Cities and Towns in Caribbean

It's a strange sight to see cruise tourists with white pants and summer dresses stroll the streets of low-key and timeworn Roseau. But the locals seem endearingly indifferent to the dribble of tourists. Here people mind their own business without being unfriendly. The mostly colourful buildings come in every style from posh with built-in double garage to wooden shacks. There are lots of churches, but none impressive, though the front of the old cathedral stills stand. During daytime, Roseau is crowded with cars and people, but at night and Sunday, Roseau is all but empty. Don't mind the few dodgy characters in the streets, the city is safe as anything can be.

The fishing village of Soufrière has a wonderful colourful church standing next to the beach. There the water is slightly warmer than elsewhere, as volcanic steam bubbles through the sand and creates a natural spa. A pool have been made and there is small snack shack for the mostly local visitors.

In North America there is a somewhat distorted sense of history. "Old" is something that has been around for 100 years. But if looking for the oldest the continent has to offer (at least in terms of the Columbian era) then you need to go where it began. The UNESCO listed Colonial City of Santo Domingo has the oldest everything; the oldest church in the Americas, the oldest university in the Americas, the oldest this and the oldest that. The old city has a great mix of remodelled, decaying and crumbling to honestly show the signs of its age. Almost any visit to the Dominican Republic will start here, and it is here the Dominican Republic, and indeed the invasion of America, began.

If you like the rough edges of St. George and colourful characters in the streets, then you will probably like Grenville too. Of a town with no more than two main streets, it’s surprisingly how bustling it is. The main attraction here is people watching. Just wander around or sit down for a drink, and take in daily life. If this isn’t fulfilling enough, then visit the old airport 3 km north of town to see the leftovers of old Soviet planes from when the US invaded Grenada in 1983.

Tiny St George’s is a serious candidate for the most charming capital in the whole Caribbean. Its setting is spectacular on a hilly peninsula with a bay to one side and the ocean to the other. A mismatch of colourful houses are spread out over the slopes and the streets are steep and cramped. Perched high up stands the Fort George, which isn’t particularly interesting, but the view are well worth the walk up here. The thing that makes St George’s so darn adorable, is the fact that it hasn’t been tarted up for the cruise tourists, not even down at the harbour. Here are just ordinary life full of characters.

Let's be honest, Port-au-Prince is by no means a pretty sight, but it's not as bad as its reputation either. The city is still recovering from the devastating 2010 earthquake. Debris are everywhere, though new grey concrete and cement have taken over. Sightseeing in Port-au-Prince are normally confined to the downtown area which includes: Iron Market, remains of the cathedral, tower of the not-so-eternal flame (it has never been lit), the museum, and a wicked voodoo art gallery. Walking around can be very overwhelming as streets are chaotic and crowded with vendors, pedestrians, buses, mototaxi, and, of course, white Toyota Landcruisers with UN or NGO logos. However, if you dare, you can always jump on one of the many mototaxi and let the driver navigate the madness. For a bit of perspective, and maybe a sundowner, take the trip up to the observatory in the hills for panoramic views over the city and valley. And from that distance, Port-au-Prince can be very appealing.

Falmouth is one fine little town. It was once the capital of the area and had the biggest marked on Jamaica, which also included slave trade, so there are some historical relics. But the town’s real charm is its bustling normality. The streets are filled with shopping mamas and fruits vendors pushing their wooden cart. Here you stroll around the town square without being hustled. The town gets particularly lively in the evening as the shops close, and the bars and food stands open. The small town charm might be lost on cruise days, when the big ships anchor up.

It’s truly understandable that most travellers limit their time in Kingston to a visit at the Bob Marley museum and an ice-cream at Devon House, for there aren’t a whole lot to see. Kingston is very spread out with two main areas, downtown and uptown. Downtown has a few landmarks, but else boring office buildings. Uptown isn’t more interesting, but is more orderly and where you find the Bob Marley museum and Devon House, the mansion for the first black millionaire in Jamaica. Though most people in Kingston are as friendly and easygoing as elsewhere on the island, don’t venture into the shantytowns on your own.

San Juan is more a patchwork of different neighbourhoods than one big city. Tourists will probably spend most of their time in overly cute Old San Juan (Viejo San Juan) with its cobblestone lanes, pastel coloured colonial houses, and historical forts. However, Old San Juan is much more than the tourist blocks near the cruise ship terminal. In the back lanes you can find cool cocktails bars and wonderful local eateries which serve rich Creol food. The infamous slum La Perla, which lies squeezed in by the city walls of polished Old San Juan and the Atlantic Ocean, is a peek into Puerto Rico's dark side, but take care down there. The posh neighbourhood of Condado, with its long beach and Atlantic surf, is where the rich hang out. Further East right next to the airport is Isla Verde with equal nice surf beaches, this is the playground for the people. Calle Loiza is also worth a look, an upcoming area for San Juan's trendy community (think tattoo parlors, salad/cocktail bars, and designer T-shirts).

From the waterfront Marigot looks amazing with pretty villas and the ruins of Fort Louis high up on the hill, but as you venture deeper into the residential areas, the scruffier it gets. However, it certainly has a lot of appeal with fine old houses with ornamented balconies. The town center has the usual range of jewelry shops, but the beach fashion boutiques are a bit more Frenchy than what you otherwise see on the Dutch side.