A friend recently called me “The Human Planner” I giggled because it’s the first time I’ve heard that about me. But when I stopped giggling I thought about it, and she’s kinda right. I plan everything.
One of the many things that have to be in order is when I decide to travel, things like what to carry in my bag, an itinerary with details like flight information, my stay address and contact info, and of course what I actually want to do, see, eat… all broken down into days.
Yeah, it sounds like a lot, and most likely irritating. In my defense it’s more like a guideline, so I know where to start off my day.
The worst part of being on vacation is being limited to time. So why would I want to start my day not knowing what I want to do, which means I’ll be wasting time thinking about where to go first and not knowing if it’s open or not. Let alone on how to get there.
In my personal experience these are a few things that work for me:

1. When should I travel? What are the best days to purchase?
   Again, in my opinion, we all have our things that work for us. There are  many who say booking your flight a few weeks before is usually the cheapest, there’s another myth that says Tuesdays at 7am is when  flights are the cheapest. Myself, I like to hunt for the best prices, and yes, I use many websites to do so. Comparing prices from Jetblue, Delta, Spirit and many airlines can be a little easier with expedia or websites similiar. One of the things that I like to use is Hopper. This app  “watches” flights for you, and let’s you know which days are cheapest and higher in rates by month and by color.  One of my favorite tricks is to open up two Jet Blue’s Fare Finder tabs side by side, and pick a one way trip. One tab gets the “from” destination while the other tab get’s the “to” option. This way i can see and play around with dates compared to prices.
   For example, let’s go to Puerto Rico:
2. I often get asked “how do you have and get so many days off of work?” How do you find the time?
   Every job is different, and I’m blessed to have one that let’s you accumulate Paid Time Off days according to how long you work there. The longer I work here, the more days I accumulate. So, If I’ve been working for a year, every month I gain a day of PTO time. Not counting the first 3 probation months, 12-3=9 PTO days that I have earned. After the first year, I earn 1.66 days or some random number like that. so in 2 months, instead of earning 2 days, I’ve gained 3. The longer I work here, the more I gain. Next year I’ll probably be gaining 2 days per month.
   Every job is different. Find out what your job offers you. Don’t be afraid to have a talk with your Human Resources Coordinator and see what benefits you gets that you actually don’t know about.
   Another thing that I keep in mind, is not calling out. (Even when I’m sick) In my mind, if I’m sick, I’m going to be sick anywhere and anyway… I might as well just go to work and not waste one of my hard earned days, doing nothing at home. (My coworkers will have to deal with all the coughing.. I know, not nice)
   Another thing to keep in mind is to manipulate your days off. Yes, this sounds mischievous. but I promise it’s not. Most jobs have holidays where you don’t have to go to work.  For example: Labor day is a day where I know I don’t have to go to work. So if I can incorporate a vacation around that time, that’s a day I don’t have to waste and can have an extra day to actually have fun and enjoy myself. Extra points for you if you sneak in your days off too.
   I only work Mondays through Friday. Let’s say Labor day is on a Monday. If I’m smart about it., my flight can be on Friday, right after I get out of work. I have Friday, Saturday, Sunday and Monday that I don’t have to worry about requesting days off. If I want to stay longer, and let’s say use up more time.. I can fly back home the following Sunday. I only have to use 4 PTO days (Tuesday-Friday), for a 10 day vacation. Isn’t that like secretly genius!?
3.  How can I afford to travel all the time?
   Yes, traveling is very expensive.  I wish I was rolling in dough, throwing dollar bills up in the sky.. but the way I get paid, and the way my bills are set up… child please. I’m a firm believer that if you really want something bad enough, you will find a way to make it happen. If I get paid bi-weekly, I budget my bills, and spending expenses accordingly. If I take out $100 every time I get paid and set it aside (and my advice– in cash and leave it at home so you won’t be tempted to spend it)  You better believe that 6 months in, you just saved $1,200.  You can take a nice vacation with $1,200.. and if you want to save more or less you can… or if you need more time, give yourself more time. Every person is different, every paycheck, responsibility is different.
   Also, I try to limit my spending when I’m saving. Which sounds pretty obvious, but I nice reality check that I give myself is — Would I rather be spending my money on dumb stuff here, or cool stuff somewhere else? ——-That usually stops me dead in my tracks.
   
