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Cruise Calendar › Winter Escape Cruises

Winter Cruises

Winter Escape Cruises

Trade the cold for sunshine. January and February are peak season in the Caribbean, Mexico and Hawaii, and the start of the season for longer voyages to South America, Antarctica and the South Pacific.

  • 1,358Sailings in January 2027
  • 1,268Sailings in February 2027
  • 24Cruise lines

Key Dates

Dates to plan around.

  • Martin Luther King Jr. Day is Monday, January 18, 2027.
  • Presidents’ Day is Monday, February 15, 2027.
  • Antarctica’s cruise season runs from about November to March.

Tips From Our Advisors

What we tell clients planning winter escape cruises.

  • Early January, after the holidays, can be good value.
  • Long weekends around MLK Day and Presidents’ Day fill quickly.
  • Southern Caribbean itineraries sail farthest from winter weather.
  • Many world cruises and long voyages begin in January.

Cruise Lines Sailing in January 2027

These lines have sailings in January 2027 in our booking engine.

More Ways to Plan

Sailing counts, cruise lines and ports come from our booking engine and refresh through the day (last updated Nov 5, 8:35 am PST). Fares and availability change often and are confirmed at booking.

Google Reviews

What Our Clients Say

Real reviews from travelers our advisors have helped, straight from Google.

Posted on Google Google
Marty Wagner profile picture
Marty Wagner
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I (we) have been booking cruises with The Cruise Company since the early 90s. Angelina is quite simply our go-to for cruise bookings...now after some 40 cruises taken! Thank you Angelina, as always, for your great personalized service!
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Haik Yapoudjian profile picture
Haik Yapoudjian
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I have booked cruises with your company for 20+ years. Most professional, VIP and Five Star Service each and every time! Thank you for helping me book 27 cruises including friend and family.
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Chrissie F profile picture
Chrissie F
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Great communication and awesome job with providing thorough information on cruise options. Quick response time! Still fighting with spouse on which cruise choice to go with and appreciate their patience with answering our on demand questions.
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Cari Brandt profile picture
Cari Brandt
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Literally the best agency I’ve worked with. Been through quite a few and none of them have compared! Thank you guys for the best vacation and making it so stress free.
Posted on Google Google
Taye Luke profile picture
Taye Luke
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
What wonderful service! I had such a fantastic trip with my family. Very easy to work with and very low stress for me. Would totally book again through this company!
Posted on Google Google
Alyssa Marques profile picture
Alyssa Marques
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
Wow! I have never had such a great experience with any other travel agency! Super professional and personable, would definitely recommend!

See all our reviews on Google →

Booked with us? Leave us a Google review →

Planning a Winter Getaway?

Tell us when you would like to travel and how you would like to get to the port. Our advisors will compare sailings, ships and cabins and find the right fit.

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