Multi-Day Private Tours in Crete & Greece — Complete 2026 Guide
Multi-day private tours in Crete start from €380 per person per day for a couple and give you access to places, people, and experiences that a single-day trip simply cannot reach. From a 2-night Cretan road trip to a 7-day island-hopping voyage combining Crete, Santorini, and Mykonos, 105 Olives Greece designs every itinerary around your pace, interests, and budget.
Multi-Day Tour Options & Prices
| Duration | Destinations | Price per couple | Includes |
|---|---|---|---|
| 2 Days | Crete East + West highlights | from €760 | Guide, transport, meals |
| 3 Days | Crete deep-dive or Crete + Santorini | from €1,140 | Guide, transport, hotel, meals |
| 5 Days | Crete + Santorini + Mykonos | from €1,900 | Guide, flights/ferries, hotels, meals |
| 7 Days | Full Greek Islands private circuit | from €2,800 | Full concierge, all logistics |
Our Most Popular Multi-Day Itineraries
2-Day Western Crete Circuit: Day 1 — Chania Old Town, Balos Lagoon by jeep, sunset at Gramvousa. Day 2 — Samaria Gorge hike (or Elafonisi beach if you prefer swimming to walking), Sfakia fish lunch on the southern coast, return to your hotel via the mountain road through Askifou. Perfectly paced, completely private.
3-Day Crete & Santorini: Days 1–2 on Crete (Knossos Palace, Heraklion food market, private cooking class in a village). Morning of Day 3: high-speed ferry to Santorini (2 hours from Heraklion). Afternoon in Oia, sunset dinner. Your guide handles all logistics — you just arrive.
5-Day Greek Islands Classic: Crete (2 days) → Santorini (1.5 days) → Mykonos (1.5 days). Private guides on each island, hand-picked boutique hotels, restaurant reservations made in advance. This is the itinerary most of our returning clients recommend to friends.
7-Day Yacht & Land Combination: 3 days of private touring across Crete by land, then 4 days aboard a skippered sailing yacht — western Crete coast south, Gavdos Island (southernmost point of Europe), return via Rethymno. The format that gets the most repeat bookings.
What Every Multi-Day Tour Includes
- Private, licensed English-speaking guide throughout
- All ground transport in a private air-conditioned vehicle
- Hotel bookings (boutique properties, personally vetted)
- Inter-island ferry or flight tickets where applicable
- Entrance fees to archaeological sites and museums
- At least one included meal per day (taverna or cooking experience)
- 24/7 WhatsApp support from your 105 Olives Greece coordinator
Why Multi-Day Over Day Trips
A single day in Crete covers the highlights. Two or more days reveals the island. On day two you wake up in a mountain village, have breakfast with the owner’s family, and take the back road that no tour bus finds. The pace slows down. You stop rushing. The people you meet stop being background scenery and become part of the story you take home.
Multi-day touring is also significantly more cost-effective per experience than stacking multiple separate day trips, since transport, guide time, and logistics are consolidated. Most couples who book a 5-day tour spend less per day than they would on three separate single-day tours.
Chat on WhatsApp — Plan Your Multi-Day Tour
Frequently Asked Questions
Can we customise the itinerary completely?
Yes — 100%. We treat every multi-day tour as a blank canvas. You tell us your interests (history, food, hiking, beaches, photography), your pace preference (relaxed or packed), and your accommodation style (village guesthouse or 5-star resort), and we design around that. Nothing is pre-set.
Do prices include accommodation?
Our 3-day+ packages include hotel bookings. We select boutique properties that match your style and handle all reservations. For 2-day tours, accommodation is optional and quoted separately on request.
How far in advance should we book?
For July and August, 6–8 weeks ahead is ideal. For May, June, September, and October, 2–3 weeks is usually sufficient. We occasionally accommodate last-minute requests (under a week) depending on availability.
Do you run multi-day tours outside Crete?
Yes — we organise private multi-day tours throughout Greece, including Santorini, Mykonos, Athens, Nafplio, and the Peloponnese. These are often combined with a Crete base, but standalone tours of other destinations are equally welcome.
Ready to design your private Greek adventure? 105 Olives Greece has been crafting tailor-made multi-day experiences since 2018.