Cruise Ports
← Back to Jost Van Dyke port guide

Cruises Calling at Jost Van Dyke

45 upcoming cruises that stop at Jost Van Dyke, British Virgin Islands. Updated regularly; always confirm with the cruise line.

Crystal Symphony
Crystal Cruises
Vancouver → New York
⚓ Calls 20 Sep 09:00 - 17:00 202639 nights29 portsDeparts 2026 Aug 17
View itinerary · 29 ports
39 days, one-way from Vancouver to New York
  1. 17 Aug 18:00Departing from Vancouver, BC Canada
  2. 18 Aug 07:00 - 17:00Victoria BC, Vancouver Island Canada
  3. 19 Aug 10:00 - 19:00Astoria OR, Oregon
  4. 21 Aug 07:00 - 16:00Eureka CA, California
  5. 22 Aug 08:00 - 19:00San Francisco, California
  6. 24 Aug - 19:00San Diego, California
  7. 25 Aug 07:00 - 16:00Ensenada, Baja California Mexico
  8. 27 Aug 08:00 - 17:00Cabo San Lucas, Baja California Mexico
  9. 28 Aug 11:00 - 19:00Puerto Vallarta, Jalisco, Mexico Riviera
  10. 31 Aug 08:00 - 17:00Acajutla, El Salvador
  11. 01 Sep 11:00 - 19:00Playa Flamingo, Costa Rica
  12. 02 Sep 07:00 - 18:00Puntarenas, Puerto Caldera, Costa Rica
  13. 04 Sep 10:00 - 17:00Manta, Ecuador
  14. 05 Sep - 19:00Guayaquil, Ecuador
  15. 07 Sep 19:00 - 09 Sep 04:00Panama City, Fuerte Amador, Balboa
  16. 09 SepPanama Canal
  17. 10 Sep 10:00 - 19:00Cartagena Colombia
  18. 12 Sep 08:00 - 19:00Santo Domingo, Dominicana
  19. 13 Sep 08:00 - 18:00Punta Cana, Dominicana
  20. 14 Sep - 18:00San Juan, Puerto Rico
  21. 15 Sep 08:00 - 18:00Marigot, St Martin Island France
  22. 16 Sep 08:00 - 18:00Roseau, Dominica
  23. 17 Sep 08:00 - 18:00Bridgetown, Barbados
  24. 18 Sep 08:00 - 18:00Castries, St Lucia Island
  25. 19 Sep 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  26. 20 Sep 09:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  27. 21 Sep 09:00 - 18:00Samana, Dominicana
  28. 22 Sep 07:00 - 14:00Grand Turk Island, Cockburn Town, Turks and Caicos
  29. 25 Sep 07:00Arriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$17300from / pp
Crystal Symphony
Crystal Cruises
San Diego → New York
⚓ Calls 20 Sep 09:00 - 17:00 202632 nights24 portsDeparts 2026 Aug 24
View itinerary · 24 ports
32 days, one-way from San Diego to New York
  1. 24 Aug 19:00Departing from San Diego, California
  2. 25 Aug 07:00 - 16:00Ensenada, Baja California Mexico
  3. 27 Aug 08:00 - 17:00Cabo San Lucas, Baja California Mexico
  4. 28 Aug 11:00 - 19:00Puerto Vallarta, Jalisco, Mexico Riviera
  5. 31 Aug 08:00 - 17:00Acajutla, El Salvador
  6. 01 Sep 11:00 - 19:00Playa Flamingo, Costa Rica
  7. 02 Sep 07:00 - 18:00Puntarenas, Puerto Caldera, Costa Rica
  8. 04 Sep 10:00 - 17:00Manta, Ecuador
  9. 05 Sep - 19:00Guayaquil, Ecuador
  10. 07 Sep 19:00 - 09 Sep 04:00Panama City, Fuerte Amador, Balboa
  11. 09 SepPanama Canal
  12. 10 Sep 10:00 - 19:00Cartagena Colombia
  13. 12 Sep 08:00 - 19:00Santo Domingo, Dominicana
  14. 13 Sep 08:00 - 18:00Punta Cana, Dominicana
  15. 14 Sep - 18:00San Juan, Puerto Rico
  16. 15 Sep 08:00 - 18:00Marigot, St Martin Island France
  17. 16 Sep 08:00 - 18:00Roseau, Dominica
  18. 17 Sep 08:00 - 18:00Bridgetown, Barbados
  19. 18 Sep 08:00 - 18:00Castries, St Lucia Island
  20. 19 Sep 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  21. 20 Sep 09:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  22. 21 Sep 09:00 - 18:00Samana, Dominicana
  23. 22 Sep 07:00 - 14:00Grand Turk Island, Cockburn Town, Turks and Caicos
  24. 25 Sep 07:00Arriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$13600from / pp
Crystal Symphony
Crystal Cruises
San Juan → New York
⚓ Calls 20 Sep 09:00 - 17:00 202611 nights10 portsDeparts 2026 Sep 14
View itinerary · 10 ports
11 days, one-way from San Juan to New York
  1. 14 Sep 18:00Departing from San Juan, Puerto Rico
  2. 15 Sep 08:00 - 18:00Marigot, St Martin Island France
  3. 16 Sep 08:00 - 18:00Roseau, Dominica
