I'd be able to tell ya after this year if there is a comparison... I'm going to both, instead of just Gulf...

From what i understand, they both have their ups and downs... I really don't know so much about Pennsic aside from the fact that its frickin' huge because it has a lot of tertiary or satellite groups that attend... I know that Gulf is basically 100% scadians, and is a lot of fun...

Well, I went to Pennsic this year and I've been to a bunch of Gulf Wars.

One pro of Gulf War is that if you hook up with someone you really like, it is easy to hook up with them again because it is smaller. The con is that it if you hook up with someone you want to avoid, it is harder to do than at Pennsic because the crowds aren't quite big enough to hide you at Gulf Wars...most of the time.

One pro of Gulf War is that you are able to party hop a lot easier than at Pennsic. The distances are smaller so you can hit several parties several times in one night...or just find a good one and hang out. And you don't have to reserve energy to climb out of the bog at the end of the evening at Gulf War. It is mostly flat.

The biggest pro for Gulf War, for me is that it is easily doable by car. Pennsic is too far away to not make it a MAJOR expedition. I have to add three to four days just for travel whereas Gulf Wars is a long drive away and I can get there and set up camp the same day if I want to.

The biggest con at Gulf Wars for me is the showers. They suck. I don't know that much about the showers at Pennsic because they allow you to have your own showers and I was lucky enough to camp with someone using a 40 gallon hot water heater for our shower. The shower situation at Gulf Wars is the biggest negative for me. But then, I sort of have a shower fetish (I have a walk-in shower that will fit three people and has jets!). I hate having to take a cold shower when it is cold outside.

The weather is good at both places as far as I'm concerned. Yes, it rained at Pennsic this year, but it wasn't so bad. It was hot, but not like Ansteorran hot...for the northerners, I can see this being an issue. I love the weather at Gulf War because you usually have a reason to snuggle up with someone at least a few nights of the week.

One of the pros of Pennsic is the shopping. It is a shopping mecca. Gulf Wars is good but it isn't the same because it doesn't have the history ...but it is getting better all the time.

I just think things are a bit friendlier at Gulf Wars than at Pennsic. It is the difference between the big city and a small town. It is exciting to visit the big city, but Gulf War is home.

After 10 Pennsics and 11 Gulf Wars, both as a atendee and a merchant. I can tell ya that there are definite differances between these wars.
Which is better is simply defined by individual taste and interpretation of "The Dream"

Gulf Wars is a BIG weekend event run by and for SCA folks who wish to continue the "dream"
Pennsic is a 2 week quasi-renfair that was SCA inspired but has been morphed in to a cash cow for some and a fantasy freakout Galaxy-Qwestairan Woodstock in garb for others. Personally i call Pennsic "Scadian Disneyland"
That being said.....I happen to LOVE both.
I have been fortunate enough to attend the "big 4" Sca wars for several years running (Pennsic, Gulf Wars, Estrella and Lillie's War) and feel that all have both good and bad attributes. What you have to ask your self is what you want to DO at these wars. The following is what I usually tell others who ask about the wars they have not attended.
Pennsic..The Good
Ya gotta go at LEAST once. Pennsic is THE top of the line event. If it's SCA, it's at Pennsic. Battles where fighters can be counted by the THOUSANDS, a merchant area that's 400+ and take DAYS to see, classes that number in the DOZENS daily, evening parties that can draw numbers higher than other wars' entire attendance, camp setups that rival Hollywood sets.....on and on. The diversity is staggering. Go! Go to Pennsic ! Then decide if it's for you.
Pennsic...The Bad
My only real bitch about this war is the lack of sca "moments" that I get. Pennsic is SOOO big. It's also VERY mundane looking. While many try (quite successfully) to keep their camps period looking, this war just does not have the "feel" of an average SCA event. If your game is marred by having non-period items and speech intruding, think twice before you go..(but DO go!)
Gulf Wars...The Good
Ok my home war so I'm a bit bias. However, in my opinion GW has THE best fighting. Not only because the number of fighters present at any GW is PERFECT for fun and learing, but also because it's the best war for the spectators. I think Gulf is the most laid back of all the wars. Classes are good and the subjects diverse. Also the permenant encampments allow for a level of A&S that is not present at any other war. Note.. the"period encampment" and The Green Dragon are VERY cool.
Gulf Wars..the Bad
Friggin' golf carts! they're (IMHO) not needed and take away from the "dream"
Estrella..The Good
Wanna fight like it's REAL? THIS IS YOUR WAR!! Estrella has the most flat out, no holds barred "gonna beat yer ass' fighting I have ever seen. While past Estrellas have been plagued by dust, dirt and a horrible lack of space, the new site is MUCH better. (there's even a BAR!) While it's a VERY long drive for us, we like the war overall. It's pretty 'period" the people are great, and the fighting is awesome to watch.
Estrella..The Bad.
The site is an organic farm, so the disposal of waste water is strictlly controlled. While the war does bring in shower trailers, they're still inadequate to the number of people. Even cooler water was NOT supposed to be dumped on the ground...Overall, it's a new site with some weird rules, but even with the long drive, it's worth it.
Lillie's War. The Good...
There's more good about Lillie's than I can say in a short missive. The people are great, very helpful and quite devoted to the "dream' without being oppressive or judgemental. The site is (IMHO) the most beautiful site i have ever been to. The classes, while fewer than other wars, are VERY well researched and presented, (not to mention complete) and to me most importantly, ther are NO golf carts, NO streetlights and very few mundane things about to quash your dream. 'SCA moments" are VERY easy to have at Lillie's
Lillie's..The Bad
Ok, we've all heard about the weather. It is after all, the midwest in high summer. The thunderstorms can be quite impressive to those who have not been thru one. High winds and violent thunderstorms are possible, but not as frequent as the horror stories make them out to be. Bring wet weather gear, stake your tent down well, and use common sense and you will enjoy this war.

Hmm, sorry this ran longer than I wanted it too..

Gulf Wars has a lot of things going for it. The Green Dragon is flat out the coolest thing ever made. Great atmosphere, entertainment and people. Although I have been attending as a merchant for a few years, I can never seem to find any large parties/badric circles/shows like Pennsic has.

I'm sorry to say that the food is a bit sad a Gulf Wars. There are a few bright spots, but overall its a bit pricey and a bit limited.

You are right that mundane items can intrude at Pennsic, but I think irs actually getting better in some ways each year. Each year there are more and more period pavilions in camps and on merchants row. Gulf Wars had the Dragon, Pennsic has Casa Bardici and Vlads.

The showers (and indeed the condition of the buildings in general on site) at GW are horrible. I know Katrina did a lot of damage, but its been two years now. Some of the structures on site actually look structurally unsound to me. At Pennsic, your camp isn't considered half-civilized unless you have your own camp shower and a semi public bar. Is this not allowed at GW?

I can't speak as to the fighting but the Fort battle looked a bit more animated than the one at Pennsic.

I disagree that Pennsic is some kind of public theme park. I think one of the biggest complaints people have are the stupid glow sticks and rave LEDs that are sold at the Coopers store. Honestly, those bug me and our camp (a camp that devotes itself to slackitude) simply won't allow you in with them. They have their uses. (We drop them in the porta johns as a navigation device) But otherwise, no.

Oh course I am a bit biased. Attendance at Pennsic: 19 years Attendance at GW: 4 years.