We are a couple in our 50s. We are thinking about a 14-day trip to Thailand. Should we book a package or try to organize it ourselves? Anyone has good experience with a travel agency specialized in this? Thanks!

We have travelled several times to Thailand and have never used a travel agency. The only difficulty we have found is the high prices of using a driver or hire car in areas where transport is limited (ie away from the capital.). It is easy to book train or air tickets on the internet but more difficult to work out how to get from airport to your hotel especially if the airport is somewhat distant to the town/city. While many posters claim to have used a travel agency to hire a vehicle/driver they always conveniently have forgotten which one!

It is very difficult to suggest a good travel agency without knowing which country you live in. I am in London and would be happy to suggest UK travel agencies and tour operators but if you happen to be in say the USA, I wouldn't have a clue. The more information you provide the more relevant and useful responses you will receive. That said, it is very easy to organise everything yourself booking flights direct with airlines, accommodation with booking.com or similar or direct with the hotels. The cost savings are significant.

Despite what is said in post #2, it is not difficult to arrange transport to and from airports or stations . Just ask your accommodation to organise or grab a taxi. Prices are not high by European or US standards. Far from it!

There are also many ride apps similar to Uber available in most cities .

I'd say it doesn't hurt to do a bit of youtube research for the trip. It's nice to have a tour guide. The city can get very crowded and some locals are used to hustling foreigners. If you want things to go smoothly and travel comfortably, hire a guide with transportation service.

We always organise our own trips so we can create an itinerary that suits our interests.
Here's the itinerary we created for 3 weeks in Thailand a few years back, note we aren't into beaches so it's beach-free.
The only bit we used an agency for was the 3 night excursion from Saigon down into the Mekong, and she also booked the internal flight for us as well.
For accommodation, my preference is booking.com and I've used them extensively for the last 12+ years.