Sailing experiences at luxury level
Your private yacht for a time – with air-conditioned cabins, private bathroom & shower cubicle, a private chef and a warm crew to pamper you!
Sailing vacations - a very special kind of luxury
Experience an indescribable feeling of freedom that can only be found on a sailing ship. The wide view to the horizon, the sea breeze blowing through your hair, the fading of everyday life, the dreamlike sunsets – all in casual yacht style. Our sailing trips are a particularly beautiful and free kind of luxury that can hardly be put into words. Come on board and feel it for yourself.
Dreamlike large yachts in classic style
Sail with us on one of our 3 luxurious, classic sailing yachts (38-54 m) with teak deck and open railing – an experience usually reserved for yacht owners. You have your own air-conditioned double cabin with plenty of storage space, portholes (small windows) and en-suite bathroom including shower cubicle. There is a large saloon and plenty of space on deck with lounging and seating options for relaxing as well as areas protected from the sun and wind.
Sail along in style - wherever the wind takes us
Follow the call of the wind with a maximum of 26 guests, experience the beauty of sailing, anchor in idyllic bays, discover picturesque islands that can only be reached by boat, explore charming harbor towns and glide through sparkling, crystal-clear water. With a bit of luck, you may even spot dolphins and whales. We sail 4-6 hours a day if possible.
With a friendly crew & fantastic service
Enjoy freshly baked rolls & cakes, a 2-course lunch, a 3-course dinner, sundowner cocktails, fine wines and exotic snacks every day. Feel the unique maritime atmosphere while our professional crew pampers and cares for you. Real sailing with the comfort of a cruise. Interact with the crew if you wish, look over their shoulders as they navigate or lend a hand.
CO-SAILORS ABOUT THEIR TIME ON BOARD:
A great pleasure
I would like to express my great pleasure at having taken part as a passenger in the wonderful, eventful and indeed exhilarating voyage with the RHEA on the occasion of the Antigua Classic Yacht Regatta 2025. Even a few days later, it was a trip that I will remember for a very, very long time.
28.04.2025 Matthias after the Antigua cruise on board the RHEA
Full of positive impressions...
The sailing trip was fantastic, great in all respects and we are still delighted with the Chronos. The flights all went smoothly and the luggage always followed us through check-in without any problems. We will probably not have travelled to the Caribbean on a sailing trip for the last time - maybe to the British Virgin Islands in a few years, who knows...
17.02.2025 Barbara and Roger after their CHRONOS cruise in the Grenadines in January
It was in 1 word: Great
It was in 1 word: Great. We really enjoyed this trip with KAIRÓS. Everyone was super friendly and they tried more than 100% to make us feel comfortable. And they succeeded. We had a fantastic vacation that we will look back on fondly.
Bertie and John after their trip to the Aeolian Islands
The Sailing Classics moment
We don't really know how to put this wonderful trip into words... We made new friends, had deep conversations, experienced wonderful nature and are wholeheartedly grateful for the great crew around Captain Lenno, who spoiled us the whole week. The crew on board made all the difference, always friendly and helpful, always smiling and with an eye for detail.
23.04.2024 - Irmi and Alex after their first sailing trip on the KAIRÓS off Corfu & the Ionian Islands
What distinguishes Sailing-Classics from sailing cruises and yacht charters?
Normal sailing cruise
On most sailing cruises, you are one of hundreds of guests on board.
You stick to a fixed route and follow it regardless of the wind and weather.
In order to keep to the schedule, a lot of motoring is required to reach each port on time.
Sailing-Classics
There is a maximum of 26 guests and 7-10 crew members on board our ships, who sail the ship and look after you with loving care.
The wind sets the course. We offer you real authentic sailing without the constraints of a fixed routing.
On average, our yachts are under sail 70% of the time. They are set several times a day and always trimmed according to the wind.
Charter vacation
You have to take care of everything yourself: Navigating, sailing, cooking, tidying up, shopping & cleaning.
Handing over and returning the yacht takes time and nerves – your vacation often begins and ends with stress instead of peace and quiet.
Charter yachts are often not in the best condition. Instead of sailing comfortably, you repair them. After all, you bear full responsibility.