  4. 17 Sep 08:00 - 18:00Bridgetown, Barbados
  5. 18 Sep 08:00 - 18:00Castries, St Lucia Island
  6. 19 Sep 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  7. 20 Sep 09:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 21 Sep 09:00 - 18:00Samana, Dominicana
  9. 22 Sep 07:00 - 14:00Grand Turk Island, Cockburn Town, Turks and Caicos
  10. 25 Sep 07:00Arriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$5000from / pp
Crystal Symphony
Crystal Cruises
Bridgetown → New York
⚓ Calls 20 Sep 09:00 - 17:00 20268 nights7 portsDeparts 2026 Sep 17
View itinerary · 7 ports
8 days, one-way from Bridgetown to New York
  1. 17 Sep 18:00Departing from Bridgetown, Barbados
  2. 18 Sep 08:00 - 18:00Castries, St Lucia Island
  3. 19 Sep 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  4. 20 Sep 09:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  5. 21 Sep 09:00 - 18:00Samana, Dominicana
  6. 22 Sep 07:00 - 14:00Grand Turk Island, Cockburn Town, Turks and Caicos
  7. 25 Sep 07:00Arriving in New York, NYC Manhattan-Brooklyn
Find this cruise to book →
$4200from / pp
Crystal Symphony
Crystal Cruises
San Juan → Fort Lauderdale
⚓ Calls 05 Nov 10:00 - 18:00 20267 nights6 portsDeparts 2026 Nov 04
View itinerary · 6 ports
7 days, one-way from San Juan to Fort Lauderdale
  1. 04 Nov 18:00Departing from San Juan, Puerto Rico
  2. 05 Nov 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 06 Nov 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  4. 07 Nov 08:00 - 18:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 08 Nov 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  6. 11 Nov 07:00Arriving in Fort Lauderdale, Port Everglades, Florida
Find this cruise to book →
$3500from / pp
Crystal Symphony
Crystal Cruises
Montreal → Fort Lauderdale
⚓ Calls 05 Nov 10:00 - 18:00 202626 nights19 portsDeparts 2026 Oct 16
View itinerary · 19 ports
26 days, one-way from Montreal to Fort Lauderdale
  1. 16 OctDeparting from Montreal, Quebec Canada
  2. 17 Oct 08:00 - 18:00Quebec City, Canada
  3. 19 Oct 08:00 - 17:00Madeleine-Magdalen Islands, Cap-aux Meules, Quebec Canada
  4. 20 Oct 07:00 - 16:00Sydney NS, Nova Scotia Canada
  5. 21 Oct 08:00 - 16:00Halifax, Nova Scotia Canada
  6. 22 Oct 10:00 - 18:00Saint John NB, New Brunswick Canada
  7. 23 Oct 09:00 - 17:00Portland OR, Oregon
  8. 24 Oct 07:00 - 16:00Boston, Massachusetts
  9. 25 Oct 10:00 - 18:00Newport RI, Rhode Island
  10. 26 Oct 07:00 - 27 Oct 18:00New York, NYC Manhattan-Brooklyn
  11. 29 Oct 11:00 - 30 Oct 17:30Kings Wharf, Bermuda
  12. 02 Nov 08:00 - 19:00Santo Domingo, Dominicana
  13. 03 Nov 08:00 - 18:00Samana, Dominicana
  14. 04 Nov - 18:00San Juan, Puerto Rico
  15. 05 Nov 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  16. 06 Nov 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  17. 07 Nov 08:00 - 18:00Gustavia St Barths, Saint-Barthelemy Island France
  18. 08 Nov 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  19. 11 Nov 07:00Arriving in Fort Lauderdale, Port Everglades, Florida
Find this cruise to book →
$12900from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 06 Nov 08:00 - 22:00 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
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from San Juan
⚓ Calls 13 Nov 10:00 - 18:00 202614 nights12 portsDeparts 2026 Nov 01
View itinerary · 12 ports
14 days, round-trip An Extended Journey into Island Delights, Hidden Coves Chic Coastlines
  1. 01 Nov 18:00Departing from San Juan, Puerto Rico
  2. 02 Nov 09:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  3. 03 Nov 09:00 - 19:00Basseterre St Kitts, Port Zante
  4. 04 Nov 09:00 - 05 Nov 01:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 05 Nov 09:00 - 17:00Anguilla Island, UK, Sandy Ground
  6. 08 Nov 08:00 - 17:00Miami, Florida
