Planning Vacations And Getaways

Good morning friends!

Today I’m talking about one of my favorite things ever



SO, How-To Plan Vacations?

Disclaimer: There is no right way or wrong way, this is just my way.

1. What Kind Of Vacation?

I find that there are two types of vacations.

1.  Vacation where you just relax and do things at your own leisure.

2. Adventure vacation where you have a full itinerary of things to see and do.

You can tell the difference because you may think you need another vacation after an adventure vacation 😉

For example: 

Back in January, Andrew and I vacationed in Miami (you can read Part 1&2 here and here) and that was a flat out vacation where we’d wake up, get breakfast, and mosey on over to the beach. Spontaneous plans and just chilling.12

And then back in November, Andrew and I went on a long weekend getaway to D.C. (you can read those here and here) and that was an adventure vacation. We had a ton that we wanted to do and see and A LOT of walking was involved. 22

2. Pick A Location

I’ve mentioned this before but Andrew and I have a pretty clear idea of the places we want to go. But once we pick a place our main deciding factors are:

-For how long? A Long Getaway or Long Weekend?

-When/What month?

3. Hopper

This is a great flight reference app.

15Once you have a place and a time frame in mind, you plug in the details and it highlights the cheaper time to fly.

So more often than not, Andrew and I are laying in bed3And I’ll look over and find him on Hopper. Of course yesterday he’s looking up trips to MIAMI (again). Green is the cheaper time and Red being the more expensive time. But this helps us narrow down what week we want to look at. 4Another favorite thing about Hopper, is that you can plug in the week you want to go and it “watches” the trip for you and will update you if/when the prices go lower or rise higher.

4. Booking Flightsunnamed

For most of our destinations we pretty much know the high, medium, and low costs so we obviously want to pay the lowest.

For example:

I’ve flown to Florida countless times and know that you can get really cheap RT flights there so I refuse to pay anything more than $250. Even $250 is high- I’d say generally our flights to Florida have ranged from $150-$200 which is fine.

D.C. is another where you can get cheap flights I’ve seen them as low at $98-$118 so I really wouldn’t want to pay more than $125, but even that is high.

California is tricky. Tickets are almost always $300-350+ of course depending where exactly you fly into. But my general thought is nothing more than $350 for me. Britt on the other hand magically found RT flights to LA for a whopping $196. I don’t know her secret but she ALWAYS manages to find some real cheap flights to most destinations.

Anyways, depending on the Hopper updates as soon as we see a low and reasonable price we book it. We’ve never actually bought tickets off of Hopper because we go onto Andrew’s old work perk-site and usually flights are $10-15 cheaper.

4. Booking Hotels + Rental Car2

This is where Andrew and I differ.

He’s more of a “lets wait it out” and I’m more of a “lets book now since the price is already good” I always get nervous of rising prices so why not just book while it’s cheap. Car included, if necessary.

But again, we generally always book through his perk-site because it’s always cheaper. And as an added bonus each time we book a trip, we get “points” which is equivalent to cash to use on our next trip.

SIDE NOTE: Sometimes I find that some of the best prices are through package deals.


I often use this for flight and hotel bookings to Florida. I’ve used it for the past 3 years on me and my sister’s yearly trip there. And I just recently found Andrew and I one for this year. For the past, now 4 times that I’ve used Expedia, for FLIGHT AND HOTEL, I usually do 4 nights/5 day stay and we spend between $430-$500 for the whole darn thing! #WIN

5. Plan & JET SET GO

Once everything is booked. I usually go to google (if I don’t already know what the plan is at whatever destination) I will always look up things online to see and do regardless and BUY TICKETS TO ANYTHING IN ADVANCE! 🙂

I’m thankful that Andrew has the travel bug in him. He’s usually the more adamant one to book the next trip before we even go on our trip. Right now we have 3 trips coming up and he’s still looking up more. His train of though it, one getaway per month… ha…But I love him for that! ❤

Any traveling tips and tricks PLEASE SHARE THEM! Also if you have any secret flight sites or apps, I’d love to know!!!!

xo, JJ


25 Comments Add yours

  1. THIS POST WAS SO HELPFUL!!! I also travel a lot, and I found that using Kayak as my search engine is super helpful. Similarly to hopper, it tells you the cheapest days and months to fly somewhere. It also has a tool that advices you as to weather or not to book the flight, and if they suspect the price to drop. I’m not too sure how that works, but I always take that into considerations. AND YES, Expedia, Travelocity, love them all! But also be sure to check the actual airline’s site too, because I found my tickets to Greece to be cheaper on the airline’s site, than Expedia, so keep an eye out for that!

