Find and compare cruises to the Caribbean in 2026 with Oceania. Get cruise deals, including last-minute deals.

Book cruises to the Caribbean in 2026 with Oceania Online and Save

Cruisebound

10 Night Caribbean - Western Cruise aboard the Insignia departing from Miami, Florida, on 2025-12-29, cruises to Cozumel, Mexico, Costa Maya, Mexico, Belize City, Belize, Roatan, Honduras, Montego Bay, Jamaica and Georgetown, Grand Cayman, Cayman Islands, starting at 3099.0 per person.

10 Night Caribbean - Western Cruise

7 Night Caribbean - Western Cruise aboard the Nautica departing from Miami, Florida, on 2026-03-10, cruises to Cozumel, Mexico, Roatan, Honduras, Harvest Caye, Belize and Costa Maya, Mexico, starting at 2199.0 per person.

7 Night Caribbean - Western Cruise

10 Night Caribbean - Western Cruise aboard the Allura departing from Miami, Florida, on 2026-12-28, cruises to Charlotte Amalie, St. Thomas, U.S. Virgin Islands, Philipsburg, St. Maarten, Gustavia, St. Barts, Port of Basseterre, St. Kitts, St. Kitts and Nevis and Tortola, B.V.I., starting at 4299.0 per person.

7 Night Caribbean - Eastern Cruise aboard the Vista departing from Miami, Florida, on 2026-12-21, cruises to Tortola, B.V.I., Charlotte Amalie, St. Thomas, U.S. Virgin Islands and Nassau, Bahamas, starting at 2999.0 per person.

7 Night Caribbean - Eastern Cruise

10 Night Mediterranean Cruise aboard the Nautica departing from Barcelona, Spain, on 2026-06-01, cruises to Villefranche, France, Florence, Italy, Civitavecchia (Rome), Italy, Ibiza, Spain, Cartagena, Colombia, Malaga, Spain, Seville, Spain, Lisbon, Portugal and Lisbon, Portugal, starting at 3199.0 per person.

10 Night Mediterranean Cruise

10 Night Caribbean - Eastern Cruise aboard the Insignia departing from Miami, Florida, on 2025-12-19, cruises to San Juan, Puerto Rico, Port of Basseterre, St. Kitts, St. Kitts and Nevis, St. John's, Antigua, Philipsburg, St. Maarten and Charlotte Amalie, St. Thomas, U.S. Virgin Islands, starting at 2999.0 per person.

10 Night Caribbean - Eastern Cruise

14 Night Transatlantic Cruise aboard the Marina departing from Miami, Florida, on 2026-04-07, cruises to Royal Naval Dockyard, Bermuda, Royal Naval Dockyard, Bermuda, Funchal, Madeira, Portugal, Gibraltar, British Territory, Cartagena, Colombia and Barcelona, Spain, starting at 2899.0 per person.

14 Night Transatlantic Cruise

12 Night Caribbean - Southern Cruise aboard the Insignia departing from Miami, Florida, on 2025-12-07, cruises to Port of Oranjestad, Aruba, Caribbean, Willemstad, Curacao, Willemstad, Curacao, St. Georges, Grenada, West Indies, Castries, St. Lucia, San Juan, Puerto Rico and San Juan, Puerto Rico, starting at 2799.0 per person.

12 Night Caribbean - Southern Cruise

9 Night Caribbean - Western Cruise aboard the Insignia departing from Bridgetown, Barbados, on 2026-02-22, cruises to Port of Oranjestad, Aruba, Caribbean, Montego Bay, Jamaica, Costa Maya, Mexico, Cozumel, Mexico and Tampa, Florida, starting at 2499.0 per person.

9 Night Caribbean - Western Cruise

12 Night Transatlantic Cruise aboard the Marina departing from Santa Cruz de Tenerife, Canary Islands, on 2025-11-17, cruises to San Sebastian, Spain, Bridgetown, Barbados, St. John's, Antigua, San Juan, Puerto Rico and Miami, Florida, starting at 2399.0 per person.

12 Night Transatlantic Cruise

Popular Sailings

Miami, Florida

Barcelona

Lisbon, Portugal

Tampa

Rome (Civitavecchia)

Explore Departure Ports

Insignia

Allura

Nautica

Vista

Marina

Browse Cruise Ships

Cozumel, Mexico

Costa Maya, Mexico

Belize City, Belize

Roatan, Honduras

Montego Bay, Jamaica

Georgetown, Grand Cayman, Cayman Islands

Oceania Cruises

Harvest Caye, Belize

Charlotte Amalie, St. Thomas, U.S. Virgin Islands

Philipsburg, St. Maarten

Gustavia, St. Barts

Port of Basseterre, St. Kitts, St. Kitts and Nevis

Tortola, B.V.I.

Nassau, Bahamas

Barcelona, Spain

Villefranche, France

Florence, Italy

Civitavecchia (Rome), Italy

Ibiza, Spain

Cartagena, Colombia

Malaga, Spain

Seville, Spain

San Juan, Puerto Rico

St. John's, Antigua

Royal Naval Dockyard, Bermuda

Funchal, Madeira, Portugal

Gibraltar, British Territory

Port of Oranjestad, Aruba, Caribbean

Willemstad, Curacao

St. Georges, Grenada, West Indies

Castries, St. Lucia

Bridgetown, Barbados

Tampa, Florida

Santa Cruz de Tenerife, Canary Islands

San Sebastian, Spain

Caribbean