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Cruises Calling at St John

45 upcoming cruises that stop at St John, U.S. Virgin Islands. Updated regularly; always confirm with the cruise line.

MSC Explora 3
MSC Explora Journeys Cruises
Quebec City → San Juan
⚓ Calls 28 Oct 08:00 - 17:00 202617 nights12 portsDeparts 2026 Oct 15
View itinerary · 12 ports
17 days, one-way from Quebec City to San Juan
  1. 15 Oct 20:00Departing from Quebec City, Canada
  2. 16 Oct 09:00 - 16:00Saguenay, Quebec Canada
  3. 17 Oct 09:00 - 18:00Sept-Iles, Quebec Canada
  4. 19 Oct 08:00 - 17:00Sydney NS, Nova Scotia Canada
  5. 20 Oct 09:00 - 17:00Halifax, Nova Scotia Canada
  6. 22 Oct 08:00 - 19:00New York, NYC Manhattan-Brooklyn
  7. 25 Oct 08:00 - 17:00Miami, Florida
  8. 28 Oct 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 29 Oct 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  10. 30 Oct 09:00 - 18:00Iles des Saintes, Guadeloupe
  11. 31 Oct 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  12. 01 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$8855from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 28 Oct 08:00 - 17:00 202614 nights11 portsDeparts 2026 Oct 25
View itinerary · 11 ports
14 days, round-trip An Extended Journey of Maritime Soul Island Zest
  1. 25 Oct 17:00Departing from Miami, Florida
  2. 28 Oct 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 29 Oct 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 30 Oct 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 31 Oct 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 01 Nov 08:00 - 18:00San Juan, Puerto Rico
  7. 02 Nov 09:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  8. 03 Nov 09:00 - 19:00Basseterre St Kitts, Port Zante
  9. 04 Nov 09:00 - 05 Nov 01:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 05 Nov 09:00 - 17:00Anguilla Island, UK, Sandy Ground
  11. 08 Nov 08:00Arriving in Miami, Florida
Find this cruise to book →
$7725from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 28 Oct 08:00 - 17:00 20267 nights6 portsDeparts 2026 Oct 25
View itinerary · 6 ports
7 days, one-way from Miami to San Juan
  1. 25 Oct 17:00Departing from Miami, Florida
  2. 28 Oct 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 29 Oct 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 30 Oct 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 31 Oct 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 01 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4310from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 29 Oct 08:00 - 18:00 202611 nights11 portsDeparts 2026 Oct 28
View itinerary · 11 ports
11 days, round-trip 11 Night Masterpieces at Sea Gems of the Leeward Islands Cruise
  1. 28 Oct 19:00Departing from San Juan, Puerto Rico
  2. 29 Oct 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 30 Oct 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 31 Oct 08:00 - 18:00Basseterre St Kitts, Port Zante
  5. 01 Nov 08:00 - 18:00Falmouth Antigua
  6. 02 Nov 08:00 - 18:00Iles des Saintes, Guadeloupe
  7. 03 Nov 08:00 - 21:30Pigeon Island, Rodney Bay, St Lucia
  8. 04 Nov 10:00 - 18:00St Georges Grenada
  9. 06 Nov 08:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  10. 07 Nov 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  11. 08 Nov 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$3417from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 11 Nov 08:00 - 18:00 202611 nights8 portsDeparts 2026 Nov 07
View itinerary · 8 ports
11 days, round-trip Miami, Fl To Miami, Fl
  1. 07 Nov 18:00Departing from Miami, Florida
  2. 10 Nov 09:00 - 19:00San Juan, Puerto Rico
  3. 11 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 12 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 13 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  6. 14 Nov 08:00 - 17:00Montserrat Island UK, Little Bay
  7. 15 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 18 NovArriving in Miami, Florida
Find this cruise to book →
$6300from / pp
Silver Shadow
Silversea Cruises
Montreal → Miami
⚓ Calls 11 Nov 08:00 - 18:00 202625 nights16 portsDeparts 2026 Oct 24
View itinerary · 16 ports
25 days, one-way from Montreal to Miami
  1. 24 Oct 20:00Departing from Montreal, Quebec Canada
  2. 25 Oct 08:00 - 23:00Quebec City, Canada
  3. 28 Oct 08:00 - 20:00Prince Edward Island, Charlottetown, Canada
  4. 30 Oct 08:00 - 23:00Halifax, Nova Scotia Canada
  5. 01 Nov 08:00 - 19:30Boston, Massachusetts
  6. 02 Nov 01:45 - 03:15Cape Cod Canal, Massachusetts
