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Finally arriving at planet Risa, the weary Enterprise crew eagerly embarks on a long overdue shore leave on the tropical paradise for two days and two nights. As some of the crew needs to stay onboard and run the ship, Captain Jonathan Archer institutes the drawing of lots to determine who can take leave. Winning a vacation himself, Archer feels both guilty for taking a break and also suffers from premature separation anxiety for leaving the Enterprise. With the comfort of T'Pol remaining onboard, the Captain is finally able to board the shuttlepod along with Trip, Reed, Mayweather and Hoshi. Everyone seems to have quite varied agendas for their short time on the planet: Mayweather plans to do some rock climbing on a cliff that changes pitch while you climb it; both Trip and Reed plan to meet some of the female aliens and ... broaden their cultural horizons; Hoshi feels she has had to rely on the Universal Translator far too much, and therefore plans to put her linguistic skills to the test with the various alien languages she hopes to encounter; while Archer booked a small cabin overlooking the ocean, and simply plans to relax with a good book and Porthos. Once the shuttlepod lands on Risa, the eager crewmates all go their separate ways.

Soon after arriving at his cabin, Archer discovers a wrapped Vulcan book on meditation, a gift to help him relax from T'Pol. Chuckling, Archer steps onto the deck to take in the breathtaking vista, and notices a beautiful alien woman and her dog in the cabin just below his. Their eyes amicably meet for a moment, and Archer senses the possibility of an unexpected romantic element to his vacation. Later, Archer hears Porthos growling as the alien woman's dog finds its way onto his porch. When the woman tracks her dog down, Archer seizes the opportunity and strikes up a conversation. The two hit it off and with Archer learns her name is Keyla and that this is the first trip to Risa for both of them. He invites Keyla to dinner, but she is forced to take a rain check due to a previous engagement. As she leaves, Archer senses promise in the air.

Viewing the stars from his deck later that evening, Archer is pleased to find Keyla on his doorstep, having just finished her previous engagement. The two discuss their respective homeworlds and pasts, but Archer senses a strong hesitation from Keyla to share the details of her own history. Continuing their discussion over breakfast, Archer learns the Suliban massacred Keyla's entire family. When Archer admits he has encountered the Suliban, Keyla suddenly floods him with questions. Hesitant to reveal any privileged information, Archer is surprised by Keyla's tenacity. Sensing something suspicious, Archer surreptitiously takes a bio-scan of Keyla and runs it through the Enterprise computer for a match. Confirming his suspicions, Archer discovers Keyla is actually a Tandaran, the same species that unjustly ran a Suliban concentration camp. Confronting Keyla with the truth, Archer refuses to let her leave until she tells him who sent her ... but his questions go unanswered when Keyla renders him unconscious by pricking him with some type of anesthetic. Waking in the morning Archer finds Keyla long gone, and sadly packs his bags to rendezvous with the shuttlepod to return to the Enterprise.

Meanwhile, Hoshi finds a friendly indigenous couple and practices her Risan with them at a quaint restaurant. As the couple bids her farewell, Hoshi is approached by a charming and handsome alien who couldn't help but overhear her previous conversation. Introducing himself as Ravis, the two hit it off, and Ravis wonders if Hoshi has ever met a language she couldn't learn ... indicating his native language might just be her Achilles heel. Up to the challenge, Hoshi convinces Ravis to both join her for lunch and attempt to teach her his extremely complex native language. Finding the language nearly impossible to learn, Hoshi's impromptu lesson continues into the night until she finally gives up on learning it in only one day. Seeing Hoshi is a little tense from her concentration, Ravis invites her to join him in the exotic steam pools to melt her tension away. A little flattered and nervous, Hoshi gives into carpe diem, and accepts Ravis' invitation. The next morning, Hoshi rolls over to find a very happy Ravis in bed beside her. Sad that she has to leave to rendezvous with the shuttlepod, the lovers lie in each other's arms, knowing that other than their time ending too soon, they wouldn't change a thing in their otherwise perfect vacation.

Elsewhere, Trip and Reed immerse themselves in a rocking nightclub, filled to the rim with exotic alien females of every description. The two bachelors have trouble targeting their prey, when suddenly the decision is made for them as two gorgeous women join them for a drink. Introducing themselves as Dee'Ahn and Latia, the flirtatious women find everything about Trip and Reed fascinating. After several rounds of Risan drinks, the women invite the fairly inebriated Reed and Trip to view the nearby subterranean gardens, filled with luminescent plant-life. Letting the ladies show them the way, Trip and Reed are led into the basement underneath the bar. Sensing something amiss, Reed questions the ladies as to how the basement could lead to a garden when suddenly the ladies turn around and demand all of the men's valuables. Still shocked and fairly intoxicated, both Reed and Trip sober up fairly quickly when the "ladies" morph right in front of them, turning into grotesque and decidedly male aliens! Held at phaser-point, Trip and Reed are helpless as the aliens tie them up and mug them. Finding their prey to be of no more value, the muggers shoot the officers unconscious and leave them tied up in the club basement for the night. Waking up in the morning with a killer hangover from both the alcohol and the phaser-blasts, Trip and Reed find themselves very much alone as the club shuts down in the daytime. Preferring not to be discovered by the Captain tied up and in their skivvies, the two spend the day frantically searching for a means of escape from their awkward predicament. Eventually smashing a nearby bottle to saw through their ropes, the officers awkwardly make their way through the then crowded club on their way back to their hotel room to pack for their return to the Enterprise.

In Sickbay, Dr. Phlox prepares to take his annual hibernation. Normally requiring six days of deep sleep per year, Phlox informs T'Pol he should be fine with only two days, and he has prepared Crewman Cutler to handle any medical situations in the meantime. Although it would not hurt Phlox to be prematurely awakened from his hibernation, he states it would be highly unpleasant and he would prefer it not to happen unless absolutely necessary. Time flies smoothly, until Mayweather contacts Enterprise and requests a shuttlepod to pick him up as he had a slight accident rock climbing. First arriving at a Risan hospital, Mayweather felt uncomfortable being treated by a doctor who has never even heard of a human before, and wished to be seen by his familiar Dr. Phlox. After arriving back on the Enterprise, Mayweather is unnerved by the absence of Phlox, but is assured by Cutler that she can handle his broken leg. The ensign also notices some trouble breathing, however, and Cutler diagnoses him having a reaction to a painkiller the Risan doctor gave him. Mayweather's reaction worsens and causes swelling which threatens to cut off his air supply, which forces Cutler and T'Pol to awaken the hibernating Phlox. After Cutler applies the appropriate hypospray, Phlox snaps out of his sleep however, the doctor is extremely disorientated and somewhat delusional due to being prematurely awakened. With the assistance of Cutler and T'Pol, the somewhat incoherent Phlox makes his way to sickbay and diagnoses the extremely concerned Mayweather. Despite his mental cloudiness, Phlox determines the problem and creates a suitable antidote for Mayweather's reaction. Once administered with the hypospray Mayweather immediately feels better, but is unable to thank the doctor as Phlox immediately collapses back into hibernation!

On Risa the next morning, the Enterprise crew members take the shuttlepod back to their ship. Each having a story to tell, but not necessarily divulging what they got up to just yet.