My Best + Worst Vacations

If you’ve been around here for awhile, you will know that I am a big, big fan of vacation! When I saw that Andrea of Momfessionals was doing a travel link-up – I was 100% on board! To travel is to live. Forever and ever, amen. So today I’m breaking down all the places I’ve been – love it or list it style. Just kidding, but I do really love that show. Without further ado…My Best + Worst Vacations!

So let’s start with all the places Iย have loved…

1. Thailand. If you’ve read here for any amount of time whatsoever you will know that the time Dane and I spent in Thailand is time I will cherish forever. The culture, the people, the food, the sights…gah! All of it was just so magical. Dane had just returned from a super long training exercise and I had been through a ton that year. That trip was just what the doctored ordered. We often say that we would love to retire in Chiang Mai!

My Best + Worst Vacations - CommuniKait

2.ย San Francisco. For my mom’s 50th birthday, instead of a party, we all went to San Francisco and I made a mental note that I wanted trips, not parties, forevermore. Though don’t get me wrong, I love a good party ๐Ÿ˜‰ We toured around the city, visited Alcatraz and then went north to weave in and out of vineyards and wineries for a few more days. It was a trip to remember and we always talk about how much fun it would be to go back!

My Best + Worst Vacations - CommuniKait

3. Italy. I’ve been to Italy six times so I guess you could say I enjoy it a little bit ๐Ÿ˜‰ย The best part is that Dane has never been (except when I FaceTime-d him in from Afghanistan during cooking school), so I have one big reason to go back! It’s one of my favorite places in the world, because there is so much to see and do, it’s nonstop hustle and bustle and oh-dear-heaven…THE FOOD! The best part is that you just walk everywhere and burn all that deliciousness off until it’s time to eat again. No complaints here!

My Best + Worst Vacations - CommuniKait

4. Hawaii. Yep, we live here and yep, these are still some of our favorite beaches, hikes and eateries in the world. Simply put? It’s hands-down one of our favorite places to be. Each and every time we go to a new beach while on vacation, we wind up comparing it to the turquoise waters and white sand in our own backyard. Call us spoiled, but you just can’t beat life in Hawaii! We have had both friends and family visit, which is like a vacation in itself for us getting to go around the island or island hop to show them all our favorite places.

My Best + Worst Vacations - CommuniKait

5. Seattle. Dane and I have both traveled to Seattle a handful of times separately and we finally got to go together a few years ago. It. Was. Magic. The food, the views, the insane amount of walking – we love it all. I know Seattle is considered the rainiest place ever (or something like that), but honestly – I will take it! For what it’s worth, it’s never rained during any of our visits.

My Best + Worst Vacations - CommuniKait

And yes, this is 100% the free cheesy photo from atop the Space Needle! HA!

Other favorite trips include: New York City, Washington, D.C., Chicago, Los Angeles, State College, PA (go Penn State!).

My Best + Worst Vacations - CommuniKait

It’s super duper hard to narrow down all the amazing places I’ve traveled and loved. There are honestly only a few that are ‘thanks, but no thanks’ for me and even then – I’m still happy I went! But, my post title would be a lie if I didn’t include the places I haven’t been crazy about, so here we go:

Costa Rica. People rave and rave about it, but we were pretty disappointed. One of those – happy we went, don’t need to go back type of places. We headed there for our honeymoon and it just…fell flat. The best day we had is pictured below where we hired a private driver to take us hiking, to waterfalls, etc.

My Best + Worst Vacations - CommuniKait

Orlando. We went for a wedding and had an extra day to play tourist. I think when you’re little and you visit Disney World is seems so magical and awesome, but as adults we kind of looked at each other like “holy crap, this place is insanely expensive! How did our parents do it?!” Kudos to all you parents out there braving those parks for the sake of your kids, you’re the real MVPs.

My Best + Worst Vacations - CommuniKait

On tap for the rest of this year we have Boston, Martha’s Vineyard, Indonesia, Taiwan, Scottsdale, a few staycations here in Hawaii and one pending trip TBD over Thanksgiving (now taking suggestions!).

What is your favorite vacation destination? And why?! Give me all the details!


  • But really, how DID our parents survive the high prices and insane crowds of Disney when we were kids? I feel like I need to thank them again for that trip right now.

    I vote Vancouver/Banff for your next trip! I’ve been dying to go there, so you can go and tell me if it’s worth it or not!

    • Kait

      Banff is in the running, actually! We REALLY want to do Alaska and then ending in Banff before coming back to Hawaii – we will see what pans out! And yes, agreed on all fronts – how did they afford it?! And keep their sanity?!