  7. 02 Nov 08:00 - 17:00Newport RI, Rhode Island
  8. 03 Nov 08:00 - 23:00New York, NYC Manhattan-Brooklyn
  9. 07 Nov 07:00Miami, Florida
  10. 10 Nov 09:00 - 19:00San Juan, Puerto Rico
  11. 11 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  12. 12 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  13. 13 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  14. 14 Nov 08:00 - 17:00Montserrat Island UK, Little Bay
  15. 15 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  16. 18 NovArriving in Miami, Florida
Find this cruise to book →
$9600from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 16 Nov 08:00 - 18:00 202614 nights14 portsDeparts 2026 Nov 08
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 08 Nov 19:00Departing from San Juan, Puerto Rico
  2. 10 Nov 09:00 - 22:00St Georges Grenada
  3. 11 Nov 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  4. 12 Nov 08:00 - 17:00Mayreau Island, Grenadines
  5. 13 Nov 10:00 - 17:00Iles des Saintes, Guadeloupe
  6. 14 Nov 08:00 - 15:00Marigot, St Martin Island France
  7. 15 Nov 07:00 - 19:00San Juan, Puerto Rico
  8. 16 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 17 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  10. 18 Nov 07:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  11. 19 Nov 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  12. 20 Nov 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  13. 21 Nov 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  14. 22 Nov 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$5893from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 16 Nov 08:00 - 18:00 202614 nights14 portsDeparts 2026 Nov 15
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 15 Nov 19:00Departing from San Juan, Puerto Rico
  2. 16 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 17 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  4. 18 Nov 07:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 19 Nov 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 20 Nov 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 21 Nov 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 22 Nov 07:00 - 19:00San Juan, Puerto Rico
  9. 24 Nov 09:00 - 22:00St Georges Grenada
  10. 25 Nov 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  11. 26 Nov 08:00 - 17:00Mayreau Island, Grenadines
  12. 27 Nov 10:00 - 17:00Iles des Saintes, Guadeloupe
  13. 28 Nov 08:00 - 15:00Marigot, St Martin Island France
  14. 29 Nov 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$5693from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 16 Nov 08:00 - 18:00 20267 nights8 portsDeparts 2026 Nov 15
View itinerary · 8 ports
7 days, round-trip 7 Night San Juan and the Virgin Islands Cruise
  1. 15 Nov 19:00Departing from San Juan, Puerto Rico
  2. 16 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 17 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  4. 18 Nov 07:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 19 Nov 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 20 Nov 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 21 Nov 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 22 Nov 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$3562from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 22 Nov 08:00 - 18:00 202612 nights9 portsDeparts 2026 Nov 18
View itinerary · 9 ports
12 days, round-trip Miami, Fl To Miami, Fl
  1. 18 Nov 18:00Departing from Miami, Florida
  2. 21 Nov 09:00 - 19:00San Juan, Puerto Rico
  3. 22 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 23 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 24 Nov 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  6. 25 Nov 08:00 - 18:00Montserrat Island UK, Little Bay
  7. 26 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  8. 27 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  9. 30 NovArriving in Miami, Florida
Find this cruise to book →
$6200from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from San Juan
⚓ Calls 25 Nov 08:00 - 17:00 202614 nights12 portsDeparts 2026 Nov 15
View itinerary · 12 ports
14 days, round-trip An Extended Journey of Tropical Harmony Natural Wonders
  1. 15 Nov 17:00Departing from San Juan, Puerto Rico
  2. 16 Nov 09:00 - 19:00Anguilla Island, UK, Sandy Ground
  3. 17 Nov 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 18 Nov 08:00 - 16:00St Croix Island USVI, Frederiksted-Christiansted, US Virgin Islands
  5. 19 Nov 08:00 - 17:00Catalina Island, Dominicana