Where do you want to go on your sailing trip?
Sailing on a luxury yacht - in the Caribbean, in the Mediterranean Sea& on the Atlantic
Do you feel like dreaming?
Browse through our sailing trips and spark your anticipation
"Small" Atlanticcrossing from the Azores to Portugal
"Big" Atlanticcrossing to the Azores
"Barefoot route" via the Atlantic to St. Martin
"small" Atlantic crossing from Gibraltar to Tenerife
Mediterranean SeaCrossing Malta-Gibraltar
A day on board a luxury sailing yacht:
You are snuggled up comfortably in your bunk. The smell of freshly baked bread rolls fills your nose. It’s time to start the day. You slip into your swimsuit and jump straight off the boat into the crystal-clear water while the morning sun shines gently. After a short swim, it’s time for breakfast.
You choose what your heart desires. While you eat, you look out over the glittering waves and the beautiful bay where you spent the night. Your captain tells you how the wind is blowing today and that a deserted island is perfectly on course. You set sail.
The sails are set and you listen to the gentle lapping of the waves. You give yourself over completely to the beauty of sailing: sitting on deck, feeling the wind in your hair, feeling free. At this very moment, a family of dolphins joins you and plays with the bow waves of the ship.
After a few minutes, the dolphins move on and you decide to read a book. This continues for the next few hours until the captain discovers a small bay. There, the chef serves you a delicious 2-course meal. You sit together with the other guests on deck – there is no seating arrangement, you are barefoot, in casual yacht style.
After lunch, you explore the small bay in a kayak, then set sail again and reach the secluded island. You travel to the island in dinghies (small inflatable boats), walk along the beach, enjoy the sun and treat yourself to a small picnic: an exotic specialty and a refreshing coconut.
Back on your temporary ship, the crew has prepared a sundowner for you to sip with relish. The chef will spoil you with a lovingly prepared 3-course menu. Full and satisfied, you end the day with a glass of wine on deck and good conversation. You are already looking forward to the next day, as the captain has announced that you will reach a charming port city tomorrow.
Happy and far away from everyday life, you fall asleep, gently cradled by the waves of the sea.
NEWSLETTER
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Who are sailing trips with Sailing-Classics ideal for?
First of all, because it is so important to us:
Everyone is welcome on board with us!
Nevertheless, you should have a slight level of physical fitness. This means that you should be able to climb stairs – even on a slight incline.
Couples who love freedom, the sea & and pleasure
Experience a relaxing break under sail with your partner. Even if your other half isn’t a big sailing fan, they’ll get their money’s worth – that’s a promise!
Singles & solo travelers who want to make new contacts
There are many single travelers on board our yachts. Thanks to the relaxed atmosphere on board and no fixed seating arrangements at mealtimes, you’ll quickly make friends and perhaps even make friends for life.
Parents with children who want to spend a relaxing time
The perfect mix of relaxation and action for families and individual parents with children – everyone can enjoy themselves with us! Children up to the age of 14 can sleep in their parents’ cabin for a special price of €450.
Friends who are looking forward to an unforgettable experience
Do you know those experiences that you and your friends still rave about years later? That’s exactly what awaits you on board our yachts. A time together that you will never forget.
WHAT OUR GUESTS SAY ABOUT THEIR SAILING EXPERIENCE:
Always in a good mood
Despite some adverse sailing weather, the crew acted super professionally and were always in a good mood, so that we felt like we had 100% sunshine.
27.04.2022 - Petra and Stephan
Chapeau!
To experience such a great wind with only 3 sailing days was of course a bit of luck, but we couldn't have expected that this wind was also used for sailing and that the sails were not reefed to half. Chapeau!
15.06.2022 - Ulrich and Dorothee
The most perfect ship
Kairós is definitely the most perfect ship - familiar & cozy!
09.12.2022 - Mareike and Jan
And a special word of praise for the crew
I'll be brief: it was very nice again and everyone was delighted! Once again, the entire crew deserves special praise... In the end, it's always the people who make something special.
16.03.2023 - Andreas and his group of friends
Very well done!
