It's hard to compete with a well-kept Spanish-colonial city for charm, romance, and splendor. The plazas, cobblestone streets, courtyard homes, and flowered balconies take you back to Spain's grand colonial era in a way that is hard to match and that can make for a very appealing retirement lifestyle. The best part is that some of the grandest Spanish colonial cities are also some of the most affordable places to think about retiring.
Top colonial city in the Americas #1: Cartagena, Colombia. Of Spain's cities on this side of the ocean, Cartagena, Colombia, is often recognized as the most beautiful, with a lot to offer potential expats or retirees. As colonial cities go in the Americas, some would argue that Cartagena is king. It is one of the world's few remaining walled cities, has been largely restored, and is very well preserved. You'll be impressed by the number of shops, cafes, and restaurants.
Cartagena combines the best of old Spanish America with the richness of the Caribbean. The courtyards and narrow streets are old Spain, while the bright colors of the houses add a Caribbean flair. The traditional Colombian cuisine on offer in places like Cafetería Bocaditos may be reminiscent of Madrid, but the women walking about with giant trays of fresh fruit balanced on their heads remind you that you're on the shores of the Caribbean. Plus, Cartagena offers a number of attractive beach areas that attract large numbers of expats. These beach areas are not in the historic center, but a few minutes away by cab.
Thinking more practically, the infrastructure in this area is great, with drinkable water, well-maintained streets, cable TV, high-speed Internet, and a convenient international airport just minutes away. The weather in Cartagena is either warm and dry or warm and humid, depending on when you go. (May through November tends to be humid.)
One downside to retirement in Cartagena can be the tourist annoyances--the ever-present vendors trying to sell you something, the scamming moneychangers, and, at times, the numbers of tourists themselves. Early-risers can avoid this by exploring places before 9 a.m. Also, if you don't like typically hot Caribbean weather, then Cartagena wouldn't be a good choice for you.
Top colonial city in the Americas #2: Colonia, Uruguay. While far less recognized than Cartagena, Colonia's Barrio Histórico (original historic center) can be an unbeatable retirement option. The Barrio Histórico is an island of history adjacent to an otherwise modern city. The neighborhood is on a peninsula, mostly surrounded by water, meaning it will never become the center of a large metro area or see any through-traffic. Yet the more-modern sections of town are close at hand.
Further, while the district itself boasts 17th century buildings, streets, and ambiance, Barrio Histórico still enjoys Uruguay's generally first-rate infrastructure. Another benefit of living in Colonia's Barrio Histórico is that it's relatively crime-free compared with almost anywhere else in Latin America. You can enjoy its inordinate number of cafes, shops, and fine dining establishments, day or night, without worrying about your personal safety or belongings.
Top colonial city in the Americas #3: Casco Viejo, Panama. Casco Viejo in Panama City is another top colonial city retirement option. Like Colonia, it's on a peninsula and not central to the rest of the city. Yet just a few minutes away, Panama City offers almost anything you could want, from modern stores and supermarkets to international-standard medical care.
On the other hand, Casco Viejo's state of restoration is nothing like that in Colonia. While Colonia's Barrio Histórico is virtually 100 percent restored, Casco Viejo is still a work-in-progress. There are many nicely restored buildings and parks, while many others are in stages of decay. You do have a good selection of shops, cafes, and nice restaurants in Casco, but petty crime can be more of a concern than in Colonia.
Top colonial city in the Americas #4: Granada, Nicaragua. Granada, Nicaragua, is situated on the giant Lake Nicaragua. This means that this city (which claims to be the oldest in the Americas) is somewhat protected from surrounding development. Granada is also a walkable city, with a good number of cafes and shops and an established community of foreign retirees. You won't find the selection of international-level fine dining that is available in Colonia, Cartagena, or Casco Viejo, but the local restaurant scene (including a few notable expat-owned restaurants) is quite good.
What I like best about Granada is that it's probably the least expensive place in the Americas to own a Spanish-colonial home. You can buy a centuries-old Spanish-colonial structure, the type with the typical center courtyard, for less than $100,000. And unlike most colonial homes in the Americas, those in Granada frequently have pools in their courtyards, something you'll appreciate in Granada's heat.
Top colonial city in the Americas #5: São Luis, Brazil. A little farther off the beaten trail is São Luis, Brazil. This is another historic center on a peninsula. This one juts from the mainland where two large rivers join the ocean. Brazil has a number of great colonial cities, including Olinda and Ouro Preto. São Luis is not necessarily the most beautiful, but it is the most fun. The most popular (and best restored) section of the historic center is between Rua do Giz and the river, with Rua da Estrela being the best place for strolling and exploring.
São Luis (capital of the state of Maranhão) is the reggae capital of Brazil, and its culture is a fascinating mix of French colonial, Dutch, African, and Portuguese influences. It's not as convenient for travel as the other colonial cities I mentioned above, but it's unbeatable if you'd like to step into the past and get away from the mainstream.
Kathleen Peddicord is the founder of the Live and Invest Overseas publishing group. With more than 25 years experience covering this beat, Kathleen reports daily on current opportunities for living, retiring, and investing overseas in her free e-letter. Her book, How To Retire Overseas--Everything You Need To Know To Live Well Abroad For Less, was recently released by Penguin Books.