Gibraltar

Clambering up the Rock of Gibraltar feels a bit like gatecrashing a primate frat party atop a historic limestone fortress-only infinitely more photogenic. This rugged chunk of British bravado dangling off Spain's southern coast has seen it all: sieges, smugglers, and even a Beatle's wedding (looking at you, Mr. Lennon). The resident Barbary macaques-charmingly mischievous furballs with strategic military protection (legend has it, Britain loses Gibraltar when the monkeys leave)-are experts at charming tourists into surrendering snacks, sunglasses, and dignity, so clutch your belongings tighter than your grandmother at bingo night. Get there early, around nine in the morning, to beat cruise-ship hordes and snag Instagram-worthy views across two continents and a sparkling strip of sea. Budget about £16 for entry fees and cable car, or hike if you're feeling masochistically adventurous, and plan at least a day ahead for tickets or guided tours. Bring comfy walking shoes, bottled water, and your steeliest poker face-show fear and the macaques will sense your weakness. But despite the occasional simian shakedown, the vistas alone-comprising sunlit straits, African mountains, and endless azure-make it worth every ounce of effort. And if nothing else? Well, you've still got a story about the time you were mugged by monkeys atop a giant pebble disputed by two nations.

If you've ever fantasized about scaling a staircase built by sadistic medieval monks with a penchant for geology, Gibraltar's Mediterranean Steps is your dream hike. Clinging precariously to the cliffs of the famed Upper Rock, this vertigo-inducing trail was originally crafted by the British military in the 18th century-no doubt as some cruel initiation rite. The path twists upward with lung-burning tenacity, rewarding your sweat and steady stream of curses with jaw-dropping views across the Strait of Gibraltar, tantalizingly close to Morocco's hazy coastline. Go early in the morning or late afternoon, when the sun paints the horizon with golden dramatics, and wear sturdy shoes and sunglasses-because nothing spoils epic panoramas like squinting or twisted ankles. Plan at least two hours, budget a modest £16 entry fee to the Nature Reserve, pack water and snacks, and brace yourself for a few curious Barbary macaques eyeing your granola bar with mugger-like intensity. Sure, you might curse each step on the way up, but trust me-afterward, with sore muscles and a cocktail in hand, you'll proudly recount conquering the Mediterranean Steps to strangers at bars, dinner parties, and dentists' offices for years to come.

Rising defiantly above Gibraltar's tangle of pubs, fish-and-chip shops, and mischievous Barbary macaques, the Moorish Castle beckons history nerds and anyone with a passing fondness for old stones-and let's be honest, the smug satisfaction of bragging rights. Built way back in the 8th century by the Moors (who, let's face it, had impeccable taste in prime real estate), this fortress tells a tale of conquest, siege, and enough political backstabbing to make Game of Thrones look tame. For optimal bragging conditions and minimal sweat, tackle the castle's crumbling ramparts early in the morning, before the sun gets aggressive and cruise ship passengers invade like modern-day Berber pirates. Bring cash (about £12 should cover entry and a cold beverage afterward), sturdy shoes, a hat you'd willingly lose to mischievous monkeys, and enough water to stave off dehydration-no one wants your travel story to include a chapter on heatstroke. And though the best view of Gibraltar might actually be from across the strait in Morocco, climbing these ancient battlements, dramatically perched between continents, is absolutely worth doing-even if only to confirm your suspicion that history is best enjoyed from above, especially when you can see two continents and openly mock the strategic mistakes of kings long gone.

Wandering through Granada's Alhambra feels like you've crashed a lavish 14th-century garden party uninvited, without the inconvenient risk of decapitation. This Moorish wonderland, part fortress, part palace, part botanical fever dream, was lovingly perched on a hillside by Nasrid royalty who clearly knew a thing or two about epic sunset views (hint: arrive late afternoon-when the sun dips low and ignites the honey-gold walls, your Instagram followers will seethe with envy). Now, the Alhambra isn't exactly an under-the-radar spot anymore-tickets vanish faster than tapas at happy hour, so book weeks ahead and brace yourself to mingle with throngs of camera-toting pilgrims. Bring comfy shoes (it's an uphill trek and sprawling property), sunscreen, bottled water, and most importantly, patience to withstand the endless selfie ballet near the Court of the Lions. Budget around €14 for day tickets, but honestly, splash for the guided tour-knowing that behind those intricate tiles and endless arabesques lurk centuries of palace intrigue and conspiracies makes it well worth the extra euros. And even if architectural grandeur isn't your usual jam, strolling through lush gardens, citrus-scented walkways, and palatial courtyards sure beats another afternoon nibbling tapas. Besides, how many other UNESCO World Heritage sites give you bragging rights to say you visited a place abandoned by romantic sultans and later used as a squat by Napoleonic troops? Exactly.