That's the biggest downside for me of working at a small company. Only one person can take a vacation at the time and in those type of companies there's often a strong hierarchy. Which means if you're the new person (and you can be the new person for 10 years) you're basically screwed. I'm lucky that my coworkers don't care about christmas, so I get to take the week between christmas and NYE off, but I didn't have a summer holiday. Coworkers have kids, so they want to spend that time with their kids (understandably) and I'm stuck in the office working overtime for the entire summer.
Imma, the fall is a lovely time to travel. Could you plan something for then so you have something to look forward to in the dog days of summer? I used to go to DC a lot. The best time was in early September. Lovely weather, no lines, and shoulder season rates. The kids were back in school and hadn't had time to plan their rampages field trips yet. It was heavenly.
One of the great joys of FIREing is that we have discovered that the worker bees have a very fixed window to enjoy a whole lot of opportunities when it comes to recreation and tourism, and since you are post-unemployed, you get to enjoy the best places during the times when the masses have to stay chained to their desks. We relocated to the heart of the Amish country in PA, earlier this year. We had been visiting the area for two decades, and had a huge concern about moving to a place that sees eight million tourists a year. We had spend many Saturdays in years past, crawling in tourist traffic, and didn't want to turn that into a lifestyle. After a few months of being here, and unwinding a bit, we finally figured out that the ONLY time our neighborhood sucks is from about 10AM to 6PM on Saturdays, from mid-spring to Christmas. That is less than 10% of the time, and we now have a very good handle of every farm road, and back alley in the land, and how to use them to get around the lines of out of state cars that stack up on those days. We just smile when people from out of town say, "you live in a beautiful place, but oh, God, that traffic".
We have also used this concept as we spent a few years roaming around the states in our motorhome, and rarely did anything the would potentially involve crowds on a weekend, or peak times. We made darn sure to find quiet places to hide on the big summer holidays. The wonderful world of RVing can really turn to shit on holidays like the 4th of July, when the campgrounds are 110% full. Occasionally full of families with a litter of screaming little brats and a $300 pop-up camper that blew two tires on the way there. Due to awesome parenting and social skills, they then decide that the way to address the sugared up, screaming little spawn, at 11pm, is to make the bonfire bigger, kick up the drinking a notch, and turn up the sorry-assed country music they and half the county are "enjoying". The amazing part is that, by the last week of August, chucklenuts like this are long gone, and great places are very lightly attended. If you really want your experience to be wonderful and uncrowded, push the limits and get there a week or two before the places are about to roll up the sidewalks for the winter. Places like the Black Hills, SD, or the coast of Maine, absolutely kick ass in the second half of September, and 80% or more of the crowds are gone. Yellowstone is another great example. They have been setting attendance records every year, and by noon on a typical mid-summer day, the place looks like a street in Manhattan. Get there the week after labor day, and it's like another planet. Without kids to accommodate, being able to take time off in fall and spring is a gift.