I agree on trying to stay at all the hotels is too much. They are all walking distance. Pick one, or maybe two, and visit the others to check out the ambiance and gauge which is the best fit for you for the next trip. I’m sure SL, Castillo, and La Amistad would show you a room if asked. Plenty of strong supporters of each, comes down to what fits your style.
Definitely book directly with Hotels. If they give a percent to Expedia or any other third party they will not give the CRT discount.
I generally spend a few days in Jaco each trip, but most stay only in SJ. Personal choice, I enjoy both.
Figuring in a trip to Jaco will definitely increase your costs. Private shuttle will run $80-$100 each way. The bus can be navigated for much cheaper (around $5) but be sure you are ready for that experience. There are some threads on taking the bus. Interbus is around $45 each way, I did it once. My opinion - not worth it.
Once in Jaco hotels are more expensive, be sure of their guest policy! and girls tend to start negotiations at a higher point than in SJ. For a six day trip I would probably stick to SJ, there will be plenty to keep you occupied. When I am in CR for less than a week, I typically skip the Jaco trip.
One advantage of trip to Jaco is it will get you out of the gulch and you can see some of CR’s beauty. If you stay six days in SJ, book a side trip somewhere that will get you out of the city for a least half a day to see some of the country. Given your luggage choice I would infer you would enjoy spending some time in the rainforest.
I agree on the dress code comment. Casual is fine. I wear jeans and a t-shirt, maybe a polo, never a button down. You don’t need to look good for the ladies, they don’t care. They do care about cleanliness!
Given the importance of presenting cleanliness, consider the volume of clean clothes you need to achieve that goal. 28 L is not a big pack, it could be a challenge depending on your packing skills. Most use a typical roller bag. You are navigating the airport to a taxi to a hotel. No need for extended carry.
Cell phone use depends on your needs and cell phone plan. All the hotels have decent wifi these days. Adequate for most everything. Communicating with the girls once you get some numbers is almost exclusively WhatsApp which is wifi I use some international minutes because I am typically on some work calls and I don’t disclose to my work contacts that I am in CR.
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