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ITINERARY
5-day late-summer and autumn itinerary in Chania
Overview
Enjoy our season-extending road trip in Chania on an itinerary where culture, food and village life take centre stage
Many of Chania’s most memorable experiences are saved for the quieter months when holidays become even more personal and highlights beyond the region’s famous beaches can shine. From exploring the city’s Old Town and immersing yourself in Crete's famous olive oil, wine and raki traditions to learning how to cook like a local and going on an off-road excursion into the White Mountains, you’ll discover what it means to live in this cherished part of Greece. So buckle up for a 5-day itinerary of Chania that celebrates all the late-summer and autumn highlights.
As an itinerary that’s been road-tested by Discover Greece, we’ve included the restaurants and experience providers that supported our journey – although there are, of course, plenty of alternatives out there. The road trip is designed to be enjoyed best during the grape or olive harvests, in late summer an autumn, but you can incorporate any part of it into your summer holiday in Chania and extend or adapt it around your interests.
Duration
5 days /370km
Best For
Food lovers, culture fans, village explorers and anyone wanting to experience Chania beyond its summer beaches
Pace
A relaxed, experience-led 5-day stay with Chania town as your base, combining easy city walking with day trips to nearby villages, vineyards, olive mills, distilleries and the White Mountains, plus one longer day on the south coast.
Why You'll Love It
- You’ll get under the skin of Chania’s Old Town, Venetian Harbour and neighbourhoods, seeing how history, architecture and everyday life blend together.
- Food is at the heart of the itinerary – from farm-to-table dinners and seafood by the sea to slow-cooked Cretan classics and hands-on cookery lessons.
- You’ll experience Chania’s harvest traditions first-hand, with vineyard visits, raki distillation and (in season) the chance to join an olive harvest.
- A 4x4 trip into the White Mountains reveals shepherd culture, highland villages and sweeping views that most summer visitors never see.
- A late-season boat trip to Loutro and the Sfakia coastline shows off Crete’s wilder, quieter side, with clear water and small harbours that feel untouched by mass tourism.
Pro Tip
Leave room in your schedule for conversation. Whether you’re picking olives, tasting wine or watching raki being distilled, the people you meet are often the highlight. Ask questions, linger a little and you’ll unlock stories and traditions you won’t find in guidebooks.
DAY 1 OVERVIEW
Chania town
20km
airplane, car, foot
2
So much of Chania’s soul is found in its old town, so this is the focus of day one of your itinerary in Chania. Best of all, with the airport just 25mins away, you can get stuck in straight away.
Walking tour of the Old Town
There’s no better way to discover Chania than wandering its streets. Your first port of call is the Venetian Harbour, with its iconic lighthouse (rebuilt by the Egyptians in the 1830s) and the many-domed Ottoman-era Giali-Tzamisi Mosque. The fort you can see at one end is the 16th-century Firka Fortress. Other highlights are the Church of Agios Nikolaos and central market, as well as the Topana district (housing Greeks during the Ottoman years) and neighbouring Jewish quarter, still preserving original architecture and numerous historical buildings.
Seafood dining with a view
You’ll be returning to the Venetian Harbour to eat throughout your stay in Chania. Our first experience of the region’s famous food is Apostolis restaurant, known for its fresh seafood and delicious assortment of local ingredients. Stuffed squid, shrimps and clams line up next to meat and vegetable-based dishes. The seven triangular-roofed brick buildings you can see from your outdoor table are the remains of the Venetian’s famous ship-repair yards, or Neoria.
DAY 2 OVERVIEW
Cooking like a local & a winery
77 km
car, foot
3
If you want to experience Chania like a local, you need to learn how to eat and drink like one. So today is dedicated to two favourite local pastimes… cooking and wine. It’s also an introduction to the Apokoronas villages, a collection of traditional settlements worth seeking out as an activity in its own right.
A cooking lesson
Our day starts at Olive Farm, in Litsarda, one of the Apokoronas villages. This small farm encompasses the principles of locally sourced, sustainable produce and offers cookery workshops in its outdoor kitchen. You’ll learn how traditions are incorporated into everyday life while preparing dishes such as kleftiko (melt-in-your-mouth, slow-cooked lamb or goat with potatoes, carrots, tomatoes, peppers, courgettes and an assortment of aromatics picked from the farm’s vegetable garden). You’ll also be introduced to tirozouli, a white, tangy homemade cheese and other dairy products.
