Classic Caribbean

Windstar Cruises

21 Dec - 28 Dec 2025 (7 Nights)

From £2,235 pp

Star Collector: Caribbean Explorations

Windstar Cruises

21 Dec 2025 - 4 Jan 2026 (14 Nights)

From £3,591 pp

Beach Fun & Sun: A Remote Caribbean Getaway

Windstar Cruises

28 Dec 2025 - 4 Jan 2026 (7 Nights)

From £2,248 pp

Beach Fun & Sun: A Remote Caribbean Getaway

Windstar Cruises

4 Jan - 11 Jan 2026 (7 Nights)

From £2,120 pp

Star Collector: Leeward & Windward Caribbean Havens

Windstar Cruises

4 Jan - 18 Jan 2026 (14 Nights)

From £3,371 pp

Star Collector: A Lesser Antilles Odyssey

Windstar Cruises

4 Jan - 25 Jan 2026 (21 Nights)

From £5,177 pp

Star Collector: The Best of the Windward & Leeward Isles

Windstar Cruises

4 Jan - 1 Feb 2026 (28 Nights)

From £6,905 pp

Star Collector: Grand Caribbean Adventure

Windstar Cruises

4 Jan - 28 Feb 2026 (55 Nights)

From £14,751 pp

Lush & Lovely Islands of the Lesser Antilles

Windstar Cruises

11 Jan - 18 Jan 2026 (7 Nights)

From £2,142 pp

Star Collector: Antilles Adventures

Windstar Cruises

11 Jan - 25 Jan 2026 (14 Nights)

From £3,461 pp

Jewels of the Windward Islands

Windstar Cruises

17 Jan - 26 Jan 2026 (9 Nights)

From £2,211 pp

Star Collector: Captivating Caribbean

Windstar Cruises

18 Jan - 1 Feb 2026 (14 Nights)

From £3,777 pp

Windward Ways & Tobago Cays

Windstar Cruises

25 Jan - 1 Feb 2026 (7 Nights)

From £2,294 pp

Star Collector: Windward Islands & Spanish New World

Windstar Cruises

25 Jan - 9 Feb 2026 (15 Nights)

From £4,118 pp

In the Wake of the Spanish Armadas

Windstar Cruises

1 Feb - 9 Feb 2026 (8 Nights)

From £2,634 pp

Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond

Windstar Cruises

1 Feb - 17 Feb 2026 (16 Nights)

From £4,214 pp