Don't forget to explore local wines. There is a wine region and wine industry in Uruguay, but not much of interest is exported.

I would like to see Montevideo on the weekend (dine, relax on the rambla, shop antiques and local crafts, weekend flea market, see the tango, museum/sights, and eat some more), Colonia del Sacramento on a weekday, and explore the rural areas inbetween on a weekday, maybe horse riding (I will stay in that rural area for a couple of nights). I am also trying to decide whether I should spend time in Carmelo or in Punta del Este. It appears that the draw of both of them is the beach. I have seen Punta del Este described as sort of a Biarritz of Uruguay. What is Carmelo compared to? Is Carmelo more luxury and Punta del Este more party-like? I am not a partier but love beautiful beaches and local culture. My inclination would be to go to both, but I am only there about five days and not sure if it would be rushing to do all of that. (When I tried to hit like 15 places in Italy in about 12 days, a very wise FTer admonished me to take it slower and I have found that invaluable advice.) Current itinerary is:

Day 1: Arrive MVD in the morning, get rental car, Punta del Este, Jose Ignacio, La Barra
Day 2: Rural areas between MVD and Colonia del Sacramento, maybe horse riding
Day 3: Colonia del Sacramento, Carmelo
Day 4: Montevideo
Day 5: Montevideo, flight out in evening

Response: I was too ambitious in my planning. I do tend to stop quite a bit while driving to take photos, so that eats up some time, but arriving at 9 AM and expecting to see Punta del Este, Jose Ignacio and La Barra all in one day is do-able if you just want to see something and move on, but to actually experience and enjoy these places, it is not do-able, especially in autumn when the sun sets by 5:30 or 5:45 PM. Even in the off-season, to fully appreciate Punta del Este, you need a full day to walk around, see the beaches, the shops, Los Dedos, soak in the beautiful views, watch the sunset, and experience the great food. It is, in my opinion, well worth visiting even in the off-season. I am sure it is a different and more energetic vibe in the summer but it was thoroughly enjoyable even in late autumn. You could spend another day on sleepy and quaint Jose Ignacio and cute La Barra.

As for Piriapolis, while it was rather quiet in the off-season, it was still lovely and worth a visit for the beautiful views and kind people one meets in town. Many shops were boarded up for the season here, so there was not as much to do, but just walking along the rambla and visiting places like Hotel Argentino made it worthwhile.

Also, I had heard that Carmelo is quite beautiful where the vineyards meet the water, but when I said that to locals, they were perplexed why I was going and told me that "beautiful" was not the word they would use to describe it. I pressed on and drove up there but never found the beautiful part. In a desperate attempt to find the beautiful part before the sun was to set, I tried to use Google maps to guide me to the Hyatt in Carmelo which I knew must be in that "beautiful" part, but alas, Google maps kept sending me down the same dirt road that was fenced off and offered no other options. The sun finally set and I gave up as I would not be able to see the beautiful part anyway at that point. There may be quite lovely parts of Carmelo, but what I saw was just a busy town.

As everyone here has said, Colonia del Sacramento is a true gem. I cannot say enough about this charming little town. One could easily stroll and linger here all day long.

WHERE TO STAY IN MONTEVIDEO: I wrote:

I have read that several people stayed at the Sheraton, but also read that it is not central to much, and according to the below US State Dept travel advisory, there are robberies and thefts there. I read suggestions to stay at Four Points but from a map, it looks like that is also not near much? Also, I cannot tell which neighborhood the Four Points is in and if it is safe, I read that it is recommended to stay perhaps in Pocitos on the water instead of downtown Montevideo because it is more enjoyable, but then read on the travel advisory that there are even burglaries and robberies there in Pocitos (see below). I have elite status with Marriott/Starwood and also Hilton so would like to stay within those properties if possible (Sheraton, Four Points, Hilton Garden Inn), but safety is my #1 concern followed by I guess hoping for an upgrade, helpful service, etc. (I do like that the Four Points is 70% cheaper in points the night I am considering staying there, but that alone is not a deciding factor for me.)