  7. 10 Nov 09:00 - 18:00Providenciales Island, Turks and Caicos Islands
  8. 11 Nov 09:00 - 16:00Puerto Plata-Amber Cove, Dominicana
  9. 12 Nov 09:00 - 17:00La Romana, Dominicana
  10. 13 Nov 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 14 Nov 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  12. 15 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$8025from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 13 Nov 10:00 - 18:00 202614 nights13 portsDeparts 2026 Nov 08
View itinerary · 13 ports
14 days, round-trip An Extended Journey of Blissful Escapes Shoreline Splendour
  1. 08 Nov 17:00Departing from Miami, Florida
  2. 10 Nov 09:00 - 18:00Providenciales Island, Turks and Caicos Islands
  3. 11 Nov 09:00 - 16:00Puerto Plata-Amber Cove, Dominicana
  4. 12 Nov 09:00 - 17:00La Romana, Dominicana
  5. 13 Nov 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 14 Nov 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  7. 15 Nov 08:00 - 17:00San Juan, Puerto Rico
  8. 16 Nov 09:00 - 19:00Anguilla Island, UK, Sandy Ground
  9. 17 Nov 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  10. 18 Nov 08:00 - 16:00St Croix Island USVI, Frederiksted-Christiansted, US Virgin Islands
  11. 19 Nov 08:00 - 17:00Catalina Island, Dominicana
  12. 20 Nov 09:00 - 17:00Puerto Plata-Amber Cove, Dominicana
  13. 22 Nov 08:00Arriving in Miami, Florida
Find this cruise to book →
$7425from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Miami → San Juan
⚓ Calls 13 Nov 10:00 - 18:00 20267 nights7 portsDeparts 2026 Nov 08
View itinerary · 7 ports
7 days, one-way from Miami to San Juan
  1. 08 Nov 17:00Departing from Miami, Florida
  2. 10 Nov 09:00 - 18:00Providenciales Island, Turks and Caicos Islands
  3. 11 Nov 09:00 - 16:00Puerto Plata-Amber Cove, Dominicana
  4. 12 Nov 09:00 - 17:00La Romana, Dominicana
  5. 13 Nov 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 14 Nov 08:00 - 19:00Gustavia St Barths, Saint-Barthelemy Island France
  7. 15 Nov 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$4125from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 15 Nov 08:00 - 14:00 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 15 Nov 08:00 - 14:00 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
Crystal Serenity
Crystal Cruises
Lisbon → Fort Lauderdale
⚓ Calls 19 Nov 09:00 - 18:00 202615 nights8 portsDeparts 2026 Nov 08
View itinerary · 8 ports
15 days, one-way from Lisbon to Fort Lauderdale
  1. 08 Nov 19:00Departing from Lisbon, Portugal
  2. 11 Nov 08:00 - 18:00Praia da Vitoria, Terceira Island Azores Portugal
  3. 12 Nov 08:00 - 17:00Ponta Delgada, Sao Miguel Island Azores Portugal
  4. 13 Nov 07:00 - 15:00Horta, Faial Island Azores Portugal
  5. 18 Nov 11:00 - 20:00St Johns Antigua, RCI Royal Beach Club
  6. 19 Nov 09:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 20 Nov 07:00 - 18:00San Juan, Puerto Rico
  8. 23 Nov 06:00Arriving in Fort Lauderdale, Port Everglades, Florida
Find this cruise to book →
$6900from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 20 Nov 09:00 - 22:00 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 20 Nov 09:00 - 22:00 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
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 20 Nov 09:00 - 22:00 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
Seabourn Ovation
Seabourn Cruises
Miami → Philipsburg St Maarten
⚓ Calls 24 Nov 08:00 - 18:00 202615 nights13 portsDeparts 2026 Nov 20
View itinerary · 13 ports
15 days, one-way from Miami to Philipsburg St Maarten
  1. 20 Nov 16:00Departing from Miami, Florida
  2. 23 Nov 10:00 - 18:00San Juan, Puerto Rico
  3. 24 Nov 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 25 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 26 Nov 08:00 - 17:00Roseau, Dominica
