Sailing Greece - Santorini to Santorini - 10 Days

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Trip Snapshot

Genders

  • Female50%
  • Male50%

Average age

44
16 Min100 Max

Start / End

  • Firá
  • Firá

Physical rating

3/5

Group size

1 - 10

Meals included

0

Highlights

  • Embark on an unforgettable 10-day yacht adventure from the iconic island of Santorini, sailing aboard a state-of-the-art 57 ft vessel through the dazzling azure waters of the Greek Cyclades.
  • Discover the diverse beauty of the Cycladic islands, including tranquil Ios with its famous Magganari beach and ancient sites like Homer's tomb, alongside Naxos, offering optional excursions to the historic Temple of Dimitra, a local microbrewery, and stunning views of Mount Zeus.
  • Immerse yourself in the cosmopolitan charm of Mykonos, where you can admire picturesque windmills, enjoy a refreshing cocktail with panoramic views over Little Venice, and experience the island's vibrant beaches and thrilling nightlife.
  • Explore a tapestry of other Cycladic gems, from strolling through the bustling markets of Syros to wandering amidst the atmospheric Venetian ruins on Paros, each island offering a unique glimpse into Greek culture and history.
  • Engage with local traditions and breathtaking landscapes on Sifnos, where you can hike scenic trails and visit artisan ceramic workshops, before being captivated by Folegandros' dramatic cliffside city of Hora, the perfect spot for sunset cocktails.
  • Indulge in the authentic flavours of Greece, dining on fresh seafood at charming local tavernas and sampling traditional Ouzo, with ample opportunities for enriching activities like snorkelling in crystal-clear bays and participating in a meaningful Naxos Wildlife and Conservation Awareness Experience.
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Free Brochure

Uncover insider tips, see a packing list and view a detailed itinerary and accommodation information.

Summary

A yacht adventure is the ideal way to experience what many consider the world’s most beautiful islands in Greece. Sail aboard our all-new, state-of-the-art 57 ft yachts, with time for hiking, snorkelling, and relaxing. Explore ancient archaeological sites and taverna-lined harbours, dine on fresh seafood and don’t forget to try the Ouzo! This 10-day round trip from Santorini will give you the chance to explore some of the treasures of the Greek Islands.

Itinerary

  • Day 1

    Santorini

    Arrival day. Join the group at 11am for a welcome meeting and safety briefing before beginning the journey through the Cyclades. We highly recommend booking pre-tour accommodation in order to have time to explore the island of Santorini.

  • Day 2

    Cyclades - Ios/Small Cyclades/Naxos

    Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos. The islands of the Cyclades offer a range of different experiences on each island.

    While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb.

    Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.

  • Day 3

    Cyclades - Ios/Small Cyclades/Naxos

    Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos. The islands of the Cyclades offer a range of different experiences on each island.

    While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb.

    Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.

  • Day 4

    Cyclades - Ios/Small Cyclades/Naxos

    Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos. The islands of the Cyclades offer a range of different experiences on each island.

    While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb.

    Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.

  • Day 5

    Mykonos

    Arrive to Mykonos and opt to visit the local windmills and enjoy a cocktail on a veranda overlooking Little Venice. The beaches and nightlife add excitement to this picturesque island.

  • Day 6

    Cyclades - Syros/Paros/Sifnos/Folegandros

    Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset. Find countless treasures and must-grab deals while strolling through the markets of Syros.

    Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop.

    No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.

  • Day 7

    Cyclades - Syros/Paros/Sifnos/Folegandros

    Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset. Find countless treasures and must-grab deals while strolling through the markets of Syros.

    Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop.

    No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.

  • Day 8

    Cyclades - Syros/Paros/Sifnos/Folegandros

    Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset. Find countless treasures and must-grab deals while strolling through the markets of Syros.

    Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop.

    No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.

  • Day 9

    Cyclades - Syros/Paros/Sifnos/Folegandros

    Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset. Find countless treasures and must-grab deals while strolling through the markets of Syros.

    Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop.

    No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.

  • Day 10

    Santorini

    Depart after breakfast. Depending on weather conditions and access, the drop-off location may vary. A shuttle transfer will take you to Santorini, where you can explore or relax before your onward journey. We highly recommend booking post-tour accommodation on the island.

What's Included

  • Accommodation

    5 twin/double bed cabins with en suite or shared facilities.

  • Meals

    Breakfasts: 0, Lunches: 0, Dinners: 0

    Vegetarian options are available on all meals throughout the adventure.

    Vegetarian options available

  • Local Guide

    Guided

    This adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.

  • Wifi

    Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.

Dates & Prices

  • Jun 2026

    from £1,104

  • Jul 2026

    from £1,288

  • Aug 2026

    from £1,564

  • Sep 2026

    from £1,514

  • Apr 2027

    from £1,781

  • May 2027

    from £1,781

  • Jun 2027

    from £1,949

  • Jul 2027

    from £1,949

  • Aug 2027

    from £1,949

  • Sep 2027

    from £1,880
  • Save 41%
    Thursday 11 Jun 2026to Saturday 20 Jun 2026
    6+ spaces of 10 leftGuaranteed Departure
    £1,859£1,104
    Best offer
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Customer reviews & ratings

(4.67 out of 5)Based on 297 reviews

  • Amazing! For me this was a magical experience! It was an amazing unique adventure!