  • Jen

    Seattle is on my list of places I want to visit. Kyle went to college in Washington and he always raves about how awesome Seattle is. I have to say my favorite trip that you have taken was Thailand, I loved following along with your amazing adventures there.

    • Kait

      I dream about Thailand all the time! The colors, people, food…all of it was just so magical!

  • You have some amazing trips on the horizon! Thailand is on my bucket list…I’ve heard nothing but great things!!

  • Haley Howell

    Great list. I live in Boston and have never been to Martha’s Vineyard- major fail. Have a great trip!

    • Kait

      We are super excited ๐Ÿ™‚

  • jillian

    italy SIX times?! Im jealous!! what are your favorite Italian cities? I went to Florence, Rome, Venice and Cinque Terre and they were beautiful. I’d like to go back and visit Lake Como and Milan (my husband is a huge AC Milan soccer fan)

    You have so many amazing trips planned for this year!

    I also loved Paris — we went for our honeymoon and I spent a month there during college.
    Turkey (although with the political situation the way it is now and Syria being so close I wouldn’t go again anytime soon which is too bad bc Istanbul is a beautiful city)
    Santorini Greece was amazing (I wouldn’t go back to Athens but I’m glad I went once)
    Barcelona, Spain — so much beautiful architecture, awesome city to do a bike ride in (we also went to Madrid but I wouldn’t go back — it was kind of dirty)
    I loved Seattle + Portland too!
    Charleston is a beautiful city you should try to visit sometime, the downtown is super walkable and there’s lots of great food. We lived there for two years.

    I’d love to go to Thailand, Switzerland, Denmark, Iceland, Southern France, India — and of course Hawaii! xoxo

    • Kait

      I’m so glad you got to visit Turkey! That is 100% on our list, but the political climate right now makes it dicey at best. Hopefully one day it will get better! Thailand is a MUST!! Literally, most magical trip ever!

  • I love this post! Italy is at the very top of my travel bucket list. I’m so jealous you’ve been there so many times! haha

    • Kait

      When you get a chance to go, you will love every bit of it! We are hoping to go in the spring of next year again so Dane can experience it!

  • I love the range of places on this list. Italy is amazing, but then Chicago – which feels “local” to me as my hometown is only 2.5 hours away – is also such a fun city to visit. Which basically goes to show that you can find a great vacation near or far, if you find what you like. It’s so too bad that you didn’t love Costa Rica though! My family was there over Christmas one year and we thought it was just so great. But then we also did have this amazing rental villa and could walk to all of these fabulous little restaurants for meals, so that always helps ๐Ÿ™‚ My greatest love for a “trip” kind of vacation is London. For a relaxing kind of vacation I’ll pretty much take the beach anywhere, but we really loved Great Exuma island in the Bahamas especially.

  • So many great adventures!! And so many more to come! Some of my favorite places I have been, Bora Bora (obviously), Bahamas, Banff B.C, so many different places in Alaska, New Orleans, and well you already live in Hawaii. I went to college in Seattle and also got married there so that holds a special place. Also lived in Scottsdale for a few years, so many good places to eat! I feel like my list of places to visit in the US is long. LOL. Can’t wait to follow along on your travels this year!

  • Let me know if you need any recs in Boston or on the Cape! I don’t know Martha’s Vineyard super well, but I can help elsewhere ๐Ÿ™‚

    Alyssa |

    • Kait

      Any Martha’s Vineyard recommendations would be awesome! We will be there this weekend through Tuesday ๐Ÿ™‚

      • Kait

        Oops! I read your comment totally wrong! Gah! Well, we will only be in Boston for the day, followed by Providence, then MV. It should be a whirlwind, but fun! ๐Ÿ™‚

  • Aw you’re coming to my neck of the woods in Boston?! When/Where about are you staying? I hate advertising but I do have some Boston posts on my blog, I can link them if you want! Martha’s Vineyard is amazinggg!!!! (I also blog about MV) I go there a few times throughout the summer, just a great place. I’d also consider checking out Nantucket if you have extra time just a little further than MV! It’s funny because my boyfriend and I have a little savings going on to go to Hawaii. I’ve been twice and fell in love so I’m dying to go back with my boyfriend and explore more territory! I swear it’s like another world down in that tropical paradise! Beautiful blog! <3

    xo, JJ

    • Kait

      Hi Jenny! Thanks so much for stopping by ๐Ÿ™‚ We are! We are only spending a day there before heading down to Providence to visit my brother-in-law at Brown, then spending the weekend in Martha’s Vineyard. We are excited ๐Ÿ™‚ If you come out to Hawaii – let me know!!

  • Pingback: How To Get The Cheapest Airfare Possible - CommuniKait()