Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? From to — only cruises that fit entirely inside your dates

My result then click any cruise row to open it

Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa

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+ pick specific cruise lines · 1 selected

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Filtering Princess ×From San Francisco, California ×13+ nights × Clear all

Showing 22 of 22 sailings

Princess · Ruby PrincessRound-trip

Mexico 16 nights Sep 17 – Oct 3, 2026 from San Francisco, California

San Francisco, California · Kauai, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Kauai, Hawaii · Honolulu, Oahu, Hawaii · Kona, Hawaii · Kahului, Maui, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Doors-Off Helicopter Tour Pearl Harbor Big Island Manta Ray Night Snorkel +2 more

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from $1,529

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Oct 23 – Nov 8, 2026 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Kahului, Maui, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Haleakalā Sunrise Pearl Harbor +2 more

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from $2,249

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Nov 8 – Nov 24, 2026 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Kahului, Maui, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Haleakalā Sunrise Pearl Harbor +2 more

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from $1,137

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Princess · Ruby PrincessRound-trip

Mexico 16 nights Nov 29 – Dec 15, 2026 from San Francisco, California

San Francisco, California · Kahului, Maui, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Kahului, Maui, Hawaii · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Haleakalā Sunrise Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor +2 more

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from $1,070

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Dec 26 – Jan 11, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Haleakalā Sunrise +2 more

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from $1,064

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Princess · Ruby PrincessRound-trip

Mexico 16 nights Jan 11 – Jan 27, 2027 from San Francisco, California

San Francisco, California · Kona, Hawaii · … · San Francisco, California6 ports

San Francisco, California · Kona, Hawaii · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Big Island Manta Ray Night Snorkel Pearl Harbor Haleakalā Sunrise +1 more

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from $1,109

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Princess · Ruby PrincessRound-trip

Mexico 16 nights Jan 27 – Feb 12, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California6 ports

San Francisco, California · Hilo, Hawaii · Kahului, Maui, Hawaii · Honolulu, Oahu, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Haleakalā Sunrise Pearl Harbor +1 more

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from $1,052

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Feb 12 – Feb 28, 2027 from San Francisco, California

San Francisco, California · Kauai, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Kauai, Hawaii · Kahului, Maui, Hawaii · Honolulu, Oahu, Hawaii · Kona, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Doors-Off Helicopter Tour Haleakalā Sunrise Pearl Harbor +2 more

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from $1,052

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Princess · Ruby PrincessRound-trip

Mexico 16 nights Feb 28 – Mar 16, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Kona, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Doors-Off Helicopter Tour +2 more

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from $1,032

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Princess · Ruby PrincessRound-trip

Mexico 16 nights Mar 16 – Apr 1, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Haleakalā Sunrise +2 more

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from $1,087

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Apr 1 – Apr 17, 2027 from San Francisco, California

San Francisco, California · Honolulu, Oahu, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Kahului, Maui, Hawaii · Hilo, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Pearl Harbor Doors-Off Helicopter Tour Haleakalā Sunrise +2 more

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from $1,368

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Princess · Ruby PrincessRound-trip

Hawaii 16 nights Sep 25 – Oct 11, 2027 from San Francisco, California

San Francisco, California · Honolulu, Oahu, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Honolulu, Oahu, Hawaii · Kona, Hawaii · Kahului, Maui, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Pearl Harbor Big Island Manta Ray Night Snorkel Haleakalā Sunrise +2 more

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from $1,524

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Hawaii 16 nights Oct 11 – Oct 27, 2027 from San Francisco, California

San Francisco, California · Kona, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Kona, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Kahului, Maui, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Big Island Manta Ray Night Snorkel Pearl Harbor Doors-Off Helicopter Tour +2 more

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from $1,519

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Hawaii 16 nights Nov 7 – Nov 23, 2027 from San Francisco, California

San Francisco, California · Honolulu, Oahu, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Hilo, Hawaii · Kona, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Pearl Harbor Haleakalā Sunrise Private Big Island Volcanoes & Lava Fields Tour fr… +2 more

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from $1,299

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Mexico 16 nights Nov 28 – Dec 14, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Kona, Hawaii · Kauai, Hawaii · Honolulu, Oahu, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Big Island Manta Ray Night Snorkel Doors-Off Helicopter Tour +2 more

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from $1,374

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Mexico 16 nights Dec 14 – Dec 30, 2027 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Haleakalā Sunrise +2 more

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from $1,636

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Hawaii 16 nights Dec 30 – Jan 15, 2028 from San Francisco, California

San Francisco, California · Honolulu, Oahu, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Kona, Hawaii · Hilo, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Pearl Harbor Doors-Off Helicopter Tour Big Island Manta Ray Night Snorkel +2 more

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from $1,669

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Mexico 16 nights Jan 15 – Jan 31, 2028 from San Francisco, California

San Francisco, California · Kona, Hawaii · … · San Francisco, California6 ports

San Francisco, California · Kona, Hawaii · Honolulu, Oahu, Hawaii · Hilo, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Big Island Manta Ray Night Snorkel Pearl Harbor Private Big Island Volcanoes & Lava Fields Tour fr… +1 more

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from $1,481

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Mexico 16 nights Jan 31 – Feb 16, 2028 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Kona, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Doors-Off Helicopter Tour +2 more

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from $1,521

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Mexico 16 nights Feb 16 – Mar 3, 2028 from San Francisco, California

San Francisco, California · Kona, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Kona, Hawaii · Kahului, Maui, Hawaii · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Big Island Manta Ray Night Snorkel Haleakalā Sunrise Private Big Island Volcanoes & Lava Fields Tour fr… +2 more

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from $1,556

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Hawaii 16 nights Mar 3 – Mar 19, 2028 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Honolulu, Oahu, Hawaii · Kahului, Maui, Hawaii · Kona, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Pearl Harbor Haleakalā Sunrise +2 more

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from $1,519

Book This Cruise@ Cruisebound

Princess · Ruby PrincessRound-trip

Hawaii 16 nights Apr 9 – Apr 25, 2028 from San Francisco, California

San Francisco, California · Hilo, Hawaii · … · San Francisco, California7 ports

San Francisco, California · Hilo, Hawaii · Kona, Hawaii · Honolulu, Oahu, Hawaii · Kauai, Hawaii · Ensenada, Mexico · San Francisco, California

★ Bucket-list Alcatraz Island Private Big Island Volcanoes & Lava Fields Tour fr…Big Island Manta Ray Night Snorkel Pearl Harbor +2 more

View → ✉ Email

from $1,524

Book This Cruise@ Cruisebound

Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara