Caribbean
Sailing the Caribbean
The Caribbean is our densest sailing ground after the Mediterranean and the winter dream: trade winds, turquoise water, white palm beaches and, from island to island, a new language, cuisine and music. Whether a sailing voyage on a yacht, a catamaran cruise, a sailing cruise on a tall ship, a boutique cruise or ultra-luxury – the Caribbean carries every form, from an intimate passage to the highest comfort.
The Windward Islands – St Lucia, Martinique and the Grenadines
The green Lesser Antilles in the south-east: the Pitons of St Lucia, French Martinique and the dreamlike anchorages of the Grenadines with the Tobago Cays, where you snorkel over coral gardens. Reliable trade winds, short hops, the picture-postcard sailing of the Caribbean.
The Leeward Islands – Antigua, St Kitts and St Barth
Further north: Antigua with its 365 beaches and historic Nelson’s Dockyard, glamorous St Barth with Gustavia, and green St Kitts. Sailing between elegant marinas and lonely bays.
The British Virgin Islands – Tortola, Jost van Dyke and the BVI
The densest anchoring ground in the Caribbean: short legs, sheltered water and legendary beach bars from Jost van Dyke to Norman Island. Ideal for yacht and catamaran, and for the relaxed voyage too.
St Maarten, Guadeloupe and the Îles des Saintes
The middle of the island chain: two-nation St Maarten, French Guadeloupe and the tiny Îles des Saintes with Terre-de-Haut – a touch of Brittany in the tropics. Fine starting points for voyages in either direction.
Barbados and the Caribbean sailing routes
Barbados with Bridgetown is a frequent port of departure and arrival, as are Fort-de-France, Philipsburg and Pointe-à-Pitre. From here the voyages run through the chain of the Antilles – and in spring the Atlantic crossing back to Europe.
Which ship for the Caribbean?
The Caribbean offers the full range – from a sailing voyage to a cruise. Every one of these voyages is arranged and booked through ivent-sailing:
- Sailing yacht with cook and skipper (Kairos, Chronos) – intimate, few guests, anchoring in bays no large ship can reach. The most personal way in.
- Catamaran cruise – spacious catamarans with a skipper aboard; by far the widest choice of catamaran routes and the most popular Caribbean experience, perfect for relaxing, snorkelling and swimming, even without any sailing experience.
- Sailing cruise on tall ships (Royal Clipper, Star Clipper, Star Flyer – the entire Star Clippers fleet) – true sailing under full canvas, the romance of the classic windjammers.
- Windjammer luxury (Sea Cloud II, Sea Cloud Spirit) – hand-set sails, grand-hotel atmosphere at sea.
- Boutique cruising (Le Ponant, Le Champlain) – French elegance, intimate ships, great cuisine.
- Ultra-luxury cruise (Silver Spirit, Silver Shadow) – suite-based, the highest level of service.
So the Grenadines dreamer who is not (yet) ready to book the grand voyage finds the right catamaran in the very same waters – and vice versa.
| Ship | Route | Period | nights | from price p.p. | |
|---|---|---|---|---|---|
| Star Flyer | Philipsburg → Philipsburg | 28.11.–05.12.2026 | 7 | from 2.575 € | View |
| Royal Clipper | St. John's (Antigua) → Bridgetown | 28.11.–05.12.2026 | 7 | from 2.840 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 29.11.–06.12.2026 | 7 | from 4.590 € | View |
| Star Flyer | Philipsburg → Philipsburg | 05.12.–12.12.2026 | 7 | from 2.500 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 05.12.–12.12.2026 | 7 | from 2.755 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 06.12.–14.12.2026 | 8 | from 5.210 € | View |
| Sea Cloud II | Bridgetown → Bridgetown | 08.12.–15.12.2026 | 7 | from 3.840 € | View |
| Star Flyer | Philipsburg → Philipsburg | 12.12.–19.12.2026 | 7 | from 2.500 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 12.12.–19.12.2026 | 7 | from 2.755 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 14.12.–21.12.2026 | 7 | from 2.860 € | View |
| Sea Cloud II | Bridgetown → Bridgetown | 15.12.–22.12.2026 | 7 | from 3.840 € | View |
| Rhea | Antigua → Antigua | 18.12.–28.12.2026 | 10 | from 5.250 € | View |
