Sailing Greece Self-Launched: Kos to Santorini Island Hop
8 days · Greece
G Adventures charges £2,100
No-markup version: ~£600 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched 8-day Aegean island hop following the same Dodecanese-to-Cyclades route as the G Adventures Kos–Santorini sailing trip — but on ferries and local boats instead of a chartered yacht. You'll start at Kos Marina where the yachts moor, then hop the lesser-visited Dodecanese (Kalymnos, Leros, Nisyros, Tilos) before crossing to Amorgos and finishing in Santorini. You can bolt on a day sail or snorkel trip on a shared yacht day-charter (typically £50–80) to get the sailing hit without the £2,000+ cabin price. Costs are rough budget-traveller estimates for peak-summer Greece (July–August); shoulder season is 20–30% cheaper.
Day-by-day
Arrive Kos and get your sea legs
Kos
Fly into Kos (or arrive by ferry from Athens/Rhodes). Base yourself in Kos Town, a 10-minute walk from Kos Marina where the G Adventures yacht joins. Explore the ancient Agora and the Asklepieion ruins, wander the harbour tavernas and pick up an ouzo. Book your onward Blue Star ferry tickets at a local travel agency or online tonight — Dodecanese ferries fill in summer.
🚌Airport bus to Kos Town (~€3) or taxi ~€35
🛏Budget guesthouse or hostel in Kos Town (£25–35)
- →Explore Kos Town harbour & old town
- →Visit the Asklepieion archaeological site
- →Book onward ferry tickets
Sail-equivalent day trip or ferry to Kalymnos
Kalymnos
Option A (the sailing hit): book a shared day sail/snorkel trip out of Kos Marina on GetYourGuide or direct with a local charter — often a 6-hour trip to Pserimos with lunch. Option B (cheaper): take the morning ferry to Kalymnos (about 1 hour, ~€12). Kalymnos is a sponge-diving island with dramatic limestone cliffs, world-famous rock climbing and a lively harbour at Pothia.
🚌Blue Star/Dodekanisos Seaways ferry Kos–Kalymnos ~€8–14
🛏Guesthouse in Pothia or Myrties beach (£25–35)
- →Shared day sail & snorkel from Kos Marina (optional, £55–75)
- →Ferry hop to Kalymnos
- →Harbour walk in Pothia
Kalymnos beaches and cliffs
Kalymnos
Slow morning — swim at Myrties or Massouri beach and look across at the islet of Telendos (a 10-minute water taxi, ~€5 return). Hike part of the climbing trails above Massouri for big Aegean views. In the afternoon catch the ferry onward to Leros (about 45–60 minutes).
🚌Local water taxi ~€5; Kalymnos–Leros ferry ~€8–12
🛏Budget rooms in Lakki or Agia Marina, Leros (£25–35)
- →Water taxi to Telendos islet
- →Coastal hike above Massouri
- →Ferry to Leros
Leros: the quiet Dodecanese
Leros
Leros is one of the least-visited islands on this route — Italian-era architecture at Lakki, a hilltop castle at Pandeli and good seafood. Rent a scooter (~€20/day) or use the local bus to get between the three main villages. In the evening take the overnight-ish or next-morning ferry toward Nisyros/Tilos.
🚌Local bus or rental scooter ~€15–25
🛏Guesthouse in Agia Marina or Pandeli (£25–35)
- →Pandeli castle & windmills
- →Scooter or bus loop of the island
- →Seafood taverna dinner
Nisyros volcano island
Nisyros
Ferry to Nisyros (via Kos or direct seasonal crossings — check Dodekanisos Seaways). Walk the rim of the Stefanos crater — one of Greece's most accessible active volcanoes — then wander the whitewashed village of Nikia perched on the caldera edge. This is exactly the kind of remote anchorage the sailing route stops at.
🚌Ferry to Nisyros ~€10–15
🛏Small guesthouse in Mandraki (£25–35)
- →Hike the Stefanos volcanic crater
- →Explore Nikia and Mandraki villages
- →Swim at Pali beach
Cross to the Cyclades: Amorgos
Amorgos
Make the crossing from the Dodecanese into the Cyclades. Ferries from Kos/Nisyros/Tilos to Amorgos run several times a week in season (3–5 hours) — check schedules on Ferryhopper and book ahead. Amorgos is the dramatic cliff-hugging island where much of 'The Big Blue' was filmed: the cliffside monastery of Hozoviotissa is unmissable.
🚌Inter-island ferry ~€20–35
🛏Guesthouse in Chora or Katapola (£28–38)
- →Ferry crossing Dodecanese → Cyclades
- →Cliff walk to Hozoviotissa monastery
- →Swim at Agia Anna beach
Amorgos to Santorini
Santorini
Morning ferry from Amorgos (Katapola) to Santorini — around 1.5–2.5 hours depending on service. Check into budget rooms in Fira or Karterados (not the caldera — those are £200+ a night). Afternoon: walk the caldera rim path toward Fira, grab a gyros, and catch the Oia sunset by local bus rather than paying for a caldera-view table.
🚌Ferry ~€12–25; local bus €2
🛏Budget rooms in Karterados or Fira (£35–50)
- →Ferry Amorgos–Santorini
- →Fira caldera rim walk
- →Oia sunset via local bus
Santorini and depart
Santorini
Morning swim at Kamari or Perissa black-sand beach, or a quick visit to Ancient Akrotiri if time allows. Local buses connect the airport and port cheaply. Check the departure flight timing — the G Adventures trip notes suggest 2pm+ flights for flexibility, and the same advice applies here.
🚌Local bus to airport €2–3
🛏None (departure day)
- →Black-sand beach swim
- →Akrotiri ruins (optional, ~€12)
- →Depart from Santorini airport or port
Self-launched vs. G Adventures
| This itinerary (self-launched) | G Adventures | |
|---|---|---|
| Price per person | ~£600 | £2,100 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £1,500 per person (71%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more G Adventures-style trips? Check them out here.~£600
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 Sailing Greece Self-Launched: Kos to Santorini Island Hop cost?+
Doing it yourself with this self-launched itinerary costs an estimated £600 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 £2,100 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £600 — a saving of roughly £1,500 (71%) 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 beaches, adventure, backpacker 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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