Sailing Yachts

For the true pleasure of sailing, charter one of these beautiful monohull sailing yachts. We feature classic yachts, performance yachts & luxury ocean-going, round the world cruisers.

Here is a selection of just some of our recommended sailing yachts. If would just like us to put together a list of recommended yachts especially for you please complete our YACHT CHARTER ENQUIRY form.

The yacht details and rates quoted are believed to be correct, but are not guaranteed.  Please note: higher rates apply at peak periods such as Christmas and New Year and rates can change. Special discounts are offered from time to time.

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Sailing Yachts
Cape Arrow Image
Cape Arrow
Southern Wind 100 RS. 4 guest cabins: 2double, 1 twin
Length In Feet: 67
Guests: 8
Crew: 4
Scuba: No
Rate per week from €47,000

Plus All Expenses
67
3,
0,
,
Cape Arrow,
Contingency Image
Contingency
Oyster
Length In Feet: 53
Guests: 6
Crew: 1
Scuba: No
Rate per week from US$10,500

Captain-only.
53
3,
0,
,
Contingency,
Ptarmigan Image
Ptarmigan
Swan 82S
Length In Feet: 82
Guests: 7
Crew: 4
Scuba: No
Rate per week from US$37,000

Plus All Expenses
82
3,
0,
,
Ptarmigan,
The Dove Image
The Dove
Custom-built world-cruising yacht. Two double guest cabins.
Length In Feet: 54
Guests: 4
Crew: 2
Scuba: No
Rate per week from US$8,800

Inclusive food.
54
3,
0,
,
The Dove,
Sedna Image
Sedna
Swan 82 sloop. 4 guest cabins: master, double and 2 twins.
Length In Feet: 82
Guests: 8
Crew: 3
Scuba: No
Rate per week from US$39,000

Plus all expenses
82
3,
0,
,
Sedna,
Regina Image
Regina
56.1m Pruva schooner. Six guest cabins: master; four double; one twin.
Length In Feet: 184
Guests: 12
Crew: 7
Scuba: No
Rate per week from 75,000 euros

PLUS all expenses
184
3,
0,
,
Regina,
Vaimiti Image
Vaimiti
Trehard
Length In Feet: 130
Guests: 10
Crew: 5
Scuba: Yes
Rate per week from US$67,000

Plus All Expenses
130
3,
0,
,
Vaimiti,
Tilly Mint Image
Tilly Mint
Discovery 67
Length In Feet: 67
Guests: 6
Crew: 2
Scuba: No
Rate per week from US$21,500

Plus All Expenses
67
3,
0,
,
Tilly Mint,
Skip
Skip'n Bou
Southern Wind
Length In Feet: 80
Guests: 6
Crew: 3
Scuba: No
Rate per week from US$28,000

Plus All Expenses
80
3,
0,
,
Skip'n Bou,
Ree Image
Ree
Valdettaro
Length In Feet: 112
Guests: 10
Crew: 6
Scuba: No
Rate per week from 52,650 euros

Plus All Expenses
112
3,
0,
,
Ree,
Ravenous Image
Ravenous
Swan
Length In Feet: 82
Guests: 6
Crew: 3
Scuba: No
Rate per week from US$33,000

Inclusive food plus bar
82
3,
0,
,
Ravenous,
Pacific Wave Image
Pacific Wave
Yacht Officine Pesaro SRL
Length In Feet: 72
Guests: 6
Crew: 2
Scuba: Yes
Rate per week from US$14,500

Inclusive food and standard bar
72
3,
0,
,
Pacific Wave,
Lady B Image
Lady B
Dubois-designed sloop, built by Vitters in 2010
Length In Feet: 112
Guests: 6
Crew: 6
Scuba: No
Rate per week from US$110,000

Plus all expences
112
3,
0,
,
Lady B,
Penelope Image
Penelope
Oyster
Length In Feet: 130
Guests: 6
Crew: 4
Scuba: No
Rate per week from 50,000 euros

Plus All Expenses
130
3,
0,
,
Penelope,
Melinka Image
Melinka
Swan 80
Length In Feet: 80
Guests: 6
Crew: 3
Scuba: No
Rate per week from US$19,500

Inclusive food & standard bar
80
3,
0,
,
Melinka,
Marae Image
Marae
Alloy Yachts
Length In Feet: 108
Guests: 6
Crew: 4
Scuba: No
Rate per week from US$59,000

Plus All Expenses
108
3,
0,
,
Marae,
On Liberty Image
On Liberty
Oyster 725 built 2015. Three guest cabins: master, double and twin.
Length In Feet: 72
Guests: 6
Crew: 2
Scuba: No
Rate per week from US$24,000

