Self-Launched Greek Islands Sailing: Santorini to Kos
8 days · Greece
G Adventures charges £1,650
No-markup version: ~£610 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Ditch the group yacht package and island-hop the Cyclades and Dodecanese on your own terms. This self-launched version of G Adventures' Santorini to Kos sailing route swaps a shared 15m yacht for a mix of budget ferry hops, affordable guesthouses, and optional local sailing day trips — giving you the same sun-soaked anchorages, taverna seafood, and snorkelling spots at a fraction of the price. You'll sail, swim, hike, and explore remote island ports just like the commercial tour, but with full freedom over your pace, your stops, and your spending. Costs below are approximate estimates per person.
Day-by-day
Arrive in Santorini — Settle In & Explore by Night
Santorini (Thira)
Fly or ferry into Santorini and check into your guesthouse or budget hotel in Fira or Perissa. Spend the afternoon getting your bearings — walk the caldera rim at Fira, catch sunset views from Oia (arrive early to beat the crowds), and grab dinner at a harbourside taverna. This is your orientation day before the ferry-hopping begins.
🚌Fly into Santorini (Thira) Airport or take a high-speed ferry from Athens Piraeus (~£40-55). Local bus from airport/port to Fira, ~£2
🛏Budget guesthouse or hostel in Fira or Perissa (e.g. Caveland Hostel or similar), ~£25-35/night
- →Walk the caldera rim path from Fira to Oia (~10km, free)
- →Watch the famous Santorini sunset from Oia or the Fira clifftops
- →Explore Fira's narrow lanes, local shops, and waterfront bars
- →Dinner at a local taverna — try grilled octopus and local Assyrtiko wine
Santorini to Amorgos — First Ferry Hop
Amorgos
Catch a morning or midday ferry from Santorini to Amorgos, one of the most dramatic and least touristy islands in the Cyclades. Known for its clifftop monastery (Hozoviotissa) and crystal-clear waters, Amorgos was famously the setting for 'The Big Blue'. Check into a simple guesthouse in Katapola or Aegiali and explore on foot.
🚌Ferry Santorini to Amorgos, ~£25-35 (book via Ferryhopper.com or DirectFerries.co.uk)
🛏Family-run guesthouse in Katapola or Aegiali, ~£25-35/night
- →Ferry crossing Santorini → Amorgos (Blue Star Ferries or SeaJets), ~£25-35
- →Visit the stunning Monastery of Hozoviotissa perched on the cliffside (free, modest dress required)
- →Swim at Agia Anna beach below the monastery
- →Evening ouzo and meze at a harbourside café in Katapola
Astypalea — The Butterfly of the Aegean
Astypalea
Take a ferry onward to Astypalea, shaped like a butterfly and straddling the Cyclades and Dodecanese. This quiet, whitewashed island has a stunning hilltop kastro, turquoise coves, and barely any tourist crowds. Hire a scooter or quad to explore the island's remote beaches.
🚌Ferry Amorgos → Astypalea (may require a brief stop at Kos or Kalymnos depending on schedule). Check ANEK Lines or Blue Star. ~£20-30
🛏Simple guesthouse or studio apartment in Skala or Chora, ~£25-35/night
- →Ferry Amorgos → Astypalea, ~£20-30
- →Explore the medieval Kastro of Astypalea and its hilltop windmills (free)
- →Scooter or quad hire to reach remote beaches like Livadia, Tzanakia, and Vatses, ~£20/day
- →Fresh fish dinner at a taverna in Pera Gialos harbour
Nisyros — Volcano Island
Nisyros
Ferry to Nisyros, a volcanic island with an active caldera you can walk right into — one of the most unique experiences in the Aegean. The main village of Mandraki is a gem of black-and-white pebble mosaics and bougainvillea-draped alleys. Don't miss the local speciality: pitties (chickpea fritters).
🚌Ferry to Nisyros via Kos or direct, ~£15-25. Local bus to volcano, ~£5 return
🛏Guesthouse or small hotel in Mandraki, ~£25-35/night
- →Ferry Astypalea → Nisyros (via Kos or direct), ~£15-25
- →Walk into the active Stefanos Crater at Polyvotis volcano (entrance ~£4)
- →Explore the village of Nikia with its circular plateia and caldera views
- →Wander the lanes of Mandraki and try local pitties and souma spirit
Tilos — Snorkelling & Hiking
Tilos
A short ferry hop to Tilos, one of the Aegean's most peaceful islands and a protected nature reserve. With excellent snorkelling off deserted beaches and easy hiking trails, this is your day to slow down and connect with the water. The island is small enough to explore fully on foot or by bicycle.
🚌Ferry Nisyros → Tilos, ~£10-15. Island is walkable or hire bicycle ~£8/day
🛏Guesthouse or pension in Livadia, ~£25-35/night
- →Ferry Nisyros → Tilos, ~£10-15
- →Snorkelling off Eristos Beach — bring your own mask or hire locally, ~£5
- →Hike to the abandoned medieval village of Mikro Horio (free)
- →Visit Tilos Castle ruins above Megalo Horio for panoramic Aegean views
Kalymnos — Sponge Divers & Rock Climbers
Kalymnos
Ferry to Kalymnos, world-famous for both its traditional sponge-diving heritage and its status as one of Europe's top rock climbing destinations. Even non-climbers will love the rugged limestone scenery, the lively port of Pothia, and the excellent fresh seafood. Visit the Nautical & Folklore Museum to learn about the island's sponge-diving tradition.
