Skippered catamaran sailing in the Caribbean with Sailing‑Dutchman is the easiest and most enjoyable way to experience a true sailing holiday.
No paperwork, no deposits, no stress — everything from navigation and anchoring to berthing is handled by an experienced skipper. All you have to do is relax and enjoy the sun, the sea, and the freedom of life on board.
Whether you’re an experienced sailor or stepping on a yacht for the first time, our skippered catamaran cruises are designed for pure enjoyment. You can take part in sailing or simply unwind on deck — the choice is entirely yours.
Sailing holidays for everyone
Our sailing experiences are open to everyone. Join as a solo traveler, book a cabin as a couple, or come on board as a family or group of friends — we’ll create the perfect setup for you.
Discover the Caribbean at your own pace
On a skippered sailing holiday, you’ll explore the Caribbean the way it’s meant to be seen — from the water. Sail between islands, anchor in hidden bays, and experience each destination’s unique vibe, with optional shore activities to make your journey even richer.
NEW YEAR’s EVE CRUISE – Martinique – Grenadines
Destinations: Martinique, St Lucia, St Vincent, Bequia, Mayreau, Tobago Cays
On / Off board: Le Marin, Martinique
Yacht: Dean 440 Espace
Dates: December 27, 2026 – 07.01.2027
Price: 1.950€
Destinations: Martinique, Dominica, Les Saintes, Guadeloupe
On board: Martinique / Off board: Guadeloupe
Yacht: Dean 440 Espace
Dates: February 07-15, 2027
Price: 1.250 €
Destinations: Trinidad, Grendada, Carriacou, Union Island, Mayreau, Tobago Cays, Bequia,St.Vincent, St. Lucia, Martinique
On board: Trinidad / Off board: Martinique
Yacht: Dean 440 Espace
Dates: December 6 – 18, 2026
Price: 1.690 €
Bridge & Breeze – Cruise for Bridge Players
Destinations: Martinique, St Lucia, St Vincent, Bequia, Mayreau, Tobago Cays
On / Off board: Le Marin, Martinique
Yacht: Dean 440 Espace / Lagoon 42 (TBC)
Dates: January 10 – 21, 2027
Price: 2.650 €
Destinations: Martinique, St Lucia, St Vincent, Bequia, Mayreau, Tobago Cays
On / Off board: Le Marin, Martinique
Yacht: Dean 440 Espace
Dates: January 10 – 21, January 24 – February 02, 2027
Price: 1.595 €
Guadeloupe > St Martin – Lazy Sailing
Destinations:
Option 1: Guadeloupe, Montserat, St Kitts and Nevis, St Eustatius, St Martin
Option 2: Guadeloupe, Antigua, Barbuda, St Baarts, Anguilla, St Martin
On board: Gudeloupe / Off board: St Martin
Yacht: Dean 440 Espace
Dates: February 18 – March 01, 2027
Price: 1.595 €
BVI Islands – Lazy Sailing
Destinations: Tortola, Norman Island, Peter Island, Cooper Island, Virgin Gorda, Anegada, Jost van Dyke
On/Off board: Tortola
Yacht: Dean 440 Espace
Dates: March 04 – 16, 2027
Price: 1.595€