| Star Flyer | Philipsburg → Philipsburg | 19.12.–26.12.2026 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 19.12.–26.12.2026 | 7 | from 2.840 € | View |
| Kairos | St. Martin → St. Martin | 20.12.–27.12.2026 | 7 | from 3.300 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 21.12.–04.01.2027 | 14 | from 9.120 € | View |
| Sea Cloud II | Bridgetown → Santo Domingo | 22.12.–04.01.2027 | 13 | from 7.640 € | View |
| Chronos | Martinique → Martinique | 22.12.–29.12.2026 | 7 | from 3.900 € | View |
| Star Flyer | Philipsburg → Philipsburg | 26.12.–02.01.2027 | 7 | from 2.650 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 26.12.–02.01.2027 | 7 | from 2.925 € | View |
| Kairos | Segel-Yacht-Reise Karibik mit der Kairos | 27.12.–03.01.2027 | 7 | on request | View |
| Chronos | Martinique → Martinique | 29.12.–06.01.2027 | 8 | from 4.400 € | View |
| Rhea | Segel-Yacht-Reise Karibik mit der Rhea | 29.12.–05.01.2027 | 7 | on request | View |
| Star Flyer | Philipsburg → Philipsburg | 02.01.–09.01.2027 | 7 | from 2.500 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 02.01.–09.01.2027 | 7 | from 2.840 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 04.01.–11.01.2027 | 7 | from 4.320 € | View |
| Star Flyer | Philipsburg → Philipsburg | 09.01.–16.01.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 09.01.–16.01.2027 | 7 | from 2.840 € | View |
| Kairos | St. Martin → BVI: Jost van Dyke / Necker Island / Tortola | 09.01.–16.01.2027 | 7 | from 3.100 € | View |
| Chronos | Martinique → Martinique | 09.01.–19.01.2027 | 10 | from 5.050 € | View |
| Rhea | Antigua → Antigua | 09.01.–19.01.2027 | 10 | from 5.050 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 11.01.–18.01.2027 | 7 | from 4.590 € | View |
| Star Flyer | Philipsburg → Philipsburg | 16.01.–23.01.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 16.01.–23.01.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 16.01.–23.01.2027 | 7 | from 3.100 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 18.01.–25.01.2027 | 7 | from 4.590 € | View |
| Chronos | Martinique → Martinique | 19.01.–26.01.2027 | 7 | from 3.800 € | View |
| Rhea | Antigua → Antigua | 19.01.–27.01.2027 | 8 | from 4.300 € | View |
| Star Flyer | Philipsburg → Philipsburg | 23.01.–30.01.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 23.01.–30.01.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 23.01.–30.01.2027 | 7 | from 3.300 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 25.01.–01.02.2027 | 7 | from 4.590 € | View |
| Star Clipper | Oranjestad → Saint George | 27.01.–06.02.2027 | 10 | from 3.680 € | View |
| Chronos | Martinique → Martinique | 27.01.–06.02.2027 | 10 | from 5.050 € | View |
| Rhea | Antigua → Antigua | 27.01.–06.02.2027 | 10 | from 5.050 € | View |
| Star Flyer | Philipsburg → Philipsburg | 30.01.–06.02.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 30.01.–06.02.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 30.01.–06.02.2027 | 7 | from 3.300 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 06.02.–13.02.2027 | 7 | from 2.840 € | View |
| Star Clipper | Saint George → Saint George | 06.02.–17.02.2027 | 11 | from 4.050 € | View |
| Rhea | Antigua → Antigua | 06.02.–17.02.2027 | 11 | from 5.350 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 06.02.–13.02.2027 | 7 | from 3.300 € | View |
| Chronos | Martinique → Martinique | 06.02.–13.02.2027 | 7 | from 3.800 € | View |
| Star Flyer | Philipsburg → Philipsburg | 13.02.–20.02.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 13.02.–20.02.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 13.02.–20.02.2027 | 7 | from 3.300 € | View |
| Chronos | Martinique → Martinique | 13.02.–23.02.2027 | 10 | from 5.050 € | View |
| Star Clipper | Saint George → Saint George | 17.02.–27.02.2027 | 10 | from 3.680 € | View |
| Rhea | Antigua → Antigua | 17.02.–27.02.2027 | 10 | from 5.050 € | View |
| Star Flyer | Philipsburg → Philipsburg | 20.02.–27.02.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 20.02.–27.02.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → Tortola (BVI) | 20.02.–27.02.2027 | 7 | from 3.300 € | View |
| Chronos | Martinique → Martinique | 23.02.–02.03.2027 | 7 | from 3.800 € | View |
