01 May 2027
Twin share
£1,368pp
Escorted tour
Sail Greece: Santorini to Mykonos by Yacht – 8 Days
Seven nights on a skippered yacht through Ios, Amorgos, the Small Cyclades, Naxos and Syros, in a group of up to 11.
8 days
From £1,368
Tour overview
This 8-day sailing trip island-hops through the Cyclades on a skippered yacht, from Santorini to Mykonos by way of some of the quietest and most beautiful islands in the Aegean. Groups have up to 11 travellers aged 15 and over, with an experienced local skipper who knows the best anchorages and harbours. You spend seven nights on board a 54 to 56ft monohull yacht with two double cabins, two twin-bunk cabins and a triple-bunk cabin, sharing five bathrooms. Breakfast and lunch are included from the second day, often eaten on deck, and evenings are spent in harbour tavernas.
You meet your skipper in Santorini and take a ferry to Ios to join the yacht. From there, you sail to Amorgos, the mountainous island made famous by the film The Big Blue, with its cliff-hanging monastery of Hozoviotissa and steep hiking paths.
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Over the following days you explore the Small Cyclades, a cluster of islands where only Koufonisia, Iraklia and Schinousa are inhabited. Days are spent swimming in crystal-clear bays, snorkelling, relaxing on deck and, time permitting, going ashore to explore whitewashed villages and empty beaches. Naxos, the largest of the Cyclades, brings sandy beaches, small villages and the olive groves around its capital, Hora, with its Venetian old town.
Sailing on to Syros, with a stop for a swim in the Bay of Gaidharos, you discover a relaxed island with an elegant neoclassical capital, Ermoupoli. A short final sail brings you to Mykonos in the late afternoon, with time to explore its windmills, Little Venice and lively waterfront before the trip ends the next morning. Routes depend on wind and weather, and the skipper adapts each day to conditions.
The physical rating is medium, with time on a moving boat and climbing on and off the yacht. This trip suits sociable, active travellers who love the sea and want to see the Greek islands from the water. Pack light in a soft bag, as storage space on board is limited. Departures run through the summer sailing season, when the Aegean is at its warmest for swimming. No sailing experience is needed to join.
Trip highlights
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Joining the yacht on Ios (Day 1)
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Amorgos and its cliffside monastery (Day 3)
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Swimming in the Small Cyclades (Day 4)
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Naxos and its Venetian old town (Day 5)
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Syros and the Bay of Gaidharos (Day 6)
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An evening in Mykonos (Day 7)
Your route
8 stops from Santorini to Mykonos
- Santorini Day 1
- Ios Day 1
- Koufonisia Day 2
- Amorgos Day 3
- Schinousa Days 4–5
- Naxos Day 6
- Delos Day 7
- Mykonos Days 7–8
Why choose this tour
The Cyclades from the water, with quiet bays few ferries reach. A local skipper and a small, sociable group.
Best suited to
- Sea lovers and swimmers
- Sociable travellers
- Solo travellers looking for a small group
- Island hoppers
Day-by-day itinerary
8 days from Santorini, Greece to Mykonos, Greece
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Day 1 · Santorini, Ios Santorini to Ios
Meet your skipper and take the ferry to the yacht.
- Hotel
- Sailing yacht
-
Day 2 · Ios Ios
Set sail into the Cyclades.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 3 · Amorgos Amorgos
Sail to the island of The Big Blue.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 4 · Koufonisia, Schinousa Small Cyclades
Swim in crystal-clear bays.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 5 · Naxos Naxos
Beaches and the old town of Hora.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 6 · Bay of Gaidharos, Syros Syros
A swim stop and an elegant island capital.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 7 · Mykonos Mykonos
A short sail to Mykonos.
- Hotel
- Sailing yacht
- Meals
- Breakfast, Lunch
-
Day 8 · Mykonos Trip ends
The trip ends at about 10am.
Where you stay
- Cyclades (7 nights) 54–56ft sailing yacht, shared cabins
Hotel names are indicative and may be replaced with a property of similar standard and location.