  6. 20 Nov 09:00 - 17:00Puerto Plata-Amber Cove, Dominicana
  7. 22 Nov 08:00 - 17:00Miami, Florida
  8. 25 Nov 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 26 Nov 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  10. 27 Nov 09:00 - 18:00Iles des Saintes, Guadeloupe
  11. 28 Nov 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  12. 29 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$6900from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 25 Nov 08:00 - 17:00 202614 nights11 portsDeparts 2026 Nov 22
View itinerary · 11 ports
14 days, round-trip An Extended Journey of Sunlit Horizons Sapphire Bays
  1. 22 Nov 17:00Departing from Miami, Florida
  2. 25 Nov 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 26 Nov 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 27 Nov 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 28 Nov 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 29 Nov 08:00 - 18:00San Juan, Puerto Rico
  7. 30 Nov 09:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  8. 01 Dec 09:00 - 19:00Basseterre St Kitts, Port Zante
  9. 02 Dec 08:00 - 18:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 04 Dec 08:00 - 18:00Grand Turk Island, Cockburn Town, Turks and Caicos
  11. 06 Dec 08:00Arriving in Miami, Florida
Find this cruise to book →
$6825from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 25 Nov 08:00 - 17:00 20267 nights6 portsDeparts 2026 Nov 22
View itinerary · 6 ports
7 days, one-way from Miami to San Juan
  1. 22 Nov 17:00Departing from Miami, Florida
  2. 25 Nov 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 26 Nov 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 27 Nov 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 28 Nov 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 29 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4125from / pp
SeaDream II
SeaDream Yacht Club Cruises
San Juan → St Thomas Island USVI
⚓ Calls 28 Nov 20268 nights10 portsDeparts 2026 Nov 27
View itinerary · 10 ports
8 days, one-way from San Juan to St Thomas Island USVI
  1. 27 NovDeparting from San Juan, Puerto Rico
  2. 28 NovSt John Island USVI, Cruz Bay, US Virgin Islands
  3. 29 NovAnguilla Island, UK, Sandy Ground
  4. 30 NovPhilipsburg St Maarten, Netherlands Antilles
  5. 30 Nov - 01 DecGustavia St Barths, Saint-Barthelemy Island France
  6. 02 DecCharlestown Nevis, Nevis Island
  7. 03 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 04 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  9. 04 DecNorman Island BVI, The Bight, UK Virgin Islands
  10. 05 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
Price on request
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 30 Nov 08:00 - 18:00 202614 nights14 portsDeparts 2026 Nov 22
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 22 Nov 19:00Departing from San Juan, Puerto Rico
  2. 24 Nov 09:00 - 22:00St Georges Grenada
  3. 25 Nov 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  4. 26 Nov 08:00 - 17:00Mayreau Island, Grenadines
  5. 27 Nov 10:00 - 17:00Iles des Saintes, Guadeloupe
  6. 28 Nov 08:00 - 15:00Marigot, St Martin Island France
  7. 29 Nov 07:00 - 19:00San Juan, Puerto Rico
  8. 30 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 01 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 02 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  11. 03 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  12. 04 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  13. 05 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  14. 06 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$5093from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 30 Nov 08:00 - 18:00 20267 nights8 portsDeparts 2026 Nov 29
View itinerary · 8 ports
7 days, round-trip 7 Night San Juan and the Virgin Islands Cruise
  1. 29 Nov 19:00Departing from San Juan, Puerto Rico
  2. 30 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 01 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 02 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 03 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 04 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 05 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 06 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$2962from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 30 Nov 08:00 - 18:00 202614 nights14 portsDeparts 2026 Nov 29
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 29 Nov 19:00Departing from San Juan, Puerto Rico