  6. 27 Nov 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  7. 28 Nov 07:00 - 21:00Bridgetown, Barbados
  8. 29 Nov 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  9. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  10. 02 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  11. 03 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  12. 04 Dec 08:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  13. 05 Dec 07:00Arriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
$7499from / pp
Seabourn Ovation
Seabourn Cruises
Miami → Bridgetown
⚓ Calls 24 Nov 08:00 - 18:00 20268 nights7 portsDeparts 2026 Nov 20
View itinerary · 7 ports
8 days, one-way from Miami to Bridgetown
  1. 20 Nov 16:00Departing from Miami, Florida
  2. 23 Nov 10:00 - 18:00San Juan, Puerto Rico
  3. 24 Nov 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 25 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 26 Nov 08:00 - 17:00Roseau, Dominica
  6. 27 Nov 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  7. 28 Nov 07:00Arriving in Bridgetown, Barbados
Find this cruise to book →
$3799from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 27 Nov 08:00 - 14:00 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
Crystal Serenity
Crystal Cruises
Fort Lauderdale → Cartagena Colombia
⚓ Calls 28 Nov 08:00 - 17:00 20268 nights7 portsDeparts 2026 Nov 23
View itinerary · 7 ports
8 days, one-way from Fort Lauderdale to Cartagena Colombia
  1. 23 Nov 19:00Departing from Fort Lauderdale, Port Everglades, Florida
  2. 24 NovParadise Island Bahamas, RCI Royal Beach Club, Atlantis Resort
  3. 26 Nov 09:00 - 18:00Samana, Dominicana
  4. 27 Nov 08:00 - 18:00San Juan, Puerto Rico
  5. 28 Nov 08:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 30 Nov 07:00 - 16:00Oranjestad Aruba, Netherlands Antilles
  7. 01 Dec 15:00Arriving in Cartagena Colombia
Find this cruise to book →
$4500from / pp
Crystal Serenity
Crystal Cruises
San Juan → Cartagena Colombia
⚓ Calls 28 Nov 08:00 - 17:00 20264 nights4 portsDeparts 2026 Nov 27
View itinerary · 4 ports
4 days, one-way from San Juan to Cartagena Colombia
  1. 27 Nov 18:00Departing from San Juan, Puerto Rico
  2. 28 Nov 08:00 - 17:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 30 Nov 07:00 - 16:00Oranjestad Aruba, Netherlands Antilles
  4. 01 Dec 15:00Arriving in Cartagena Colombia
Find this cruise to book →
$2600from / pp
Star Flyer
Star Clippers Cruises
Round-trip from Philipsburg St Maarten
⚓ Calls 30 Nov 20267 nights12 portsDeparts 2026 Nov 28
View itinerary · 12 ports
7 days, round-trip 7 Night Treasure Islands Cruise
  1. 28 NovDeparting from Philipsburg St Maarten, Netherlands Antilles
  2. 29 NovAnguilla Island, UK, Sandy Ground
  3. 30 NovJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 30 NovTortola Island BVI, Road Town, UK Virgin Islands
  5. 01 DecNorman Island BVI, The Bight, UK Virgin Islands
  6. 01 DecNorman Island BVI, The Bight, UK Virgin Islands
  7. 02 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  8. 02 Deccoastal cruising
  9. 03 DecBasseterre St Kitts, Port Zante
  10. 03 DecSaint Kitts island
  11. 04 DecGustavia St Barths, Saint-Barthelemy Island France
  12. 05 DecArriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
Price on request
Seabourn Quest
Seabourn Cruises
Round-trip from Miami
⚓ Calls 03 Dec 07:00 - 14:00 202614 nights11 portsDeparts 2026 Nov 22
View itinerary · 11 ports
14 days, round-trip Leeward Island Jewels
  1. 22 Nov 16:00Departing from Miami, Florida
  2. 25 Nov 10:00 - 18:00San Juan, Puerto Rico
  3. 26 Nov 08:00 - 17:00Anguilla Island, UK, Sandy Ground
  4. 27 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 28 Nov 08:00 - 17:00Roseau, Dominica
  6. 29 Nov 08:00 - 18:00Fort-de-France, Martinique
  7. 30 Nov 08:00 - 17:00Iles des Saintes, Guadeloupe
