Luxury Sailing Experiences

Your private yacht for a limited time – with air-conditioned cabins, private bathroom & shower cubicle, a private chef and a friendly crew to pamper you!

Trip start

Exclusive sailing trips for fall & winter

28/12
 - 
04/01/2026

New Year's Eve from St. Lucia to the Grenadines

Sailing Yacht Journey
24/01
 - 
31/01/2026

Sailing trip in the BVIs

Sailing Yacht Journey
25/01
 - 
04/02/2026

10 nights island hopping from Grenada

Sailing Yacht Journey
17/02
 - 
03/03/2026

In sailing paradise: Island hopping from/to Antigua

Segel-Yacht-Reise
31/01
 - 
10/02/2026

Island hopping from Martinique via Dominica & Guadeloupe to Antigua

Sailing Yacht Journey
18/02
 - 
24/02/2026

Sailing and exploring the BVIs

Sailing Yacht Journey
03/03
 - 
10/03/2026

Sailing trip around Antigua and to Barbuda

Sailing Yacht Journey
04/12
 - 
20/12/2025

On the "barefoot route" across the Atlantic

Crossing

Sailing in paradise

Caribbean sailing vacation

A sailing trip through the Caribbean with SAILING-CLASSICS is pure joie de vivre under white sails. Between turquoise waters, palm-fringed bays and gentle trade winds, you will experience the sea at its most beautiful. On board our large, comfortable yachts, you will sail from island to island, enjoy swimming stops in crystal-clear lagoons and the sunset with a cool drink on deck. Whether lively markets, colorful colonial towns or secluded dream beaches – every stage brings new impressions and the incomparable feeling of freedom at sea.

Unsere Schiffe

Chronos

Fantastic large yacht in classic style

54m length, 1000m² sail area, max. 26 passengers and 10 crew members

13 cabins with private bathroom, shower and air conditioning

Cruising area: Summer in the western Mediterranean Sea, winter in the Caribbean

Dinghy for shore excursions, water sports equipment

Your sailing boutique hotel!”

Rhea

Fantastic large yacht in classic style

54m length, 1000m² sail area, max. 25 passengers and 10 crew members

13 cabins with private bathroom, shower and air conditioning

Cruising area: Summer in the western Mediterranean Sea, winter in the Caribbean

Dinghy for shore excursions, water sports equipment

Your sailing boutique hotel!”

“Your private yacht for a limited time!”

Kairós

Sailing yacht in classic style

38m length, 556m² sail area, max. 16 passengers and 7 crew members

13 cabins with private bathroom, shower and air conditioning

Cruising area: summer in the Adriatic, winter in the Caribbean

Dinghy for shore excursions, water sports equipment

Where our yachts are at home

From Caribbean ease to Mediterranean flair – our sailing trips combine relaxation,
adventure and the fascination of unique coastal landscapes.
Mediterranean Sea

Mediterranean island dreams under white sails

Caribbean
Dream bays, sea, freedom
Atlantic
From the Canary Islands to Cape Verde

Your sailing trip -
optimally planned

Still not sure which sailing trip suits you best? Our experts will take time for you, answer your questions and work with you to find the perfect route. Simply arrange your personal consultation – free of charge and without obligation.

Stylish sailing for
beginners and experienced sailors

Follow the call of the wind with a maximum of 26 guests, experience the beauty of sailing, anchor in idyllic bays, discover picturesque islands, explore charming harbor towns and glide through crystal-clear waters. With a bit of luck, you may even spot dolphins and whales. If possible, we sail 4-6 hours a day.

Exclusive insights into our sailing trips

First comes the newsletter. Then comes the journey.

Sign up for our newsletter and be the first to find out about new sailing trips, exclusive offers and highlights from our most beautiful sailing areas.

What our guests say about their time on board

High praise

This is the fifth time we have enjoyed a trip with Sailing Classics, this time between the Greek islands. And in November we want to sail across the Atlantic with...

Everything optimal

I will remember these two weeks for a long time to come, because there was a good balance between shore leave, swimming, sailing and wonderful weather. The crew was outstanding...

blick-auf-die-segel-der-chronos-vor-der-amalfikueste

A special experience

You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

blick-von-der-chronso-auf-den-sonnenaufgang

A special experience

You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

Absolutely marvelous charter

It was an absolutely marvelous charter. Loved every minute of it. I have chartered boats a number of times, and I have never had such a friendly, positive, and accommodating...

It was marvelous

About 10 days ago, we had zero sailing experience and no idea what to expect as a family with two young kids (ages 5 and 7) boarding a 3-night charter...

A special experience

You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

An all-round successful trip

It was an all-round successful trip, from the organization and information beforehand to the support and care on board! Captain Nico and his crew did a great job, so that...

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 experience of crossing Atlanticis something special!

We have just passed the Ampere Seamount, an ocean mountain that rises from a depth of over 4,000 m to 56 m at the surface. According to research from the...

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.

News, tips & stories
from our sailing blog

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Caribbean under sail - perfect for solo travelers

Discover our special offers for solo travelers in the Caribbean:

🎉Christmas & New Year’s Eve without single cabin supplement

🏝️Bis 31.03.2026: half single cabin supplement on all Caribbean voyages

⛵Tip: Combine two weeks and secure a multi-week discount