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 →
Guadeloupe
Remove all
Cabin charter

Winter ’27: Catamaran sailing trip Caribbean from Guadeloupe

Pointe à PitreRound trip
06.02.2027 – 20.02.202715 daysapprox. 300 nm
CatamaranLagoon 42 or similar42 feet
AtlanticCaribbean Guadeloupe
Windbeutel Reisen
Leave a review
from 1,898 €
View trip
Cabin charter

Welcome to Paradise – Catamaran sailing – two weeks in the Caribbean under sail

GuadeloupeRound trip
06.02.2027 – 19.02.202714 daysca. 250 sm
CatamaranLagoon400S240 feet
Caribbean Antigua and BarbudaDominicaGuadeloupe
Segelschule Meersburg
Leave a review
from 1,890 €
View trip
Cabin charter

Caribbean Sailing Trip from Martinique to Sint Maarten

Martinique→Sint Maarten
10.02.2027 – 19.02.202710 daysca. 450 sm
Tall shipThree-mast clipper249 feet
Caribbean Antigua and BarbudaDominicaGuadeloupeMartiniqueSaint LuciaSint Maarten (NL)St Kitts and NevisSt Vincent and the GrenadinesTrinidad and Tobago
INMARIS Windjammer Worldwide
(5)
from 8,950 €
View trip
Cabin charter

An adventurous voyage of discovery: Martinique – Sint Maarten

Le Marin, Martinique→Marigot, Saint Martin
13.02.2027 – 27.02.202715 daysapprox. 400 nm
MonohullSwan 65 S&S65 feet
Caribbean AnguillaAntigua and BarbudaDominicaGuadeloupeMartiniqueMontserratSaint BarthélemySint EustatiusSint Maarten (NL)St Kitts and Nevis
Swan 65 Ilios
(5)
from 1,750 €
View trip
Regatta sailing

RORC CARIBBEAN 600 2027

AntiguaRound trip
18.02.2027 – 27.02.202710 daysca. 650 sm
MonohullSwan 5151 feet
Caribbean AnguillaAntigua and BarbudaGuadeloupeMontserratSabaSaint BarthélemySaint Martin (FR)Sint Maarten (NL)St Kitts and Nevis
Swan 51 Eira
Leave a review
from 2,700 €
View trip
Cabin charter

Sailing voyage Antigua & Lesser Antilles | Caribbean island hopping on a tall ship

Falmouth Harbor, AntiguaRound trip
19.02.2027 – 26.02.20278 daysca. 250 sm
Tall shipThree-masted schooner144 feet
Caribbean Antigua and BarbudaGuadeloupeMontserratSt Kitts and Nevis
Rederij van Linschoten
(7)
from 2,138 €
View trip
Cabin charter

Winter ’27: Catamaran sailing trip Caribbean from Guadeloupe

Pointe à PitreRound trip
20.02.2027 – 06.03.202715 daysapprox. 300 nm
CatamaranLagoon 42 or similar42 feet
AtlanticCaribbean Guadeloupe
Windbeutel Reisen
Leave a review
from 1,998 €
View trip
Cabin charter

Welcome to Paradise – Catamaran sailing – two weeks in the Caribbean under sail

GuadeloupeRound trip
20.02.2027 – 05.03.202714 daysca. 250 sm
CatamaranLagoon400S240 feet
Caribbean Antigua and BarbudaDominicaGuadeloupe
Segelschule Meersburg
Leave a review
from 1,890 €
View trip
Cabin charter

Holiday sailing trip in the Caribbean on a Lagoon 42 – Lesser Antilles from Martinique

MartiniqueRound trip
20.02.2027 – 06.03.202715 daysapprox. 280 nm
CatamaranLagoon 4242 feet
Caribbean Antigua and BarbudaDominicaGrenadaGuadeloupeMartiniqueSaint LuciaSt Vincent and the Grenadines
Christopher Daniell
Leave a review
from 2,000 €
View trip
Cabin charter

Caribbean sailing trip from Sint Maarten to Martinique

Sint Maarten→Martinique
22.02.2027 – 04.03.202711 daysapprox. 245 nm
Tall shipThree-mast clipper249 feet
Caribbean Antigua and BarbudaDominicaGuadeloupeMartiniqueMontserratSabaSaint Martin (FR)Sint Maarten (NL)St Kitts and Nevis
INMARIS Windjammer Worldwide
(5)
from 9,675 €
View trip
Cabin charter

Catamaran cabin charter from Martinique to St. Martin

Le Marin / Martinique→Simpson Bay Sint Maarten
27.02.2027 – 13.03.202715 daysapprox. 320 nm
CatamaranLagoon 450S45 feet
Caribbean Antigua and BarbudaDominicaGuadeloupeMartiniqueSaint BarthélemySaint Martin (FR)Sint Maarten (NL)
Segelwolf.com
Leave a review
from 1,898 €
View trip
Cabin charter

Sailing voyage Antigua & Lesser Antilles | Caribbean island hopping on a tall ship

Falmouth Harbor, AntiguaRound trip
28.02.2027 – 07.03.20278 daysca. 250 sm
Tall shipThree-masted schooner144 feet
Caribbean Antigua and BarbudaGuadeloupeMontserratSt Kitts and Nevis
Rederij van Linschoten
(7)
from 2,138 €
View trip
Cabin charter

CARIBBEAN HANG OUT CRUISE SINT MAARTEN – ANTIGUA

Sint Maarten→Antigua
19.03.2027 – 26.03.20278 daysapprox. 150 nm
MonohullSwan 5151 feet
Caribbean AnguillaAntigua and BarbudaGuadeloupeSaint BarthélemySint Maarten (NL)
Swan 51 Eira
Leave a review
from 1,550 €
View trip
Cabin charter

Holiday sailing trip in the Caribbean on a Lagoon 42 – Lesser Antilles from Martinique

MartiniqueRound trip
20.03.2027 – 03.04.202715 daysapprox. 280 nm
CatamaranLagoon 4242 feet
Caribbean Antigua and BarbudaDominicaGrenadaGuadeloupeMartiniqueSaint LuciaSt Vincent and the Grenadines
Christopher Daniell
Leave a review
from 2,000 €
View trip
Cabin charter

CARIBBEAN TRIP: THE GREATER ANTILLES & DISCOVERY ROUTE FROM MARTINIQUE

Fort de FranceRound trip
21.03.2027 – 03.04.202714 daysca. 350 sm
MonohullBeneteau Cyclades 50.550.5 feet
Caribbean Antigua and BarbudaDominicaGuadeloupeMartinique
Blauwasser Segelreisen
Leave a review
from 1,200 €
View trip