Grand Princess Sailing Dates and Sailing Calendar

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Dec 14, 2025

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan, Tortola, Pointe-a-Pitre, Roseau, St George's, Bridgetown, San Juan

14 Nights

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$3,334

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 21, 2025

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Holiday Cruise

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

Ports: San Juan, Tortola, Pointe-a-Pitre, Roseau, St George's, Bridgetown, San Juan

7 Nights

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$839

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 21, 2025

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, Tortola, Pointe-a-Pitre, Roseau, St George's, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, St Vincent, Bridgetown, San Juan

14 Nights

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$5,294

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 28, 2025

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Holiday Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, St Vincent, Bridgetown, San Juan

7 Nights

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$1,209

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 28, 2025

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, St Vincent, Bridgetown, San Juan, St Thomas, Basseterre, Castries, St George's, Bridgetown, San Juan

14 Nights

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$2,057

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 4, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and St. Lucia Cruise

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

Ports: San Juan, St Thomas, Basseterre, Castries, St George's, Bridgetown, San Juan

7 Nights

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$854

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 4, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Basseterre, Castries, St George's, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

14 Nights

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$1,428

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

7 Nights

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$684

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

14 Nights

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$1,376

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

7 Nights

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$722

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, Pointe-a-Pitre, Bridgetown, San Juan

14 Nights

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$1,314

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 25, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Pointe-a-Pitre, Bridgetown, San Juan

7 Nights

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$631

Interior Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 25, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Pointe-a-Pitre, Bridgetown, San Juan, Tortola, Basseterre, St John's, Roseau, Bridgetown, San Juan

14 Nights

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$2,742

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and St. Kitts Cruise

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

Ports: San Juan, Tortola, Basseterre, St John's, Roseau, Bridgetown, San Juan

7 Nights

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$707

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, Tortola, Basseterre, St John's, Roseau, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, Basseterre, Castries, San Juan

14 Nights

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$1,459

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2026

(Sunday)

7 Night Southern Caribbean with Antigua and St. Kitts Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Basseterre, Castries, San Juan

7 Nights

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$787

Interior Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Basseterre, Castries, San Juan, Basseterre, Roseau, Castries, St George's, Bridgetown, San Juan

14 Nights

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$1,626

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and St. Kitts Cruise

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

Ports: San Juan, Basseterre, Roseau, Castries, St George's, Bridgetown, San Juan

7 Nights

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$742

Interior Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2026

(Sunday)

14 Night Southern Caribbean Adventurer Cruise

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

Ports: San Juan, Basseterre, Roseau, Castries, St George's, Bridgetown, San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

14 Nights

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$1,266

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 22, 2026

(Sunday)

7 Night Southern Caribbean with Barbados and Antigua Cruise

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

Ports: San Juan, St Thomas, Sint Maarten, St John's, Roseau, Bridgetown, San Juan

7 Nights

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$593

Interior Stateroom (double occupancy)

Includes taxes & feesLearn More

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