Inclusive food.
72
3,
0,
,
On Liberty,
Domicil Image
Domicil
SRF Holland
Length In Feet: 85
Guests: 4
Crew: 2
Scuba: No
Rate per week from US$17,500

Inclusive food and standard bar
85
3,
0,
,
Domicil,
Destiny Image
Destiny
Hylas
Length In Feet: 70
Guests: 6
Crew: 2
Scuba: No
Rate per week from US$20,225

Inclusive food & standard bar
70
3,
0,
,
Destiny,
Elena Image
Elena
Classic Schooner built in 2009 to original Herreshoff plans
Length In Feet: 180
Guests: 8
Crew: 8
Scuba: No
Rate per week from 80,000 euros

Plus all expences
180
3,
0,
,
Elena,
Marie Image
Marie
Vitters
Length In Feet: 180
Guests: 8
Crew: 8
Scuba: Yes
Rate per week from US$200,000

Plus All Expenses
180
3,
0,
,
Marie,
Sayang Image
Sayang
Jeanneau
Length In Feet: 54
Guests: 8
Crew: 2
Scuba: No
Rate per week from US$8,900

Inclusive food and standard bar
54
3,
0,
,
Sayang,
Jupiter Image
Jupiter
Giorgetti & Magrini ketch. 4 guest cabins: 1 double, 3 twins.
Length In Feet: 100
Guests: 8
Crew: 3
Scuba: No
Rate per week from US$35,000

Plus all expenses
100
3,
0,
,
Jupiter,
Rapture Image
Rapture
Southern Wind 100 DS yacht. 4 guest cabins: 2 double, 2 twin.
Length In Feet: 99
Guests: 8
Crew: 4
Scuba: No
Rate per week from US$45,000

Plus all expenses
99
3,
0,
,
Rapture,
Leopard 3 Image
Leopard 3
30m Farr100 performance yacht. 5 guests cabins: master, 2 doubles, 2 singles.
Length In Feet: 98
Guests: 8
Crew: 4
Scuba: No
Rate per week from US$38,500

PLUS all expenses
98
3,
0,
,
Leopard 3,
Dharma Image
Dharma
29m Southern Wind sloop. 4 guest cabins: master two double (1 with Pullman) and single cabin.
Length In Feet: 95
Guests: 8
Crew: 4
Scuba: No
Rate per week from 30,000 euros

Plus all expences
95
3,
0,
,
Dharma,
Silent Wings Image
Silent Wings
16.8m Jeanneau sloop. 2 guest cabins: master, double/twin
Length In Feet: 55
Guests: 4
Crew: 2
Scuba: No
Rate per week from US$11,820

Inclusive food and standard bar
55
3,
0,
,
Silent Wings,
Lush Image
Lush
27.1m Oyster sloop. 4 guest cabins: master and 3 doubles.
Length In Feet: 89
Guests: 8
Crew: 4
Scuba: No
Rate per week from US$45,000

Plus all expences
89
3,
0,
,
Lush,
Germania Nova Image
Germania Nova
55.4m classic schooner. 5 guest cabins: master and 4 doubles.
Length In Feet: 181
Guests: 10
Crew: 13
Scuba: No
Rate per week from US$95,000

Plus all expences
181
3,
0,
,
Germania Nova,
Chronos Image
Chronos
54.6m Staysail Ketch. 13 cabins: master, 10 double, 2 twin.
Length In Feet: 180
Guests: 26
Crew: 8
Scuba: No
Rate per week from 55,000 euros

Plus all expences
180
3,
0,
,
Chronos,
Twilight Image
Twilight
38.1m Dubois-designed Oyster. 4 cabins: master, 2 double, 1 twin.
Length In Feet: 125
Guests: 8
Crew: 5
Scuba: No
Rate per week from US$90,000

