female solo travel

Sailing, Takes Me Away. . .

~ Solo Chick Traveler ~ Leave a comment
From the boat


When I was a little girl, I loved playing with paper dolls. Wardrobes made of paper hanging onto bodies formed from cardboard with little tabs folded over shoulders and around waists and legs. It was temporary, a strong breeze could render them naked once again. Easy to change if I changed my mind. 

J stepping into my eye line was a lot like that. Hanging there, against blue skies and cotton ball clouds, a fifty shades of aqua backdrop bordered by island sand. Did I say stepped into?. . . I meant sailed. The background and my friend Pat’s boat (and Pat for that matter) were all familiar–the cardboard constant. Making J the paper outfit overlaid on top.  New. Different.

But what I was really grooving on that morning–besides my love of water, boating and snorkeling the reef–was my essay placing in the contest I’d entered.  It would be published in the next few days.  I had champagne and was planning to celebrate with mimosas. 

Earlier I’d shared the news with my close writing friend and she’d offered to build me a website.  After the toasting and enthusiastic congratulations, I floated what I thought was a crazy idea.  I wasn’t a big enough deal to warrant a website.

Pat nods and J says, “You probably should have a website.”  

His words spread on me like frosting–a nice feeling on top of the nice feeling I’m already having.

The wind picks up the farther we get out, so I man (woman?) one of the winches adjusting the sails, prompting Pat to make a compliment about my strength in relation to my gender. To which I quip, “I like to be all the Spice Girls.”  I’m sporty, at times scary, other times posh, and have been ginger.  I’ve tucked my frilly dress up into the leg band of my underwear so it didn’t get caught in my bike spokes, riding in wedges for miles. 

I  break into a really bad cover of “If you wannabe my lover, you gotta get with my friends.”

J chimes in from his winch, “I never understood that song.  Sure, I’ll get with your friends.”

I laugh into the gap extending to let this new interpretation settle in.  Clever. Sexy.  I’ll never hear the song the same way again.  

Another tab of J’s paper folds over.

I watch his back muscles roll underneath his shirt.  The way a sleeve folds into the crevice of a flexed bicep. And I watch myself watch, wondering what I’m up to.

Two weeks later I’m climbing aboard again and as we get ready to sail, I go down to link my phone with the Bluetooth speaker in the salon.  At my elbow is suddenly J asking, “Need any help?”

My knee jerk response to this question is always, no.  Because it hits me like an insult, implying I’m somehow incapable.  But in that instant, I see how it pushes others away.  I turn away in the circumference of this realization, a fighter pilot who’s just fired a missile but wishes she could take it back. It’s early and I secretly hope for another chance to play it differently.

A tab folds over.

We sail on and he says other things I like and jive with. And I notice myself watching his lips as much as I’m listening to the words coming out of them. Sometimes he does a little smirk and it makes me smile. I like his lips. I think the smirk makes him look cute.

Coming from self-awareness, he shares about needing to have his own personal space and how hard it is to have it in Key West.  How it’s all cramped living quarters for this huge chunk of change and he’s not really down with it.  Neither am I, that’s why I have a camper.  Neither is Pat, he’s on a boat tied to a mooring ball.  J couldn’t find a boat he and an insurance company could agree on so he applied for a job in Indiana.

There it is, the eroding of our island community conversation I’ve had with more people than I’d like.

“I’m so tired of saying goodbye to cool people,” I stare past him in a quiet moment of memoriam to all those who have gone before him. I feel his paper flutter in the winds of change.

I’m Off the Market Until My Book’s ON the Market

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“I’m off the market until my book’s ON the market.”  That’s what I said, and I meant it.  I was drawing a thou shalt not cross line in the sand. I should know better.

The last time I did that was after taking a trip with a guy I’d been dating for a few months.  We found a cheap deal to Vegas to escape winter in Wisconsin and thaw out for a while.  When we got there he invited his friends in Vegas over and they hung out pretty much the entire four days and three nights smoking pot in our hotel room while I complained about it to my sister on the lobby’s payphone. Had my car starting on fire on the way to the airport been a sign?  That’s right, on fire. The brakes locked up, causing friction to build and ignite something under the hood.  

I’ve never seen the metaphor as crystal clear as I do in this instant.

By the time we got back the relationship was also in flames. Our break-up was the final straw breaking the camel’s back–the camel’s back being my attempts at having relationships. This break-up, on top of a string of other break-ups, on top of my recent divorce had me assessing my already poor track record with men.

I said to my bestie Renee on our next girls night out, “Thirty days. I’m benching myself for thirty days. No flirting, calling, kissing, hugging or fucking for thirty days.” 

The next weekend on our next night out, a tall, dark and handsome (it may be cliche, but it’s also hella accurate) half of a twinset (which made him even more sexy)was buying me drinks and asking for my number.  Had to give him the brush off for three weeks, after which I fell madly in bed with him.  He was definitely one of the better choices I’d made.  Perhaps my brief hiatus had performed some kind of reset to the ‘my type’ presets.

And now, many years later I’m doing the same thing but for different reasons.  To continue with the sports allegory, like athletes not having sex before a big game–I doubt Lance Armstrong banged anyone the night before Tour de France–I’m not risking diffusing my energy, either.  I’m too easily distracted when I’m attracted. 

The I’m-off-the-market-until-my-book’s-on-the-market statement was made a few weeks ago, to much applause from those close to me who know this about me and support my focus.  Evidently cuing the Universe: “Let’s send Jen a nice boy.”  