🚌Ferry Tilos → Kalymnos, ~£15-20. Local buses and taxis available on island
🛏Budget hotel or guesthouse in Pothia or Myrties, ~£25-35/night
- →Ferry Tilos → Kalymnos, ~£15-20
- →Visit the Nautical & Folklore Museum of Kalymnos (sponge-diving heritage), ~£3
- →Walk or taxi up to Kastelli Byzantine castle for views over the port
- →Optional: beginner rock climbing session with a local guide via GetYourGuide, ~£45
- →Browse the sponge market in Pothia and pick up a natural sponge souvenir
Leros — Art Deco Harbours & Hidden Coves
Leros
Take the ferry to Leros, a lesser-known gem with a surprisingly charming Italian Art Deco waterfront (a legacy of Italian occupation), a magnificent hilltop castle, and some of the calmest, most swimmable bays in the Dodecanese. Hire a bicycle and spend the day circling the island at your own pace.
🚌Ferry Kalymnos → Leros, ~£10-15. Bicycle hire ~£8/day
🛏Guesthouse or studio in Agia Marina or Alinda, ~£25-35/night
- →Ferry Kalymnos → Leros, ~£10-15
- →Explore the waterfront of Lakki with its striking Art Deco architecture (free)
- →Hike up to the Castle of Panteli for sweeping views over the island (~£2 entry)
- →Swim at Pandeli or Vromolithos beach
- →Fresh seafood dinner in Agia Marina harbour
Arrive Kos — Ancient Ruins & Farewell Swim
Kos
Final ferry hop into Kos, the birthplace of Hippocrates and a vibrant island with ancient ruins, a lively harbour town, and excellent beaches. Spend your last day exploring the archaeological site of the Asklepion, the ancient Agora, and the plane tree of Hippocrates before a farewell meal at a harbour taverna.
🚌Ferry Leros → Kos, ~£10-15. Bicycle hire is the best way to get around Kos Town (~£8/day). Fly home from Kos Airport (KGS) or ferry to Athens
🛏Budget hotel or hostel in Kos Town, ~£25-35/night (or depart same evening by ferry)
- →Ferry Leros → Kos, ~£10-15
- →Visit the Asklepion ancient healing sanctuary (~£8 entry)
- →Explore Kos Town's ancient Agora and the Knights' Castle (entrance ~£4)
- →Cycle to Paradise or Tigaki Beach for a final swim (bike hire ~£8/day)
- →Farewell dinner of grilled fish and Mythos beer at Kos harbour
Self-launched vs. G Adventures
| This itinerary (self-launched) | G Adventures | |
|---|---|---|
| Price per person | ~£610 | £1,650 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £1,040 per person (63%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more G Adventures-style trips? Check them out here.~£610
estimated per person
You never pay Travel Crew for this — you pay hostels, transport, and activity providers directly, the same as if you'd booked it all yourself.
This publishes your dates so other travellers can find and join you — no tour operator needed.
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Frequently asked questions
How much does Self-Launched Greek Islands Sailing: Santorini to Kos cost?+
Doing it yourself with this self-launched itinerary costs an estimated £610 per person for 8 days in Greece. This is an AI-generated estimate based on typical budget-traveller prices — actual costs will vary by season and how you book.
Is this cheaper than booking with G Adventures?+
Yes — G Adventures charges around £1,650 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £610 — a saving of roughly £1,040 (63%) per person.
How long is the Greece trip?+
This itinerary runs 8 days, covering 8 day-by-day stops through Greece.
How do I join this trip?+
You can join an existing open departure using this itinerary if one is scheduled, or launch your own departure with your own dates and invite other travellers to join you — no tour operator required.
Isn't it easier to just use a tour operator?+
Well, yes, a tour operator will book all the individual parts of your travel for you and provide a guide. That's obvious, but doing this has the potential to save the group thousands, which can in turn improve your itinerary substantially or save you huge amounts of money. Also, when you launch a departure, Travel Crew has tools in place to help you book the individual sections of the trip or make it easier for you to do this as a group. Really, you do not need a middle man. If you are more comfortable paying more and using a middle man, then you should certainly do this.
Is it safer to book through a tour operator?+
Arguably, there isn't much difference. A self-launched trip runs on the same principle as a group travel crew: collective responsibility, everyone looking out for each other, the same way it would if a group of friends organised the trip themselves — because that's exactly what's happening. You should always take out travel insurance before you go, self-launched or not; that doesn't change either way. Every open departure is published publicly with real dates and a real trip organiser, so it's never an anonymous arrangement, and our support team is reachable any time you need help, including in an emergency while you're away. Longer-term, we're building direct relationships with ground DMCs in popular destinations, offered as an optional paid add-on for extra on-the-ground support. Ultimately, though, the group is responsible for its own conduct and safety on a self-launched trip, same as on any trip you plan yourself.
What kind of trip is this?+
This is a adventure, beaches, culture trip through Greece, self-launched rather than run by a tour operator — you organise it with a group you find or bring yourself.
Would you like to name the operator, name the trip, or have any suggestions about how to improve this itinerary?
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