Welcome to Day 2 of Planning A Trip!
The very first thing I do when it comes down to planning is booking the flights, which may seem sort of obvious to some, since they tend to vary more in price than anything else. They’re also much harder to cancel than a hotel reservation, so booking the flights means we’re really going on a trip!
I always do quite a bit of Googling when I’m looking to go somewhere. Some frequent searches are “Best Time To Visit Puerto Rico” or “Monthly Weather Charleston”. I always like to cross reference the search results of these with the Google Flights fare schedule, and it usually yields some pretty good information. The average temperatures and number of rainy days sometimes scarcely vary between the busiest travel times and the shoulder season, which allows you to save some money and travel during a slower season that’s only a few degrees cooler.
I always at least try to fly loyally. Even when I know I’m going to fly JetBlue, I still use Google Flights while doing my research. I love how visually everything is laid out, and you can really see how the price varies between dates. I just make sure to use their awesome filters so I’m only seeing nonstop flights from JetBlue.
I’m also at a place in my life where I’m traveling domestically pretty heavily (trying to take advantage of that TSA Precheck!) and not as much internationally, which is an entirely different animal.
To be quite honest, the early steps of planning (re: hotels and rental cars) are hands down my least favorite aspects of traveling. I really don’t care about hotels much for 95% of my travels. Since I don’t do much beach or resort travel, there’s no reason to spend thousands of dollars per night on somewhere that essentially just needs to have a bed and a shower.
Since I’m looking to explore the location I’m in and not the hotel, I tend to also travel pretty loyally to Marriott, so I always check their website directly first to check to see what kind of rates they’re offering (for more about why I travel loyally, check out my How I Afford To Travel post!)
Depending on the location I’m traveling to, and whether or not I have a car, I’ll generally consider staying outside the city center to get $100 off the room price and free parking. In places like Austin this has worked greatly to my advantage, especially since we were only actually spending one day in Downtown Austin. In Nashville, however, Mac and I were mostly exploring the Gulch and Broadway, so we opted to stay right downtown within walking distance of almost everything, taking a few Ubers when necessary, since it was so much cheaper than renting a car and staying farther away from everything we wanted to do.
The last step of hotel research that I do is all about bed bugs. It’s important to preface this by saying my germaphobia in general is what my mom calls “neurotic” and what I call “thorough”. I wipe down every surface in the entire hotel room with an antibacterial wipe as soon as I get there, and I absolutely never walk around on a hotel floor with bare feet. This sort of paranoia extends into bed bugs as well. The internet is super helpful in finding out if the place you’re going has any sort of record with bed bugs. In places like Manhattan and San Francisco, which see so many travelers from all corners of the globe, it can be really hard to find an affordable hotel that has zero reports, so something within a three or four year grace period I’ll usually let slide. This is just another reason I prefer to stay at a Marriott over an Airbnb when possible, because big hotels tend to have facility management and protocols in place if a traveler brings along some unwanted friends; plus, their reputation is on the line. It’s always advised to do your own bed bug investigation once you check in.
For rental cars, I don’t shop loyally as much. I’ve found Hertz to generally have some of the best prices, especially if you have AAA. While I was under 25 they waived the young driver fee which was huge (plus, you can add on a second driver for free if they are also a AAA member). B tends to also get some pretty great rates with his “perks at work” program, so those can be worth looking into as well.
I also think it’s pretty important and responsible to start making a travel budget. Once I have an idea on the most affordable options, what kind of attractions we’re doing, and such, I’ll start to break down the budget. For San Francisco, it looked like this.
Different people will, of course, have a different idea of their budget based on varying priorities (some might think budgeting almost $40 for coffee is ludicrous, but exploring coffee culture is important to us, especially in somewhere as significant in the coffee world as San Francisco!) I also way overestimated for transportation, quite frankly because I wasn’t interested in spending time researching those costs and we walked a lot. But it’s always better to overestimate and allow yourself some wiggle room!
