Trying damn hard to stay frugal in San Francisco

My wife and I have a looming trip to one of our favorite cities, San Francisco, to celebrate the birthday of a friend of ours.  But, there is no getting around the fact that San Francisco is not the cheapest place to tootle around in, and our friends of ours are definitely not on the fast track to retirement.

So, what's a frugal retire by 40 guy to do?  How am I supposed to NOT be a complete tool with our gang, have some fun and stay focused on our drive towards jobless bliss?

Well, my wife and I have tried our best to make sense out of maximizing our fun in one of our favorite cities - which, of course, will include paying for a few drinks for the birthday boy! - and minimize the costs of the trip so we stay within our budget. This is an art as much as it is a science, so there isn't a right or wrong way to approach this.

The key is to be real with yourself.  Know that you will probably spend at least some money that you wouldn't ordinarily spend, and as long as you're reasonable about these expenses, it's okay.  Financial independence is a process.  Just like Superbowl teams in the NFL lose games along the way, you too will find yourself spending more than you probably should have at times.

We try to make up for our mistakes by living more frugally after a larger expense - or, if we see it coming, pre-frugalize our life a little more so things don't get as "extreme" after.  If you are dedicated to retiring early, it'll happen.  Avoid the tendency to stress out over a few larger expenses in the year.  That's just life.

Our San Francisco goals are simple and achievable:

• Live VERY cheap until the trip - We know that we're going to spend more money during our weekend in San Francisco than we ordinarily would hanging around the house.  Knowing that, we are living as cheaply as we can now to build up enough of a buffer that, hopefully by the end of the trip, we will still be around our normally-budgeted expenditures.  For example, we usually budget some going out to eat money during the month, but we aren't touching a penny of that money until we get to the "city by the bay".
• Use Uber instead of a rental car - I have never tried Uber, but one of our friends who will be in San Francisco with us has.  Parking in the city is extremely expensive, so there is no way that a rental car would be the most cost-effective way to travel during the weekend.  A taxi might have worked as well, but quite honestly, we're going off of the recommendation of our friend that Uber is the cheapest option.  This might save us a hundred dollars or more in parking by the end of the weekend.
• Split the cost of meals - Although it might be easier on the ol' cranium to just assign one person to be the designated payer for the evening's dinner, this tends to wind up more expensive than simply splitting the cost of the meal.  Why?  Even though others at the table know that their turn to pay will eventually come, diners still tend to order more expensive items because they are not paying that night (psychology is interesting, isn't it?).  In the end, we will all spend more money if we do not split the check.
• Brunch!  One of our days in the city will consist of a nice brunch on a cruise around the Bay.  While the cost of the cruise itself is certainly more than a lunch, it remains far cheaper than the cost of a separate breakfast, lunch and whatever entertainment we'd otherwise be doing during that time.  Thus, we eat like absolute fucking kings while on the cruise to get our money's worth and enjoy the savings.  Win-Win, I'm In.

This is our first real trip with those outside of the family since we decided to start living frugally to achieve financial independence at a very early age.  It will be a test for us to determine what works and what doesn't, but we reasonably believe that our goals, outlined above, are a good target to aim for.  Minimizing food costs will be most important, followed by keeping local travel expenses down as much as possible.

Do you travel on the cheap?  What tricks do you use to keep your expenses low, but fun high?