Many thanks again to the entire Sailing-Classics team for this wonderful trip, including the birthday promotion on May 29. - Very well done! Once again, greetings and thanks to the crew of the Kairos!
15.06.2023 - Utz
Your private yacht for a limited time
Our luxury sailing yachts in classic style
RHEA
Titan of well-being and serenity
RHEA is one of the largest classic sailing yachts in the world. She sails in winter in the Caribbean and in summer, after the Atlanticcrossing, mostly in Greece and in the eastern Mediterranean Sea.
54m
Yacht length
1000m²
Sail area
10
Crew members
26
Guest capacity
CHRONOS
Leader of the Titans and the march of time
CHRONOS is the sister ship of the RHEA and therefore also one of the largest classic sailing yachts in the world. She sails mainly in the west Mediterranean Sea on the Côte d’Azur, in Italy & in the Caribbean islands.
54m
Yacht length
1000m²
Sail area
10
Crew members
26
Guest capacity
KAIRÓS
Seize the right moment
We launched this sailing concept in 2007 with the KAIRÓS. At 38m, she is slightly smaller and therefore perfect for island hopping in Croatia, Corfu & the Ionian Islands, Sicily and the Peloponnese.
38m
Yacht length
556m²
Sail area
07
Crew members
16
Guest capacity
How it all began
THE HISTORY OF SAILING-CLASSICS
In 2001, Andreas Steidle-Sailer (our founder) visited the Voiles de Saint-Tropez, the most important sailing regatta on the Côte d’Azur.
There he spotted the newly restored yacht “Endeavour” – a classically elegant beauty. As a passionate sailor and lover of classic yachts, he was so enthusiastic about this ship that he absolutely wanted to sail on it for a few days.
But he realized that apart from the extremely expensive full charters, there was no way to sail on these luxury yachts. Driven by the motivation to make this sailing experience possible, he founded SAILING-CLASSICS in 2007 after much preparatory work. A concept that is still unique today.
But be careful: Before you arrange a personal meeting with us now, you should know:
There is a risk of addiction – 70% of our guests come back!
Some have been on board more than 14 times. Often even with friends they have made on board. That’s why we affectionately call our ships “Friendships”.
VOTES FROM OUR CO-SAILORS:
Wonderful days on the CHRONOS
We had 4 wonderful days on the Chronos with the best weather, very nice fellow travelers and a top-notch staff on board! Everything is simply great! Therefore gladly again!
03.07.2024 - Anita and Tom after their taster cruise on the Amalfi Coast in June
The Sailing Classics moment
We don't really know how to put this wonderful trip into words... We made new friends, had deep conversations, experienced wonderful nature and are wholeheartedly grateful for the great crew around Captain Lenno, who spoiled us the whole week. The crew on board made all the difference, always friendly and helpful, always smiling and with an eye for detail.
23.04.2024 - Irmi and Alex after their first sailing trip on the KAIRÓS off Corfu & the Ionian Islands
It was an unforgettable and wonderful trip!
It was an unforgettable, wonderful trip. Everything was perfect! A super great ship and a great crew who spoilt us. We quickly grew together with the other guests and friendships developed. And all this in a fantastic sailing area, what more could you want?
22.03.2024 - Ina, Bernhard, Timo and Desi after their trip to the Grenadines
Many thanks to the whole team
We had a trip with KAIRÓS that could not have been better. Many thanks to the whole team and not least to our fantastic crew!
13.10.2023 - Martin and his family after their cruise off Sicily
A dream trip across the Atlantic
It was a dream trip... Every morning during the RHEA cruise I got up in the dark and, after greeting the night shift crew, sat down on a bench with a headlamp and started writing into the dawn. Organizing your life - is there a better way to do this than during a three-week crossing through an empty world (which is by no means empty under the keel)? ... A wonderful time, ... especially the two stops that allowed us to take a dip in the 5,000 meter deep Atlantic. So all this will remain unforgettable, a lifelong dream...
30.03.2023 - Peter
Questions & Answers
Do I need sailing experience to get on board?
No, you don’t need to, just a desire for the sea! Many of our guests get their first taste of the sea with us. Once they have experienced it, most of them want to go sailing again and again.
