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BY POPULAR DEMAND! With our January sailing SOLD OUT we’ve added a second cruise to Cuba! We invite you to join us in November as we sail to historic Cuba with 1,300 of your closest Olivia friends and continue our celebration of our 30th Anniversary of Olivia Travel with a Thanksgiving/Friendsgiving Festival!

Set sail from Fort Lauderdale, FL and spend a full day and night in Havana—cruise along the Malecon in a Classic Car; discover the art of savoring Cuban coffee, rum and cigars; visit Hemingway’s home, haunts and inspirations, or revel in a night of music and dance at a Cuban Cabaret. Next, we sail around the southern coast of Cuba to Cienfuegos, where you’ll experience the heart of Cuban life, culture and history. This UNESCO site will charm you with its mix of French neo-classical architecture and Afro-Cuban spirit. Learn about its rich history as a hub of art, music and commerce or take a trip to nearby Trinidad or Santa Clara. Dive deep into the culture and history of Cuba with our carefully curated tours. We’ll continue our cruise to popular Georgetown in the Grand Cayman Islands, and our final stop is in Cozumel, the heart of the Mayan culture. Round-trip from Fort Lauderdale, FL, January is the perfect time to enjoy tropical sun-kissed days and star-filled nights. Combine this unique itinerary with a stellar Anniversary line-up of entertainment, along with the incredible Team Olivia, and you’ll be on your way to a vacation you won’t forget!


  • Fort Lauderdale, FL
  • Havana, Cuba
  • Cienfuegos, Cuba
  • Georgetown, Grand Cayman Islands
  • Cozumel, Mexico
  • Fort Lauderdale, FL

To learn more about your ship, Holland America's ms Veendam, click here.


  • Accommodations for 8 days/7 nights on board Holland America's ms Veendam
  • All meals, including room service (specialty restaurants have a nominal charge)
  • Gratuities, port charges, and taxes (covered in NDA fees)
  • Expert naturalists
  • Olivia’s signature 30th Anniversary of Travel entertainment and programming
  • Olivia staff assistance throughout

To learn more about your trip, please click here. For more information about what’s not included, and other things you should know before you go, please click here.


For room options, pricing and availability, please click here.


Olivia is happy to offer payments plans and accepts VISA, MasterCard and Discover: Payment Plan.


Call 800-631-6277 or 415-962-5700 option 1 for more information or to secure your space now!

For Reservations Call: (800) 631-6277 M-F 8:30am-5:30pm Pacific
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Olivia Travel is the premiere lesbian travel company providing amazing cruise and resort vacations for lesbians worldwide. We create unforgettable holidays for women from all over the world. Vacation with us and you will never be the same!