Sailing trips

Cabin charter, sailing holidays and sailing trips

From day trips to ocean crossings – for beginners and experienced sailors.

To display the location search, we need your consent to load Google Maps services. Data will be transmitted to third parties.

More Information
Enable location search


Custom charter Can't find your dream trip? Plan your custom sailing trip – no obligation & free of charge. Enquire now →
7 - 9 days
Caribbean
Remove all
Cabin charter

3 crew spots: One week in the Caribbean on a catamaran – Martinique ↔ St. Lucia, 4–11

Le Marin, MArtiniqueRound trip
04.12.2026 – 11.12.20268 daysapprox. 150 nm
CatamaranLagoon 4646 feet
Caribbean Martinique
Florian
Leave a review
from 900 €
View trip
TOP
Cabin charter

Caribbean Christmas Cruise

St LuciaRound trip
19.12.2026 – 26.12.20268 daysca. 250 sm
MonohullSwan 5151 feet
Caribbean DominicaGuadeloupeMartiniqueSaint Lucia
Swan 51 Eira
Leave a review
from 1,280 €
View trip
Cabin charter

Christmas sailing in the Caribbean from St Martin

Marigot, St MartinRound trip
20.12.2026 – 27.12.20268 daysapprox. 200 nm
Tall shipKAIRÓS124 feet
Caribbean AnguillaSabaSaint BarthélemySaint Martin (FR)Sint Maarten (NL)
Sailing-Classics
Leave a review
from 3,500 €
View trip
Cabin charter

Christmas sailing from Martinique

Sainte AnneRound trip
22.12.2026 – 29.12.20268 daysca. 250 sm
Tall shipCHRONOS177 feet
Caribbean DominicaGuadeloupeMartinique
Sailing-Classics
Leave a review
from 4,000 €
View trip
Cabin charter

Sailing trip in Belize

PlacenciaRound trip
26.12.2026 – 02.01.20278 daysapprox. 150 nm
CatamaranLagoon41 feet
Caribbean Belize
Rocket Science Sailing
(12)
from 2,142 €
View trip
Cabin charter

New Year sailing in the Caribbean from St Martin

Marigot, St MartinRound trip
27.12.2026 – 03.01.20278 daysapprox. 200 nm
Tall shipKAIRÓS124 feet
Caribbean AnguillaSabaSaint BarthélemySaint Martin (FR)Sint Maarten (NL)
Sailing-Classics
Leave a review
from 3,900 €
View trip
Cabin charter

New Year's voyage from Antigua

Falmouth HarbourRound trip
29.12.2026 – 05.01.20278 daysca. 250 sm
Tall shipRHEA177 feet
Caribbean Antigua and Barbuda
Sailing-Classics
Leave a review
from 3,850 €
View trip
Cabin charter

New Year's Eve sailing in the Caribbean

Sainte AnneRound trip
29.12.2026 – 06.01.20279 daysca. 250 sm
Tall shipCHRONOS177 feet
Caribbean MartiniqueSt Vincent and the Grenadines
Sailing-Classics
Leave a review
from 4,500 €
View trip
Cabin charter

Active Sailing San Blas Panama Caribbean on TopSail Schooner Eendracht

Portobelo, Panama→Shelter Bay, Panama
09.01.2027 – 16.01.20278 daysapprox. 200 nm
Tall shipTop Sail Schooner196 feet
Caribbean Panama
Sailing Vessel Eendracht
Leave a review
from 2,150 €
View trip
Cabin charter

Sailing in the BVIs from St Martin

Marigot→Trellis Bay
09.01.2027 – 16.01.20278 daysapprox. 200 nm
Tall shipKAIRÓS124 feet
Caribbean British Virgin IslandsSaint Martin (FR)Sint Maarten (NL)
Sailing-Classics
Leave a review
from 3,300 €
View trip
Cabin charter

Island hopping in the BVIs

Trellis BayRound trip
16.01.2027 – 23.01.20278 daysapprox. 200 nm
Tall shipKAIRÓS124 feet
Caribbean British Virgin Islands
Sailing-Classics
Leave a review
from 3,500 €
View trip
Cabin charter

Island hopping from Antigua

Falmouth HarbourRound trip
19.01.2027 – 27.01.20279 daysca. 250 sm
Tall shipRHEA177 feet
Caribbean Antigua and BarbudaSabaSaint BarthélemySt Kitts and Nevis
Sailing-Classics
Leave a review
from 4,300 €
View trip
Cabin charter

Caribbean sailing voyage: Martinique – Dominica – Îles des Saintes

Sainte Anne / MartiniqueRound trip
19.01.2027 – 26.01.20278 daysapprox. 200 nm
Tall shipCHRONOS177 feet
Caribbean DominicaMartinique
Sailing-Classics
Leave a review
from 3,900 €
View trip
Cabin charter

GaySail Exclusive British Virgin Islands

Tortoal→Tortola
23.01.2027 – 30.01.20278 daysapprox. 150 nm
CatamaranLagoon 4545 feet
Caribbean British Virgin Islands
Amstel 18-2
Leave a review
from 1,595 €
View trip
Cabin charter

Island hopping in the BVIs

Trellis BayRound trip
23.01.2027 – 30.01.20278 daysapprox. 200 nm
Tall shipKAIRÓS124 feet
Caribbean British Virgin Islands
Sailing-Classics
Leave a review
from 3,500 €
View trip