If you look at all the colorful cities in the world, I will go out on a limb here and say that the densest accumulation of colorful cities can be found in Italy and in the Caribbean. But even Italy, often featured in my lists of The Most Colorful Cities In The World and The Most Colorful Cities In Europe, finds it hard to beat the many vibrant cities and harbor towns found in the Caribbean. It must have something to do with the generally happy vibe, the love of life and music, and the picture-perfect setting of most islands that invite their people to paint the town red. And pink. And blue.
Here are some of the most colorful cities in the Caribbean, stretching across all islands, each as pretty as the next. All are obviously chosen for their color, but also for their overall vibrant atmosphere.
So, what are you waiting for? Go and get your color fix on one of these lovely islands.
1. Havana, Cuba
Let’s start with a double, or even triple, whammy here, because not only is Havana’s architecture bright and colorful but so are its ubiquitous vintage cars. And then there is Trinidad, an hour or so down the road. Cuba is such a gorgeous island, with its resilient and resourceful people, and it shows in the colors that are all around. From the tall French-colonial townhouses in Havana to the low, non-frill residences in Trinidad, the styles could not be more different, but what brings them together is the cheerful splash of color that goes so well with the music that greets you at every corner.
Pro Tip: Explore old Havana on a locally sourced walking tour, learning about its challenging history while enjoying this lively city.
2. San Juan, Puerto Rico
San Juan, the capital and largest city of Puerto Rico, has a 500-year-old history, with some 400 buildings dating to the 16th and 17th centuries. It is the Old San Juan overlooking the Atlantic, which is the most colorful spot on the island. The beautiful candy-colored buildings are a legacy of the Spanish, who invaded Puerto Rico and surrounding lands in the 1500s, making for a painful history. But despite the terrible record, the buildings are now so much part of the San Juan cityscape that when politicians wanted to flatten the old buildings to make space for new developments in the 1940s, locals fought for the preservation of the colonial buildings, and today they are well-loved and cared for. They were named a UNESCO World Heritage site in 1983.
Pro Tip: For a very colorful stay, why not rent an apartment in an orange building right in the center of Old San Juan?
3. Willemstad, Curacao
The island of Curacao is a constituent country of the Netherlands, and that is pretty obvious as soon as you look at Willemstad, its capital city. The cityscape is like Amsterdam dipped in candy colors. The typically tall Dutch buildings, with their frilled facades, even stand by a canal, but that is where the Caribbean and the historic Spanish, Portuguese, South American, African, and even Sephardic Jewish influences take over, making for a truly unique Curacao style that has been awarded UNESCO World Heritage status due to its distinctiveness. Add to the colorful architecture a rainbow-colored (and at night, lit up) bridge, plenty of twinkle lights, street art, and the turquoise sea, and you’ll need sunglasses not just for the sun. This is probably the most colorful of the Caribbean selection of colorful cities, and it is so vibrant that anywhere you visit after Willemstad will seem sad and dull.
Pro Tip: Did you know that Curacao is the “C” of the ABC Islands? The “A” and “B” are Aruba and Bonaire, and you can explore all three in style on a crewed yacht.
4. Oranjestad, Aruba
Though you’d be excused to be thinking that, with Aruba also being a Dutch-Caribbean island, Oranjestad would look a lot like our previous city, you are actually wrong. Yes, there are similarities, of course, with many buildings resembling the typically Dutch style, but there are just as many which are very different, somehow more ornate, more elaborately decorated. But just as colorful and vibrant. Especially around the harbor, with its bright, big buildings and the small, just as dazzling boats moored at the end of the pontoon.
Pro Tip: To add even more color and a dash of festivities, every Tuesday the Bon Bini Festival, Bon Bini meaning “welcome” in the local indigenous language of Papiamento, takes place at the blue (!) Fort Zoutman.
