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Cruising with Olivia on the Caribbean


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Entertainment on the Olivia Cruise
lesbian travels, leisha hailey, olivia cruise

Vickie Shaw interviewing Leisha Hailey on the Olivia Cruise.

© Kathy Belge
One of the things that makes Olivia different from a mainstream cruise is their stellar line up of lesbian-specific entertainment. The cruises I was on had a great mix of musicians, comedians, performance artists and one L Word star.

There are two shows nightly for the main entertainment. Each guest, when they registered for the cruise received either a late or early dinner time. Those with an early dinner, ate first and saw the show later. The late diners watched the show and then ate.

Leisha Hailey was a featured guest on both of my Cruises and I have to admit that her "show" was the a bit of a letdown. She was simply interviewed by one of the comedians. It was nice, but not up to the caliber of the other entertainment.

The Indigo Girls and Olivia co-founder Meg Christian sang on the 20th anniversary cruise.

Olivia hires some of the best comedians in the business. And who doesn't want to laugh on vacation? Comedians Vickie Shaw, Dana Goldberg, Karen Williams, Julie Goldman (from the Big Gay Sketch Show) and Elvira Kurt put on fantastic shows. All of them drew some of their comedy from things that were happening on the ship and that added to the appeal.

Main stage entertainers Halcyon and Vicci Martinez both sang with a folk-rock vibe and the incredible Julie Wolf serenaded the late night crowds in the Ocean Lounge piano bar. The Wau Wau sisters brought a special blend of comedy, acrobatics and burlesque that almost defies explanation. And Suede serenaded with her silky voice and stellar trumpet playing.

Olivia is pretty loyal to their entertainers, so you're sure to see some of the same performers on their trips.

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