(Half of) The world is my oyster, so where should I go?
September 17, 2016 5:57 AM   Subscribe

I'm flying out of the Caribbean on a Wednesday and need to arrive in South Africa on Sunday. Where should a solo traveler spend a couple-day stopover in between the two?

The travel and the time change eat up about two days, so if I left on Wednesday morning I could arrive by Thursday late afternoon, leaving two or three days to see somewhere new. Criteria: should be roughly on the way, so most of Asia, Australia, Mexico, and the western US are out. East coast, South America, Europe, and Africa are viable. The city should be reasonably accessible by air - doesn't need to be a major hub, but should have an airport with enough activity that I won't need to add two or three extra connections just to get in. And finally, the destination should be compact and easy enough to navigate that I'd have a chance of having a meaningful experience with limited time. Budget is not an issue - this will be a free stopover as part of a miles award ticket (star alliance), so while I'll have to check routing and seat availability, I don't need to worry so much about whether it's typically expensive to reach.

I like art, history, good food, and distinctive ambiance. I don't care about the beach, and while I really enjoy the outdoors this seems like too little time to stray far from civilization (though maybe I'm wrong about this!). My default idea is to spend a couple days in NYC - it doesn't add any extra travel time, there's plenty to do, and I'm familiar enough with the place that the stress of figuring out logistics and language and social norms wouldn't be overwhelming during a brief visit. But I also wonder if I should be more adventurous with this opportunity. What do you seasoned travelers think?
posted by exutima to Travel & Transportation (6 answers total) 1 user marked this as a favorite
I would say London since it's easy to navigate, language isn't an issue and London definitely has the items you are looking for. Does South African Airways (which is Star Alliance) fly from there?

Other Star Alliance hubs that might work are Toronto, Brussels, Frankfurt, Lisbon. Maybe Singapore? Paris or Madrid, maybe?
posted by TORunner at 6:22 AM on September 17, 2016

Barcelona. Food, culture, art, people watching. Areas of interest are very walkable and not too far apart.
posted by CrazyLemonade at 8:00 AM on September 17, 2016 [1 favorite]

Buenos Aires? It will be spring time, and you should be able to get direct flights back to South Africa.
posted by Gomez_in_the_South at 8:56 AM on September 17, 2016

Addis Ababa, Ethiopia, with a side trip to Lalibela if you have time.
posted by bluedaisy at 9:58 AM on September 17, 2016

Caribbean -> Rio de Janeiro (2 days) -> Jo'burg

It looks like Avianca and South African Airways would work for you on this route

Another option would be to get to Johannesburg on Thursday/Friday and add a weekend trip to the Seychelles or Mauritius
posted by Kwadeng at 10:08 AM on September 17, 2016

Non-awful, relatively comfortable ways to do this on Star Alliance (do check with your ticketing carrier that stops to change planes don't count as "stopovers") would be home to Miami on whatever Star carriers are available (if a US/ESTA-requiring stop is possible/not annoying for you!), then:

- on to Johannesburg via Istanbul on Turkish Airlines (great food, cheap on the ground, very rewarding and compact even for short visits)


- on to Johannesburg via Frankfurt or Zurich on Lufthansa or Swiss (slightly more boring layovers, but a lot of interesting nearby places if you weren't into the cities themselves; also probably a better reputation in terms of in-flight experience, especially if you are in a premium class)

From the non-US Caribbean your options are a bit more limited for trans-Atlantic Star Alliance flights. Air Canada has a number of flights that would go Islands/Toronto or Montreal/Europe, and then a new carrier on to South Africa, but two stopovers may break the ticketing rules. United can get you to Newark or Washington for the South African Airways flight from JFK to JNB.

The Avianca connection is interesting and there are many options (I see Aruba/Barbados/Cancun/Curacao/Havana(!)/Punta Cana/San Juan PR/Santo Domingo - Bogota - Sao Paulo, then on to Johannesburg on South African!) but it's two stops, and I wonder about Brazilian transit visas and how easy it is to get them if you're on an island without a Brazilian diplomatic post?

Also look at Copa Airlines out of Panama; they also link many islands and Sao Paulo via Panama City for that SAA flight.

The only other one-stop from the region on Star I can see is Havana-Beijing-Johannesburg on Air China. Beijing is definitely worth a stop and there's a visa-free transit deal you can do depending on your passport. I would assume this route would be WIDE OPEN in terms of availability.

Finally, my personal preference were I in business or first, had loads of time and no restrictions: Caribbean to Buenos Aires via Bogota on Avianca, Air New Zealand to Auckland and then Perth, and then South African Airways on to Johannesburg.
posted by mdonley at 9:04 AM on September 19, 2016

« Older The Professor is Not Quite In   |   The Third Man--How many different ways can you... Newer »
This thread is closed to new comments.