Life certainly has a way of working itself out lately–as does my budget. Just as I recently posted about why I’ll never regret a dime I spend on vacations, I go ahead and spend a ridonculous amount of money to extend my most recent trip to Kauai, nearly pushing myself into the “Piss, what have I done” vein of disbelief.
But even after filling in all of the (very ugly) numbers in my spreadsheet, I have to admit that I sit here typing this post with a huge shit grin on my face after returning from a pretty epic island-hopping adventure.
Vegas or Bust–$1K in Flight Changes
Originally, I was supposed to be flying to meet my BF in Kauai after he’d been in Vegas for a conference. After working my tail off to find a pretty amazing combination of deals that scored me a cheap R/T flight from Boston, I realized that the dates conflicted with some project and work responsibilities–after I had already booked the non-refundable flight combo on Expedia.
A quick snap of the Vegas Strip
Cost to fix my oversight? A cool $1K in flight changes.
At the end of the day, I realized that the work I had to do was worth far more than the initial bite of the flight extravaganza, so I finagled a series of flights that would allow me to be in Boston a few days longer and also visit my BF in Vegas thanks to a 3.5 hour layover. After running through the airport Home Alone-style and grabbing a cab, I met him and his colleague for a quick round of drinks atop the Cosmopolitan hotel, which was a nice way to kick off the vacation.
Kauai Turns into Maui which Turns into Oahu
For the next round of could-have-been-completely-avoided-had-I-planned-better expenses, the adventure began in Kauai, where I originally had planned to spend a three-day long weekend. When I got there, I fell in love with the island, and I was relishing the time with my BF as we hadn’t seen each other much lately due to his crazy work travel schedule. After a few days on island time, I decided to continue the adventure rather than head home (he originally had planned to continue on to Maui to meet up with a friend while I would come back to Boston).
Cost to extend my vacation to include Maui and Oahu? Another ~$600 (I was able to use some of the credit I had from cancelling my initial flight to Kauai which saved me from dropping another $700 or so). But as you can see from my pictures here, it can be hard to leave paradise when you’re there and know you have an option to stay longer:
Walking along the private beach where we stayed in Kauai
Caves we found while exploring Kauai
View from our sunset catamaran tour in Kauai
View from Kauai Helicopter Tour of Na Pali Coast
View from Kauai Helicopter Tour of Na Pali Coast
Sunrise view from our balcony at the Maui Marriott Ocean Club
Waterfall on Road to Hana in Maui
If Headed to California, Why Not Stop in Napa?!
On the way home, we also decided to stay an extra day in San Francisco, which necessitated a trip to Napa again for some wine tasting. 
Duckhorn Vineyards Napa CA
In total, I spent just about $3K on this trip. While that’s a nauseating sum considering at least $1,500 or more could have been avoided had I done a better job planning, I’m still in the camp of not regretting the decision to stay longer. Flight delays and extra expenses be damned; we had a hell of a good time!
That being said, I have my work cut out for me to save up and find creative ways to cut expenses for our upcoming trips to Quebec and Portugal….
What are your upcoming travel plans?
Jen
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Your trip sounds amazing! I can't wait until I can go back to Kauai.
Thanks, Michelle! It was quite a week–so happy I got to cross some things off the life list while there
Those pictures make it worth it, in my mind!
It was pretty amazing! We definitely thought about how people say they'll go back, but then we realized we have no idea when that could be and why not just stay if we can now?
Wow those pics alone are worth the cost.
We have nothing major planned for this year other than maybe a short getaway. We're going to Vegas in January for my birthday and it's all going to be funded by rewards points. 
Ahhh…reward points! Those definitely helped us trim expenses on this trip. A bday trip to Vegas sounds great–you'll have a blast!!
I can understand the desire to stay in Hawaii longer. It's a hard place to leave! Look I'm in no position to judge for the cost at all (my post on Monday-lol!) so I will just say that I hope you find your way back on track soon. I know it can be kind of a hangover to see how much you spent. I have some domestic trips I'm taking (detroit, portland/seattle, and st. louis), all which were paid for with southwest points save for about $125 or so. It's going to be pretty frugal overall.