  8. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  9. 02 Dec 08:00 - 17:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  10. 03 Dec 07:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 06 Dec 07:00Arriving in Miami, Florida
Find this cruise to book →
$5999from / pp
SeaDream II
SeaDream Yacht Club Cruises
San Juan → St Thomas Island USVI
⚓ Calls 03 Dec 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 04 Dec 09:00 - 22:00 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 04 Dec 09:00 - 22:00 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 04 Dec 09:00 - 22:00 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
SeaDream II
SeaDream Yacht Club Cruises
Round-trip from St Thomas Island USVI
⚓ Calls 07 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
Round-trip from Miami
⚓ Calls 07 Dec 08:00 - 14:00 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
SeaDream I
SeaDream Yacht Club Cruises
St Johns Antigua → San Juan
⚓ Calls 10 Dec 20267 nights9 portsDeparts 2026 Dec 05
View itinerary · 9 ports
7 days, one-way from St Johns Antigua to San Juan
  1. 05 DecDeparting from St Johns Antigua, RCI Royal Beach Club
  2. 06 DecOranjestad Aruba, Netherlands Antilles
  3. 06 Dec - 07 DecGustavia St Barths, Saint-Barthelemy Island France
  4. 08 DecCharlestown Nevis, Nevis Island
  5. 09 DecAnguilla Island, UK, Sandy Ground
  6. 10 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 11 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  8. 11 DecNorman Island BVI, The Bight, UK Virgin Islands
  9. 12 DecArriving in San Juan, Puerto Rico
Find this cruise to book →
$5219from / pp
Crystal Symphony
Crystal Cruises
Round-trip from Fort Lauderdale
⚓ Calls 14 Dec 10:00 - 18:00 202617 nights14 portsDeparts 2026 Dec 03
View itinerary · 14 ports
17 days, round-trip 17 Night Roundtrip Fort Lauderdale Cruise
  1. 03 Dec 18:00Departing from Fort Lauderdale, Port Everglades, Florida
  2. 06 Dec 09:00 - 19:00Tortola Island BVI, Road Town, UK Virgin Islands
  3. 07 Dec 08:00 - 18:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 08 Dec 08:00 - 17:00Pointe-a-Pitre, Grande-Terre Island Guadeloupe
  5. 09 Dec 08:00 - 18:00Saint Vincent Island, Kingstown, Grenadines
  6. 10 Dec 08:00 - 18:00Castries, St Lucia Island
  7. 11 Dec 08:00 - 18:00Fort-de-France, Martinique
  8. 12 Dec 08:00 - 16:00Basseterre St Kitts, Port Zante
  9. 13 Dec - 18:00San Juan, Puerto Rico
  10. 14 Dec 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 15 Dec 08:00 - 18:00Marigot, St Martin Island France
  12. 16 Dec 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  13. 17 Dec 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  14. 20 Dec 07:00Arriving in Fort Lauderdale, Port Everglades, Florida
Find this cruise to book →
$7500from / pp
Star Flyer
Star Clippers Cruises
Round-trip from Philipsburg St Maarten
⚓ Calls 14 Dec 20267 nights12 portsDeparts 2026 Dec 12
View itinerary · 12 ports
7 days, round-trip 7 Night Treasure Islands Cruise
  1. 12 DecDeparting from Philipsburg St Maarten, Netherlands Antilles
  2. 13 DecAnguilla Island, UK, Sandy Ground
  3. 14 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 14 DecTortola Island BVI, Road Town, UK Virgin Islands
  5. 15 DecNorman Island BVI, The Bight, UK Virgin Islands
  6. 15 DecNorman Island BVI, The Bight, UK Virgin Islands
  7. 16 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  8. 16 Deccoastal cruising
  9. 17 DecBasseterre St Kitts, Port Zante
  10. 17 DecSaint Kitts island
  11. 18 DecGustavia St Barths, Saint-Barthelemy Island France
  12. 19 DecArriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
Price on request
Crystal Symphony
Crystal Cruises
San Juan → Fort Lauderdale
⚓ Calls 14 Dec 10:00 - 18:00 20267 nights6 portsDeparts 2026 Dec 13
View itinerary · 6 ports
7 days, one-way from San Juan to Fort Lauderdale
