It was two hours into the flight before the sleeping tablets, assisted by a crippling exhaustion borne of crushing anxiety and the misery of nausea, finally did their job and allowed Dean to slip into an uneasy rest.
Sam let out a sigh of relief as he sunk back ino his seat, weighed down by Dean's head lolling heavily on his shoulder; warm, shaky breaths, tainted by the tang of recycled alcohol, huffing damply into the crook of his neck.
Bobby leaned forward to look round Dean's still form at the younger Winchester, "y'ok under there boy?"
Sam nodded with a smile, scared to utter a word in case it disturbed Dean.
Eight hours with Dean's head resting on his sagging shoulder; he could see himself walking with a stoop for the next six months, but even that was infinitely preferable to Dean spending another second of this flight awake, and horribly, miserably aware of his surroundings.
The hours of the flight began to tick down; Sam was able to spend the next couple of hours working his way through the Dan Brown book, concentrating admirably despite the infuriating distraction of Dean's spiky fringe tickling his face. Dean had barely stirred, gradually calming into a deeper and deeper sleep, his face burrowing further into his brother's neck until Sam was convinced he was going to have teethmarks there by the time the plane landed.
In fact, Sam, against his better judgement, was daring to think fate may have cut them a break; a relatively pain, panic and vomit-free flight to their vacation was more than either of them could have dared hope.
His heart, therefore, sunk to his boots when he heard the pilot's reassuring voice crackling over the intercom that he was switching on the 'fasten seatbelts' light due to stormy conditions out over the pacific coast, and that they were heading for 'a little turbulence'; "nothing at all to worry about!" he finished glibly.
"S'easy for you to say …" Sam whispered to himself sourly, glancing towards Bobby in dismay; "perhaps it's just a precaution…" Bobby muttered hopefully.
Sam felt Dean shift slightly, squashing his nose firmly against Sam's jaw with a muffled sigh.
It was a half an hour before the plane gave it's first rattling judder, followed closely by another.
Glancing across the cabin, Sam caught a glimpse of misty tendrils of cloud wafting across the plane's wing as another shudder gripped the plane.
Sam's gaze turned to his sleeping brother as the timbre of the plane's engines rose through a rolling lurch from a hum to a strained buzz.
Bobby leaned over; "he okay?" he whispered, genuine concern in his eyes, his head bobbing from side to side as the plane jolted again.
"Yeah, so far," Sam mouthed; hoping, praying even, that Dean would sleep through this rocky patch.
No sooner had the words left his lips then Dean gave a quiet moan, and rubbed the heel of his hand across unfocussed, tired eyes as they fluttered open; he sat up, momentarily disorientated by his nap.
Sam gritted his teeth, loosing a stream of muttered invective on Winchester luck as Dean sat back in his seat, and glanced absently at Bobby who smiled weakly, cringing as the plane gave a gut-wrenching lurch.
Dean's sleep-glazed, vacant eyes suddenly widened in fear. He turned to Sam who suddenly could see the very real possibility of a panic-stricken break for the emergency exit.
"It's just a bit of turbulence, dude; nothing to worry about the pilot said," Sam urgently adopted his most soothing tone, "just a bit of stupid stormy stuff over the coast."
Dean gave a yelp as the plane shimmied, bucking as more and more wispy cloud tumbled over it's wings like sea-fret over a still ocean.
Letting out a gasp, Dean made a grab for Sam, only the seatbelt across his thighs stopping him from practically climbing into Sam's lap; such was his need to be close to something solid and reliable; something he trusted; his brother.
Shaking, unco-ordinated fingers guided by terror-glazed unseeing eyes clawed, panic-stricken at the buckle.
It broke Sam's heart to do it; gently but firmly pulling Dean's cold, clammy hands away from the belt buckle and holding them both tightly out of harms way, an action which Sam hoped, as well as saving Dean from himself, would bring him some small comfort.
"No Dean," Sam scolded gently, "you need this on; to keep you safe in your seat while we fly through this cloudbank. Pilot says it won't take long, before things smooth out."
Dean burrowed back into his seat, both his hands still gripping Sam's in a crushing grip, puffing out harsh panting breaths as, in his increasingly waking state, he fought to maintain some semblance of control.
Sam tried again to reassure Dean; "this plane's built to withstand way more than this crappy bit of cloud, it's nothing to worry about, I promise."
Dean flinched as Bobby's hand reached up behind him to squeeze his shoulder; "trust ya brother, boy; we ain't in trouble, I promise ya."
Gradually the cloud began to thin, and pale shafts of sunlight once again penetrated the cabin. The rocking and rolling of the plane subsided to a gentle sway until after a few moments, the soft ping of the 'fasten seatbelts' sign switching off heralded the end of the turbulence, and Sam was able to slip his crushed fingers out of Dean's sweaty fists, and try to wiggle some blood back into them.
"See, told you we weren't in trouble; it was just turbulence," smiled Sam.
"S-stupid freakin' turbulence" Dean murmured shakily, transferring his bone crushing grip once again to the arms of the seat rather than his brother's maimed fingers.
He opened his eyes a crack on feeling a soft pat on his arm to see Bobby, holding out a plastic tumbler of dry ginger and a couple of tablets.
"C'mon son, you must be thirsty, those sleepin' tablets give ya real dry mouth."
Dean eyed the drink reluctantly; now he was awake, his fractious belly was already starting to voice it's disapproval at his situation, but he had to admit; he was thirsty.
It was like Bobby could read his mind.
"The ginger'll help settle ya stomach, kid, c'mon, jus' a coupla sips."
Dean recognised the Dramamine and Sominex tablets in the older man's hand; "I reckon you're about due for your next dose of these."
Taking the tumbler with a shaking hand, Dean managed to sip enough to choke down the tablets.
"Okay son, the entertaining bit's over now;" Bobby smiled, "why don't you try an' get ya head down for the rest of the trip – we're halfway there." Sam nodded his enthusiastic agreement with that suggestion, his hand slipping back over Dean's in a discreet and quietly appreciated gesture of reassurance and unity.
He didn't go back to his book until Dean had sunk once again into a deep, medication-induced sleep.
Dean jerked awake as a hand gently jostled his shoulder; "wake up dude, we're there."
Blinking back a momentary confusion, Dean looked around the cabin, squinting sleepily at his travelling companions.
"Look;" Sam's pointed finger guided his vision toward the windows. Dean stared intently, trying to focus his vision past the rows of passengers between him and the windows.
He could see grass and buildings gliding past as the plane taxied to it's berth.
Dean's head dropped limply back into the headrest of the seat, and he closed his eyes, sighing with incalculable relief.
The whole experience of leaving the plane, collecting luggage, and the courtesy coach trip to the resort passed Dean by in a medication induced haze as he trailed along on rubber legs between Sam and Bobby, muzzy-headed and still skirting the edge of sleep.
They eventually stepped out of the coach and found themselves standing, bathed in the late afternoon sunlight before a low, whitewashed building surrounded by softly swaying palms and the chittering of crickets, a gentle chorus to the soporific rumble of the sea in the distance.
A festival of hibiscus and kukui blossom brought a riot of colour to the terraced grounds around them, as a tiny fountain tinkled into a sparkling pond, a delicate latticework of pink and white orchids clinging to it's rocky edges, looking down onto the tiny flashes of vermillion which darted haphazardly between the glistening ripples.
The three men stood and stared, each of them losing the power to speak, to blink, even to think.
It was the most beautiful sight they had ever seen.