Start, for example, with a trial cruise or in a beginner’s area such as Sardinia – Corsica or Corfu & the Ionian Islands. We will be happy to advise you in a personal consultation.
-> To the beginner areas
-> To the taster trips
-> Get non-binding advice
What if I get seasick?
First of all, very few people actually get seasick (only 0.5%). Often there is only concern and when you come on board you quickly realize how stable a sailing ship of this size is in the water.
This is because the large sail area and the ballast keel (60 tons for RHEA & CHRONOS) support the ship. Unlike ferries or motor yachts, a sailing ship is therefore much calmer in the water and there is NO unpleasant rolling motion.
There are also lots of tips and tricks for avoiding seasickness:
- Make sure you eat a normal diet that is not too heavy or contains histamine and take plenty of vitamin C. Fruit is available on board at all times.
- Stay on deck for the first few hours and watch the horizon. This will help your body and your vestibular system to get used to the movement of the boat.
- Drink enough. We provide you with ginger tea and other drinks free of charge the whole time. Ginger tea in particular is not only healthy and delicious, but also a great insider tip against seasickness.
We or your crew on board will be happy to advise you. Just in case, we recommend taking light medication against motion sickness.
If you are worried about getting seasick, why not book a trial cruise first or choose a “beginner’s area” at Mediterranean Sea such as Sardinia – Corsica or Croatia/Corfu.
Are the sailing trips also suitable for solo travelers & singles?
Absolutely. Many guests travel alone. Thanks to the relaxed atmosphere on board, you will quickly make friends. There is no fixed seating arrangement – everyone chats to everyone else. As this often leads to real friendships, we affectionately call our yachts “Friendships”.
When booking, you can choose whether you would like to share the cabin with a second person of the same sex.
Or whether you would like guaranteed single use of the cabin. For single use in the low season we add 50% and in the high season* we add 80%.
*July 1 – October 1 week, Christmas, New Year, Regatta, Atlanticcrossing east-west (barefoot route)
Can I also actively participate in sailing?
Yes, you can. After instruction from the crew, you can take the helm yourself and help with trimming, setting and stowing the sails and navigating.
Many a die-hard blue water or regatta sailor has already been impressed by the great sailing characteristics of RHEA, CHRONOS and KAIRÓS and even wanted to sign on with us afterwards.
But complete sailing novices are also welcome to help out with the sailing if they want to.
Are there places of retreat on board?
Yes, there is. CHRONOS and RHEA are about 20 times the size of a typical 44-foot charter yacht (13 m), which is normally sailed by 6-8 people. Each guest has a small charter yacht to themselves.
The large open teak deck offers plenty of space for relaxing, reading, daydreaming or watching the passing scenery.
We sail about 4-6 hours a day. Afterwards you can swim, snorkel, go to the beach, go on a shore excursion or stroll through a nearby harbor village. Everyone can ‘do their own thing’ on board to a certain extent.
During the meal, you sit together with the other guests. In our experience, guests quickly get to know each other and great friendships develop.
Do I have to take part in all activities?
No, you don’t have to take part in all activities. You are always free to decide. After all, it’s your sailing experience and you want it to be just the way you want it. There is no peer pressure with us!
What activities are there?
Most people are already very enthusiastic about sailing itself. The freedom of the seas, the deceleration on board, the beauty of sailing & nature.
You can also go on shore excursions to explore charming harbor towns, go hiking, relax on the beach, visit sights, enjoy local specialties, browse small stores, experience wine tasting and much more. Depending on the area, there are great & varied possibilities!
You can enjoy a wide variety of water sports from our ships. From stand-up paddling, water skiing, wakeboarding and kneeboarding, banana boating or donut boating to snorkeling, swimming or wave kayaking, everything is included.
What about safety on board?
Your safety is our top priority. As a commercial shipping company, we adhere to much higher safety standards than recreational sailors.
It starts with the professional crew:
The captain and helmsman must have completed a nautical college and could also drive a large cruise ship with their patents.
The deck crew has proven sailing qualifications and undergoes regular safety training for crew and guests.
The ships themselves were built and tested in accordance with the latest, very high Dutch safety requirements. They are licensed to sail worldwide. Despite their speed, the ships are extremely stable and safe.