    ALSO, I love Andrew’s logic, one trip a month. That sounds like the dream! Hope you lovebirds have fun on all your trips! xx

    Liked by 1 person

    1. xoJenny says:

      I had no idea that Kayak kept track of the weather, holy moly that’s extremely handy! That’s so notable thanks for that tip! And you’re so right sometimes on the actual airlines the flights ARE cheaper, we noticed that when we were booking Andrew’s flight home on JetBlue all the sites were like close to 300ish which he was SO close to buying but luckily there was an error on Priceline so he just went directly to the site and there it was like $250 or something not to mention better flight times too!!! His logic is very very good and I love it too but burns a hole in my wallet hahah


  2. K.M. Sutton says:

    Love all these tips and tricks!:) I usually purchase my flights Tuesday after three or on Wednesday. They are the cheapest days to book and it hasn’t failed me yet.
    Also at least a month out they are way cheaper (though for some reason that six week mark they get pricey again…airlines🙄)
    I am the same way if I find a great deal I try to book it right away. The few times I have gotten greedy it has gone up🤣🙈
    Do you ever do air BnB? I am obsessed and have found such cute places to stay at!

    Liked by 1 person

    1. xoJenny says:

      You’re so right Tuesday’s and Wednesday’s are for sure the cheapest days to fly. It sucks because majority of our trips we try to keep short (typically do Thurs-Mon) because less days to take off from work (esp when Monday’s are holidays) so we always miss those Tuesday and Wednesday deals. It’s a crazy price difference! And no we haven’t done Airbnb yet, we ALWAYS look at the options and they’re great BUTTT this is where I tell Andrew, “I told you so” because he waits too darn long to book them so they end up getting taken. I hear great things about BnBing so hopefully one day I get to experience it! xoxoxo

      Liked by 1 person

      1. K.M. Sutton says:

        Not just to fly, but also book them on those days :)) Airlines get more traffic at the beginning and ending of a work week, so that Tuesday after three to Wednesday evenings (Some people say Thursday mornings too but I always book on Tuesdays after Three) is that best time to buy tickets.
        Also erasing your web browser also helps a lot! I always forget about that. Airlines take note of what you search so will jack the prices up. Airlines…
        So many tricks to the trade!
        And yes flying in the middle of the week is always cheaper but who can do that? ~Eyeroll emoji~
        Haha. That is funny. yes you definitely have to jump on them! I hope you do too! It is definitely a different vibe then a hotel! Eeeek your trip is ALMOST here! 😀 ❤

        Liked by 1 person

      2. xoJenny says:

        WHATTTT OMG had no idea….you’re seriously such a good travel guide ❤ ❤


  3. koraihweb says:

    I do use hopper and it is a life saver! I got round trip flights to Spain for 400. (yay) I also almost always use airbnb or homeaway. They have cheap, cute, affordable houses or apartments. And you can pick what you need or not and put them in the app. We also always buy all tickets or anything before hand. It makes the vacations a thousand times less stressful! Loved the post!
    xoxo Koraih

    Liked by 1 person

    1. xoJenny says:

      YAY I’m so glad you’re a hopper user too! $400 to Spain is a GREAT deal. I’ve seen flights from where I am to Hawaii for like $650 before when they’re usually always 850+, thats when I knew I could trust Hopper lol And I haven’t gotten around to trying AirBnB but everyone I know that’s used it has said great things about their experience! Every time we go to book it, we usually wait too long and it gets taken!

      Liked by 1 person

      1. koraihweb says:

        Yes….that happened with me many times! I will try and book but they will say that it is taken! Hopper is great! It gives us soooo many great deals! I always wanted to go to Hawaii. Next thing going on hopper!

  4. ughmango says:

    This was so helpful!! I do travel quite a lot (not as much as you but every now and then) and I always use so much time to make sure I book cheapest flights and hotels.. I have never heard about hopper before but I am definitely going to download it right away 🤗

    Liked by 1 person

    1. xoJenny says:

      I never really used to travel as heavily as I do now either. Only because I work a pretty good job and can afford it now haha but yess Hopper is a great reference tool when looking at flights. And usually when you see low prices on there, it’s good to check other sites and the actual airline to compare! Where’s the next place you wish to travel to? xo


  5. I am more of the type 1 of vacation planner and hubby is defos type 2. We are pretty much opposites in every way! But I like that, keeps things exciting. This post seriously makes me wanna plan a vacay so bad!