5. Bridgetown, Barbados
Head from the Dutch Caribbean to the British Caribbean with Bridgetown, the capital of Barbados. Bridgetown is known for its British colonial architecture with some Barbadian flair and a dash of indigenous Bajan culture and color. Formerly known as the Town of Saint Michael, Bridgetown is generally simply called “The City” or “Town” by the locals, and its old section has achieved UNESCO World Heritage status. Walking along the Careenage, the inner natural harbor, you’ll see buildings in every color imaginable, and together with the clear water and colorful boats, this area makes for a vibrant excursion.
Pro Tip: Head to the Cheapside Street Market for more color in the shape of fresh fruit and vegetable produce, and plenty of local arts and crafts that make for bright souvenirs.
6. Cockburn Town, Turks And Caicos
Cockburn Town is the capital city of the Turks and Caicos archipelago, located on the largest island, Grand Turk. The small capital is eminently walkable and best explored on foot. Most of the historic buildings, all in the British-Colonial Bermudian style, can be found along Queen Street and Front Street, both running parallel to the beach. Most of the original colonial-style buildings had to be restored repeatedly because Grand Turk lies in the hurricane belt, but it is an homage to the lovely and colorful historic architecture that the buildings are kept in their original style, with the pastel colors dominating and complementing the white beach and turquoise sea.
Pro Tip: Walk along the coast to the Grand Turk Lighthouse, which, even without access to its tower, offers great views across the bay and has a little snack and souvenir shop on the grounds.
7. Philipsburg, St. Maarten
St. Maarten, in the Leeward Islands Archipelago, is a popular stop for cruise ships and offers a two-in-one bonus. Half the island is Dutch, called Sint Maarten with Philipsburg as its capital, and the other half is French, called Saint Martin with Marigot as capital. Different architecture, even different currency, but both gorgeous and colorful throughout. With there being no physical border and the movement between the Dutch and the French part completely open, you can not only visit the two colorful capitals but also enjoy the very different food scenes, with the French side offering fresh croissants and French cuisine, while the Dutch part’s restaurant scene is more international, probably due to the influx of cruise ships.
Pro Tip: There are plenty of organized tours that take in both parts of the island, helping visitors forgo the need to rent a car.
8. Santo Domingo, Dominican Republic
From one island split in two to another: The Dominican Republic shares the island Hispaniola with Haiti (see below), and its capital, Santo Domingo, is widely touted as the oldest city in the Caribbean, founded in the late 1400s. This statement means that it is the oldest European settlement in the New World — which does not consider its indigenous history, of course. But the fact remains that the old part of Santo Domingo, called the Zona Colonial, is a gorgeous, well preserved, and vibrant area, also designated a UNESCO World Heritage Site.
While the architecture is a mix of ancient brick buildings and more decorative colonial residences, there are plenty of pops of color throughout the Zona Colonial, from pastel pink or orange churches to the candy-colored street Calle Jose Reyes and the lively Mercado Modelo, with its orange and yellow outside and vibrantly colored produce inside.
Pro Tip: There is a lot of history to take in, so why not go on a free walking tour to learn more about it?
9. Port-Au-Prince, Haiti
The Caribbean’s second-largest city, it is also one of the poorest, with the city, and the country, still trying to recover from the devastating 2010 earthquake. But proving the nation’s resilience, Port-au-Prince is still bustling, welcoming, and well worth seeing. It was the earthquake and the destruction of the already rickety slum shanty towns that lead to the art project Beauty versus Poverty: Jalousie in Colors, a project that saw the restoration of the shanty towns while adding a splash of color, making residents become part of the community’s improvement and raising levels of happiness. While I do not normally agree with “slum tourism,” this is a valuable project and definitely worth a visit.
Pro Tip: Port-au-Prince’s historic Iron Market was lovingly restored after the earthquake and now stands in its old red and green splendor once more, making it a must-see when visiting.
Wherever you look in the Caribbean, a pop of color is never far away. Be it the natural shades of white beaches, green countryside, and turquoise seas, or the old town centers harking back to the island’s colonial history. Add the flair of the locals and the happy tourists, and vibrancy is assured.