  2. 30 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 01 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 02 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 03 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 04 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 05 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 06 Dec 07:00 - 19:00San Juan, Puerto Rico
  9. 08 Dec 09:00 - 22:00St Georges Grenada
  10. 09 Dec 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  11. 10 Dec 08:00 - 16:30Mayreau Island, Grenadines
  12. 11 Dec 11:00 - 18:00Deshaies, Basse-Terre Island Guadeloupe
  13. 12 Dec 08:00 - 15:00Marigot, St Martin Island France
  14. 13 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$5093from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 04 Dec 08:00 - 18:00 202610 nights7 portsDeparts 2026 Nov 30
View itinerary · 7 ports
10 days, round-trip Miami, Fl To Miami, Fl
  1. 30 Nov 18:00Departing from Miami, Florida
  2. 03 Dec 09:00 - 19:00San Juan, Puerto Rico
  3. 04 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 05 Dec 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 06 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  6. 07 Dec 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 10 DecArriving in Miami, Florida
Find this cruise to book →
$5700from / pp
Ritz-Carlton Ilma
Ritz-Carlton Yacht Collection Cruises
Round-trip from San Juan
⚓ Calls 06 Dec 08:00 - 19:00 20263 nights4 portsDeparts 2026 Dec 04
View itinerary · 4 ports
3 days, round-trip 3 Night San Juan to San Juan Cruise
  1. 04 Dec 18:00Departing from San Juan, Puerto Rico
  2. 05 Dec 08:00 - 19:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  3. 06 Dec 08:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 07 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4100from / pp
Emerald Sakara
Emerald Cruises
San Juan → St Thomas Island USVI
⚓ Calls 08 Dec 20266 nights7 portsDeparts 2026 Dec 07
View itinerary · 7 ports
6 days, one-way from San Juan to St Thomas Island USVI
  1. 07 DecDeparting from San Juan, Puerto Rico
  2. 08 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  3. 09 DecCharlestown Nevis, Nevis Island
  4. 10 DecFalmouth Antigua
  5. 11 DecGustavia St Barths, Saint-Barthelemy Island France
  6. 12 DecAnguilla Island, UK, Sandy Ground
  7. 13 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
$5045from / pp
Emerald Sakara
Emerald Cruises
Miami → St Thomas Island USVI
⚓ Calls 08 Dec 202613 nights13 portsDeparts 2026 Nov 30
View itinerary · 13 ports
13 days, one-way from Miami to St Thomas Island USVI
  1. 30 NovDeparting from Miami, Florida
  2. 01 DecNassau, Bahamas, New Providence Island
  3. 02 DecExuma Islands, Bahamas, George Town
  4. 03 DecSan Salvador Island Bahamas, Cockburn Town
  5. 04 DecLong Island Bahamas, Clarence Town, Calypso Cove
  6. 05 DecGrand Turk Island, Cockburn Town, Turks and Caicos
  7. 07 DecSan Juan, Puerto Rico
  8. 08 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  9. 09 DecCharlestown Nevis, Nevis Island
  10. 10 DecFalmouth Antigua
  11. 11 DecGustavia St Barths, Saint-Barthelemy Island France
  12. 12 DecAnguilla Island, UK, Sandy Ground
  13. 13 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
$10890from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 09 Dec 09:00 - 18:00 20267 nights6 portsDeparts 2026 Dec 06
View itinerary · 6 ports
7 days, one-way from Miami to San Juan
  1. 06 Dec 17:00Departing from Miami, Florida
  2. 09 Dec 09:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 10 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 11 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 12 Dec 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  6. 13 Dec 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4235from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 09 Dec 09:00 - 18:00 202614 nights11 portsDeparts 2026 Dec 06
View itinerary · 11 ports
14 days, round-trip An Extended Journey through Islands of Scenic Wonder Coastal History
  1. 06 Dec 17:00Departing from Miami, Florida
  2. 09 Dec 09:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 10 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 11 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 12 Dec 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  6. 13 Dec 08:00 - 18:00San Juan, Puerto Rico
  7. 14 Dec 09:00 - 19:00Anguilla Island, UK, Sandy Ground