What's included
Included
- Accommodation 7 nights aboard a sailing yacht
- Meals 6 breakfasts and 6 lunches
- Ferry from Santorini to Ios
- Sailing between the islands with a local skipper
- Swimming and snorkelling stops
Not included
- Flights
- Meals not included 1 breakfast and 7 dinners
- Harbour and port fees where applicable
- Tips, travel insurance and personal spending
This trip might not be for you if…
Honest disclaimer — please read
- You get seasick
- You want private bathrooms — five are shared on board
- You want space — cabins are compact
- You want a fixed itinerary — routes depend on the weather
Good to know
Meals by day
Breakfast: Days 2–7 · Lunch: Days 2–7 · Dinner: none included
FCDO advice
UK FCDO travel advice for Greece
In pictures
Departures & prices
From £1,368 per person, twin share, tour only. 42 upcoming departures.
11 May 2027
Twin share
£1,368pp
15 May 2027
Twin share
£1,368pp
25 May 2027
Twin share
£1,368pp
29 May 2027
Twin share
£1,368pp
08 Jun 2027
Twin share
£1,418pp
12 Jun 2027
Twin share
£1,368pp
22 Jun 2027
Twin share
£1,368pp
26 Jun 2027
Twin share
£1,368pp
06 Jul 2027
Twin share
£1,368pp
10 Jul 2027
Twin share
£1,368pp
24 Jul 2027
Twin share
£1,368pp
03 Aug 2027
Twin share
£1,368pp
17 Aug 2027
Twin share
£1,368pp
21 Aug 2027
Twin share
£1,368pp
31 Aug 2027
Twin share
£1,408pp
04 Sept 2027
Twin share
£1,408pp
14 Sept 2027
Twin share
£1,408pp
28 Sept 2027
Twin share
£1,408pp
02 Oct 2027
Twin share
£1,368pp
29 Apr 2028
Twin share
£1,433pp
09 May 2028
Twin share
£1,433pp
13 May 2028
Twin share
£1,433pp
23 May 2028
Twin share
£1,433pp
27 May 2028
Twin share
£1,433pp
06 Jun 2028
Twin share
£1,433pp
10 Jun 2028
Twin share
£1,433pp
20 Jun 2028
Twin share
£1,433pp
24 Jun 2028
Twin share
£1,433pp
04 Jul 2028
Twin share
£1,433pp
08 Jul 2028
Twin share
£1,433pp
18 Jul 2028
Twin share
£1,433pp
22 Jul 2028
Twin share
£1,433pp
01 Aug 2028
Twin share
£1,433pp
05 Aug 2028
Twin share
£1,433pp
15 Aug 2028
Twin share
£1,433pp
19 Aug 2028
Twin share
£1,433pp
29 Aug 2028
Twin share
£1,473pp
02 Sept 2028
Twin share
£1,473pp
12 Sept 2028
Twin share
£1,473pp
16 Sept 2028
Twin share
£1,473pp
26 Sept 2028
Twin share
£1,473pp
Frequently asked questions
How do I book this tour?
Tap any "Enquire" button on the page and one of our travel specialists will be in touch within 24 hours (often same day). We'll confirm availability on your preferred date, run through anything you need to know, and only ask for the deposit once you've decided.
What financial protection do I get?
Every Travelisto booking is 100% financially protected. Your money is held in a ring-fenced Trust account until you return from your trip, and we are members of the Protected Trust Services scheme (PTS 6035). Most tours also include ATOL protection where flights are part of the package.
What is the yacht like?
A 54 to 56ft monohull with five compact cabins and five shared bathrooms.
Do I need sailing experience?
No, the skipper sails the yacht, though you are welcome to help.
Can the route change?
Yes, the skipper adapts the route to wind and weather.
Are dinners included?
No, evenings are usually spent in harbour tavernas.
What is the minimum age?
The minimum age is 15.
How many people travel together?
Up to 11 travellers, with a local skipper.
Can you tailor the trip?
Yes — every escorted tour can be modified into a private tailor-made version with your own dates, adjusted pace, upgraded hotels and add-on extensions. Tell us what you'd like changed when you enquire and we'll quote it both ways so you can compare.
What if my flight is delayed or cancelled?
If your international flight is part of your booking through us, we re-book at no cost. If you've booked flights separately, the tour's local team holds your transfer slot until you arrive. We strongly recommend a comprehensive travel insurance policy that includes delay and cancellation cover.
ATOL protected
100% financially protected in a Trust bank account
PTS 6035
4.7 on Trustpilot
Tailor-made option
Not quite the right fit? Make it tailor-made.
If this group tour doesn't match your ideal trip, our specialists will turn it into a private tailor-made journey — your own dates, your own pace, upgraded hotels where you want them, and the parts you don't love swapped out. Same destinations, just rebuilt around you.
Contact us for a tailor-made version of this itinerary