The line has announced 17 Cuba voyages, five in 2019 and a further 12 in 2020.
Itineraries will showcase the best of Cuban culture through a range of “immersive” land excursions.
2019 departures are available to book now.
Silver Wind will depart San Juan on February 14 on a seven-night voyage to Fort Lauderdale.
The itinerary will include visits to Havana and Santiago de Cuba, and the Bahamian island of Bimini.
Recently lengthened Silver Spirit will depart San Juan on a 10-night voyage on February 22 with an overnight in Santiago de Cuba, calls in Cienfuegos and Havana and stops in George Town, Key West and Bimini, ending in Fort Lauderdale.
Departing San Juan on March 31, Silver Wind overnight in Santiago de Cuba, Havana and Cienfuegos during its 10-night voyage. The itinerary also features George Town and Bimini.
Silver Wind will sail a second itinerary next year, a nine-night round-trip from Fort Lauderdale departing April 10 stopping overnight in Santiago de Cuba and Havana. Other calls include Bimini, Nassau and Port Canaveral.
Finally, Silver Whisper will also sail a second itinerary, a 14-night voyage departing Fort Lauderdale on November 22.
The round-trip voyage will visit Cienfuegos and include overnights in Santiago de Cuba and Havana, giving guests time to experience local life.
Other calls include Grand Cayman, Cozumel, Belize City and Key West.
Silversea’s 2020 voyages will open for bookings in the near future.
Roberto Martinoli, Silversea chief executive, said: "Cuba is a remarkable island and we are delighted to offer our guests the opportunity to discover the most authentic sights, sounds and flavours of its culture, as they connect with its people on thoughtfully orchestrated voyages."
Peter Shanks, Silversea managing director UK and Ireland, added: "We are thrilled to announce the addition of Cuba to our 2019 and 2020 voyage collections.
“Cuba is arguably the fastest growing destination in the Caribbean, and one that many luxury travellers are eager to explore, knowing that they can be uniquely enriched by a fresh perspective on the people, traditions and natural wonders of this island nation."