How I Plan My Vacations

This post is somewhat similar to my Wanderlust post. Vacations and traveling is very important to me, and I make it a point to get away every 4-5 months. If I wait much longer I tend to get bogged down with every day life. I also never leave my last planned vacation without having another lined up.

I plan my vacations around the same times yearly. I like to get somewhere warmer if I can in the winter months like January-February. I like to celebrate spring and get away in May. I also like to get away in October. I tend not to travel in summer unless it’s something I can’t resist (like Disney World!) because my husband’s family has a beach house and it’s easy for us to get down to the shore.

First step, who am I traveling with? My best friend and my husband are my two travel partners. I also have a friend that moves around the country every two years and I make a point to get out to see her in her new location. I haven’t done a full travel alone and stay on my own vacation, but I am the type of person who would be fully content traveling alone. I know this isn’t common, for a woman especially but even for a man, and this would make plenty of people feel uncomfortable. I am the opposite, I would revel in the solitude, I always have.

Second step of planning, do I want to drive or fly? This dictates a lot of my planning and gives me a budget to work with. Flying is more expensive and if you don’t rent a car you have to stay within a certain area to get around easily. I recently went to Nashville with my best friend and we drove out there. It was a long drive that I wouldn’t do again, but we were able to rent a cheap, but beautiful, Airbnb that we wouldn’t have rented had we flown out.

Third, what am I looking to do? Is this a vacation with outdoor activities? Do I plan on shopping and eating? Or am I going for a specific purpose? Activities usually dictate the length of my vacations, especially if there is a special purpose I am going for. My next vacation is with my best friend again and we are doing a spa weekend in the Poconos.


Fourth, you guessed it, I make lists. If you have not figured this out yet, I obsessively make lists. I plan costs and itinerary of how my days will look. I also check on Pinterest and Tripadvisor for restaurants and other things to do in the location I’m going. I plan a full itinerary and break down the time. This is a little obsessive, and if this isn’t your style don’t bother. I just love this part of planning!

Fifth, I plan my outfits based on my itinerary. I love planning outfits! The outfits I pick will change constantly, whether because of weather or my preferences it depends. For my honeymoon, I was making outfit lists for at least six months. I’m also an over packer, especially if I’m driving to a vacation. I do recommend planning what you will be bringing with you to avoid forgetting important items and having to buy something while on vacation.

Finally, I book everything! I get my tickets, my lodging, and buy any necessary items I need for the location. Booking also feels so final, and it’s a great feeling! Having the money I work for going towards something I truly enjoy and not a bill or groceries is great too.

Did I miss anything in my travel plans? How do you prepare to travel? Let me know in the comments!


  1. Sally

    November 2, 2017 at 1:04 am

    Ahhh I can never resist Disney World either! But I’m from Florida so I suppose it’s a little different, Lol. I like your tips and I TOTALLY get the whole “If I don’t plan in advance it won’t happen” feeling. I like the idea of having a really detailed itinerary and outfit haul for a vacation – I’m also list-obsessed so it’s half the fun!

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