Vacation Planning-The Balancing Act of Neuroticism and Having a Good Itinerary

When planning a vacation, there are two types of people; those who plan almost all days down to the minute (raises hand) and those who like to live spontaneously and go with the flow (kudos to you!). I noticed my neurotic planning for vacations get to a new level when I started modeling full time. Our schedules are generally handed to us the night before so it makes planning ahead virtually impossible. If you have any model/actor/freelance friends, you’ll know what I’m talking about. There is a lot of cancelling and a lot of rescheduling when it comes to planning anything more than two days ahead for us. There are times when I’ve received an amazing job offer that I couldn’t pass on, that falls right in the middle of our planned vacation, so we’ve had to cancel and reschedule everything for next year. It’s expensive, it sucks, but work is work and I’m not about to give up an amazing job for another model to swoop in and grab. Therefore, when I plan my vacations I like to have full control of my off duty time to plan ahead, albeit cautious that I may have to reschedule.

When I was younger, I had the kind of dad who planned beautiful itineraries for us for any family vacation we took which I appreciated more than ever. We always knew where we’d be staying and what we’d have planned to see each day. I liked the regimen of having these guidelines so we wouldn’t get anywhere and potentially miss the must-see spots. On a different note, I also always liked having plans from anything as simple as where my friends and I would be going to dinner. It made sense to me, from my dad’s influence, to have a general idea of a place to see or go so you wouldn’t waste time not knowing what to do (I’m also half-German, can you tell?). 

In recent years, I’ve noticed my neuroticism with planning has sometimes gone too far. I’ve Yelped and researched every potential site, restaurant, and bar we’ve gone to in order to check things off the list, leaving out any room for the fun that comes with spontaneity. I’ve become frustrated if things haven’t gone according to my (super) detailed plan, which has definitely dampened the mood on what should have been a fun, relaxing holiday. 

After some thought I realized that over-planning was possible when mixed with a little spontaneity. I’ve recently talked about the importance of being open to change on my friend’s podcast, HeyChange! You can listen to our chat here. While we delve into change on a grander scale like the fact that change is what keeps life lively, in this article I try and tackle change in smaller terms, like planning a vacation. Here are some guidelines I tend to follow whether I have a month to plan a trip or a few hours. The act of balancing pre-planning and impulsiveness generally makes for an extremely enjoyable trip, work or vacation. 

  • Book your tickets well in advance, if possible!
    • For plane travel, I sometimes find it’s worth the investment to buy your tickets early with trip protection (only if the protection includes cancellation for any reason, not solely related to injury, death or sickness). Unfortunately, I end up having to book last minute which unfortunately costs a lot more… however if your work permits it, book ASAP! I don’t think I’ve ever seen a plane ticket price go down over time. Try checking Skyscanner to see best times to book travel. If you can be flexible with your dates this is a great option as they show you a calendar and how much each day would cost to travel.
    • I take the Amtrak train frequently and always book tickets up to over a year in advance for popular holiday weekends. If I have to cancel, Amtrak lets you get your money back or travel credit if you cancel up to a minute before your travel. That way I can book a roundtrip for ~$70 versus ~$500+ last minute.
       
  • Same goes for accommodation. Airbnb is my favorite way of staying in a new city. You get to live like a local and the hosts generally have cool city guides of their favorite coffee shops, restaurants and sights. It’s more personal and I like the coziness of staying in someone else’s home! I have a saved list for a bunch of popular cities of my favorite Airbnbs ready to go if I need to book last minute if they’re available.
     
  • Hotel Tonight is also a great way to save on an indulgent night at a nice hotel. This is a great option for a staycation or if you want to treat yourself to one or two nights at a nicer hotel. They let you book a room that day or up to a week in advance and you can usually get a great deal of ~$100+ off per night.  These are the rooms they couldn’t fill last minute so they are inclined to sell them for a lot cheaper!
     