| Star Clipper | Saint George → St. John's (Antigua) | 27.02.–06.03.2027 | 7 | from 2.575 € | View |
| Star Flyer | Philipsburg → Philipsburg | 27.02.–06.03.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 27.02.–06.03.2027 | 7 | from 2.840 € | View |
| Kairos | BVI: Tortola / Virgin Gorda / Jost van Dyke / (Anegada) → St. Martin | 27.02.–06.03.2027 | 7 | from 3.300 € | View |
| Rhea | Antigua → Antigua | 27.02.–06.03.2027 | 7 | from 3.800 € | View |
| Chronos | Martinique → Martinique | 03.03.–13.03.2027 | 10 | from 5.050 € | View |
| Sea Cloud II | Philipsburg → Philipsburg | 05.03.–15.03.2027 | 10 | from 6.111 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 06.03.–13.03.2027 | 7 | from 2.575 € | View |
| Star Flyer | Philipsburg → Philipsburg | 06.03.–13.03.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 06.03.–13.03.2027 | 7 | from 2.840 € | View |
| Kairos | St. Martin → St. Martin | 06.03.–13.03.2027 | 7 | from 3.100 € | View |
| Rhea | Antigua → Antigua | 06.03.–13.03.2027 | 7 | from 3.800 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 13.03.–20.03.2027 | 7 | from 2.575 € | View |
| Star Flyer | Philipsburg → Philipsburg | 13.03.–20.03.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 13.03.–20.03.2027 | 7 | from 2.840 € | View |
| Kairos | St. Martin → St. Martin | 13.03.–20.03.2027 | 7 | from 3.500 € | View |
| Rhea | Antigua → St. Martin | 13.03.–23.03.2027 | 10 | from 5.150 € | View |
| Chronos | Martinique → Martinique | 13.03.–20.03.2027 | 7 | from 3.800 € | View |
| Sea Cloud II | Philipsburg → Philipsburg | 15.03.–25.03.2027 | 10 | from 6.111 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 20.03.–27.03.2027 | 7 | from 2.575 € | View |
| Star Flyer | Philipsburg → Philipsburg | 20.03.–27.03.2027 | 7 | from 2.575 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 20.03.–27.03.2027 | 7 | from 2.840 € | View |
| Kairos | St. Martin → St. Martin | 20.03.–27.03.2027 | 7 | from 3.400 € | View |
| Chronos | Martinique → Martinique | 20.03.–29.03.2027 | 9 | from 4.700 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 27.03.–03.04.2027 | 7 | from 2.575 € | View |
| Kairos | St. Martin → Antigua | 27.03.–03.04.2027 | 7 | from 3.300 € | View |
| Chronos | Martinique → Antigua | 29.03.–05.04.2027 | 7 | from 3.700 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 20.11.–27.11.2027 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 20.11.–27.11.2027 | 7 | from 2.825 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 27.11.–05.12.2027 | 8 | from 5.210 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 27.11.–04.12.2027 | 7 | from 2.535 € | View |
| Star Flyer | Philipsburg → Philipsburg | 27.11.–04.12.2027 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 27.11.–04.12.2027 | 7 | from 2.825 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 04.12.–11.12.2027 | 7 | from 2.470 € | View |
| Star Flyer | Philipsburg → Philipsburg | 04.12.–11.12.2027 | 7 | from 2.470 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 04.12.–11.12.2027 | 7 | from 2.750 € | View |
| Sea Cloud Spirit | Philipsburg → Philipsburg | 05.12.–12.12.2027 | 7 | from 4.106 € | View |
| Sea Cloud II | Bridgetown → Bridgetown | 07.12.–14.12.2027 | 7 | from 4.097 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 11.12.–18.12.2027 | 7 | from 2.470 € | View |
| Star Flyer | Philipsburg → Philipsburg | 11.12.–18.12.2027 | 7 | from 2.470 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 11.12.–18.12.2027 | 7 | from 2.750 € | View |
| Sea Cloud Spirit | Philipsburg → Willemstad | 12.12.–20.12.2027 | 8 | from 4.692 € | View |
| Sea Cloud II | Bridgetown → Bridgetown | 14.12.–21.12.2027 | 7 | from 4.097 € | View |
| Chronos | Martinique → Martinique | 15.12.–22.12.2027 | 7 | from 3.800 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 18.12.–27.12.2027 | 9 | from 3.255 € | View |
| Star Flyer | Philipsburg → Philipsburg | 18.12.–27.12.2027 | 9 | from 3.255 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 18.12.–29.12.2027 | 11 | from 4.440 € | View |
| Sea Cloud II | Bridgetown → Santo Domingo | 21.12.–05.01.2028 | 15 | from 8.798 € | View |
| Kairos | Tobago → Tobago | 22.12.–29.12.2027 | 7 | from 3.300 € | View |