    Liked by 1 person

    1. xoJenny says:

      LOL same AND not to mention opposites attract 😉 I feel like when theres two different types it keeps things alive and interesting! xo

      Liked by 1 person

  6. ayrgalaxy says:

    This is fantastic. Great tips! I’ve never heard of Hopper but it sounds like a really great app to use to plan in advance. I’d love to travel to many places so I’ll have to check that app out, thanks! 😉
    And that’s crazy that he wants to travel once a month, #wheredoyoufindallthatmoney lol but it’s great! Traveling is actually really good for you as you get to experience things outside your everyday routine/environment. 🙂

    Liked by 1 person

    1. xoJenny says:

      I think Andrew thinks we have a money tree in our nonexistent backyard lmao he’s wild! I love his idea of going on one every month and would love to make it a reality but not always can I make it work haha The app has helped us soo much in all the trips we’ve taken- whenever they send us a low price alert it gets us buzzing to book something. But also if you do use it/rely on it just double check traveling sites and actual airline sites because we did notice the other day that sometimes they have slightly better flight times or sometimes even a little bit cheaper prices than hopper. But in any regards its always good to do research!!! I hope you guys get to take your Japan trip soon!!! xoxo

      Liked by 1 person

      1. ayrgalaxy says:

        Lmao. Well I would say three vacations a year is really good. I csn barely get one in and I know that’s not enough lol. Hopefully when the gremlin gets older we can travel more and take road trips.
        I hope so too. If we go to Japan I don’t wanna bring my son along lol. It sounds mean but I feel like he’s gonna hold us back from experiencing things and going to places we want to see. Lol.

        Liked by 1 person

      2. xoJenny says:

        No its so true, and of course I know you don’t mean it in a mean way lol but it’s definitely A LOT harder to travel with a child, even like an ‘older’ child, you don’t get to really thoroughly take everything in…annnnddd its one less human to pay for 😉

        Liked by 1 person

  7. lifeofangela says:

    I love planning trips. It’s always me who plans things, and Rory is happy to come along XD
    I just love knowing that everything is taken care of, I get crazy organized and make lists and plans, and like you, I book everything in advance. Rory tends to leave most of it to me, cause he knows I love to plan these things 🙂

    Liked by 1 person

    1. xoJenny says:

      LOL I’m mostly the planner too… girls are just better at handling everything 😉 But I’m super particular too, I need to make sure the itinerary is set and planned and everything is booked or reserved. It’s the best way to make sure stuff gets done when you do it yourself 🙂

      Liked by 1 person

  8. helloitsjo says:

    I’m literally planning trips ALLL THE TIMEEE , so thank you for this!!!! your photos are just so cute, I love them hehe I’m obsessed with booking holidays at the mo and to be able to see when is cheapest etc. is so perfect!!! xx

    Liked by 1 person

    1. xoJenny says:

      Me too whether I’m planning trips for real or just scoping out potential trips I feel like I’m always looking! The thought of traveling just gets me to excited and it’s fun to have something to look forward to! Do you have any trips lined up?!!? xoxo

      Liked by 1 person

      1. helloitsjo says:

        literally STORY OF MY LIFE! It’s just something to look forward to you’re right!!! I actually have quite a few lined up!! Lucky to have Amsterdam, Spain and Portugal in the next couple months so will have to do plenty of posts on them all hehe!!! xxx

        Liked by 1 person

  9. I love this post Jenny, so detailed, well thought out and organised. That Hopper app is so handy. I definitely agree with Andrew- one trip per month is the ideal!!! I can’t believe you go on yearly trips to Florida with your sister, living the dream! And you have so much travel coming up, how exciting. Booking activities in advance is always a good idea, and makes you even more excited for your trip knowing what you have planned! I’m definitely #teamJenny when it comes to hotel bookings, the sooner the booked the better and once that’s done everything for the holiday is sorted too – no worrying about having to book a hotel! Ps I love the pic of you and Andrew in DC- gorgeous! xx

    Liked by 1 person

    1. xoJenny says:

      When you said “so detailed, well thought out and organised” you just get me!!!!! That is so me in the nutshell. I’m a freak when it comes to stuff like that haha (The Virgo in me) But yes Florida is sooo easy to travel to from here, it’s really the cheapest place to fly and stay and it helps that they have nice hot weather, beautiful beaches, palm trees, and DISNEY! Which you get to explore soon-ish!!! EEK!!!!! 🙂 🙂 ❤


  10. RahulYuvi says:

    Interesting post ! Beautifully Written & wonderful Clicks !

    As for getaways , We too visited a beautiful Hill station in North India recently !

    And Here ‘s a short write up from my recently updated Travel Diary :

    My ‘With Family’ story of a near perfect Hill Station !!(Photograph based short story )

    Hope you find it interesting ! 🙂

    Liked by 1 person

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