  8. 15 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  9. 16 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  10. 18 Dec 08:00 - 18:00Grand Turk Island, Cockburn Town, Turks and Caicos
  11. 20 Dec 08:00Arriving in Miami, Florida
Find this cruise to book →
$7070from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from San Juan
⚓ Calls 09 Dec 09:00 - 18:00 202614 nights11 portsDeparts 2026 Nov 29
View itinerary · 11 ports
14 days, round-trip An Extended Journey through Golden Shores Island Grace
  1. 29 Nov 18:00Departing from San Juan, Puerto Rico
  2. 30 Nov 09:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  3. 01 Dec 09:00 - 19:00Basseterre St Kitts, Port Zante
  4. 02 Dec 08:00 - 18:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 04 Dec 08:00 - 18:00Grand Turk Island, Cockburn Town, Turks and Caicos
  6. 06 Dec 08:00 - 17:00Miami, Florida
  7. 09 Dec 09:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  8. 10 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  9. 11 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  10. 12 Dec 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  11. 13 Dec 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$7140from / pp
Ritz-Carlton Ilma
Ritz-Carlton Yacht Collection Cruises
Round-trip from San Juan
⚓ Calls 10 Dec 08:00 - 19:00 20264 nights5 portsDeparts 2026 Dec 07
View itinerary · 5 ports
4 days, round-trip 4 Night San Juan to San Juan Cruise
  1. 07 Dec 18:00Departing from San Juan, Puerto Rico
  2. 08 Dec 09:00 - 23:59Gustavia St Barths, Saint-Barthelemy Island France
  3. 09 Dec 08:00 - 19:00Marigot, St Martin Island France
  4. 10 Dec 08:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  5. 11 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4900from / pp
SeaDream II
SeaDream Yacht Club Cruises
Round-trip from St Thomas Island USVI
⚓ Calls 11 Dec 20267 nights7 portsDeparts 2026 Dec 05
View itinerary · 7 ports
7 days, round-trip 7 Night Charlotte Amalie to Charlotte Amalie Cruise
  1. 05 DecDeparting from St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  2. 06 DecSan Juan, Puerto Rico
  3. 07 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 08 Dec - 09 DecGustavia St Barths, Saint-Barthelemy Island France
  5. 10 DecAnguilla Island, UK, Sandy Ground
  6. 11 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  7. 12 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
Price on request
Silver Shadow
Silversea Cruises
Miami → San Juan
⚓ Calls 13 Dec 13:00 - 19:00 202610 nights9 portsDeparts 2026 Dec 10
View itinerary · 9 ports
10 days, one-way from Miami to San Juan
  1. 10 Dec 18:00Departing from Miami, Florida
  2. 13 Dec 13:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 14 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  4. 15 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  5. 16 Dec 08:00 - 18:00Iles des Saintes, Guadeloupe
  6. 17 Dec 08:00 - 18:00Fort-de-France, Martinique
  7. 18 Dec 08:00 - 17:00Montserrat Island UK, Little Bay
  8. 19 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  9. 20 DecArriving in San Juan, Puerto Rico
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$5100from / pp
Ritz-Carlton Ilma
Ritz-Carlton Yacht Collection Cruises
Round-trip from San Juan
⚓ Calls 13 Dec 08:00 - 19:00 20263 nights4 portsDeparts 2026 Dec 11
View itinerary · 4 ports
3 days, round-trip 3 Night San Juan to San Juan Cruise
  1. 11 Dec 18:00Departing from San Juan, Puerto Rico
  2. 12 Dec 08:00 - 19:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  3. 13 Dec 08:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 14 Dec 07:00Arriving in San Juan, Puerto Rico
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$4100from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 14 Dec 08:00 - 18:00 202614 nights14 portsDeparts 2026 Dec 06
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 06 Dec 19:00Departing from San Juan, Puerto Rico
  2. 08 Dec 09:00 - 22:00St Georges Grenada
  3. 09 Dec 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  4. 10 Dec 08:00 - 16:30Mayreau Island, Grenadines
  5. 11 Dec 11:00 - 18:00Deshaies, Basse-Terre Island Guadeloupe
  6. 12 Dec 08:00 - 15:00Marigot, St Martin Island France
  7. 13 Dec 07:00 - 19:00San Juan, Puerto Rico
  8. 14 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 15 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 16 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  11. 17 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  12. 18 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  13. 19 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  14. 20 Dec 07:00Arriving in San Juan, Puerto Rico