  • Book a few restaurants in advance! The popular must-see restaurants are always booked last minute and no one likes to wait in line for an hour with a hangry girlfriend attached at their hip (guilty as the hangry girlfriend!) When I plan a trip, solo or with a friend, I like to book a few restaurants in advance so we have options where we want to go. I’ll book a couple different cuisines for popular days (Thursday through Sunday) so we can see what we feel like at that moment. And if you feel like being spontaneous and hitting up a place you stumble upon instead, so be it! Yelp lets you make reservations through Opentable and I find their app/website easier to use/more reliable than the actual Opentable website. Resy is also a great app for last minute reservations at popular restaurants in a select number of cities. Sometimes they have a fee but this fee generally helps you get into restaurants that may not take reservations and for popular times.
    • I also like having a bunch of ‘bookmarked’ restaurants under my Yelp account, that way if I’m in a city and am not sure where to go for the best ice cream or a cute local coffee shop, I can pull up my Yelp account and see what I’ve bookmarked in the past.
       
  • Have a small bag always packed and ready to go with the essentials; underwear, toothbrush & toothpaste, deodorant, t-shirt, passport and a charger. That way, if you need to run last minute you can just grab this bag, add a few things and be ready to go. This is the number one sanity saver I’ve finally learned as a model for 5+ years. It helps. Trust me! If you have a bit more time to plan you can still take these essentials with you as a base and add whatever extras you need. Although, it’s always so much easier and stress free to travel with as little as possible. (Which also makes me continually rethink my entire closet and how much “stuff” I actually need when I’m generally fine for weeks on end with a small suitcase filled with my essentials…)
     
  • If you’re heading to a new city for the first time, or if you’d like to see a city you already know in a new light, try doing a free walking tour on your first or second day of arrival. It’s a great way to get a gist of your bearings and see where you’d like to go back to and check out in greater detail on the rest of your trip. Just type in “Free City Walking Tours” into google for whatever city you plan to visit. Almost all of them have great options! In Europe, Sandemans Walking Tours are exceptional!
     
  • Look into best options for transit depending on your length of stay in each city. Some offer weekly metro passes while others have deals for the day. It will help you save a lot of money that you could spend on a drink or two instead;)
    • In Japan they offer a rail pass that is significantly cheaper if you plan to travel all over the country for a week or more. For seven consecutive days, an ordinary rail pass will cost around $260 USD for unlimited travel, while some trains last minute can cost up to that much for one trip. (For Japan specifically make sure to book well in advance, as they have to send it in the mail to you and you then get it verified at any Japan Rail Pass station once you’re there).
       
  • Ask your friends for their recommendations! There’s no better way to see how a local lives than by getting suggestions from your friends, family and friends of friends. With Yelp, you can rest assured you’ll find some incredibly tasty, trendy spots but to live a little off the beaten path ask around for some of your friend’s favorite spots. In some cities, Yelp isn’t even popular so it’s nice to get a list of must-see restaurants, bars and museums from a pal.
    • On that note, don’t be afraid to check in with friends about staying with them either. Of course make sure and not overstay, I find 1-3 days is plenty and can save you a ton of cash which leaves you room to book last minute, expensive plane trips. Always bring a gift; flowers or wine are a great option and I always try to leave another bottle of wine and/or a card to show my appreciation...and two bottles of wine are so much cheaper than some hotel options!
       
  • Similar to checking out a walking tour your first or second day of arrival, I also love getting my workout in by going for a run, sans map, my first day in a new city. You can get lost and explore, while getting a good sweat in and see what spots you’d like to check out in more detail later on. If you’re only there for a day or two it’s a nice way to feel like you’ve ‘seen’ the city rather than relying on a treadmill or no workout at all.
     
  • Last but not least, try your best to meal prep for the flight! It’s an absolute pain in the butt, but once you get to the airport and see the options you have (for upwards of $15+ for a bleak salad), you’ll be so incredibly proud of yourself for that little extra prep (your seatmates on the plane will be extremely jealous too!) With the Tupperware you bring you’re not only helping cut down on plastic but you can use that Tupperware later on in the trip for future meals. I always end up bringing oatmeal with me so I can use the container the next morning as a bowl for breakfast! And if you’re up for it, you can do a little grocery shop or take home leftovers from dinner with you on the flight back. Anything you can do to avoid buying food at an airport will be extremely beneficial on your wallet and your health!
    • I also have a banana case I got in Japan, yes, a banana case! It keeps them nice and fresh and perfectly shaped with no squish happening. I know you’re jealous!

I hope these tips help you with your pre-planning desires. Advance planning allows for seamless travel, but of course try to be open to change. Flights will be delayed and canceled, restaurants will be booked, you may even get sick, but being well-prepared and flexible reduces potential stress...which we all need, considering how difficult travel can be these days! Bon Voyage!