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Day One: Chely Wright and the Sock Debacle

Hit the high seas with Curve's advice guru as she shares her adventures on an Olivia Caribbean Sun Cruise.

How did I pack a 52-pound suitcase and still forget socks? As I’m sitting on the plane on my way to my fourth trip with Olivia, I realize I only packed two pair of dress socks and that was it. Luckily I find a “Life is Good” store at the Orlando airport, but the only pairs I can find are blue with pink hearts. Really? For Dipstick? But what can I do, I can’t risk blisters, so I buy them and stick them in the bottom of my suitcase.

I make my way to my hotel and as I enter the lobby a Melissa Etheridge song just happens to come on over the sound system and Cynthia Nixon is being interviewed on TV. Am I entering some kind of lesbian dream world? 

After checking in, I head down to the bar where groups of women have gathered, excited about the upcoming journey. In the morning, we begin what will be a day of standing in line. Line to catch the shuttle to the ship, line to go through security, a line to check in, a line for the buffet.  But ever time we stand it line, it’s an opportunity to meet new people. Who knew waiting could be so fun?

Newly out lesbian singer Chely Wright is the first night’s performer and she talks a much as she sings, about hiding, living in the closet, painful break-ups, contemplating suicide. Geez, part of me wants her to sing. Her story is depressing me. Unlike most of the artists performing this week, Chely leaves the ship after her show. She tells us she wishes she could stay. I wish she could too, I think her life would be truly changed if she had the opportunity to see women being so free and open.

After Chely’s show, we head up to the pool deck for the sail away party with DJ Lisa Pittman, one of my favorite DJS on the planet. We dance outside as night falls and our ship heads out for two days at sea.

Tip of the Day: Bring your own coffee. The coffee on cruise ships is notoriously bad. Bring along a few packets of Starbucks via to get you through the day.