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Caribbean Sailings

Winter season from early December through to late March

28 November 2026 - Classic Yachtsman's 7 Nights

Royal Clipper
St. John's - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

28 November 2026 - Treasure Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,005
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

05 December 2026 - Windward Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,155
EARLY BOOKING DISCOUNT 20% - LAST BOOKING DATE 30 Apr, 2026.

05 December 2026 - Leeward Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £1,950
EARLY BOOKING DISCOUNT 20% - LAST BOOKING DATE 30 Apr, 2026.

12 December 2026 - Grenadine Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,155
EARLY BOOKING DISCOUNT 20% - LAST BOOKING DATE 30 Apr, 2026.

12 December 2026 - Treasure Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £1,950
EARLY BOOKING DISCOUNT 20% - LAST BOOKING DATE 30 Apr, 2026.

19 December 2026 - Windward Islands Christmas Cruise 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

19 December 2026 - Leeward Islands Christmas Cruise 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,005
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

26 December 2026 - Grenadine Islands New Year's Cruise 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,275
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

26 December 2026 - Treasure Islands New Year's Cruise 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,060
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

02 January 2027 - Windward Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

02 January 2027 - Leeward Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £1,950
EARLY BOOKING DISCOUNT 20% - LAST BOOKING DATE 30 Apr, 2026.

09 January 2027 - Grenadine Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

09 January 2027 - Treasure Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,005
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

16 January 2027 - Windward Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

16 January 2027 - Leeward Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,005
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

23 January 2027 - Grenadine Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

23 January 2027 - Treasure Islands 7 Nights

Star Flyer
St. Maarten - St. Maarten RATES FROM £2,005
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

27 January 2027 - Aruba to Grenada 10 Nights

Star Clipper
Oranjestad - St. George's RATES FROM £2,860
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.

30 January 2027 - Windward Islands 7 Nights

Royal Clipper
Bridgetown - Bridgetown RATES FROM £2,215
EARLY BOOKING DISCOUNT 10% - LAST BOOKING DATE 30 Apr, 2026.