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$5093from / pp
SeaDream I
SeaDream Yacht Club Cruises
San Juan → St Thomas Island USVI
⚓ Calls 14 Dec 20267 nights10 portsDeparts 2026 Dec 12
View itinerary · 10 ports
7 days, one-way from San Juan to St Thomas Island USVI
  1. 12 DecDeparting from San Juan, Puerto Rico
  2. 13 DecSan Juan, Puerto Rico
  3. 14 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  4. 15 DecPhilipsburg St Maarten, Netherlands Antilles
  5. 15 DecPhilipsburg St Maarten, Netherlands Antilles
  6. 15 Dec - 16 DecGustavia St Barths, Saint-Barthelemy Island France
  7. 17 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 18 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  9. 18 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  10. 19 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
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$4819from / pp
Emerald Sakara
Emerald Cruises
Round-trip from St Thomas Island USVI
⚓ Calls 14 Dec 20267 nights8 portsDeparts 2026 Dec 13
View itinerary · 8 ports
7 days, round-trip 7 Night Vibes of the Virgin Islands Cruise
  1. 13 DecDeparting from St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  2. 14 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  3. 15 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 15 Dec - 16 DecNorman Island BVI, The Bight, UK Virgin Islands
  5. 17 DecAnguilla Island, UK, Sandy Ground
  6. 17 Dec - 18 DecPhilipsburg St Maarten, Netherlands Antilles
  7. 18 Dec - 19 DecGustavia St Barths, Saint-Barthelemy Island France
  8. 20 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
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$4278from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 14 Dec 08:00 - 18:00 20267 nights8 portsDeparts 2026 Dec 13
View itinerary · 8 ports
7 days, round-trip 7 Night San Juan and the Virgin Islands Cruise
  1. 13 Dec 19:00Departing from San Juan, Puerto Rico
  2. 14 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 15 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 16 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 17 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 18 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 19 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 20 Dec 07:00Arriving in San Juan, Puerto Rico
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$2962from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 14 Dec 08:00 - 18:00 202614 nights14 portsDeparts 2026 Dec 13
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 13 Dec 19:00Departing from San Juan, Puerto Rico
  2. 14 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 15 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 16 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 17 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  6. 18 Dec 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 19 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 20 Dec 07:00 - 19:00San Juan, Puerto Rico
  9. 22 Dec 09:00 - 22:00St Georges Grenada
  10. 23 Dec 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  11. 24 Dec 08:00 - 16:30Mayreau Island, Grenadines
  12. 25 Dec 11:00 - 18:00Deshaies, Basse-Terre Island Guadeloupe
  13. 26 Dec 08:00 - 15:00Marigot, St Martin Island France
  14. 27 Dec 07:00Arriving in San Juan, Puerto Rico
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$4993from / pp
Silver Ray
Silversea Cruises
Round-trip from Miami
⚓ Calls 15 Dec 08:00 - 18:00 202611 nights8 portsDeparts 2026 Dec 11
View itinerary · 8 ports
11 days, round-trip Miami, Fl To Miami, Fl
  1. 11 Dec 18:00Departing from Miami, Florida
  2. 14 Dec 09:00 - 19:00San Juan, Puerto Rico
  3. 15 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 16 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  5. 17 Dec 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  6. 18 Dec 08:00 - 17:00Deshaies, Basse-Terre Island Guadeloupe
  7. 19 Dec 08:00 - 13:30Tortola Island BVI, Road Town, UK Virgin Islands
  8. 22 DecArriving in Miami, Florida
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$7100from / pp
MSC Explora 1
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 16 Dec 08:00 - 17:00 202615 nights12 portsDeparts 2026 Dec 05
View itinerary · 12 ports
15 days, one-way from Miami to San Juan
  1. 05 Dec 17:00Departing from Miami, Florida
  2. 07 Dec 09:00 - 20:00Cozumel, Mexico, Riviera Maya