Response: I guess like anything else, it all depends on where you want to be and what you want to do. I booked the Four Points and had intended to stay there two nights, and they did upgrade me to a king one -bedroom suite which was nice. The hotel property was stylish and comfortable, and the breakfast was fine. However, they had major issues with their temperature control during the first day and night (heat did not work and it just continued to get colder) and I decided to cancel my second night there and move over to the Sheraton at Punta Carretas. I am so glad that I did. The Four Points was actually quite a good location for the things that I wanted to do that first day which was some shopping and visiting downtown landmarks, eating down at Marcado del Puerto, going to a club for local music and tango, etc. All of these things were a (seriously!) $2-4 USD Uber ride from the hotel so I ended up just leaving my car at the Four Points and taking Uber all over downtown. The hotel location was central enough to these places but still in a safe area of town. However, when I moved over to the Sheraton, I saw a whole different side of Montevideo that was so relaxing and enjoyable. Walking along the rambla there starting near the Sheraton and walking all the way to downtown, or riding one of the (free) bikes the Sheraton offers the other direction up toward the zoo or through Pocitos - it was an enjoyable way to wrap up a visit to Montevideo. While the Sheraton could not upgrade me to a suite the first night, they did upgrade to a 1 bedroom king suite the second night that I tacked on there and the suite was large and comfortable. My original concern based on posts I read here on FT was that the Sheraton was by itself without anything else to see there near it. That is just not the case. It is not near downtown - that is true (though it is an hour walk from downtown). But it is in the middle of a residential area where people live, go to eat, shop, and walk their dogs. It was right in the middle of where I wanted to be at that time. As for safety, the area near the Sheraton in Punta Carretas is definitely safe. While the US State Department information is helpful to consider, I think I was unnecessarily overconcerned.

WHERE TO BUY: I wrote:

I am interested in purchasing some items that I can use to furnish my home - maybe a locally woven wool blanket or rug, maybe something silver for the dining room, maybe something leather, etc. I am also interested in antiques for the home. Does anyone have any recommendations for shops to visit to find antiques and local crafts?

Response: There was a great antique store in La Barra, and the Montevideo flea market was definitely an experience to be had. But the wool at Manos del Uruguay really was tremendous and leather shops can be found around as well. There were plenty of shops around to purchase locally made items.

SIESTA TIME: I wrote:

I read that it is after lunch, but then also read that it is about 5-8 or 7-9 PM before dinner. If shops and restaurants close for this, approximately what time should I plan for them to be closed - late afternoon or evening?

I never encountered this. I was told that stores in towns like Punta del Este do not close during those hours, but in some other parts of Uruguay, these hours are observed. I still never figured out what time the hours were. I think maybe it is more observed in the smaller towns in the countryside.

TANGO: I wrote:

I read about Baar FunFun as a place to see a tango show. Any other recommendations?

The hotels all recommend a place called El Milongon to see tango. It is a dinner show. I did not attend so cannot say for sure but I got the impression that it was sort of like the Medieval Times of tango, but I may have gotten the wrong impression. I believe the price was about $65 USD. I ended up going to Baar FunFun which presented local folklore music and tango music (without the tango dancing) until about midnight, and then after midnight, had a bit of tango dancing and candombe music. The tango dancers were quite good - they danced only three songs but were very skilled. If you Google enough, there are tango classes all around town but it was difficult to get current information as they seem move around and change quite a bit.

US DOLLARS VS. UY PESOS: I wrote:

I have read that much of Uruguay accepts USD. Is this also true in smaller towns like Colonia del Sacramento? I am not sure how much of my money should be converted to UY Pesos or if I can get by on USD alone.

Response: I really never encountered any place that did not accept USD, even at the toll booths, but it was sometimes just much easier to use UY Pesos, so it was worth taking out some local currency at the bank, but I did not need more than $3000 UY Pesos for the whole week.

SAFETY/SECURITY: I wrote:

Many threads here state that as long as one exercises normal precautions, one should be fairly safe. However, there has been mention of not underestimating the street violence and in fact one FTer had an attempted robbery. The most recent entry (I think updated January 2018) on the US State Dept. website is listed below. I do want to see the old town and definitely have lunch at the Mercato del Puerto. I have read that it is busiest on weekends, so I assume that makes it safer. Any tips on how to do old town and the Rambla safely but alone? Are the downtown flea markets safe to shop in alone?

"Crime: There is a high level of crime in Montevideo, and street crime in particular is common throughout the capital city. Maintain situational awareness and practice good personal security at all times. Even in areas with large numbers of tourists, such as Ciudad Vieja, the Rambla, and areas around the U.S. Embassy, armed robberies of both individuals and businesses occur, along with carjackings and auto thefts. Thefts, burglaries and robberies are common in upscale residential neighborhoods as well, including Punta Carretas, Pocitos, and Carrasco. Montevideo continues to experience armed robberies at business establishments, and criminals may use improvised explosives to conduct robberies or to steal from ATMs. Criminals break car windows to steal valuables from vehicles that are parked or stuck in traffic. Sometimes, robbers approach their victims on motorcycles to rob them. . . During the summer months (December-March), many cities in Uruguay experience an increase in the number of petty street crimes, residential burglaries, and robberies, especially in beach towns such as Punta del Este, la Paloma, Cabo Polonio, la Pedrera, and Punta del Diablo."