Traveling with Jenny pt 1.

Hey guys, today I’m going to do a tag that I was nominated for a few weeks back by Lisa: From Dream to Plan  So I’ll be incorporating the tag as well as putting my own little spin to it!

And as much as I love packing my bags traveling, I’m no expert by any means but I will share what I do know and what I have learned from past experiences!

I really should change the title of this post to

Traveling with Jenny AND Andrew

Because you know, he’s my traveling partner and together we have a great syncretism  when it comes to our adventures 🙂

So to start off, whenever we fly out anywhere its always from Logan International Airport which is of course out of Boston. Therefore, we see this view every single time and as in MK terms #jetsetgo


This topic is not new to us because we’re constantly talking about our next destination. So with that said, Andrew and I have a pretty good idea of all the places we want to visit, how long we’d want to spend in each place, and around what months we want to go.

So for starters…

1. WEATHER! We always check what is the best month to travel to said destination

2. We jump onto the HOPPER app, I mentioned a few posts ago and check the weeks/weekends that will be the cheapest time to travel there.

So it goes back and forth a lot; simultaneously, he’ll look up one place, I’ll look up another and when we find something good we’ll focus on that specific place.

One last thing- I know a lot of companies do this so look into it; but we both have “Company Perks” which is a website (through your job) where you can go through and purchase anything at a discounted price. So with Andrew’s last company we’ve noticed that they supply the cheapest flights, hotels, and car rentals so we always book through them (we luckily still have access even though he no longer is employed with them) And with each purchase they give us “WOW points” which is basically free money to put towards our next purchase. We noticed that whatever cheap flight is on Hopper, this site is always about $10 cheaper if not more. Total win.

1. How Do We Get To The Actual Place? 

So once we’ve arrived to said destination’s airport; we usually always RENT A CAR and it usually ends up being with HERTZ. Remember those WOW points, well usually after buying flights and hotels we can basically get a rental car for free.

Unless by chance the hotel is fairly close to the airport and we know that we will not be needing a car to get around during our stay then we’ll just UBER! But that hasn’t happened yet.

[Side Note: Being from Boston, parking is a huge thing ($$$) so we make sure to look that all up in advance as well. Parking at hotel, places we want to visit during our stay, etc]

Between the two of us, he’s the better driver 😉

2. Where Are We Staying?

Andrew is the king of doing research for hotel stays. He out of the two of us is the one that reads between the lines, checks reviews, location, and gets all the fine details. Me on the other hand will do all that too but very briefly.

Needless to say we’ve had really great stays at each place we’ve been to thus far!

3. How Do We Get Around?

Like I mentioned before; we generally have a rental car. But we prefer to not drive it around if it’s not necessary. So when we pick a hotel we make sure its around, close, near to things we want to do.

My favorite thing though is to just give myself a walking tour of the area. You never know what kind of amazing things you can find along the way! We just try to be as efficient without a car as possible, but sometimes you may need one!

4. What To See/Do?

With each destination we pick, we know what we came there to do…

Whether its the beach, downtown area, museums, parks we make sure to hit what we want to see. And aside from what we know, I like to google “things to do” beforehand, I ask around to people who have traveled there before. But most importantly- the FOOD. You cannot travel somewhere and not be excited to try different foods. That is a total must and ALSO Andrew’s expertise. He always finds us the best places to eat at.

And that concludes The Traveling Tag! If anyone who travels near and far and has some great tips then snag this tag and share with us all 🙂 Thanks Lisa for the nomination!

xo, JJ


34 thoughts on “Traveling with Jenny pt 1.

  1. ayrgalaxy says:

    I think it’s good that you plan ahead because you know exactly how much you’ll be spending and you also have time to prepare. Weather is definitely one of the things everyone should look into it because it can change the experience of said place.
    I’ll have to remember to look into renting a car if I ever go somewhere. Very important. I haven’t tried uber or lyft yet. I don’t feel comfortable riding with a stranger but at least I won’t be alone.
    I’m the type of person that researches EVERYTHING. Our trip to Japan is currently being planned (by me of course). I’m the one who’s researching how much it will cost, places to see (that’s the main thing), where we will stay and for how long. Won’t be easy planning this trip BUT I’m excited and I have time to plan it. So excited lol!
    Anyway, great tips doll!

    Liked by 1 person

    • xoJenny says:

      NO WAY!!! You’re planning a Japan trip!!! Ah totally jelly. I hear Toyko is amazing (do you know where in Japan you’re looking to go- not that I know any of the locations lol) but wow, that’s gonna be good. My mouth is watering just thinking about all the yummy food you’ll be able to try there! I sometimes dread taking ubers or lyfts, they’re getting more and more expensive with the demand for them….but of course if its on someone elses card, I’ll jump right in haha

      Liked by 1 person

      • ayrgalaxy says:

        YESSS! That will probably be my #1 out of country vacation. Won’t be for a couple more years, but on the bright side, that will allow for our savings to grow just in time for it. 🙂
        And… We want to go to so many places, definitely Tokyo, Gunma prefecture, Kyoto, hopefully Ibaraki to the Tsukuba Circuit if they have any car events. I do have a “bucket list” of things I want to see though when I go. I would like to visit a shrine. 🙂
        But yeaaahh! Food is what I’m most excited about! I want to visit ramen shops! 😀 ❤

        Liked by 1 person

    • xoJenny says:

      It really is so handy!! A lot of my coworkers that travel often got me hooked on it! They use it so often, but I love it for the updates and reminders on prices/price changes, really handy!