Plus all expences
125
3,
0,
,
Twilight,
Sailing Yachts
Cape Arrow
€47,000
67
3,
0,
,
Cape Arrow,
Contingency
US$10,500
53
3,
0,
,
Contingency,
Ptarmigan
US$37,000
82
3,
0,
,
Ptarmigan,
The Dove
US$8,800
54
3,
0,
,
The Dove,
Sedna
US$39,000
82
3,
0,
,
Sedna,
Regina
75,000 euros
184
3,
0,
,
Regina,
Vaimiti
US$67,000
130
3,
0,
,
Vaimiti,
Tilly Mint
US$21,500
67
3,
0,
,
Tilly Mint,
Skip'n Bou
US$28,000
80
3,
0,
,
Skip'n Bou,
Ree
52,640 euros
112
3,
0,
,
Ree,
Ravenous
US$33,000
82
3,
0,
,
Ravenous,
Pacific Wave
US$14,500
72
3,
0,
,
Pacific Wave,
Lady B
US$110,000
112
3,
0,
,
Lady B,
Penelope
50,000 euros
130
3,
0,
,
Penelope,
Melinka
US$19,500
80
3,
0,
,
Melinka,
Marae
US$59,000
108
3,
0,
,
Marae,
On Liberty
US$24,000
72
3,
0,
,
On Liberty,
Domicil
US$17,500
85
3,
0,
,
Domicil,
Destiny
US$20,225
70
3,
0,
,
Destiny,
Elena
80,000 euros
Elena Image

The elegant ELENA was built in 2009 to the original 1910 drawings by designer Nathaniel G Herreshoff of the record-breaking racing schooner Elena that participated in the 1928 King’s Cup Trans-Atlantic Race from New York to Santander. This luxurious new 55m Elena features modern comforts yet maintains the classical interior reminiscent of a period country home. She is an exciting choice for lovers of large classic yachts. For more information please contact: charters@caribbeansail.com

