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Departing from Puerto Rico Cruise Specials

We've gathered all of the Departing from Puerto Rico cruise specials ordered by sail date. Click on a special and select a sail date to get a single cruise quote from the cruise agency that posted that particular special. To search through all cruise itineraries (not just Departing from Puerto Rico cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

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Explora Journeys, EXPLORA III
Discount
EXPLORA III15 Night An Extended Journey Of Sparkling Skies Dramatic Natura from $16535
15 Night - An Extended Journey Through Wild Beauty and Tropical Festivities - Starting in San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan
2026 Sails: Dec 13 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey10 Nights Caribbean Holiday Cruise from $1,979 pp plus OBC
10 Night - Caribbean Holiday Cruise : Antigua, Martinique & Saint Barthelemy - Starting in San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Gustavia, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
2026 Sails: Dec 18 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey10 Nights Caribbean Holiday Cruise from $1823 pp
10 Night - Caribbean Holiday Cruise : Antigua, Martinique & Saint Barthelemy - Starting in San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Gustavia, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
2026 Sails: Dec 18 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I7 Nights A Journey Of Caribbean Celebrations & Island Wonders from $6800 pp
7 Night - A Journey of Caribbean Celebrations & Island Wonders - Starting in San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 20 Get a Quote
Princess Cruises, Crown Princess
Discount
Crown Princess7 Nights Southern Caribbean With Barbados Holiday Cruise from $913 pp
7 Night - Southern Caribbean with Barbados and St. Lucia Holiday - Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, St Lucia, Barbados, San Juan, Puerto Rico
2026 Sails: Dec 27 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III8 Night A Journey Of Spectacular Festivities & Caribbean Wonders from $7410
8 Night - A Journey of Spectacular Festivities & Caribbean Wonders - Starting in San Juan, St Johns AG, Antigua, Pointe-a-Pitre, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Samana, Puerto Plata, Dominican Republic, Miami
2026 Sails: Dec 28 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III16 NT Extended Journey Of Caribbean Celebrations & Tropical Idyll fom$17325
16 Night - An Extended Journey of Caribbean Celebrations & Tropical Idylls - Starting in San Juan, St Johns AG, Antigua, Pointe-a-Pitre, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Samana, Puerto Plata, Dominican Republic, Miami, St John VI (Cruz Bay), US Virgin Islands, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Basseterre, San Juan
2026 Sails: Dec 28 Get a Quote
Princess Cruises, Crown Princess
Discount
Crown Princess7 Nights Southern Caribbean Cruise With Barbados from $1163 pp
7 Night - Southern Caribbean with Barbados and St. Kitts - Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Kitts, Dominica, Grenada, Barbados, San Juan, Puerto Rico
2027 Sails: Jan 3 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I7 NT A Journey Of Caribbean Delicacies & Idyllic Islands from $4270 pp
7 Night - A Journey of Caribbean Delicacies & Idyllic Islands - Starting in San Juan, St Maarten / Philipsburg, St Johns AG, Antigua, Little Bay, Tortola / Road Town, Miami
2027 Sails: Jan 4 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey9 Nights Eastern Caribbean Cruise from $1,959 pp plus OBC
9 Night - Southern Caribbean Cruise : St.Barts, Antigua & Tortola - Starting in San Juan, Virgin Gorda, Gustavia, Philipsburg, St Johns AG, Basseterre, St Kitts, Road Town, Tortola, Miami, Florida
2027 Sails: Jan 5 Get a Quote

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Departing from Puerto Rico Cruise Specials