      Liked by 1 person

    • xoJenny says:

      Okay, I’ve never done Airbnb but on so many occasions we were so close to booking one but then I always end up choosing a hotel because something about it makes me nervoufor some odd reason….but you like it?!!? Tell me more! I get concerned because a lot of the times we fly late at night so how do you get the key? And are they clean? No on bothers you? Lolz so many questions.

      Liked by 1 person

      • jacqueliinejoy says:

        Hahaha. Yeah it’s basically like booking a hotel. The owner of the house will usually leave a key box at the door and email you with a passcode to get the key. So it doesn’t matter what time you get in. The houses are clean, and usually there is a set of instructions left for you on wifi passwords, what you should do with dishes if you choose to use them, linen, all that shit. No one usually bothers us in regards to the house. Just a text before checkout asking if we enjoyed our stay. I hella like to cook, and it’s a nice way to keep everyone under one roof. So I get to see all the local markets and shit. Meet people.

        Liked by 1 person

  2. 50shad3s0fjay says:

    The perfect post. I agree, walking is the best form of exploring and you never know what gems you may find! Also I always google ‘things to do’ in said place before visiting too then I message my bestie like right, we have to do this haha. Company Perks sounds great, I’ve never heard of that before but yay for discounted prices. I can’t wait to see where you visit next xx

    Liked by 1 person

    • xoJenny says:

      Right walking is the best way to do it (and cheapest) The only downfall is not knowing if some areas are sketchy lol I do the same when I google things, Ill screen shot them and send them to whoever I’m going with and I’m like “we’re going to do this” haha xoxo

      Liked by 1 person

  3. Mackenzie says:

    I need to get that Hopper app- I’ve never heard of it, but it sounds like a necessity!!!!!! I always forget to account for parking- yesterday I was in SF for like 2 hours and it was $17 dollars. CRAZY! Ya’ll are professional little travel bugs. I gained so many good points from this post! Thanks for sharing, love!

    Liked by 1 person

    • xoJenny says:

      Hopper is sooo handy! I love it because you can look ahead to see when the cheapest time to fly out will be and if you know which days you’re going to fly out it keeps track of when the prices go down (or rise, grr) but I have like 5 different trips that “I’m watching” and as soon as I see it at it’s lowest, I jump on it! Glad you found use of this ❤ ❤

      Liked by 1 person

  4. K.M. Sutton says:

    Love reading your travel tips! Especially about cars! As I expand my wanderlusting, definitely looking into driving more and this was incredibly helpful!
    I agree though, the best way to explore a place is by walking! ❤

    Liked by 1 person

  5. Milena ☁️ says:

    Shoutout to the cutest travel couple! Thank you so much for sharing this post – it’s super helpful and really relevant as Dave and I starting to think about our next travel plans at the moment! Hopper sounds like such a lifesaving app! I can’t even remember how many times I’ve checked flights on all the different budget airlines, multiple times a week, just to see if they go up or down and I really hate that anxiety you get if you don’t book them right then! I am definitely downloading this app! I hope it works for the UK too! And checking the weather is definitely the number one thing to do first! We started looked at Zanzibar and got really excited about affordable prices only to find that when we wanted to go is the rainy season over there! Haha. Walking is definitely my favourite way to get around when on holiday so I love staying somewhere that is either quite small or staying right in the centre! When we went to Iceland, we were quite far from the city centre and had to get a bus and they were so unreliable a lot of the time – not great when it’s cold! We haven’t ever rented a car but it does seem like a really sensible option, especially if you want to visit lots of different places! Hahahaha food is definitely a highlight of travelling! xxx

    Liked by 1 person

    • xoJenny says:

      Aw thank girlie, although I could totallly say the same thing about you and Dave!! You two have some of the best traveling excursions! I feel like I need to write down tips from you!!! But yeah, walking is my favorite source of transportation (and it helps that its the cheapest) We always tryyy to stay right in the center too but its not always the cheapest option so we resort to renting a car which has it’s perks for sure and luckily Andrew is a good driver haha. Where is Zanzibar? Let me know if Hopper works for you- it really is a great way to keep track of flights. The notifications they send are so helpful but also so very tempting when you see such a low fare price especially for us wanderlusters 🙂


  6. fromdreamtoplan says:

    I finally had the time to sit down and read your answers! So cool you’ve found a great travel partner! Plus, I love how you structured the post 🙂 Thank you for partecipating!

    Liked by 1 person

  7. sarahscupofbeauty says:

    Such a fun tag!! Reading your post, makes me want to go on a trip so badly!!! The planning beforehand is already part of the journey! I just love it! Having the right travel partner is so incredibly important! Glad we have ours ;). xoxo Sarah

    Liked by 1 person

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