Why?  I mean, Why now?  I’ve been in Key West on and off for four years, and now suddenly my good friend who rarely invites me sailing, invited me to sail with a friend of his who’s just learned how and wants some practice.  A captain.  Sure, why not.  It’s not bad enough he’s cute, funny, helpful and has great lips–he can sail and has a sense of adventure.  Am I being tested or something?  

This is bad timing.  Good guy. . . bad timing.  Feels like I’m just hitting my stride with my book writing.  

Tales from the Side of the Road

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No, I’m not broken down, everything works fine, I could leave anytime. But I don’t want to—-I’m in Key West. And everyone pays a high price to be here. I pay in guts, not money. I take chances; chances most people would be uncomfortable taking. It’s sometimes uncomfortable for me too, but I’ll take it over being a slave to corporate America any day. The price of my lifestyle is risk but with that risk comes great rewards—-freedom being one of my favorites.

I have good Spidey-senses and let my intuition be my guide; most of the time. Tonight was not one of those times. I hear their walkie-talkies before I hear them knock.

“Are you alone in there?” Always the first question.

You mean besides the fool who told me to park here? Is what I think but don’t say. “Yep. Just me and my kitty.”

They answer with the looks of disbelief that I’ve come to know so well (and actually kind of get off on). That boost that comes from being what I’ve always been—unconventional—never gets old. It only encourages me; adds fuel to my fire.

They let me stay after stern warning and one even helps me lift the steps into my camper back up.

I learned my lesson: don’t let anyone have the final say on where I lay. If it feels wrong, then move. I was not surprised by my middle of the night visitors, I was surprised that I’d let myself park somewhere that I felt in my gut wasn’t right.

Sexy Key West–Steamy Summer #3

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It didn’t take long for him to end up back in my bed. Well, I did have to tow about 7,000 pounds (camper weight plus way too much clothes and way too many pairs of shoes) about seven hours, but now that his mouth is enveloping and exploring my pussy, these numbers all fade away. The only thing to count–and that counts–is how many orgasms I’m going to end up having. And if history has a way of repeating itself, and I assure you this being our fourth or fifth rodeo shows that it does, then there will be too many to count and I’ll be rendered incapable of performing math calculations after my third.

These parts of ours are like perfect puzzle pieces held together by velcro. Based on how they fit, they seem to have been made from molds designed for the ultimate carnal pleasure. And all we have to do is brush by each other and we’re connected, locked in once again to acting out our fantasies in my boudoir.

Ahhhh Key West, the place where the moped shuttle driver invited on my first visit here: “Let your freak flag fly!!” That was four years ago and I still remember it. I had a silent response to him: I’ve been looking for a place like that. I’m still doing my best to honor it, too.

We need a place to let loose our inner selves without judgement and this island offers it. For me, this time around, that’s alternating between a two-item wardrobe: my volunteer park uniform that as I fulfill the twenty hours a week at the admission gate in exchange for my free site and utilities and my bikini. It also includes writing the most and the best, in my opinion, that my creative mind has to spill.

It also means fucking my ex/now friends-with-a-generous-benefit-package as often and and as kinkily (that’s probably not a real word) as I want. Wherever I want. It means getting naked at the Garden of Eden, the clothing optional rooftop bar that towers over the heavily bar laden Duval street. It means groping while shopping. Kissing around corners. Exposing my ass in alleyways where you can catch a quick dick in the dark without anyone noticing or not caring if they do.

This boy is my playmate in every sense of the word and I’m oh so glad to be back for more fun and games. I’m here for a few months–including October for Fantasy Fest–let’s see what kind of trouble I can get into before going back to reality–I mean, the mainland.

Like a Cherry Tootsie Pop

Where In the World is Jennifer Montero?

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My blog is my online journal–rough and raw. It’s me throwing paint at the canvas and being more concerned about the colors I have chosen than the strokes, shape and impression. The first baby steps in an effort to express myself, the birth of creativity. My live processing of what happens in this mad world.

I use the term mad in the most endearing Alice In Wonderland kind of a way. I take the potion often, the red pill, and it takes me through the wardrobe and behind the wizard’s curtain, finding the truth rooted in love. Something pierces the illusion and sets its sites on my fear. I find that if I keep moving, don’t establish, stay in the humbled state of unknowing then those magical moments happen a lot more often and my grip on the world loosens. My mind, released, naturally rises to the only home it knows–the one of infinite possibilities.

I post about my gut reactions and often about the sucker punches to the gut that life has a way of throwing when you’re busy looking the other direction. There’s a lot of things I’m still trying to make sense of or things I thought I already understood, learned the lesson but here it is, back again for another round. I seem to have a deep instinctive need to try to figure things out, look at them another way and grow and advance on the game board of Life.

Jason Isbell talked about touring in an interview. He said he felt stagnant when he was home yet his relationships were strained by him being on the road. Can’t decide which is harder. Doesn’t really feel made for either one of them. I can relate. I don’t find the safety and security that others find there, in stability. I don’t share their ambitions. Longing to break out of the crowd of popular opinion. I’m a wanderer, a wonderer and I live on the fringe.

“If you’re not living on the edge, you’re taking up too much space.” Cool thing to say as the first American to summit Everest. And I agree.

One more thing. I call it solo chick traveler because I usually am, solo. Sometimes with someone, but usually not for long. The constant and common denominator is always me and I make my moves quite independently even if it may look otherwise.

Where in the world is Jennifer Montero because it rhymes and because of the three last names I have had, Montero is my favorite. Compliments of my Colombian ex-husband.