Next up, the more fun part of planning, is deciding what to do! When going someplace totally new, it can be overwhelming trying to understand giant lists of neighborhoods, attractions and restaurants. Google Drive is invaluable in these early stages. It gives you an opportunity to put all of the information you’ve found down in one place and go back to it no matter where you are. Plus, when you’re traveling with someone else you can both work on the planning doc together! In these early stages, I’ll write down everything I find, highlighting the neighborhood next to it. Then later on down the road, I don’t have to go back and find this information when I try to find a place to eat after the attraction. Then, once I’ve found pretty much everything there is to find in the destination, I can start eliminating things until the list gets down to a more manageable size. After that, cross-referencing the attractions and restaurants can help me prioritize everything and get an idea for what is manageable, and what is actually 2 hours outside of the city!
I use blogs and Instagram accounts quite frequently in my research process, especially in looking at finding restaurants. Where locals go to spend their hard earned cash on a Wednesday night is exactly where I want to be eating on vacation. Eater is also one of my favorite resources, to find out what’s popping right now, or where the quintessential cuisine of your destination can be found.
I can be somewhat of an obsessive planner (or a control freak, depending on who you ask). I spend so much time researching a destination before I arrive to make sure I eliminate things I don’t care to see, aka things that are frequently the top results on Google. I’ve tried to develop a balancing act of having a plan, while not overbooking myself to the point of every sight just becoming an item on a checklist.
My sister and I travel best when we have at least some sort of a schedule. I love finding the local food scene, but Michaela has celiac’s disease; so this could lead to some stressful and hangry moments were it not for proper planning beforehand. When we went to Nashville, we did a broad overview of what each day would look like, so I could spend some time finding gluten free places in the area that worked with Mac’s dietary restrictions, while also letting me explore Nashville’s culinary identity. In the end, it looked something like this.
Looking at this schedule, it almost looks like we were jam packed for the entire trip. But realistically, we still had so much time to fit in other activities around this schedule (we even went to two more museums than we planned!) We’ve been practicing getting in each other’s faces for 23 years, so needless to say we can be pretty good at it when the hanger starts getting in. We knew after many trips to NYC together that having an idea of what we were doing each day – and having a place with good celiac reviews nearby – was going to make our trip the best and smoothest it could possibly be. When visiting familiar destinations like NYC, we’ll usually just pick somewhat of a starting point for the day and work our way to the end point on a very loose schedule.
A look at how I planned to go to San Francisco with B is a lot different, but the core Google Drive is still there!
Once we decided to go to San Francisco, we quickly realized that this city is just as expensive as everyone says. All of my normal planning avenues were failing me. We didn’t want to stay outside of the city when we wouldn’t have a car, and even the lower tiered Marriott’s were more costly than I would have liked. I was ready to book a room at the chic Hotel Zoe, when B found an amazing price for an Airbnb in Nob Hill. Since it was more centrally located and in more of a local neighborhood, we decided it would be a better option for us than staying near Fisherman’s Wharf.
I desperately wanted to go to Yosemite, but we quickly realized it wasn’t really feasible this trip. Instead, we opted for some more time spent outside of the city in Napa, Muir Woods, and Sausalito; and decided to save Half Dome for its own special trip. A fair share of logistic hurdles arose while planning (making sure we were around to hang out with Bryan’s sister and brother in law on the weekend, not leaving our suitcases in the car EVER to avoid break-ins, etc), but with some time spent arranging attractions like puzzle pieces, we found a way to fit in everywhere we wanted to see without feeling rushed.
With B, food isn’t as much of an issue as it can be with my sister (through no fault of her own). Knowing we could both eat anywhere, we decided to plan our dinners ahead of time, so we could find the best meals at the best prices and enjoy some date nights during the trip; figuring we would be able to grab a burrito or something quick for lunch along the way.
Sketching out a loose itinerary was particularly helpful for this trip, since we had to book some things in advance. Once I compiled a list into (you guessed it) Google Docs of all the activities available to us, we were able to funnel everything into priority attractions, secondary attractions, and the things we really didn’t need to see. We tried to plan only 2-3 things (including meals) each day, giving us additional time to explore as we went, but making sure we didn’t miss anything we really wanted to see. Then, depending on how each day unfolded, we could pick items from the secondary list to hit up, should we find the time.
A great tip I’ve found for trying to plan out your travel days is to always look at tours. Even if you don’t plan on taking one, tours can give you a good idea of what you can fit into one day (for example, Muir Woods and Sausalito is a popular tour bus combination, so I knew we could do them both in one day).
Make sure you stop by next Wednesday for the third installment of Planning A Trip!
(The photos in this post were all taken in Paris!)
xo, C
The Sol Compass 