Island Hopping in Greece - Santorini To Santorini

Trip code: GVSS

Trip Highlights

  • Gear up for a brilliant Yacht adventure on the Sea of Crete.
  • Learn the ropes of sailing from an experienced skipper.
  • Explore some of the most beautiful groupings of Greek Islands.
  • Swim or Snorkel in the pristine turquoise waters.
  • Laze around like a beach bum by the white sandy shores.
  • Binge on delicious fresh seafood.
  • Hit the many highlights of Cyclades as you map your way to Mykonos & back.
  • Wander through whitewashed villages on Paros.
  • Enjoy the party life on Mykonos and get some Insta-worthy shots!
  • Discover Venetian architecture on Naxos.

Tour Details


Have you always dreamt of getting close to the enchanting city of Santorini which glows with its white-washed houses with the blue roofs? Well, Go Discover Abroad brings to you the perfect 10-days round trip around the islands of Greece, that starts and ends at Santorini. Hop on a yacht and get started with the adventurous journey that'll give you a chance to explore the picturesque Greek islands like Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos. No matter whether you are on your gap year in Greece or just looking for a perfect family vacation - this tour will offer you the best that this part of the world has in store!


Day 1 - Arrival in Santorini and off to the Cyclades

Welcome to Greece! Your journey begins today. Make sure to reach Santorini before 11 AM, when you’ll be joining others in your group for a welcome meet and safety briefing before starting your sailing adventure. Get on the Mediterranean Sailing Yacht and let's sail off to the Cyclades.

Day 2 - 4 Exploring the Cyclades

Have your list of places hands-on ready as you’re going to set sail today and your journey is as far as your imagination. Now don’t let your imaginations run too wild for the skipper will be still in-charge! Share your plans for the day with your experienced skipper for he’ll be taking you places today. The itinerary for the day will be planned according to the desires of the group so that each of you can have a bombastic experience out on the sea. 

While circling the Southern Cyclades you should definitely keep places like Syros, Naxos, Temple of Dimitra, Manganari Beach, the famous Homer’s tomb and the list goes on. Enjoy the views of Mt. Zeus while enjoying lunch in a local tavern or stop by a local ceramic workshop in Sifnos.

Day 5 - Head off to Mykonos

Arrive in style to Mykonos and explore this glamour island of Greece! Visit the local windmills or enjoy an amazing brunch on a verandah overlooking the stunning Little Venice. Beyond its exciting beaches, Mykonos is also famous for its amazing nightlife. So you should definitely hit the clubs to have a blast! 

Day 6 - 9 From Mykonos to the Cyclades

Now, as we head back, you'll have more time to explore all that you've missed out in the first round! Some amazing things that we've kept on the itinerary are Syros Island Excursion, Paros Island Excursion, Folegandros Island Excursion and more. There would surely be space for impromptu plans, so you can just hop on the yacht and get started.

Day 10 - Return from the Cyclades to Santorini

As the fun-filled island hopping trip comes to an end, we would like you to book your return flights from here. You can also continue to explore the Greek mainland, and head off to Athens!

Dates & Cost

Price Includes
  • 9 nights aboard a 52ft grand sailing yacht.
  • Fully licensed skipper.
  • Snorkeling equipment.
Price Excludes
  • International/Domestic Airfare.
  • Visa Fees.
  • Insurance expenses (can be purchased from us at minimal cost).
  • Cost of Vaccinations.
  • Additional tours and activities (not included as paid for in the itinerary).
  • Airport transfers (available at extra cost).
  • No meals included.



Accommodation - 4 twin/double bed cabins, 3 bathrooms, 3 showers.

A NOTE REGARDING SMALL SPACES ON SAILBOATS: - Please note that the rooming for these boats is assigned upon arrival and neither particular cabins, nor berths can be guaranteed. You will be sharing a bunk or double bed with your travel partner or one of your fellow passengers of the same sex and sharing the bathrooms onboard. - Please be aware that as this is a real sailboat and not a cruise vessel and the space on board is tight. The sleeping quarters on sailboats are generally kept to a minimum size in order to maximize public space and performance. - It may be possible to smell engine and/or diesel fumes when in the cabins, due to their proximity to the engine room. Most travel is done during the day, so it is unlikely you will be in the cabin when the engine is running. - Some people are not comfortable with the type of close quarter arrangements typically found on sailboats, however if a real sailing experience on a real sailboat is what you are after, then this experience should more than make up for cramped quarters. - Opportunities to sleep in open air on main deck are often available. - Please note that the skipper may also be sharing the ship's quarters and amenities with you. - Power onboard is 220V on European 2 pin sockets. Please note that this is not suitable for sleeping aid machines, as the power source may not always be operating. Bringing a battery pack is recommended.


Meals Included - No meals included

Eating is a big part of traveling. Travelling with Go Discover Abroad you experience the vast array of wonderful food that is available out in the world. Generally meals are not included in the trip price when there is a choice of eating options, to give you the maximum flexibility in deciding where, what and with whom to eat. It also gives you more budgeting flexibility, though generally food is cheap. Our groups tend to eat together to enable you to taste a larger variety of dishes and enjoy each other's company. There is no obligation to do this though. Your CEO will be able to suggest favourite restaurants during your trip. The above information applies to Go Discover Abroad group trips. For Independent trips please check the itinerary for details of meals included. For all trips please refer to the meals included and budget information for included meals and meal budgets. On our Greek sailing trips, the Go Discover Abroad Skipper/CEO will help you make a food kitty, where around EUR 75 per person, per week will be added to the kitty for small food items on board to cover breakfasts, lunches and the odd dinner. Breakfasts and lunches are prepared by yourself, and most dinners are taken ashore at local restaurants.