The hull of the ships is also divided into many small sections, each with powerful pumps. This means that if water should enter the ship, it can be pumped out quickly and precisely. So far, however, no such incident has ever occurred.
All our ships are inspected and approved annually by the authorized classification society (a kind of TÜV). You will also receive an annual refit at our trusted shipyard.
Furthermore, our ships are well equipped with extensive safety equipment. From life rafts to a 96 nm radar, an emergency generator, radar buoys (Epirb and Sart), satellite and radio systems as well as emergency medical equipment, fire protection systems and extensive emergency plans, everything is included and this equipment is also checked annually.
Just as important – should something happen: With us, all guests are insured in accordance with the international standards for cruise and passenger ships and are not – as co-sailors – personally responsible, as is usual with charter yachts.
If you have any further questions, we will of course be happy to answer them in person.
How much storage space is there in your cabin?
The cabins on board are very spacious. There is a closet where you can hang clothes as well as individual compartments.
There is plenty of space under your bed to store travel bags. However, we still recommend a foldable bag and not a suitcase.
The bathroom also has plenty of space and a lockable shower cubicle so that the bathroom stays dry while you shower. There is also a hairdryer.
Do I have to take towels with me?
No, you don’t have to. Large & small shower towels and large bath towels are provided in your cabin. These can be changed daily on request.
Does my cabin have windows?
Yes, your cabin has 2 portholes (round windows) through which daylight enters.
What about the catering on board?
There is always a chef on board our ships who will spoil you every day.
What you can expect:
- A daily changing breakfast buffet with freshly baked rolls or bread, sweet pastries such as cakes, pancakes, crepes, croissants or muffins, fresh fruit & vegetables, with various toppings such as cheese, sausage & jam, egg dishes, yogurt, muesli and juice.
- A 2-course lunch with main course and dessert.
- Coffee with smoothie & freshly baked cake.
- A changing afternoon snack with ingredients & specialties from the region.
- A delicious sundowner cocktail (not included).
- A 3-course dinner with starter, main course and dessert.
Water, tea, coffee and fruit are available free of charge throughout the day.
Alcoholic drinks and soft drinks are available at moderate prices at the ship’s bar.
If you have any intolerances, please let us know in good time so that we can prepare everything for you.
What additional costs should I expect?
Soft drinks and alcoholic beverages, motorized water sports and excursions organized by us are subject to a charge. We strive to offer all these things at moderate prices and are far below the prices of other cruises.
A good guideline for ancillary costs on board is 10% of the cruise price. However, individual consumer behavior varies greatly and the cost of excursions also varies greatly depending on the area.
Tips on board are also not included in the cruise price. A “tip box” is available for this on the day before your departure. The captain will divide the amount among all crew members present.
Do we anchor in a bay at night or are we in the harbor?
Both and. On some days you will anchor in bays, on other days you will lie in the harbor. This depends very much on the area, the wind & weather and the route. If you have a preference, please talk to us and we will recommend a sailing trip based on this.
What language is spoken on board?
The onboard language of our international crew is English, with the guests is communicated in German and English. As a rule, people on yachts are on first-name terms.
Fellow sailors about their time on board
Always in a good mood
Despite some adverse sailing weather, the crew acted super professionally and were always in a good mood, so that we felt like we had 100% sunshine.
27.04.2022 - Petra and Stephan
Chapeau!
To experience such a great wind with only 3 sailing days was of course a bit of luck, but we couldn't have expected that this wind was also used for sailing and that the sails were not reefed to half. Chapeau!
15.06.2022 - Ulrich and Dorothee
The most perfect ship
Kairós is definitely the most perfect ship - familiar & cozy!
09.12.2022 - Mareike and Jan
And a special word of praise for the crew
I'll be brief: it was very nice again and everyone was delighted! Once again, the entire crew deserves special praise... In the end, it's always the people who make something special.
16.03.2023 - Andreas and his group of friends
Very well done!
Many thanks again to the entire Sailing-Classics team for this wonderful trip, including the birthday promotion on May 29. - Very well done! Once again, greetings and thanks to the crew of the Kairos!
15.06.2023 - Utz
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