Wine-tasting
From cheese, it’s a natural progression to wine. Wine-making in Crete goes back 4,000 years and many of the indigenous grapes can be traced back centuries. Amongst the wineries you can visit is Dourakis, in Alikambos. You’ll sample reds made with a blend of Syrah and Kotsifali grapes (deep-coloured and complex) and Carignan (a variety that thrives in the Mediterranean) as well as international stalwarts (Cabernet Sauvignon and Merlot) and delicate whites from organically grown Vidiano and Malvasia. And you’ll be especially impressed by how they pair with local cheeses… from yellow, piquant graviera to smooth-white myzithra and anthotiro. You’ll also have the option of touring the vineyard in the surrounding area, especially enjoyable in late summer when the grape harvest is in full swing.
The farm-to-table experience
Farm-to-table is the theme of dinner, too, as you return to the Venetian Harbour. Salis restaurant specialises in working with local producers as well as growing many of its own ingredients. Its dishes are traditional but at the same time inventive… much like the region and its people. There’s also a great list of local wine labels, so you can put your newly acquired knowledge into practice.
DAY 3 OVERVIEW
Olive oil & Raki
65 km
car, foot
3
You delve even deeper into the social fabric of Chania as you explore the two products no self-respecting local household can be without… olive oil and raki. If you’re lucky enough to visit in late October or November (as we did), you can take part in the olive harvest. (Note that the exact dates olives are picked depends on the weather and visiting an olive press is a privilege you can enjoy at any time of year.) Your afternoon is spent in a raki distillery.
Olive-picking
Your day begins in the olive groves just outside the village of Tsivaras, at the Melissakis Olive Mill, picking olives. There are numerous olive presses in the Apokoronas villages, from small cold presses producing extra-virgin olive oil the old-fashioned way to state-of-the-art cold-extraction facilities, such as this one. What they have in common is that their produce contributes to the Protected Designation of Origin status of the area. The highlight is experiencing the olives you’ve picked being turned into smooth, golden, peppery olive oil ….a taste you’ll never forget.
The rakokazana experience
Your next stop is the Peroulakis Distillery, in Xirosterni, for an initiation into Chania’s rakokazana (raki distillation) tradition. The best late-season grapes are turned into tsikoudia (as raki is known in Crete), 40% proof firewater as part of a community affair, with music, singing and food aplenty. The Peroulakis Distillery embodies that culture. You watch a traditional distillery being fired up and the pure, clear raki begin to flow as you sit down to a meal of stewed meat and Cretan wedding pilaf. Try the rakomelo, infused with honey and herbs and served as an appetiser or aperitif.
The authentic dining scene
Back in the Old Town for the night, your gastronomic tour continues at Chrisostomos restaurant, with authentic Cretan flavours slow-cooked in a wood-fired oven and plenty more Cretan hospitality. Some suggestions are beef stifado (stewed with baby onions), synglino (cured pork) and anything with local vegetables (mushrooms, peppers, wild greens…). The olive oil you dunk your homemade bread into will take on a whole new meaning.
DAY 4 OVERVIEW
Into the white mountains
62 km
car, foot
2
There’s a change of scenery for the fourth day of your Chania itinerary as you head into Crete’s tallest mountain range. As you’re about to find out, the White Mountains are also home to villages and some of Chania’s most hidden traditions.
Jeep Safari in the White Mountains
You shift gear with a 4x4 Jeep Safari into the Lefka Ori (as the White Mountains are known in Greek) with Uncharted Escapes. You’ll pass villages and vineyards that have made their home in this rugged terrain and you’ll learn all about the life of a shepherd by visiting a mitato – a round, stone-built hut, designed for protection against the strong winds and used to store cheese as it matures. The view from 1,400m up is sublime. Finally, you visit Theriso, a village synonymous with Eleftherios Venizelos, a revolutionary hero and one of Greece’s first prime ministers. Venizelos’ mother came from the village and it was here, in 1905, that he organised a Revolutionary Assembly that led to the independence of Crete and its union with Greece.
The creative dining scene
After a day in the mountains, it’s back to the Venetian Harbour for dinner at Pallas, a restaurant specialising in traditional Cretan food with a modern Mediterranean twist. From your outdoor table overlooking the harbour, the sight of the setting sun and the Egyptian lighthouse is something else.
DAY 5 OVERVIEW
Sfakia
146 km
boat, car, foot
3
Your attention turns to the sea today as you head to the southern coastline for a boat trip. Depending on your time of visit and the weather conditions, you can look forward to wonderfully clear water, with swimming enjoyable until late-October.
