First-time visit to South America itinerary review please.

We have been to several countries in South America and love Peru, Argentina and Chile the most. Also, adored the Galapagos Islands.

We have been to Colombia, but not Medellin. I am sure it is interesting, but think you would find Peru way more interesting.
You don't have much time in Lima. I suggest you spend enough time there to do two full days of touring. There is much to see there and nearby. Be sure to use a great tour company. We used PeruAgency.com for tours and they were great and not expensive.

We did a four day tour of Cuzco, the Sacred Valley and Machu Picchu in 2019 and it was special, we had a private guide/driver with a university education. Price was only $799 pp that included nice hotels, some meals and admissions.
Cuzco needs more than a day to see, also, the Sacred Valley between that city and MP had MANY ancient sites to visit. We did several and they were definitely worth seeing.

Don't try to do this on your own, take a tour. Not sure what you are doing with Cuzco and MP you list both on the 26 and 27,
Haven't been to Bolivia, but have researched and you need to know that the country is primitive. How do you plan to tour this country? DON'T try it on our own.

Also, Consider Chile and Argentina, they are great.

I believe that you can get a Bolivia visa at the border, and as you are not American or Israeli you won't have to pay $160 for it.

Edit: India passports fall in group 2 so $30 at consulate but 24 hour service not same day. I believe there is a consulate in Cusco.

I thought Peru was not too difficult without a tour, there is Uber in Lima and Cusco and online driving services like taxidatum.com for airport pickup, taxi tours point A to point B, or someone to wait for you while you do a hike. Peru is a gentle country so no need to buffer yourself from the local population with a tour to prevent theft.

I think Cusco and Lake Titicaca deserve more time. Lima is an enormous city with lots a traffic. If you don't have time to spend there (recommended) I would fly directly to Cusco and skip Lima. If you flew on Delta or LATAM from LAX or ATL you could get travel to Cusco on a single ticket. LATAM, the national airline, is a SkyTeam member.

Adding: Cusco through Bolivia are all in the 11,000-13,000 feet range, so some nights in Medellin would help acclimate to the very high altitude. Some go right to Ollantaytambo from Cusco airport (taxidatum.com private 2 hour transfer $34 cash) which is at 9000 feet as an acclimation step, great ruins there and it’s easy to day trip to Machu Picchu.

Also adding: I have found for Europe that tours cost per day about 2.5 times more than independent travel. For Peru it’s about 5 times more expensive, tour vs independent travel.

Further: Avianca flies nonstop Bogota>>Cusco if that fits in somewhere, I.e. you’re fine skipping Lima altogether and want to visit Colombia. Bogata at 7000 feet would help acclimate. No experience personally but would expect crime/hassle in Bogota..

For what it’s worth: I would spend the whole time in Peru. I was just there 4 weeks, so much to do.

For those planning to do it yourself going from Cuzco to Machu Picchu, be prepared to deal with some terrible highways in several places. The roads are so bad that traffic slows down to 5MPH to avoid destroying the undercarriage of their vehicles.

Further, there are many great ancient sites to visit on the way to MP, how will you know where they are and which ones are the best and having a guide explain the history.

Also, you will need to take the train for the final transit to Agua Callentes.

Our tour for four days cost us only $799 pp and that include very nice hotels, some meals, transport, the guide/driver and admissions.

I am trying to avoid “do my trip” syndrome, but responding to Geo above:

You can purchase your Machu Picchu tickets here, most want circuit 2 since it includes partial panorama and tour of the ruins, Spanish only website but can use the translate feature on your browser. Tickets for 2025 go on sale in a few weeks. Buy at least 3 months in advance for high season (Jun-Aug). Sunrise tickets are not advised due to mist and fog, tickets after about 10 am usually have better visibility. A huge advantage of not being on a tour is that if it is rainy or a time of poor visibility, you can just hang out and wait for things to clear. Tours are rushed through, often early AM when there is poor visibility.

Trains Ollantaytambo to Machu Picchu Pueblo (AKA Aguas Calientes) start at about $100 round trip, see IncaRail and Peru Rail for tickets, early and late trains cheapest. Luggage is not allowed on the trains.

Of course you need to sync your MP ticket admission time with the train times. Shuttle up and down the mountain can be purchased here, unless you are staying at the $2000/night hotel at the ruins it is the only vehicle service allowed up to the ruins, tickets are good all day
https://comprar.consettur.com/

Taxidatum.com is a godsend for the independent traveler. I used them 8 times sometimes with odd pickups like 4 am, completely reliable, here's an example of a taxi tour, https://taxidatum.com/chincheros-maras-moray-taxi-tour, from Ollantaytambo to Cusco with 3 stops in the Sacred Valley on the way, $60 cash for up to 4 people, more for a van. The driver will wait for you at each stop. Or Cusco airport to Ollantaytambo with no stops, $34 cash, driver will have a sign with your name as you exit the airport. There is also a tour from Cusco to Pisac and the 4 ruins above Cusco, also $60, and the driver will wait for you at each stop. Payment cash in soles is OK. With 3 people these driver services become super economical.

Adding that there are buses for tourists that do major runs like Cusco to Puno with a guide and several stops on the way, like https://www.inkaexpressbus.com/inka-express-puno-cusco

If you did this you can stop in Puno for a Lake Titicaca boat tour on your way to Bolivia. Peru also has sand boarding at places like Huacachina and Nasca. That tail end of your trip racing from Bolivia to Santiago is too fast.

One "school of thought" regarding travel is to dash around as quickly as possible in an effort (usually futile) to "see everything." I'm not going to argue against it; it's a perfectly legitimate way to travel if you happen to like it, and are immune to exhaustion. But note that you will be travelling great distances, sometimes spending hours on buses, just to see a few places very briefly. Furthermore, there may be places in your itinerary where the proposed dashing may be unrealistic. Looking at "v2", here are some potential problems:

24 Feb.: As you're flying to Cusco, you'll have only the morning to get your Bolivia visa -- have you considered what you will do if you can't get your Bolivia visa on that Monday morning? Much as I like Latin America, I'll admit that things don't always happen promptly or punctually there -- smart travellers are not going to assume that everything will to happen when it's supposed to happen, and right on time. (Note, too, that mainly because of unpredictable weather in the high Andes mountains, flights there are sometimes delayed for hours, or even for the day.)

28 Feb -- 1 March: Are you taking a tour bus to La Paz, which will stop for a while in Puno and in Copacabana? For if the bus you board on 28 Feb. is an ordinary passenger bus, then it's hard to see how you are going to get back to Peru (where Puno is), then on to Copacabana in Bolivia, and then back to La Paz, all on 1 March.

1-2 March: It seems you are spending no time in La Paz at all, except just to sleep there from late 1 March to early 2 March. You won't even legitimately be able to tell your friends that you "saw" La Paz, except for what you might have seen from the bus windows as you entered the city or left it.

6-8 March: It seems you will have only 24 hours in San Pedro Atacama, and only between 36 and 48 hours in Santiago. Now I'm sure these are great places to visit, provided you have enough time really to see them; but it seems you'll be doing a lot of travelling, over long distances, just to "glimpse" them. (And note that if you are interested in sand-boarding, you may want to consider Huacachina Peru, a desert-oasis resort set amidst sand dunes.)

Anyway, if seeing as much as possible, if only briefly, is your preferred travel mode, then definitely proceed with either of your two itineraries; as long as buses, planes, and visa offices operate punctually according to their respective schedules, and without cancellations or mishaps (though I never count on it on my own travels), either of your two itineraries should work. However, since you acknowledged being open to other suggestions, mine would be the same as Toby's above -- spend your entire 14 full days in Peru.