Sail the Day - Skiathos Sailing Trips

Sail the Day - Skiathos Sailing Trips

Sail the Day - Skiathos Sailing Trips
5
Scuba & SnorkellingBoat ToursPrivate ToursFood ToursDay Trips
About
Real Sailing experience in small groups or in private. You will enjoy a fantastic time on board including Snorkeling,Swimming and a delicious meal freshly prepared on the boat served by Captain Stefanos
Skiathos Town, Skiathos, Greece
Meets animal welfare guidelines

Awards
Travelers' Choice
2023

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(117 reviews)
(80 reviews)
(52 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles905 reviews
Excellent
896
Very good
4
Average
1
Poor
0
Terrible
5

Peter
7 contributions
5.0 of 5 bubbles
Aug 2021
One of those perfect days that will live long in the memory. I am so glad I stumbled on sail the day when I was looking last minute for a yacht charter for my family.

Stefanos really earned trust with a super quick response to my query sharing all the information I needed; it made it an easy decision to book and arriving at the quay the next day he met us with a broad smile and Nini (not sure of correct spelling), his wise, gentle and very cute sea dog. I knew it would be a special day.

Once all the guests arrived he made sure, in a brilliantly inclusive way, that we all knew a bit about each other. He was also careful to find out what everybody wanted from the day and incorporated that into the experience.

With the introductions done, the sails went up quickly and before we knew it we dropped anchor at the first of many excellent snorkelling stops during the day.

The undoubted highlight, and there were many so this is praise indeed, was a magical lunch. After mooring in a beautiful bay Stefanos sent us off swimming whilst he prepared the food. In about 20 odd minutes he had somehow whipped up a truly memorable and delicious feast with a seafood meze masterpiece as the main element, as well lots of other local treats spinning around it. How he achieved this level of culinary excellence in a yacht galley, whilst still being an excellent host, I have no idea, but the Michelin guide would do well to take a charter with him.

After lunch we lazed in the bay before setting sail again for some more sight seeing. Everyone got a turn at the helm, if they wanted, and the fact that he sets off a bit later than the other boats (10:30am) meant the sail back was under a beautiful golden early evening sun.

As a son of Liverpool, drifting gently back to port to the sound of John Lennon’s imagine felt very fitting: “Imagine all the people livin' life in peace” summed up the day and seemed very representative of Stephanos’s generosity, humility and spirit. Heartfelt thanks for an amazing day.
Written August 16, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

fivedays2016
Bedfordshire, UK310 contributions
5.0 of 5 bubbles
Aug 2020 • Family
By far the best day of our holiday and the best boat trip I have ever been on by a mile. This was the third time we have sailed with Stefanos - he is an absolute master at what he does and has created something quite unique and very special. I think others have tried to re-create his format but I have heard that they just don’t compare. You set sail at 10.30 and return after sunset, stopping at several beautiful locations for snorkelling, swimming and amazing lunch. I think the maximum Stefanos sails with is 10/11 so it’s very personal, nothing like the big noisy boats that hold 50/100 people. If you want an experience that will stay with you forever then book ‘Sail the Day’. Covid measures also in place, so it all felt very safe. Thankyou Stefanos for another unforgettable day.
Written September 2, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Charlie R
Ferndown, UK60 contributions
5.0 of 5 bubbles
Sep 2021
'Who cares' ? Captain Stefanos cares very much .... A day sailing around the islands off Skiathos in the Aegean Sea is a day that will last long in the memory with 'Sail the Day' and Stefanos. Sail the Day is so much more than most other boat trips that any of us can select along the port in Skiathos town. Captain Stefanos is a big Greek man, full of character who wears his heart on his sleeve and is passionate about making the day so much fun for everyone. He so wants each person to experience not just just the beautiful turquoise clear waters of any boat trip, but also infectiously encourages you to loosen up from our comfort zone by trying (and teaching each person) snorkelling and sailing and to eat the fresh shell fish caught by himself just minutes before cooking. To me, he is a mix of a Greek philosopher like Socrates and Crocodile Dundee and is instrumental in making the experience so much fun with his frequent jingle style quotes such as 'who cares' and 'one day we are going to die' and many many more funny one liners :-). My trip was also enhanced by my fellow 9 passengers who were all hilarious and whom we all bonded with so quickly thanks again to Stefanos and his inclusive style of team building from the moment we set sail. The trip itself was magical with plenty of swimming stops and a huge lunch and the opportunity to jump of the bow in the early evening, before sailing back into Skiathos against the backdrop of a stunning sunset. It is also worth pointing that Stefanos also has an assistant in his little dig called Nini who could have performed on a Disney set with his joyful little character. You won't regret booking this trip and you won't need your camera as Stefanos takes numerous photographs throughout the day and forwards them on to you. A man of true star quality and a trip everyone visiting Skiathos must do in my opinion
Written September 24, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

