Imagine gliding through the crystal-clear, deep-blue waters of the Caribbean aboard the CHRONOS or RHEA—the trade winds filling the sails as you sit on the teak deck and watch the sunlight glisten on the waves. Welcome to Sailors Paradise!
Join us for an incomparably stylish and authentic Caribbean experience, far from mass tourism and the usual routes of large cruise ships.
The Caribbean is so much more than a dream in postcard colors. Aboard the CHRONOS and RHEA, you’ll experience this island paradise from a very special perspective. Our itineraries take you to places accessible only by boat—secluded coves, pristine beaches, charming islands, each with its own unique character. But what they all have in common is the Caribbean “vibe” and the cheerfulness of the locals, the ever-present “reggae” featuring the unforgettable Bob Marley, the endless beaches, and above all, the exuberant tropical nature that sometimes grows almost vertically up volcanic cones. It’s contagious, and some people never want to leave…
Our sailing trips offer island hopping with genuine, authentic sailing on huge yachts. It’s both relaxing and exhilarating…
For example, we’ll take you to the Grenadines and the Tobago Cays—three small, palm-fringed sandy islands—and the surrounding Horseshoe Reef. It’s ideal for a beach barbecue, or for swimming, kayaking, and snorkeling. Or you can watch the locals fishing and see how they often sell their catch to us right on the spot…
Our experienced crew will make sure you feel completely at home on board while you experience the thrill of sailing up close. If you’d like, you can also actively participate in the sailing, take the helm, or set the sails—under the guidance of our professionals, of course. With a length of 54 m, a weight of 370 t, and a sail area of 1,000 m², the CHRONOS and RHEA are ideally suited for sailing in the trade winds. No other sailing area has such consistent wind conditions, as the trade winds blow 9 out of 10 days… (We’re only in the Caribbean during the winter, outside of hurricane season.) The distances between the islands can also be easily covered in sailing trips lasting 4–6 hours.
After an eventful day at sea, a culinary highlight awaits you: freshly prepared delicacies from the ship’s galley, which you can enjoy under the starry sky while the gentle rocking of the ship lulls you to sleep.
In addition to sailing, the focus is, of course, on exploring the diverse islands. Unlike the large cruise ships, our trips take you to hidden gems off the beaten path. Whether you’re strolling through the charming fishing village of Clifton on Union Island or joining our good friend Alex, a local guide on St. Vincent, for a short walk—past the film sets of *Pirates of the Caribbean*, surrounded by papayas, mangoes, breadfruit, bananas, cacao, nutmeg and cashew trees, tamarinds, taro plants, goats, chickens, cows, and cattle egrets all around us—all the way to a waterfall in a small botanical garden.
For nature lovers, the Caribbean islands offer countless possibilities: hikes through dense rainforests, a visit to the botanical gardens on St. Lucia, or a kayaking tour through the fascinating mangrove forests. While out at sea, we can usually spot schools of flying fish, frigatebirds soaring on the updrafts in front of the masts, and sometimes even whales (humpback or sperm whales), with the former occasionally leaping high out of the water. At anchor, there are often sea turtles and a great many fish to observe. But also the starry sky at night and the brief yet intense downpours—it’s both a delight and an adventure all in one.
And, of course, culinary delights are a must: Try local specialties such as fresh fish, spicy jerk chicken, or a refreshing rum punch at a cozy beach bar.
Aboard the CHRONOS and RHEA, you’ll enjoy not only authentic sailing experiences but also the highest level of comfort. The ships combine the nostalgic charm of historic tall ships with modern amenities. With a maximum capacity of 26 guests, you’ll find a private, intimate atmosphere that leaves plenty of room for individual preferences—whether you’re relaxing in a comfortable cabin or enjoying the spacious deck with a view of the endless sea.
We place special emphasis on the shared experience on board. At Sailing-Classics, a family-like atmosphere quickly develops, providing space for relaxed conversations and new friendships. The small groups and personalized attention make every trip a personal experience, where you decide for yourself how active or relaxed your day will be.
A trip through the Caribbean with Sailing-Classics is much more than just a vacation—it’s a journey of discovery on the water, a journey of self-discovery. You’ll experience the Caribbean at its most authentic and enjoy the freedom that only the wind and the sea can offer. Whether you’re seeking adventure, want to experience the authenticity of the Caribbean, or simply want to unwind—on board Sailing-Classics, you’ll find your very own personal retreat.
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
