You can cruise from San Diego to the Hawaiian Islands in the fall, winter and spring months. Two cruise lines offer the voyages. They are luxury cruise lines that specialize in longer trips to exotic destinations. See the calendar of departures below.
17-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Maui (Hawaii), Hilo (Hawaii), Kona (Hawaii), Honolulu (Hawaii), Kauai (Hawaii) and Ensenada (Mexico).
• 2026 departure: January 10.
18-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Hilo (Hawaii), Kona (Hawaii), Maui (Hawaii), Honolulu (Hawaii), Kauai (Hawaii) and Ensenada (Mexico).
• 2026 departure: January 27.
35-day cruise to Hawaii & the South Pacific on Holland America Line. Round-trip from San Diego to Maui (Hawaii), Hilo (Hawaii), Honolulu (Hawaii), Kauai (Hawaii), Kona (Hawaii), Fanning Island (Kiribati), Raiatea, Tahiti, Moorea, Fakarava and Nuku Hiva.
• 2026 departure: February 14.
35-day day cruise to Hawaii & the South Pacific on Holland America Line. Round-trip from San Diego to Maui (Hawaii), Kauai (Hawaii), Honolulu (Hawaii), Kona (Hawaii), Fanning Island (Kiribati), Rangiroa, Huahine, Raiatea, Tahiti, Moorea, Fakarava and Nuku Hiva.
• 2026 departure: October 15.
18-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Kauai (Hawaii), Honolulu (Hawaii), Hilo (Hawaii), Kona (Hawaii), Maui (Hawaii) and Ensenada (Mexico).
• 2026 departure: November 19.
17-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Honolulu (Hawaii), Maui (Hawaii), Kauai (Hawaii), Hilo (Hawaii), Kona (Hawaii) and Ensenada (Mexico).
• 2027 departure: January 9.
18-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Kauai (Hawaii), Honolulu (Hawaii), Maui (Hawaii), Hilo (Hawaii), Kona (Hawaii) and Ensenada (Mexico).
• 2027 departure: January 26.
35-day cruise to Hawaii & the South Pacific on Holland America Line. Round-trip from San Diego to Kona (Hawaii), Maui (Hawaii), Honolulu (Hawaii), Kauai (Hawaii), Fanning Island (Kiribati), Raiatea, Tahiti, Moorea, Fakarava and Nuku Hiva.
• 2027 departure: February 13.
35-day cruise to Hawaii & the South Pacific on Holland America Line. Round-trip from San Diego to Kona (Hawaii), Maui (Hawaii), Honolulu (Hawaii), Kauai (Hawaii), Hilo (Hawaii), Fanning Island (Kiribati), Rangiroa, Huahine, Bora Bora, Raiatea, Tahiti, Moorea, Fakarava and Nuku Hiva.
• 2027 departure: October 14.
18-day cruise to Hawaii on Holland America Line. Round-trip from San Diego to Hilo (Hawaii), Kona (Hawaii), Maui (Hawaii), Honolulu (Hawaii), Kauai (Hawaii) and Ensenada (Mexico).
• 2027 departure: November 18.