Caribbean
While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today are drawn not only by the island's mild climate and beautiful beaches but also its cultural riches. Havana has a wealth of colonial buildings and vintage automobiles, as well as intimate paladares that serve local dishes and street parties that move to the rhythms of mambo and salsa. On the country's southern coast, Cienfuegos has elegant mansions and a 19th-century street plan that earned it a place on UNESCO's list of World Heritage sites.
21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]
![21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]](/images/packages/18-virgin_gorda-port-highlight-592x445 "21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]")
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan 04 2026 | Feb 21 2026
Port: Philipsburg, St. Maarten to Bridgetown
( Note: Optional tours are available from most ports for an additional charge. )
![21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]](/images/packages/extraimages/8601_18-map-lesser_ant_odyssey_1_4_2026 "21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]")
7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]
![7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]](/images/packages/17-basseterre-st-kitts "7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]")
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan 07 2026 | Jan 11 2026 | Feb 28 2026
Port: Philipsburg, St. Maarten to Bridgetown
( Note: Optional tours are available from most ports for an additional charge. )
![7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]](/images/packages/extraimages/1211_17-map-lush_lovely_1_11_2026 "7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]")
10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]
![10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]](/images/packages/3-bluewaters_regional(1).jpg "10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]")
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
( Note: Optional tours are available from most ports for an additional charge. )
![10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]](/images/packages/extraimages/1015_3-blue_waters_rev_12_18_2021.jpg "10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]")
17 Days - Star Collector: Hidden Gems of the Caribbean [Philipsburg, St. Maarten to Phili]
![17 Days - Star Collector: Hidden Gems of the Caribbean [Philipsburg, St. Maarten to Phili]](/images/packages/2-2026-hidden-gems-of-caribbean-regional.jpg "17 Days - Star Collector: Hidden Gems of the Caribbean [Philipsburg, St. Maarten to Phili]")
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
( Note: Optional tours are available from most ports for an additional charge. )
![17 Days - Star Collector: Hidden Gems of the Caribbean [Philipsburg, St. Maarten to Phili]](/images/packages/extraimages/7138_2026-sc_round_trip_philipsburg_1_14_2026.jpg "17 Days - Star Collector: Hidden Gems of the Caribbean [Philipsburg, St. Maarten to Phili]")
8 Days - Star Seeker Christening Sailing[Miami to San Juan]
![8 Days - Star Seeker Christening Sailing[Miami to San Juan]](/images/packages/pkg-8.jpg "8 Days - Star Seeker Christening Sailing[Miami to San Juan]")
Cruise Line: Windstar cruises
Ship: Star Seeker
Sailing Dates: Jan 15 2026
Port: Miami to San Juan
( Note: Optional tours are available from most ports for an additional charge. )
![8 Days - Star Seeker Christening Sailing[Miami to San Juan]](/images/packages/extraimages/9464_Star-Seeker-Christening-Sailing.jpg "8 Days - Star Seeker Christening Sailing[Miami to San Juan]")
8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]
![8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]](/images/packages/16-oranjestad-aruba "8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]")
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Feb 01 2026
Port: Oranjestad to Colon
( Note: Optional tours are available from most ports for an additional charge. )
![8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]](/images/packages/extraimages/1721_16-map-wake_sp_armada_2_1_2026 "8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]")
7 Days - New World Caribbean Trio[San Juan to Colon]
![7 Days - New World Caribbean Trio[San Juan to Colon]](/images/packages/Untitled-3pkg.jpg "7 Days - New World Caribbean Trio[San Juan to Colon]")
Cruise Line: Windstar cruises
Ship: Star Seeker
Sailing Dates: Apr 06 2026
Port: San Juan to Colon
( Note: Optional tours are available from most ports for an additional charge. )
![7 Days - New World Caribbean Trio[San Juan to Colon]](/images/packages/extraimages/6220_Panama-1-map.jpg "7 Days - New World Caribbean Trio[San Juan to Colon]")
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