4. Where can I  live where traveling?
   Everyone has different preferences. Many people appreciate hotels, while I don’t mind them.. they’re not my go-to. I have never had an issue with Airbnb, and they have done me well. I’ve used them for almost every single trip, Puerto Rico 4 times, Cuba 3 times, Paris, Madrid and others.
   My mindset when traveling is to live how the locals live, I want to experience the culture and I can’t do that from a fancy hotel room. When I stay in an airbnb I get a homey feel to things. One of the best things about airbnb is also the fact that you get to earn credits when you refer someone. They save money, and I save money on my next trip. ( So if you guys haven’t signed up and do, please use my link when booking, I would appreciate you forever. My friend Cintia recently when to Cuba, and we she stayed at her airbnb she saved $40, while I earned $20 off my next booking, so when I went to Bermuda, I already had a $20 off coupon waiting for me at check out. It’s a win-win!
5.  Where do I pick where I should stay?
   Alright, so you have your flight picked out, you’ve saved up some cash and you decided you’re going to stay at airbnb (hopefully you used my link too) now the question is what neighborhood should you stay in? There are so many options, how can you possibly decide where to stay. Super easy.
   This is probably my best tip that I can give you.
   First off, start making a list of all the things you want to see. Maybe all the places you want to eat too.  After you’re done with your whole list order them in order of importance to you. What are the places you possibly cannot miss? Will you go home and regret that you didn’t see something?
   For example, when going to Paris, on everyone’s list is the Eiffel Tower, but is there anything around that neighborhood you want to see as well? Maybe the Arc de Triomphe?
   When you make a list of all the things you want to see, get on google maps or even an old school map if you like to be cool like me. Mark down all the locations from your list, and the neighborhood that has the most points win. You save so much on transportation costs because you’ve chosen a place to live that’s close to all the venues you want to experience. Plus you can always visit the other locations by neighborhood.. I’ll explain in the next point.
6. How do I make an itinerary?
   You’ve chosen where you want to stay, and now it’s time for you to have some order. Try making a list by days. Add the Date and the information needed. If my flight is on August 16th, I’m going to need to write the flight number, the time of my flight, what time is boarding, my confirmation code, and other information I might need like my terminal, gate or even seat numbers. I know we have boarding passes, but sometimes having everything in one place is very helpful. Make sure you list the time you arrive as well. Estimating time after is helpful as well. If my flight lands at 10pm, I’ll probably need time to go through customs, grab my bag if I checked it in, and figure out how I’m getting to my hotel or airbnb. (Make sure you google how long the taxi drive is as well, or if it’s even worth it. Public transportation can be easy to figure out and way cheaper than a cab. If I landed by 10pm, I should be at my destination around 11pm, and instead of you having to look through emails, if you wrote down your address in your itinerary you already have your address handy. Writing down your hosts name is also a nice way to remind you to greet them accordingly, also that way you know who to ask for, write down their contact information as well, incase you need anything as well, like maybe extra towels, a cab number or even the wifi password.
   Now let’s get to the fun stuff, all the things you want to see and do. I group things together by neighborhood. When visiting Bermuda, I knew I wanted to see the unfinished church in St. Georges, I also wanted to stop by St. Peter’s church and also visit the crystal caves and see some Warwick shipwrecks. Doing all of these in one day is possible, but because their locations are so scattered, it wouldn’t make sense to do so. Plus I’ll be rushing to try to make sure everything is still open. If I make a day trip to St. Georges and see everything I want to see there, I only have to pay one cab fare over there, and don’t need to go back because that day is done. I can plan to see the shipwrecks which are in a complete different neighborhood the next day. Not only do you save money on transportation back and forth, you also save time.
   Another piece of advice I can offer is to group things together by leisure or activity. If you’re planning a day at the beach, it only makes sense to do more water activities that day like parasailing, or jetskiing. Don’t confuse your day (or your body) with walking around historic sites all day, and then going snorkeling. It’s two completely different activities, and they both definitely require different kind of clothing. On day one of Bermuda it was mostly sight seeing, so we knew to wear sneakers, and we were mentally prepared to walk into different venues. If I had on a bathing suit, walking into a church randomly with my chest exposed, it wouldn’t be the most appropriate.(True story, this has happened)

These are a few of my favorite tips when I’m planning my next trip. I hope they have helped you. I know it sounds like a lot, but remember that everyone is different, you don’t have to do everything as listed. Many times, I use my itinerary as a guideline of my vacation. I don’t always do every single thing as described. Remember to have fun and let the wind take you. Safely of course. Make friends with people, be open to new experiences and most importantly make memories.
Happy planning, and of course, if you have any questions or tips you also want to share, feel free to drop me a line.
Happy Traveling,