A boat trip to Loutro
The magic of taking a boat trip is that you can visit beaches that are inaccessible (or very difficult to reach) by car. Our day-trip was with Notos Mare Marine Adventures, heading west from Hora Sfakion towards Glyka Nera (a fabulous, isolated swimming spot that translates as Sweet Water) and on to Marmara beach. The only other way of getting here is to hike down the 6km ravine behind the beach. On the way back, you stop at Loutro, a village accessible only by sea, to enjoy a Greek coffee and traditional Sfakia pies.
Hora Sfakion
Returning to Hora Sfakion (the capital of the Sfakia region), you can look forward to an early dinner with fantastic seafood and local dishes at Livikon, a taverna right by the sea. The fish soup comes highly recommended. But before you sit down, pass by the Dourountous Bakery to stock up on Cretan kritsinia (seed-crusted, dried breadsticks) and paximadia (rusks), made from traditional recipes.
A short goodbye
You’ll be excused for not wanting your off-season Chania adventure to end. One tip is to extend your stay and walk the Samaria Gorge (one of Europe’s iconic hikes) but there are plenty of outdoor activities that will tempt you. And you’ll long to return for another taste of the olive oil and wine. Above all, it’s the way the locals have made you feel that you’ll remember most. But it’s time’s to catch your flight and say goodbye. For now.
Road-testing the itinerary for you
In road-testing our 5-day late-summer and autumn road trip to Chania, we invited a team of German media to live the experience for themselves. Here’s what they had to say.
★★★★★
“At every step, the visitor realizes very quickly that he falls on history. Under almost every square meter of Chania there is a testimony of the past.”
- Jan Schäfer for Siegener Zeitung ⇩
"The best aroma comes from the olive oil when the olives are still quite a bit unripe and need about two more days to ripen’, the olive mill manager explains when he returns to the production facility."
- Reinhard Fanslau for Emsland Kurier ⇩
“And then suddenly there is Loutro. The smallest and most beautiful coastal village, that I have ever seen: white houses with blue shutters, like colored spots in the brown landscape. Beautiful.”
- Lisa Krause for Fuldaer Zeitung ⇩
How our Travel Specialists help
Send your request
Share a few details about the trip you have in mind. We’ll connect you with a vetted Travel Specialist who’ll typically reply within 24 hours (Monday-Friday).
Shape your itinerary together
You’ll work one-to-one with the specialist to refine the route, pace, accommodation and experiences, and add any local tips or activities you’re interested in.
Finalise your trip
Once you’re happy with the schedule and inclusions, your Travel Specialist prepares the final trip plan and takes care of the booking for you.
FAQs
Is this itinerary suitable for a first-time visit to Chania?
Yes. It less on peak-season beach-hopping and more on Chania’s Old Town, food culture, village life and mountain traditions, giving first-time visitors a deeper, more local introduction to the region.
Do I need a car for this trip?
A car is necessary for many of the experiences – olive mills, wineries, villages and the drive into Sfakia. The highlights of Chania Old Town can be enjoyed on foot and some activities (Jeep tour, boat trip) are guided, but you’ll still appreciate the flexibility of driving.
Where will I be based?
The itinerary assumes you stay in or near Chania town for all five nights, using it as a base for day trips. If you prefer, you can add one overnight in Sfakia or a nearby south-coast village at the end.
What’s the best time of year to follow this itinerary?
It’s designed for late summer and autumn, especially late-September-October when harvest activities are in full swing and the Old Town and villages are quieter. You can adapt elements into a summer holiday, but some harvest experiences may not be available.
Will I still be able to swim in late summer and autumn?
Often yes. In most years the sea around Chania stays warm enough for comfortable swimming into October, especially on south-facing coasts. By November it becomes more weather-dependent but you can still have sunny, swimmable days.
Is this itinerary family-friendly?
It can be, especially for older children or teens who enjoy food experiences, boats and light exploring. Note that cookery classes, winery visits and raki distillation are slower-paced, adult-oriented experiences, so families may want to adjust the balance with more active options.
Do I have to drink alcohol to enjoy the wine and raki experiences?
No. You can still join vineyard tours, learn about grape varieties and production, and take part in the social side of raki distillation without drinking. Just let hosts know in advance so they can adjust tastings.
How active is the itinerary – do I need hiking experience?
You don’t need technical hiking experience. Most walking is around the Old Town, villages or short stretches on mountain and coastal stops.