| Chronos | Martinique → Martinique | 22.12.–29.12.2027 | 7 | from 3.900 € | View |
| Rhea | Antigua → Antigua | 22.12.–29.12.2027 | 7 | from 3.900 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 27.12.–03.01.2028 | 7 | from 2.600 € | View |
| Star Flyer | Philipsburg → Philipsburg | 27.12.–03.01.2028 | 7 | from 2.600 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 29.12.–08.01.2028 | 10 | from 4.155 € | View |
| Chronos | Martinique → Martinique | 29.12.–05.01.2028 | 8 | from 4.400 € | View |
| Rhea | Antigua → Antigua | 29.12.–06.01.2028 | 8 | from 5.050 € | View |
| Star Clipper | St. John's (Antigua) → St. John's (Antigua) | 03.01.–08.01.2028 | 5 | from 1.765 € | View |
| Star Flyer | Philipsburg → Philipsburg | 03.01.–08.01.2028 | 5 | from 1.765 € | View |
| Star Flyer | Philipsburg → Philipsburg | 08.01.–15.01.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 08.01.–15.01.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 15.01.–22.01.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 15.01.–22.01.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 22.01.–29.01.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 22.01.–29.01.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 29.01.–05.02.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 29.01.–05.02.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 05.02.–12.02.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 05.02.–12.02.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 12.02.–19.02.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 12.02.–19.02.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 19.02.–26.02.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 19.02.–26.02.2028 | 7 | from 2.825 € | View |
| Star Flyer | Philipsburg → Philipsburg | 26.02.–04.03.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 26.02.–04.03.2028 | 7 | from 2.825 € | View |
| Star Clipper | Oranjestad → Saint George | 04.03.–11.03.2028 | 7 | from 2.535 € | View |
| Star Flyer | Philipsburg → Philipsburg | 04.03.–11.03.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 04.03.–11.03.2028 | 7 | from 2.825 € | View |
| Sea Cloud II | Bridgetown → Philipsburg | 07.03.–17.03.2028 | 10 | from 5.855 € | View |
| Star Flyer | Philipsburg → Philipsburg | 11.03.–18.03.2028 | 7 | from 2.535 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 11.03.–18.03.2028 | 7 | from 2.825 € | View |
| Star Clipper | Saint George → Saint George | 11.03.–22.03.2028 | 11 | from 3.985 € | View |
| Sea Cloud II | Philipsburg → Philipsburg | 17.03.–27.03.2028 | 10 | from 5.855 € | View |
| Royal Clipper | Bridgetown → Bridgetown | 18.03.–25.03.2028 | 7 | from 2.825 € | View |
| Star Clipper | Saint George → St. John's (Antigua) | 22.03.–01.04.2028 | 10 | from 3.625 € | View |
| Sea Cloud II | Philipsburg → Philipsburg | 27.03.–03.04.2028 | 7 | from 4.095 € | View |
Frequently asked questions
What makes the Caribbean special for sailing?
Steady trade winds, warm turquoise water and short hops between very different islands - each with its own language, cuisine and music. Sail in the morning, anchor, snorkel and swim in the afternoon.
Which ports do the Caribbean voyages start from?
Frequent ports of departure and arrival are Bridgetown (Barbados), Fort-de-France (Martinique), Philipsburg (St Maarten) and Pointe-à-Pitre (Guadeloupe). You will find the exact port with each voyage in the list.
When is the best time to sail the Caribbean?
The main season runs from December to April - dry, sunny and with steady trade winds. The hurricane season from August to October is avoided.
Is the Caribbean suitable for beginners?
Yes. On yacht and catamaran a skipper is aboard, so no sailing experience is needed. The British Virgin Islands and the Grenadines are especially sheltered and ideal for a relaxed start.
What should you not miss in the Caribbean?
The Tobago Cays with turtles, the Pitons of St Lucia, a beach bar on Jost van Dyke and Nelson's Dockyard on Antigua. We are glad to tell you which islands lie on your route in a personal conversation.
Which ship suits your Caribbean?
Talk to us - we will find the right solution for your voyage.