180
3,
0,
,
Elena,
Marie
US$200,000
180
3,
0,
,
Marie,
Sayang
US$8,900
54
3,
0,
,
Sayang,
Jupiter
US$35,000
100
3,
0,
,
Jupiter,
Rapture
US$45,000
99
3,
0,
,
Rapture,
Leopard 3
US$38,500
98
3,
0,
,
Leopard 3,
Dharma
30,000 euros
95
3,
0,
,
Dharma,
Silent Wings
US$11,820
55
3,
0,
,
Silent Wings,
Lush
US$45,000
89
3,
0,
,
Lush,
Germania Nova
US$95,000
181
3,
0,
,
Germania Nova,
Chronos
55,000 euros
180
3,
0,
,
Chronos,
Twilight
US$90,000
125
3,
0,
,
Twilight,
Sailing Yachts
Cape Arrow Image
Cape Arrow
Southern Wind 100 RS. 4 guest cabins: 2double, 1 twin
Length In Feet: 67
Guests: 8
Crew: 4
Scuba: No
€47,000
67
3,
0,
,
Cape Arrow,
Contingency Image
Contingency
Oyster
Length In Feet: 53
Guests: 6
Crew: 1
Scuba: No
US$10,500
53
3,
0,
,
Contingency,
Ptarmigan Image
Ptarmigan
Swan 82S
Length In Feet: 82
Guests: 7
Crew: 4
Scuba: No
US$37,000
82
3,
0,
,
Ptarmigan,
The Dove Image
The Dove
Custom-built world-cruising yacht. Two double guest cabins.
Length In Feet: 54
Guests: 4
Crew: 2
Scuba: No
US$8,800
54
3,
0,
,
The Dove,
Sedna Image
Sedna
Swan 82 sloop. 4 guest cabins: master, double and 2 twins.
Length In Feet: 82
Guests: 8
Crew: 3
Scuba: No
US$39,000
82
3,
0,
,
Sedna,
Regina Image
Regina
... Read More
56.1m Pruva schooner. Six guest cabins: master; four double; one twin.
Length In Feet: 184
Guests: 12
Crew: 7
Scuba: No
75,000 euros
184
3,
0,
,
Regina,
Vaimiti Image
Vaimiti
Trehard
Length In Feet: 130
Guests: 10
Crew: 5
Scuba: Yes
US$67,000
130
3,
0,
,
Vaimiti,
Tilly Mint Image
Tilly Mint
Discovery 67
Length In Feet: 67
Guests: 6
Crew: 2
Scuba: No
US$21,500
67
3,
0,
,
Tilly Mint,
Skip
Skip'n Bou
Southern Wind
Length In Feet: 80
Guests: 6
Crew: 3
Scuba: No
US$28,000
80
3,
0,
,
Skip'n Bou,
Ree Image
Ree
Valdettaro
Length In Feet: 112
Guests: 10
Crew: 6
Scuba: No
52,640 euros
112
3,
0,
,
Ree,
Ravenous Image
Ravenous
Swan
Length In Feet: 82
Guests: 6
Crew: 3
Scuba: No
US$33,000
82
3,
0,
,
Ravenous,
Pacific Wave Image
Pacific Wave
Yacht Officine Pesaro SRL
Length In Feet: 72
Guests: 6
Crew: 2
Scuba: Yes
US$14,500
72
3,
0,
,
Pacific Wave,
Lady B Image
Lady B
Dubois-designed sloop, built by Vitters in 2010
Length In Feet: 112
Guests: 6
Crew: 6
Scuba: No
US$110,000
112
3,
0,
,
Lady B,
Penelope Image
Penelope
Oyster
Length In Feet: 130
Guests: 6
Crew: 4
Scuba: No
50,000 euros
130
3,
0,
,
Penelope,
Melinka Image
Melinka
Swan 80
Length In Feet: 80
Guests: 6
Crew: 3
Scuba: No
US$19,500
80
3,
0,
,
Melinka,
Marae Image
Marae
Alloy Yachts
Length In Feet: 108
Guests: 6
Crew: 4
Scuba: No
US$59,000
108
3,
0,
,
Marae,
On Liberty Image
On Liberty
Oyster 725 built 2015. Three guest cabins: master, double and twin.
Length In Feet: 72
Guests: 6
Crew: 2
Scuba: No
US$24,000
72
3,
0,
,
On Liberty,
Domicil Image
Domicil
SRF Holland
Length In Feet: 85
Guests: 4
Crew: 2
Scuba: No
US$17,500
85
3,
0,
,
Domicil,
Destiny Image
Destiny
Hylas
Length In Feet: 70
Guests: 6
Crew: 2
Scuba: No
US$20,225
70
3,
0,
,
Destiny,
Elena Image
Elena
The elegant ELENA was built in 2009 to the original 1910 drawings by designer Nathaniel G Herreshoff of the record-breaking racing schooner Elena that participated in the 1928 King’s Cup Trans-Atlantic Race from New York to Santander. ... Read More
Classic Schooner built in 2009 to original Herreshoff plans
Length In Feet: 180
Guests: 8
Crew: 8
Scuba: No
80,000 euros
180
3,
0,
,
Elena,
Marie Image
Marie
Vitters
Length In Feet: 180
Guests: 8
Crew: 8
Scuba: Yes
US$200,000
180
3,
0,
,
Marie,
Sayang Image
Sayang
Jeanneau
Length In Feet: 54
Guests: 8
Crew: 2
Scuba: No
US$8,900
54
3,
0,
,
Sayang,
Jupiter Image
Jupiter
Giorgetti & Magrini ketch. 4 guest cabins: 1 double, 3 twins.
Length In Feet: 100
Guests: 8
Crew: 3
Scuba: No
US$35,000
100
3,
0,
,
Jupiter,
Rapture Image
Rapture
Southern Wind 100 DS yacht. 4 guest cabins: 2 double, 2 twin.
Length In Feet: 99
Guests: 8
Crew: 4
Scuba: No
US$45,000
99
3,
0,
,
Rapture,
Leopard 3 Image
Leopard 3
30m Farr100 performance yacht. 5 guests cabins: master, 2 doubles, 2 singles.
Length In Feet: 98
Guests: 8
Crew: 4
Scuba: No
US$38,500
98
3,
0,
,
Leopard 3,
Dharma Image
Dharma
29m Southern Wind sloop. 4 guest cabins: master two double (1 with Pullman) and single cabin.
Length In Feet: 95
Guests: 8
Crew: 4
Scuba: No
30,000 euros
95
3,
0,
,
Dharma,
Silent Wings Image
Silent Wings
16.8m Jeanneau sloop. 2 guest cabins: master, double/twin
Length In Feet: 55
Guests: 4
Crew: 2
Scuba: No
US$11,820
55
3,
0,
,
Silent Wings,
Lush Image
Lush
27.1m Oyster sloop. 4 guest cabins: master and 3 doubles.
Length In Feet: 89
Guests: 8
Crew: 4
Scuba: No
US$45,000
89
3,
0,
,
Lush,
Germania Nova Image
Germania Nova
55.4m classic schooner. 5 guest cabins: master and 4 doubles.
Length In Feet: 181
Guests: 10
Crew: 13
Scuba: No
US$95,000
181
3,
0,
,
Germania Nova,
Chronos Image
Chronos
54.6m Staysail Ketch. 13 cabins: master, 10 double, 2 twin.
Length In Feet: 180
Guests: 26
Crew: 8
Scuba: No
55,000 euros
180
3,
0,
,
Chronos,
Twilight Image
Twilight
38.1m Dubois-designed Oyster. 4 cabins: master, 2 double, 1 twin.
Length In Feet: 125
Guests: 8
Crew: 5
Scuba: No
US$90,000
125
3,
0,
,
Twilight,
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