  1. 13 Dec 18:00Departing from San Juan, Puerto Rico
  2. 14 Dec 10:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 15 Dec 08:00 - 18:00Marigot, St Martin Island France
  4. 16 Dec 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  5. 17 Dec 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  6. 20 Dec 07:00Arriving in Fort Lauderdale, Port Everglades, Florida
Find this cruise to book →
$3700from / pp
Emerald Azzurra
Emerald Cruises
Round-trip from Marigot
⚓ Calls 16 Dec 20266 nights9 portsDeparts 2026 Dec 14
View itinerary · 9 ports
6 days, round-trip 7 Night Cruising the Leeward Islands with Chef Rachel Hargrove Cruise
  1. 14 DecDeparting from Marigot, St Martin Island France
  2. 14 DecAnguilla Island, UK, Sandy Ground
  3. 15 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 15 Dec - 16 DecNorman Island BVI, The Bight, UK Virgin Islands
  5. 16 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 17 DecAnegada Island BVI, UK Virgin Islands
  7. 18 DecSaba Island, Netherlands Antilles
  8. 18 Dec - 19 DecGustavia St Barths, Saint-Barthelemy Island France
  9. 20 DecArriving in Marigot, St Martin Island France
Find this cruise to book →
$4585from / pp
Seabourn Quest
Seabourn Cruises
Round-trip from Miami
⚓ Calls 17 Dec 07:00 - 14:00 202614 nights11 portsDeparts 2026 Dec 06
View itinerary · 11 ports
14 days, round-trip Leeward Island Jewels
  1. 06 Dec 16:00Departing from Miami, Florida
  2. 09 Dec 10:00 - 18:00San Juan, Puerto Rico
  3. 10 Dec 08:00 - 17:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 11 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 12 Dec 08:00 - 17:00Roseau, Dominica
  6. 13 Dec 08:00 - 18:00Fort-de-France, Martinique
  7. 14 Dec 08:00 - 17:00Iles des Saintes, Guadeloupe
  8. 15 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  9. 16 Dec 08:00 - 17:00Anguilla Island, UK, Sandy Ground
  10. 17 Dec 07:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 20 Dec 07:00Arriving in Miami, Florida
Find this cruise to book →
$5999from / pp
SeaDream I
SeaDream Yacht Club Cruises
San Juan → St Thomas Island USVI
⚓ Calls 17 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
Find this cruise to book →
$4819from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 18 Dec 09:00 - 22:00 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
Find this cruise to book →
$5093from / pp
SeaDream II
SeaDream Yacht Club Cruises
St Thomas Island USVI → San Juan
⚓ Calls 18 Dec 20267 nights10 portsDeparts 2026 Dec 12
View itinerary · 10 ports
7 days, one-way from St Thomas Island USVI to San Juan
  1. 12 DecDeparting from St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  2. 13 DecPhilipsburg St Maarten, Netherlands Antilles
  3. 13 DecPhilipsburg St Maarten, Netherlands Antilles
  4. 13 Dec - 14 DecGustavia St Barths, Saint-Barthelemy Island France
  5. 15 DecFalmouth Antigua
  6. 16 DecCharlestown Nevis, Nevis Island
  7. 17 DecVirgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  8. 17 DecNorman Island BVI, The Bight, UK Virgin Islands
  9. 18 DecJost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  10. 19 DecArriving in San Juan, Puerto Rico
Find this cruise to book →
$4819from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 18 Dec 09:00 - 22:00 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
Find this cruise to book →
$2962from / pp
Star Pride
Windstar Cruises
Round-trip from San Juan
⚓ Calls 18 Dec 09:00 - 22:00 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
Find this cruise to book →
$4993from / pp
Silver Shadow
Silversea Cruises
Miami → San Juan
⚓ Calls 19 Dec 08:00 - 18:00 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
Find this cruise to book →
$5100from / pp
Le Bougainville
Ponant Cruises
Round-trip from Fort-de-France
