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? — 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 1 selected · clear Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines · 1 selected
Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
Must visit a specific port
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Filtering South America ×Costa ×3–5 nights × Clear all
Showing 32 of 32 sailings
Costa · Costa DiademaRound-trip
South America 3 nights Nov 23 – Nov 26, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-Day
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from $979
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Costa · Costa DiademaRound-trip
South America 3 nights Nov 25 – Nov 28, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-Day
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from $709
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Costa · Costa DiademaRound-trip
South America 3 nights Nov 26 – Nov 29, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-Day
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from $979
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Costa · Costa DiademaRound-trip
South America 4 nights Nov 28 – Dec 2, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $733
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Costa · Costa DiademaRound-trip
South America 4 nights Nov 29 – Dec 3, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $1,085
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 2 – Dec 5, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-Day
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from $559
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 3 – Dec 6, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-Day
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from $919
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Costa · Costa DiademaRound-trip
South America 4 nights Dec 5 – Dec 9, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $733
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Costa · Costa DiademaRound-trip
South America 4 nights Dec 6 – Dec 10, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $1,085
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 9 – Dec 12, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-Day
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from $599
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 10 – Dec 13, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-Day
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from $959
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Costa · Costa DiademaRound-trip
South America 4 nights Dec 12 – Dec 16, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $713
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Costa · Costa DiademaRound-trip
South America 4 nights Dec 13 – Dec 17, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $1,115
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 16 – Dec 19, 2026 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-Day
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from $599
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Costa · Costa DiademaRound-trip
South America 3 nights Dec 17 – Dec 20, 2026 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-Day
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from $959
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Costa · Costa SerenaOne-way
South America 5 nights Jan 5 – Jan 10, 2027 from Buenos Aires, Argentina to Rio de Janeiro, Brazil
Buenos Aires, Argentina · Montevideo, Uruguay · Camboriú, Brazil · Iiha Grande(Rio De Janeiro), Brazil · Rio de Janeiro, Brazil
★ Bucket-list El Teatro ColónMercado del PuertoUnipraias ParkLopes Mendes Beach +1 more
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from $1,065
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Costa · Costa SerenaOne-way
South America 3 nights Mar 13 – Mar 16, 2027 from Rio de Janeiro, Brazil to Buenos Aires, Argentina
Rio de Janeiro, Brazil · Buenos Aires, Argentina
★ Bucket-list Private Full-Day Rio HighlightsEl Teatro Colón
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from $613
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Costa · Costa SerenaRound-trip
South America 3 nights Mar 16 – Mar 19, 2027 from Buenos Aires, Argentina
Buenos Aires, Argentina · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list El Teatro ColónMercado del Puerto
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from $637
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Costa · Costa DiademaOne-way
South America 4 nights Mar 17 – Mar 21, 2027 from Buenos Aires, Argentina to Santos (Sao Paulo), Brazil
Buenos Aires, Argentina · Montevideo, Uruguay · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list El Teatro ColónMercado del PuertoPrivate Santos Full-Day
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from $821
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Costa · Costa SerenaRound-trip
South America 3 nights Mar 17 – Mar 20, 2027 from Montevideo, Uruguay
Montevideo, Uruguay · Buenos Aires, Argentina · Montevideo, Uruguay
★ Bucket-list Mercado del PuertoEl Teatro Colón
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from $497
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Costa · Costa DiademaOne-way
South America 3 nights Mar 18 – Mar 21, 2027 from Montevideo, Uruguay to Santos (Sao Paulo), Brazil
Montevideo, Uruguay · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Mercado del PuertoPrivate Santos Full-Day
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from $619
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Costa · Costa SerenaRound-trip
South America 4 nights Mar 19 – Mar 23, 2027 from Buenos Aires, Argentina
Buenos Aires, Argentina · Montevideo, Uruguay · Punta del Este, Uruguay · Buenos Aires, Argentina
★ Bucket-list El Teatro ColónMercado del Puerto
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from $673
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Costa · Costa DiademaRound-trip
South America 4 nights Mar 20 – Mar 24, 2027 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $663
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Costa · Costa SerenaRound-trip
South America 4 nights Mar 20 – Mar 24, 2027 from Montevideo, Uruguay
Montevideo, Uruguay · Punta del Este, Uruguay · Buenos Aires, Argentina · Montevideo, Uruguay
★ Bucket-list Mercado del PuertoEl Teatro Colón
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from $603
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Costa · Costa DiademaRound-trip
South America 4 nights Mar 21 – Mar 25, 2027 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $1,045
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Costa · Costa DiademaRound-trip
South America 3 nights Mar 24 – Mar 27, 2027 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $593
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Costa · Costa DiademaRound-trip
South America 3 nights Mar 25 – Mar 28, 2027 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $975
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Costa · Costa DiademaRound-trip
South America 4 nights Mar 27 – Mar 31, 2027 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $713
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Costa · Costa DiademaRound-trip
South America 4 nights Mar 28 – Apr 1, 2027 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $1,075
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Costa · Costa DiademaRound-trip
South America 3 nights Mar 31 – Apr 3, 2027 from Itajai, Brazil
Itajai, Brazil · Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
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from $653
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Costa · Costa DiademaRound-trip
South America 3 nights Apr 1 – Apr 4, 2027 from Santos (Sao Paulo), Brazil
Santos (Sao Paulo), Brazil · Ilhabela, Brazil · Itajai, Brazil · Santos (Sao Paulo), Brazil
★ Bucket-list Private Santos Full-DayPrivate Superboat to Castelhanos & Hidden Atlantic…
View →
from $925
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Costa · Costa SerenaRound-trip
South America 4 nights Apr 1 – Apr 5, 2027 from Buenos Aires, Argentina
Buenos Aires, Argentina · Montevideo, Uruguay · Punta del Este, Uruguay · Buenos Aires, Argentina
★ Bucket-list El Teatro ColónMercado del Puerto
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from $663
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.

19 lines
aboard
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