Valiant Lady Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day Valiant Lady itineraries, please click one of the Valiant Lady sailing dates below.

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Nov 14, 2026

(Saturday)

6 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Tortola, St John's, Castries, Basseterre, San Juan

6 Nights

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Nov 20, 2026

(Friday)

8 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Charlotte Amalie (St Thomas), Willemstad (Curacao), Oranjestad, Basseterre, Philipsburg (St. Maarten), San Juan

8 Nights

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Nov 28, 2026

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Charlotte Amalie (St Thomas), Tortola, Basseterre, St John's, Philipsburg (St. Maarten), San Juan

7 Nights

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Dec 5, 2026

(Saturday)

7 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), Fort de France, Basseterre, San Juan

7 Nights

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Dec 12, 2026

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Philipsburg (St. Maarten), Bridgetown, Castries, Fort de France, Basseterre, San Juan

7 Nights

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Dec 19, 2026

(Saturday)

7 Night Southern Caribbean Holiday Voyage Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Basseterre, Fort de France, Oranjestad, Willemstad (Curacao), San Juan

7 Nights

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Dec 26, 2026

(Saturday)

7 Night Southern Caribbean New Years Voyage Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Philipsburg (St. Maarten), Fort de France, Bridgetown, Castries, St John's, San Juan

7 Nights

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Jan 2, 2027

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Tortola, Bridgetown, Castries, St John's, Philipsburg (St. Maarten), San Juan

7 Nights

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Jan 9, 2027

(Saturday)

7 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), Fort de France, Basseterre, San Juan

7 Nights

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Insider (double occupancy)

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Jan 16, 2027

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Philipsburg (St. Maarten), Bridgetown, Castries, Fort de France, Basseterre, San Juan

7 Nights

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Jan 23, 2027

(Saturday)

6 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Tortola, Basseterre, St John's, Castries, San Juan

6 Nights

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Jan 29, 2027

(Friday)

8 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), Bonaire, Fort de France, Philipsburg (St. Maarten), San Juan

8 Nights

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Feb 6, 2027

(Saturday)

7 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), St John's, Philipsburg (St. Maarten), San Juan

7 Nights

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Feb 13, 2027

(Saturday)

7 Night Sisters at Sea Voyage Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Samana, Grand Turk, Cabo Rojo, San Juan

7 Nights

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Feb 20, 2027

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Tortola, Castries, Bridgetown, Roseau, Philipsburg (St. Maarten), San Juan

7 Nights

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Feb 27, 2027

(Saturday)

7 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), Fort de France, Basseterre, San Juan

7 Nights

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Insider (double occupancy)

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Mar 6, 2027

(Saturday)

7 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Philipsburg (St. Maarten), Bridgetown, Castries, St John's, Tortola, San Juan

7 Nights

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Insider (double occupancy)

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Mar 13, 2027

(Saturday)

6 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Tortola, Basseterre, St John's, Castries, San Juan

6 Nights

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Insider (double occupancy)

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Mar 19, 2027

(Friday)

8 Night Southern Caribbean Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Charlotte Amalie (St Thomas), Bridgetown, Kingstown, Roseau, Philipsburg (St. Maarten), San Juan

8 Nights

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Insider (double occupancy)

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Apr 3, 2027

(Saturday)

7 Night Southern Caribbean and Aruban Nights Cruise

From San Juan, Puerto Rico to San Juan, Puerto Rico

Ports: San Juan, Oranjestad, Willemstad (Curacao), Fort de France, Basseterre, San Juan

7 Nights

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