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How To Plan A Vacation Without Going Crazy

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Ciao friends! We are off to Italy today and excited doesn’t even begin to describe how I’m feeling! I’ll be traveling with my boyfriend Jesse and his sister Tara, and we have a ton of fun together so I know it’s going to be a trip we will cherish for a lifetime. Italy has always been at the top of my list and this is the first trip overseas I’ve planned 100% on my own.

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Dress: Sugarlips c/o | Hat: Tilly’s | Bag: Free People | Shoes: Amazon | Sunglasses: Zero UV c/o

While I’m certainly no expert, (and am praying that the trip is super organized once we get there), I’ve definitely learned a few things when it comes to planning a vacation along the way and felt I should share them with you guys.

  1. First and probably the most obvious, plan it as far in advance as you possibly can. This is especially true if you are planning a family vacation, as you have a lot more to think about and prepare. We planned this trip only 4-5 months ahead of time and it was not enough time. I ran into so many high-stress situations such as hotels and Air Bnb’s being completely sold out with only one or two options remaining, and I also found I didn’t get to take as much time to plan our daily activities as I would have liked (although sometimes I do like to have zero plans and see where it takes us – part of the adventure!) We ended up only being able to book hotels as the Air Bnb options were limited, but in the future I would love to do a trip with only Air Bnb to really immerse myself in what it would be like to live in that place.
  2. Use discount sites and double check before purchasing anything. I found everything from our flights to our hotel prices varied from site to site, so I basically would find a hotel that looked good and type it into google to see what other booking sites had the hotel, and would choose from there. For flights I used Vayama, and for hotels I used Hotels.com and Booking.com. I’m not saying these sites will always be the best, but they were for the places and flights I booked. [UPDATE: I had a terrible, terrible experience with Vayama and would not recommend them. Please do not book through them, and double check your protection policies with any booking sites you use with regards to cancelled or delayed flights]
  3. Email your hotels to find out about tours and activities. I’ve been emailing our hotels to find out what type of tours and activities they recommend and it has been so SO helpful. Whether you’re going on a cruise vacation that stops for tours (similar to how https://www.zegrahm.com/small-ship-cruises works) or are staying somewhere local, this step can be vital to know what to expect when you land abroad. When you google a generic tourist tour you’ll find a TON of sites and it’s pretty overwhelming — and hard to know what’s legit or not. I definitely like TripAdvisor for this as well, but it’s worth it to email your hotel too – after all you’ll be speaking to a local who knows what’s best in their area.
  4. Ask your friends and social media platforms for recommendations. This has been extremely helpful as well – there’s no one I trust more than my own community. I’ve posted on various platforms, multiple times so that I make sure people see that I’d like recommendations and I’ve found that people respond every time.
  5. For my vegans!!! Make sure to find at least a few restaurants you know have vegan options ahead of time. I like to use Happy Cow, or google “best vegan restaurants in ___”. I also recently discovered this app Vegan Passport, which allows you to type in the country you’re visiting and brings up a small letter to your waiter in their native language, explaining you are vegan and what you can and cannot eat. You don’t have to try to read it, just hand them the phone so they can read off the app. I’m excited to try this and think it’s going to be a life-saver. When we were in Greece, most people spoke English so it was okay but there was the occasional language barrier that’s stressful to both parties and this will just be easier.

I think that’s all the tips I have for now, but I’ll be sure to let you guys know how the trip plays out and if I have any tips after the fact! Thanks for reading, as always xoxo

Photos: Gabi Wells

10 Comments

  1. Thursday, August 31, 2017 / 5:08 am

    This was so interesting! I can’t wait to see your posts from Italy, it’s such a gorgeous country! Planning a big trip on your own can be so stressful – thanks for these awesome trips! I love turning to Pinterest and reading lots of others bloggers recommendations, too, as I find they always have the best tips when it comes to cheap and easy prices! Ha!

    I hope you’re having a lovely Thursday!
    Michael
    https://www.mileinmyglasses.com

    • Thursday, August 31, 2017 / 2:27 pm

      Thanks Michael! Pinterest is a great point — I got a ton of inspo from pinterest and instagram! 🙂 Hope your day is going great as well!

  2. Natali
    Thursday, August 31, 2017 / 11:18 am

    You are looking so SO cute and girly in this summery and flawless outfit!
    Enjoy your trip to Italy and have the best of holidays there. 🙂

    https://lartoffashion.com

  3. Tuesday, September 5, 2017 / 1:37 am

    I love your bright red slides with the muted blue patterned dress! Enjoy your trip!

  4. Sunday, September 10, 2017 / 4:09 am

    Planning a big trip on your own can be so stressful – thanks for these awesome trips.Hope your day is going great as wel

  5. Sunday, September 10, 2017 / 12:42 pm

    Looking forward to pictures from the trip! Just found your blog today and I love it! Especially the “champagne lifestyle on a beer budget” header…so relatable

  6. Thursday, September 14, 2017 / 5:03 pm

    Wow love your pictures! The colors are amazingly vibrant. What do you use to edit your pictures?

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