    Arlene Oct, 2024 Verified

  • It was a magical experience. An opportunity to do things and see things that are amazing. Wonderful experience. A chance to see and do things you never expected

    Frances Oct, 2024 Verified

Essential trip information

Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.

Frequently asked questions

  • What is the primary style of this tour?

    This is a marine-style yacht adventure, ideal for experiencing the Greek Islands through sailing, hiking, snorkeling, and relaxing.

  • What are the main highlights of this Greek Islands sailing trip?

    Key highlights include sailing through the pristine waters, capturing iconic snapshots on Santorini, wandering through whitewashed villages on Paros, enjoying the nightlife on Mykonos, and discovering Venetian architecture on Naxos.

  • What kind of accommodation is provided on the yacht?

    The tour offers accommodation in 5 twin/double bed cabins, which may have en suite or shared facilities. Please note that specific cabins cannot be guaranteed, and sleeping quarters are designed to be snug to maximize public space.

  • What should I know about the space and amenities on board the yacht?

    Space onboard is limited, especially in cabins. Beds are approximately 1.8 meters (6 feet) long. Fresh water for showers is limited to one quick shower per person per day. Electrical outlets are European 2-pin (240V) and only operational when in port; an external battery pack is recommended for personal electronics, and CPAP machines cannot be accommodated due to inconsistent power.

  • Am I expected to help with duties on the yacht?

    Yes, this is a self-catering trip, and all participants are expected to help with keeping the boat tidy, including cleaning up after themselves, washing dishes, and emptying bins when ashore.

  • Are meals included in the tour price?

    Generally, meals are not included to provide flexibility. However, a 'food kitty' of approximately EUR 90 per person per trip is collected to cover small food items for self-prepared breakfasts, lunches, and occasional dinners onboard. Most dinners are taken ashore at local restaurants.

  • What is the physical rating for this tour, and what level of fitness is required?

    This tour has a physical rating of 3. Travelers should have an average level of fitness and mobility, able to walk unaided, climb 3-4 flights of stairs, step on and off small boats, carry their own luggage, and be comfortable moving around the yacht in waves.

  • Are there any health considerations or medical forms required for this trip?

    It is recommended to consult your travel doctor for up-to-date medical information. People prone to seasickness should come prepared. Travelers with pre-existing medical conditions are required to complete a medical questionnaire signed by their physician to ensure they meet the trip's physical demands. Please note, constant power for sleep apnea/CPAP machines is not available onboard.

  • What is the maximum group size for this sailing tour?

    The maximum group size is 10 travelers, with an average group size of 6.

  • Who will be leading the tour, and what is their role?

    A fully licensed Skipper/CEO (Chief Experience Officer) will lead the tour. Their role includes safely navigating the yacht, taking charge of sailing, ensuring safety onboard, providing information about the islands, offering suggestions for activities and local dining, and facilitating a great group experience. They may also request help with sailing tasks.

  • What currency is used in Greece, and what should I know about money exchange?

    The only currency accepted in Greece is the EURO. You can exchange foreign currency or traveler's checks at banks or 'kiosko' money exchange points, keeping in mind that banks are typically open from 8:00 AM until 2:00 PM and closed on national holidays.

  • Is tipping customary in Greece, and what are the guidelines?

    Tipping is customary in Europe. A standard rule is 10% of the bill for wait/hospitality staff and €1 or €2 for other service providers. For your Skipper CEO, a minimum guideline of 10 EUR per person per day is suggested, and for local guides, 10-20% depending on service quality and length.

  • How much emergency money should I bring for this trip?

    It is recommended to have access to at least an additional USD $200 (or equivalent in EURO) as an emergency fund for unforeseen circumstances.

  • What kind of optional activities can I expect during the trip?

    Optional activities may include exploring archaeological sites, enjoying taverna-lined harbors, visiting local markets, uncovering Venetian ruins, hiking trails, stopping at ceramic workshops, and experiencing the nightlife and cocktail spots on islands like Mykonos. A budget of up to €175 (approx. $200 USD) is recommended for these activities.

  • Is travel insurance compulsory for this trip?

    Yes, travel insurance is compulsory. You must have a policy that covers medical expenses, including emergency evacuation and repatriation, with a minimum coverage of USD 200,000.

  • Is there an extra cost for solo travelers?

    No, there is no single supplement for solo travelers on our group trips. You will be paired in twin or multi-share accommodation with someone of the same sex.

  • How flexible is the tour itinerary?

    The itinerary is flexible and will be tailored to meet the desires of the group and prevailing weather conditions. Your Skipper will advise of any necessary or desirable alterations, typically on Day 1 of the tour.

  • What type of luggage should I bring?

    Due to limited space on the yacht, only soft-sided luggage, such as a mid-sized backpack or soft duffel bag (less than 15kg), is permitted. Hard suitcases are not suitable.
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