shellyb87
Birmingham, England55 contributions
5.0 of 5 bubbles
Sep 2020 • Couples
My husband and I booked this trip in a recommendation. We had been on the run of the mill boat trip to see a couple of beaches which was ok at a push. But this is like no other boat trip, it's an experience and a great one at that. There was 9 people on our trip, me and my husband and 7 others who turned out to be a great bunch of people, who helped make it a lovely day. Phones and valuables are kept safe but accessible once you get on the boat, you are offered plenty of cold bottles of water for the trip. Captain Stephanos is a character as is his little dog Nini, shes adorable. It was a little windy at times on our trip which made for a great days sailing. We each got a chance to steer the boat, help with the sails, drop the anchor etc. before we got escorted off by Nini for a spot of snorkeling while Stephanos prepared lunch. Lunch is not a posh affair with table clothes and wine glasses, it's another great experience, get involved and enjoy it all, the food and the company. We met Captain Stelios at this point as he swam across from his boat and joined us for lunch. After lunch another dip while Stephanos cleared away we then had a choice of more sailing or more snorkeling, we chose sailing and enjoyed a relaxing trip with music playing. One more stop to jump off the boat into the sunset, even Nini had a little swim. Then back to shore. Reading back over my review really doesn't do it justice, some details have been left out so as to not spoil the surprises for when you take the trip. It really is not just another boat trip it is THE boat trip and if you do nothing else all holiday make sure you take this trip with Captain Stephanos and Princess Nini.
Written September 14, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Rebecca
6 contributions
5.0 of 5 bubbles
Jul 2022
Having never been on a sailing boat before, I was a little apprehensive prior to the trip, but Captain Stefanos soon put me & my friends at ease with his knowledge and showmanship. I would have to say this was one of the best experiences of my life, it was not only exhilarating and scary at the same time, it was relaxed and very enjoyable. The scenery around these islands are simply stunning and I would thoroughly recommend this boat trip for anyone visiting Skiathos, I intend to rebook when I return! Becky
Written July 21, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Charlotte D
2 contributions
5.0 of 5 bubbles
Aug 2021 • Family
Absolutely amazing - again! We sailed with Stefanos and princess Nini (the dog) in August 2020 as a family of four and had the most amazing time that we booked again for this year and took my husband’s parents and sister’s family too. Our group had children aged from 8 to 16 and six adults - everyone had the best time and all had a go as skipper, sailing us through the beautiful Aegean Sea.
Top highlight of the holiday! Snorkelling, sailing, amazing food (how is it even possible to create such incredible food on the boat!), fantastic company, the best skipper/ host you could hope for in Stefanos and… we even saw dolphins - lots of them playing in the waves of our boat and leaping through the water! So good you can’t help thinking about when you can go again…
Written September 12, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

nicholad
United Kingdom18 contributions
5.0 of 5 bubbles
Aug 2020
What a wonderful sailing trip- I highly recommend Sail the Day. Captain Stefanos ensured the day was highly enjoyable from start to finish. At the start of the trip he asked all of his guests what they wanted from the day and he made sure everyone got their wish. One young guest asked to see dolphins and we did, Amazing! Stefanos sails you to some wonderful beaches, keeps everyone entertained, prepares delicious food for lunch and ensures you have the most perfect day.
Written August 26, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Paul M
London, UK4 contributions
5.0 of 5 bubbles
Aug 2020
Firstly. STOP. Ask yourself what you really want from a day at sea in the Greek Islands. If you want mainstream, Mamma Mia, mass tourist, mediocrity, book some other dull day with a dreary sea dog gouging you and your bored family or friends.

Then, think about a mega-relaxed, yet involving day MC-ed and masterfully skippered by Stephanos.

My family of eight enjoyed a real day to treasure with this philosophical and honestly, deep-thinking man and his delightful salty sea dog, Ninni (apologies for any spelling errors).

If you want an experience, not another day in your life. Do. Not. Hesitate. Book this trip, IF you can.
Written August 7, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Saxgirl
cheshire71 contributions
5.0 of 5 bubbles
Aug 2022 • Couples
Hubby and I sailed with Stefanos last week and we had an absolute blast ! Spent the whole day laughing with some fabulous people, eating amazingly fresh and sometimes surprising food, drinking quite a lot of lemonade (honest!), swimming and snorkelling and engines off for a good sail whilst the wind was up (learnt quite a few tips even though I’ve sailed many times.. Stefanos is a great teacher). Was a bit reluctant to part with my cash before booking , but turns out it was great value because we had the most gorgeously memorable day, highly recommend if you have a sense of humour and adventure. Many thanks Stefanos! Linda and Mel X
Written September 3, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Frankfurt4
77 contributions
5.0 of 5 bubbles
Sep 2020 • Family
Stefanos did a great job on his sailing yacht showing us beautiful swimming and snorkeling bays and sailing us to Skopelos with the added bonus of an exquisite seafood lunch on board.

He is an excellent sailor and looks very well after the safety of his guests.

We will be back next time on Skiathos!
Written September 15, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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