Please welcome a newbie (me) to Thorntree . . .
I am planning to quit my job in July and want my first travel adventure immediately after finishing to be something that will truly satiate my wanderlust . . .
I have been to Cuba three times before in the last 10 years (1 week in Santiago in March '98; 10 days in Havana/Cienfuegos in Jan '00; 1 week in Havana in July '06), but have never done two trips that always seem to come highly recommended from other travelers. . . (1) the roadtrip around the island, and (2) carnaval in Santiago.
I am sure many of you have done one or both of these, and I'd be very grateful for any thoughts/suggestions/impressions of the pros and cons of each of these, and particularly if anyone was at Carnaval in Santiago in recent years and can report on whether it's a fun people-watching party experience, or just an endless nightmare of drunken tourists . . . or something else ??
Many thanks in advance!
smallnwise


Carnival in Santiago, a drunken nightmare? That depends on how much drunkeness you can handle before it becomes, in your view, a nightmare. But definitely far fewer drunken tourists than locals. Santiago is an authentic street festival, albeit not as glamourous (or as much a tourist attraction) as Carnival in Rio, Trinidad, or New Orleans.
A road trip around the island is a terrific thing to do, and can be done in several ways: (1) by bus; (2) by rental car; and (3) by bicycle. Or some combination of those modes of transport.
If you opt to do it by bus, you'll want to use the Viazul line whenever you can, and take the less reliable, more crowded Astro buses only on routes where the Viazul does not run (for example, west from Santiago and on around the "foot" of Cuba), or to the various lovely beaches along the coast north of Holguin.
If you do choose to travel by bus, I would suggest that you get off at various places and find some other mode of transportation (rental car, hire-car-with-driver, or bicycle) to do out-of-city, off-main-route places in the area.
If you can afford to make the trip by rental car, that is wonderful, because in Cuba, unlike many other countries, this does not necessarily isolate you from the locals. Since thousands of Cubans of all ages and professions hitchhike, any one with any sensitivity does not pass them by. Besides the wonderful service they offer as guides--invaluable in a country where road signage is minimal to non-existant--you have a chance to talk with a true cross-section of society (assuming you speak Spanish). And they are wonderfully hospiable. While they can't invite you to stay in their homes (foreigners are allowed to stay only in places licenced for such, and a homeowner who hosts a foreign guest without such a licence risks a heavy fine and even loss of their property), many will invite you to coffee, a meal, a visit around their community. There is no better way to get to know the island, top to bottom, east to west.
Bicycle is an equally wonderful way to do a road trip around Cuba, as roads are relatively good, especially for bikes, because once outside major cities, most routes have little traffic. One exception would be the heavily-trafficked Carretera Central which runs down the hot middle of the island and through a number of provincial capitals between Havana and Santiago. It carries a lot of truck traffic which makes it unpleasant for cyclists. However, it's quite easy to jump on a Viazul bus with your bike for the boring bits, and once you're into a scenic or otherwise interesting area, hop off and continue riding.
If you do your road trip in a motorized vehicle, lodging is not much of an issue, as you would rarely be more than an hour from hotel, villa, campismo, or a selection of casas licenced to host foreigners. But if traveling by bike, you have to plan your trip a bit more carefully, to make sure that you know where the places which you can legally stay are located along whatever route you're traveling. The lack of advertising in Cuba means that these are not always self-evident.

Thanks for all the tips, ttjpdo!
A followup question re Carnaval: I do speak Spanish and had no trouble arranging a casa to stay in by simply chatting with people on the street the last time I was in Santiago. But that was 9 years ago . . . Word on the street (in Havana last summer) was that Santiago is much more heavily visited by tourists now (and perhaps particularly around Carnaval?), so I am curious if I would need to arrange housing in advance? Any thoughts on whether it's good to get there before the festivities begin, or just in general about which dates in July would be best to be there?
As for the drunkenness issue, I am definitely one who likes to drink, but I also like to dance (casino, rueda, etc.). So a huge drunken, dancing party is a dream come true for me. A huge, public display of extreme drunkenness where everyone is too trashed to dance and/or getting pushy and violent (thinking of Carnival in some other countries) is not my thing, although my gut instinct is that this latter, less pleasant scenario would not be the case in Santiago. Am I right?

