The Old Town of Dubrovnik is magical, more than capable of leaving you entranced if you can ignore the teeming swarms of tourists. Fortunately I booked my break for early October, and so wasn't too overwhelmed despite staying smack bang in the centre, in the epicentre of traffic. A stroll round its stone alleyways and squares almost doubles as a workout with its sheer number of steps, and indeed I felt no small amount of concern for the huge numbers of elderly tourists as they scaled the city walls with looks of manic determination in their eyes. But keep up with these superhuman geriatrics and you'll discover no end of cobbled back streets, little tumbledown cottages with petite gardens, a stonking great church, and a lovely little harbour perfect for an evening drink.
The city walls are the main draw for most tourists as they offer searching views of the town centre below, but for some proper gasp-inducing views head up to the fort above the city. You can take a cable car or hike up, but make sure you use the actual path rather than attempt an off-road climb, which saw me crawl clumsily through a number of brier bushes only to be stared down by a herd of mountain goats and forced to bid a hasty retreat.
Once at the top there's a delightful war museum which will enlighten you (for those of you in the dark) about the Yugoslav Wars and Croatia's role in it. I have to say, despite reading up on it, I was still largely confused so it was a handy, albeit slightly one-sided, look at the conflict and its ravaging effect on Dubrovnik. There's a selection of artifacts including some heavy duty rifles, videos, and the bloke in charge actually fought in the war. My conversation with him was one of the highlights of my trip - though brief, I got a real sense of the history of the city beyond its current incarnation which can be hard to imagine when you're strolling past endless restaurants and gift shops. He was no soldier, merely a volunteer, but he was forced to take a stand in the hills above the city to defend it from marauding Serbs, armed with only a pistol against airstrikes and tanks. Remarkable really.
You'll be able to gaze over the terracotta-roofed houses of the old town below, and take in the island of Lokrum just off the shore. This is worth a half-day visit, being only ten minutes away, and is a secluded, wooded escape from the city. There's a dead sea pool, a fort or two, and a couple of rocky areas on which to lounge like a sun lizard and take dips in the sea.
To really get the most out of your trip, I recommend stepping away from the Old Town and heading towards Lapad, on the west side of city. A hilly forest stands in your way, featuring a number of delightful hiking paths, one of which has an absolutely stunning view of the Elaphite Islands, rocky cliffs, and the open sea. Head down and you'll find yourself in a bay which, were I to return to Dubrovnik, I would surely stay in or near. Utterly peaceful and sheltered, you can swim from one side to the other unimpeded. A waterside cave bar lets you take a dip mid-drink, and when night draws in you can head inside into the real-life cave for some atmospheric partying.
A kayaking trip or just a ferry to the aforementioned Elaphite Islands is a must-do. Lopud (not to be confused with Lapad) is the main island, and from there kayaking tours generally start. Mine took me from one island to another, where we hopped off and cycled around for a while as our guide related his alternate version of history to us. Having thought I'd finally got a grasp on why and by whom the war was fought, I soon discovered I was now seeing things in black and white. Turns out it's not always bad guys versus good guys! Who knew.
Also worthwhile is a cycling trip across the countryside behind Dubrovnik towards Montenegro. This region, known as Konavle, is the main wine-growing area and so look for a trip which includes wine tasting. We made our way up and down a number of dusty hillsides, across a bracing river for a spot of lunch, and on our way back stopped off at a vineyard for a glass or two of local vino, which a number of my group took such a liking to they took back a case to Canada.
As far as beaches go, you won't be building many sand castles. It's mostly rock or pebble, but the azure water is so inviting you surely won't be spending too much time out of the sea anyway. The majority of the touristy nightlife goes on in the Old Town, and this is where you'll find the majority of the restaurants. Check out Taj Mahal, oddly enough a Bosnian restaurant, which serves some oaky-tasting delicacies from across the border. There's endless pizza and pasta joints and a good number of seafood places, though prices are more London-esque than one might expect.