⚓ Calls 19 Dec - 15:00 20267 nights8 portsDeparts 2026 Dec 16
View itinerary · 8 ports
7 days, round-trip 7 Night Caribbean Flavors Cruise
  1. 16 Dec 21:30Departing from Fort-de-France, Martinique
  2. 17 Dec 12:00 - 20:30St Johns Antigua, RCI Royal Beach Club
  3. 18 Dec 12:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 19 Dec - 15:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  5. 20 Dec 07:00 - 22:30Gustavia St Barths, Saint-Barthelemy Island France
  6. 21 Dec 08:30 - 23:00Deshaies, Basse-Terre Island Guadeloupe
  7. 22 Dec 07:00 - 21:00Marie-Galante Island Guadeloupe, Saint Louis, Gran-Bourg
  8. 23 Dec 07:00Arriving in Fort-de-France, Martinique
Find this cruise to book →
$6100from / pp
Wind Surf
Windstar Cruises
Round-trip from Philipsburg St Maarten
⚓ Calls 23 Dec 19:00 - 24 Dec 22:00 20267 nights8 portsDeparts 2026 Dec 19
View itinerary · 8 ports
7 days, round-trip 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise
  1. 19 Dec 19:00Departing from Philipsburg St Maarten, Netherlands Antilles
  2. 20 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  3. 21 Dec 08:00 - 18:00Falmouth Antigua
  4. 22 Dec 08:00 - 18:00Anguilla Island, UK, Sandy Ground
  5. 23 Dec 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  6. 23 Dec 19:00 - 24 Dec 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 25 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 26 Dec 06:00Arriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
$3267from / pp
Wind Surf
Windstar Cruises
Round-trip from Philipsburg St Maarten
⚓ Calls 23 Dec 19:00 - 24 Dec 22:00 202614 nights15 portsDeparts 2026 Dec 19
View itinerary · 15 ports
14 days, round-trip 14 Night Star Collector Caribbean Explorations Cruise
  1. 19 Dec 19:00Departing from Philipsburg St Maarten, Netherlands Antilles
  2. 20 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  3. 21 Dec 08:00 - 18:00Falmouth Antigua
  4. 22 Dec 08:00 - 18:00Anguilla Island, UK, Sandy Ground
  5. 23 Dec 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  6. 23 Dec 19:00 - 24 Dec 22:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 25 Dec 08:00 - 17:00Prickly Pear Island BVI, UK Virgin Islands
  8. 26 Dec 06:00 - 19:00Philipsburg St Maarten, Netherlands Antilles
  9. 27 Dec 08:00 - 22:00Gustavia St Barths, Saint-Barthelemy Island France
  10. 28 Dec 08:00 - 17:00Charlestown Nevis, Nevis Island
  11. 29 Dec 08:00 - 16:00Roseau, Dominica
  12. 30 Dec 08:00 - 17:00Mayreau Island, Grenadines
  13. 31 Dec 12:00 - 18:00Iles des Saintes, Guadeloupe
  14. 01 Jan 08:00 - 22:00Basseterre St Kitts, Port Zante
  15. 02 Jan 06:00Arriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
$5619from / pp
MSC Explora 3
MSC Explora Journeys Cruises
Round-trip from San Juan
⚓ Calls 25 Dec 12:00 - 18:00 202615 nights12 portsDeparts 2026 Dec 13
View itinerary · 12 ports
15 days, round-trip An Extended Journey through Wild Beauty and Tropical Festivities
  1. 13 Dec 18:00Departing from San Juan, Puerto Rico
  2. 14 Dec 09:00 - 19:00Anguilla Island, UK, Sandy Ground
  3. 15 Dec 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 16 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 18 Dec 08:00 - 18:00Grand Turk Island, Cockburn Town, Turks and Caicos
  6. 20 Dec 08:00 - 17:00Miami, Florida
  7. 22 Dec 09:00 - 18:00Ocho Rios, Jamaica
  8. 24 Dec 09:00 - 18:00Catalina Island, Dominicana
  9. 25 Dec 12:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  10. 26 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  11. 27 Dec 08:00 - 21:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  12. 28 Dec 08:00Arriving in San Juan, Puerto Rico
Find this cruise to book →
$8810from / pp

Itineraries and prices change — always confirm with the cruise line before booking. Some links are affiliate links that may earn us a commission at no extra cost to you.