SMALLNWISE: Others on the branch may have a different opinion on this, but I do not think there is any such thing as a Cuban too drunk to dance. Certainly I have never been anywhere in Cuba where the locals were too trashed to dance--well.
Pushy and violent? Well, no probably not. Although Santiago being more Caribbean than Latino, and Caribbean folks being more outspoken and direct, in certain ways, causes some people (not me) to think of them as "pushy"--even when they're not drinking. But you have been to Santiago before; it it didn't bother you then, it probably won't bother you now. There is a jinetero scene in Santiago, as there is, in fact, all over Cuba. There was a long thread on this a page or two back, which you might want to skim. The consensus (I think) was that just how aggressive the jineteros varies A LOT, depending on how much it is being cracked down on, or not, at a given time. I have been there when it was very bad, and also when it hardly seemed to exist at all.
Pickpocketing and the like is widespread in all street festivals, the Santiago Carnival being no exception. Don't take anything with you into the crowd that you would get upset about if you lost. But violence, not much, I would say. Maybe there is fighting, sometimes--usually, when there's too much drinking. But I don't recall any.
If you are planning to stay in a licenced casa, you should know that there's really no such thing as "arranging in advance." I mean, you can ARRANGE in advance, but since casa owners have no way of collecting from you in advance, they have no way of knowing whether you will actually show up, so they will almost certainly rent out the room to the first person who shows up. So I think what you might want to do, especially around Carnival time, is go a few days early and nail something down. (By renting it in advance.) You could use those days leading up to Carnival to make local friends, which might make the Carnival that much more fun. Also, if they are friends, and not "frens" (the ones who approach you in the street with, "Hey, my fren,"), they will probably look out for you.
But back to lodging, it's pretty certain that places which are listed on the internet will fill up quickly, but there are a lot of other casas, which aren't promoted on the internet, that are slower to fill up. Lots over around Avenida de las Americas, both sides of the boulevard and for a few blocks back--this in the general vicinity of Hotel Santiago and Hotel Las Americas. Also some very nice casas in the suburb of Vista Alegre. They will naturally be much quieter than anything in city centre--this assuming you do not intend to party 24/7 during your stay in the city, and might want to get some sleep now and then.

I would say the carnaval is nothing spectacular; it's like many people gathering and dancing, drinking cheap beer on the street and there is the odd fistfight among drunk macho men who can't land a fist correctly. It's not dangerous but I wouldn't call it spectacular, either. Do not expect to see fancy costumes, carriages and the like. It's more like a street party. Not too many tourists around. But expect to be hassled a bit, Santiago is somewhat more prone to hasslers than other places, although opinions very on this.
If you have to choose between the two, the roadtrip is infinitely more interesting in my opinion. It does cost a bit, but it's well worth the ffort, time and money. Pick some off the beaten track places, polish your Spanish and hit the road.

Ttjpdo # 3: “If you are planning to stay in a licenced casa, you should know that there's really no such thing as "arranging in advance."
Ok, finally after many months I have found something I disagree with you about…lol…

Yor # 4:” Do not expect to see fancy costumes, carriages and the like.”
Another missing feeling from the 80’s where they were exactly like that. Hopefully when 1 cuc = 1 cup they will have a glorious come back. Go figure when....

Truetown: I actually was not speaking for myself or any of us who regularly go to Cuba when I said "there is no such thing as arranging in advance." Those of us who personally know casa owners, if they say they will have a room for us, they will have that room ready and waiting. But I do not think a first-time visitor to Cuba, or anyone who does not have a "special relationship" with someone can count on the room they arranged being available when they get there. It stands to reason that if casa owners can't count on a visitor showing up, visitors can't count on the room being there if they do show up. We have even had reports on this branch of a room arranged by the famous Pototo being occupied when the tourists who had reserved it arrived.
Anyway, I did amend my own comment "no such thing as arranging in advance" to "You can ARRANGE in advance, but no way to know" if the room will actually be there when you arrive.
If you, or any other poster to this branch can GUARANTEE that a room reserved (without pre-payment) will in fact be waiting for a visitor when s/he arrives, then I think you should post that information when an OP asks how it can be done. And screw the other posters who say you shouldn't do that because it would be "advertising." If it's info people want, and you know how to do it, post it. Or at least tell the OP to PM you, and provide that info to them privately.

Thanks ttjpdo although I was just kidding your subsequent responses are always more accurate than the previous ones. You are a great help to all: new and old time travelers to Cuba IMHO.
Just allow me a comment:
In this country PRESTIGE is king as money sometimes can’t solve things you can with it everywhere else…