is a perfect time to visit Tuscany with mild temperatures and fewer crowds which makes it perfect to visit to historic towns, the countryside, and the coastline. Besides Florence, which is crowded all year round, late spring isn’t packed with tourists, so you will surely enjoy your time there.
HOW TO GET AROUND TUSCANY
Renting a car is one of the best ways to explore Tuscany. It provides the freedom to visit remote villages, scenic countryside, and vineyards at your own pace. The smaller towns are not easily accessible by public transport, so if you want to visit places like Volterra, Pienza, Montalcino, and the countryside of Val Orcia, the best way is by car.
Tuscany has a reliable train system connecting major cities and towns. Florence, Siena, Lucca, and Pisa are all easily connected, whereas San Gimignano and Siena are better by bus.
To check prices and book I recommend using “Discover Cars”. It’s a car rental website that includes offerings from all major rental companies as well as lots of smaller local agencies.
If you prefer an easier approach, guided tours are a convenient way to see Tuscany’s highlights. Options include wine tours, cultural tours, and day trips to cities like Lucca, Pisa, Siena and San Gimgnano.