For the last few years, reboots are all the rage in the entertainment industry.  Old movies are becoming new again, sometimes claiming to be better than the original.  What if you could do the same with a trip? Have you ever had a trip that you wish you could recreate from the beginning the same way Hollywood does its movies recently? We did this with San Diego. Traveling was better the second time around!

The First San Diego Trip

A few years ago, we paired up with another couple for a quick trip to sunny fall San Diego, California.  It was our first couples’ trip and it seemed super exciting! We planned everything around watching the Chargers (back when they were in San Diego) play the Denver Broncos and it all sounded so fun. While the game was fun, the rest of our trip didn’t work out as planned.  Reflecting back on it, I wouldn’t say it was a bad trip, but it wasn’t a great one either.

Catching a little NFL action at the Chargers vs. Broncos game in San Diego.

What we did wrong:

  • We planned a trip with another couple with whom we had incompatible travel styles.
  • Unfortunately, this meant we didn’t spend our time in San Diego the way we would have liked.  
  • And, as a way to break up some of the monotony, we decided to go to SeaWorld.
We have grown a lot as travelers and no longer patronize places like SeaWorld.

This first trip wasn’t necessarily wrong, but it just didn’t fit us and our travel style.  Recognizing this fact early on in our relationship has allowed us to shape future travels since that time.  We learned pretty early what we do and don’t like in our travel pursuits. Our first trip to San Diego played a role in this and was a great learning experience.

The San Diego Reboot

In hopes of spending some time by the ocean, we returned to San Diego, in late spring, by ourselves, 5.5 years after our first trip. Our reboot trip to San Diego was so much better because we made some key changes in our travel itinerary and style.  Admittedly, there are hundreds of different types of travelers and travel styles. It is not a one-size-fits-all world.  But it is important to find out what travel style works for you and rock it. For most trips, we like full days full of sightseeing, activities, and good food. From the place we stayed to the things we did during our second time in the city, we enjoyed this trip much more!

What We Did Differently


On our first trip ride sharing wasn’t readily available. So, we took taxis everywhere we went. Luckily there were 4 of us to split the costs, but this is still expensive! On our reboot trip, we primarily opted for Uber to the few places we couldn’t walk. The downtown area is highly walkable, so we clocked a lot of miles on foot, as usual.


We stayed at Paradise Point Resort during our first trip. This area is beautiful, and we enjoyed our stay here. However, it is in the Mission Bay area which is located a good distance from the core of downtown San Diego. We splurged a bit on our second trip and stayed at the massive Manchester Grand Hyatt right at Seaport Village for our second visit. While this was more expensive, the hotel offered many nice amenities, and the central location was within walking distance to nearly everything we wanted to see in the immediate area.


We were really excited to try some of the excellent food San Diego has to offer. We weren’t able to experience much of the food scene on our first visit. Our second trip allowed us to eat at a variety of hot spots downtown and in the Gaslamp District, as well as in Little Italy and even on Coronado Island. It was great to experience a better range of offerings.


As mentioned earlier, our first visit was centered around a football game. We also decided to visit Seaworld to break up some of time. We have grown a lot since then and made choices on our second trip that were more responsible. Changing things up also allowed us to experience more in our time in San Diego. Not only did we venture further into the Gaslamp Quarter and Little Italy on our second trip, but we took the ferry to Coronado Island and spent a day at the beach. We also enjoyed exploring Balboa Park. Of course, we engaged in daily strolls around the harbor, Seaport Village, and the Port of San Diego too.

Plan Your Reboot Trip

Have a trip that you might like to rewrite? Determine what about it you just didn’t like and things you wish you had do-overs on! Once you know this, then you can start to narrow down the things that did or didn’t work for you. Things that did work, you may or may not want to repeat. If you’re looking for an entirely new experience, try staying in a new area, planning new activities, and eating at the places you didn’t make it before. You may want to consider a new budget or visiting at a different time of year.

Because we want to see as much of the world as we can within the limits of our vacation days, we have been avoiding returning to the same places multiple times.  However, there are exceptions. Our first experience to San Diego warranted a second trip. We had so much fun and I’m so glad we were able to do a reboot trip. If you have ever found yourself in a similar situation, you might want to consider planning a reboot trip too!  If Hollywood can rewrite a happy ending to a movie, there’s no reason traveler’s can’t rewrite a happy ending to a trip!

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  1. Excellent post with lots of great ideas for a reboot trip. Many times, people will say, “if only we could redo the trip to. . . .” This post sets one’s soul free to do exactly that!

  2. Glad you were able to plan a “reboot” trip! It is true that we learn from our travel mistakes the first time around.

  3. I’m so glad you had another opportunity to visit San Diego. It’s a terrific area with so many things to do and places to see. One of my favorite things was strolling around Balboa Park and checking out the museums.

  4. Isn’t it great to grow as travellers and understand what you really want and use your time well. It’s so nice to have someone who enjoys travel in the same way as you do!

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