  3. 08 Dec 09:00 - 18:00Costa Maya, Mexico, Riviera Maya
  4. 09 Dec 08:00 - 18:00Santo Tomas de Castilla, Puerto Barrios, Guatemala
  5. 10 Dec 07:00 - 18:00Belize City
  6. 11 Dec 08:00 - 14:00Roatan Island, Carnival Isla Tropicale-Coxen Hole, Honduras
  7. 13 Dec 08:00 - 17:00Miami, Florida
  8. 16 Dec 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 17 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  10. 18 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  11. 19 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  12. 20 Dec 08:00Arriving in San Juan, Puerto Rico
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$6650from / pp
MSC Explora 1
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 16 Dec 08:00 - 17:00 202614 nights11 portsDeparts 2026 Dec 13
View itinerary · 11 ports
14 days, round-trip An Extended Journey of Island Calm Coastal Retreats
  1. 13 Dec 17:00Departing from Miami, Florida
  2. 16 Dec 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 17 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 18 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 19 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 20 Dec 08:00 - 18:00San Juan, Puerto Rico
  7. 21 Dec 09:00 - 19:00Basseterre St Kitts, Port Zante
  8. 22 Dec 08:00 - 19:00Tortola Island BVI, Road Town, UK Virgin Islands
  9. 23 Dec 08:00 - 24 Dec 01:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 24 Dec 09:00 - 17:00Anguilla Island, UK, Sandy Ground
  11. 27 Dec 08:00Arriving in Miami, Florida
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$7630from / pp
MSC Explora 1
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 16 Dec 08:00 - 17:00 20267 nights6 portsDeparts 2026 Dec 13
View itinerary · 6 ports
7 days, one-way from Miami to San Juan
  1. 13 Dec 17:00Departing from Miami, Florida
  2. 16 Dec 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 17 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 18 Dec 09:00 - 18:00Iles des Saintes, Guadeloupe
  5. 19 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  6. 20 Dec 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$3745from / pp
Ritz-Carlton Ilma
Ritz-Carlton Yacht Collection Cruises
Round-trip from San Juan
⚓ Calls 20 Dec 09:00 - 19:00 20267 nights7 portsDeparts 2026 Dec 14
View itinerary · 7 ports
7 days, round-trip 7 Night San Juan to San Juan Cruise
  1. 14 Dec 18:00Departing from San Juan, Puerto Rico
  2. 16 Dec 08:00 - 19:00St Georges Grenada
  3. 17 Dec 08:00 - 19:00Canouan Island, Grenadines
  4. 18 Dec 08:00 - 14:00Soufriere, St Lucia Island
  5. 19 Dec 10:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  6. 20 Dec 09:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  7. 21 Dec 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$7800from / pp
SeaDream I
SeaDream Yacht Club Cruises
Round-trip from St Thomas Island USVI
⚓ Calls 20 Dec 20268 nights11 portsDeparts 2026 Dec 19
View itinerary · 11 ports
8 days, round-trip 8 Night Charlotte Amalie to Charlotte Amalie Cruise
  1. 19 DecDeparting from St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  2. 20 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  3. 21 DecNorman Island BVI, The Bight, UK Virgin Islands
  4. 21 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  5. 22 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 23 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  7. 23 DecBeef Island BVI, UK Virgin Islands
  8. 24 DecMarigot, St Martin Island France
  9. 25 DecAnguilla Island, UK, Sandy Ground
  10. 25 Dec - 26 DecGustavia St Barths, Saint-Barthelemy Island France
  11. 27 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
$5979from / pp
Emerald Sakara
Emerald Cruises
Round-trip from St Thomas Island USVI
⚓ Calls 21 Dec 20267 nights8 portsDeparts 2026 Dec 20
View itinerary · 8 ports
7 days, round-trip 7 Night Vibes of the Virgin Islands Cruise
  1. 20 DecDeparting from St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  2. 21 DecSt John Island USVI, Cruz Bay, US Virgin Islands
  3. 22 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 22 Dec - 23 DecNorman Island BVI, The Bight, UK Virgin Islands
  5. 24 DecAnguilla Island, UK, Sandy Ground
  6. 24 Dec - 25 DecPhilipsburg St Maarten, Netherlands Antilles
  7. 25 Dec - 26 DecGustavia St Barths, Saint-Barthelemy Island France
  8. 27 DecArriving in St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
Find this cruise to book →
$4278from / pp
Silver Spirit
Silversea Cruises
Round-trip from Bridgetown
⚓ Calls 24 Dec 08:00 - 18:00 20268 nights8 portsDeparts 2026 Dec 19
View itinerary · 8 ports
8 days, round-trip Bridgetown To Bridgetown
  1. 19 Dec 23:00Departing from Bridgetown, Barbados
  2. 20 Dec 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  3. 21 Dec 08:00 - 18:00Fort-de-France, Martinique
  4. 22 Dec 08:00 - 18:00Roseau, Dominica
  5. 23 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  6. 24 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  7. 26 Dec 08:00 - 18:00Castries, St Lucia Island
  8. 27 DecArriving in Bridgetown, Barbados
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$6100from / pp
Silver Shadow
Silversea Cruises
Round-trip from San Juan
⚓ Calls 28 Dec 08:00 - 18:00 202614 nights13 portsDeparts 2026 Dec 20
View itinerary · 13 ports
14 days, round-trip San Juan To San Juan
  1. 20 Dec 19:00Departing from San Juan, Puerto Rico
  2. 21 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 22 Dec 09:00 - 18:30Montserrat Island UK, Little Bay
  4. 23 Dec 08:30 - 18:00Castries, St Lucia Island
  5. 24 Dec 08:00 - 18:00Fort-de-France, Martinique
  6. 26 Dec 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  7. 27 Dec 07:00San Juan, Puerto Rico
  8. 28 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 29 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  10. 30 Dec 08:00 - 17:00Iles des Saintes, Guadeloupe
  11. 31 Dec 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  12. 02 Jan 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  13. 03 JanArriving in San Juan, Puerto Rico
Find this cruise to book →
$8700from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 28 Dec 08:00 - 18:00 202614 nights14 portsDeparts 2026 Dec 20
View itinerary · 14 ports
14 days, round-trip 14 Night Star Collector Lovely Leewards Cruise
  1. 20 Dec 19:00Departing from San Juan, Puerto Rico
  2. 22 Dec 09:00 - 22:00St Georges Grenada
  3. 23 Dec 08:00 - 22:00Bequia Island, Port Elizabeth, Grenadines
  4. 24 Dec 08:00 - 16:30Mayreau Island, Grenadines
  5. 25 Dec 11:00 - 18:00Deshaies, Basse-Terre Island Guadeloupe
  6. 26 Dec 08:00 - 15:00Marigot, St Martin Island France
  7. 27 Dec 07:00 - 19:00San Juan, Puerto Rico
  8. 28 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 29 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 30 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  11. 31 Dec 08:00 - 22:00Philipsburg St Maarten, Netherlands Antilles
  12. 01 Jan 09:00 - 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  13. 02 Jan 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  14. 03 Jan 07:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$6293from / pp
MSC Explora 1
MSC Explora Journeys Cruises
Round-trip from San Juan
⚓ Calls 31 Dec 09:00 - 16:00 202615 nights13 portsDeparts 2026 Dec 20
View itinerary · 13 ports
15 days, round-trip An Extended Journey into Island Bliss Lively Celebrations
  1. 20 Dec 18:00Departing from San Juan, Puerto Rico
  2. 21 Dec 09:00 - 19:00Basseterre St Kitts, Port Zante
  3. 22 Dec 08:00 - 19:00Tortola Island BVI, Road Town, UK Virgin Islands
  4. 23 Dec 08:00 - 24 Dec 01:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 24 Dec 09:00 - 17:00Anguilla Island, UK, Sandy Ground
  6. 27 Dec 08:00 - 17:00Miami, Florida
  7. 29 Dec 08:00 - 17:00Puerto Plata-Amber Cove, Dominicana
  8. 30 Dec 08:00 - 17:00Catalina Island, Dominicana
  9. 31 Dec 09:00 - 16:00St John Island USVI, Cruz Bay, US Virgin Islands
  10. 01 Jan 12:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 02 Jan 08:00 - 17:00Basseterre St Kitts, Port Zante
  12. 03 Jan 08:00 - 21:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  13. 04 Jan 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$12280from / pp
Silver Ray
Silversea Cruises
Round-trip from Miami
⚓ Calls 01 Jan 08:00 - 17:00 202714 nights9 portsDeparts 2026 Dec 22
View itinerary · 9 ports
14 days, round-trip Miami, Fl To Miami, Fl
  1. 22 Dec 18:00Departing from Miami, Florida
  2. 24 Dec 09:00 - 17:00Grand Turk Island, Cockburn Town, Turks and Caicos
  3. 26 Dec 09:00 - 18:00Basseterre St Kitts, Port Zante
  4. 28 Dec 08:00 - 22:00Oranjestad Aruba, Netherlands Antilles
  5. 29 Dec 08:00 - 22:00Kralendijk Bonaire, Netherlands Antilles
  6. 30 Dec 08:00 - 19:00Willemstad Curacao, Netherlands Antilles
  7. 01 Jan 08:00 - 17:00St John Island USVI, Cruz Bay, US Virgin Islands
  8. 02 Jan 07:00 - 15:00San Juan, Puerto Rico
  9. 05 JanArriving in Miami, Florida
Find this cruise to book →
$10700from / pp

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