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Yes! I'm already planning my budget fast for the next month or so to get right back on the wagon. The good thing is that savings is still in tact–just have to work a bit harder next month to bring in enough to off-set these crazy extras. I've never done something like this before, but I've always wanted to. One and done sounds great to me!
DAMN–well done on all those trips costing you so little out of pocket!! Is St. Louis for FinCon??
I don't see any issue with this. Yes, it was more money ,but you can't put a price on great memories. Some people think they can, but you need to live it up when you are there and I think you did just that.
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Definitely–this thought was something we actually talked about when I was deciding to stay. That and what I wrote to Mike above about how people always say they'll go back but never do. Figured I'd seize this opportunity to the fullest!
Sounds like you had an amazing trip, and it was all worth it!!
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It was great! I have a ton of work to catch up on now, but I wouldn't have it any other way
Those pictures are so beautiful! I can understand why you would want to stay longer, especially if you are not tied to a job.
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It was my first test into the location independent thing, but I didn't get nearly enough work done which will have to change in the future. It was a good test to see what went right and what went wrong so I can learn for better balance if there's ever a next time (although I don't see the extending thing happening much because I winced thinking about how I could have avoided so much of the cost).
Those pictures are awesome! I bet the real life view was even better! We're actually headed to visit my girlfriend's mom next month in Ohio, then heading to Boston in July!
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Nice!! Welcome (in advance) to Boston–you'll love it here! Let me know if you need any tips about what to see, where to eat, etc. I'm always happy to help!
It is incredibly hard to leave paradise!
And honestly, it wasn't as though you were mindless spending your money either, which is vastly different. Seeing everyone's travel pics has me revved up to go on our trip. Is it summer yet?
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I thought that exact same thing when returning to Boston and it being 50 degrees…haha! Isn't your vacation coming up soon? So exciting!!
Amazing pictures! I'd love to visit Kauai someday – passed on an opportunity a few years ago and I still regret it! When it comes to spending money on vacation, I confess I tend to see it as no object. I'm really good at pre-planning and finding deals on flights and accommodations, but I don't want to miss out on fun experiences when they present themselves. So, no judging!
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Thanks, Kendal! Yes, finding deals prior to trip is usually my MO. I'm not really sure what happened this time, but I do appreciate the experience and what I've learned through it. That being said, it's time to be super frugal for some time moving forward!
Oh..I am so jealous. I really really want to go to Hawaii! No plans beyond the cottage this year, alas..
I'd love a cottage getaway! We were joking that even though this was a vacation, it wasn't really one where you could just sit back and relax much because we were always on the move. Not that I'm complaining in the least bit!
You should definitely get to Hawaii–check out the TravelZoo deals and JetBlue getaways if there's a hub where you live–that's what got me there cheaply in the beginning!
Definitely not making a habit out of this!! It was the first time I've ever done something like this and while it was exciting and liberating, I don't think my frugal side can handle spending so much money all the time…haha!! But if it was a one time thing, I'm glad I was able to do it!
The total number hurts, but it's probably cheaper than flying out to Vegas, San Fran and Hawaii on 3 different occasions. Looks like you had a great trip! B and I won't take a honeymoon right after we get married but if we were, Kauai would be on the top of our list.
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Haha…it definitely does! Luckily everything fit into the budget this month thanks to some extra hustles in these last two weeks of the month. I think it did work out better not having to do R/T flights to and from Boston for each destination so at least there was a bit of a silver lining (besides the obvious of having a great trip!).
Definitely check out Kauai–it's so gorgeous!
looks like an awesome holiday! I hate having to pay extra to change trains, flights and other bookings but also end up doing quite a lot of it. Have fun!
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Thanks, Pauline! Hope you enjoyed your time in Paris
Hey, if you can afford it and don't regret it, it's A-OK in my book! I've actually got a very busy travel schedule planned in the near future. I'm heading away for the long weekend, the in July I'm going to Cuba for a week for my honeymoon, then a week after I get back, I'm going to Quebec City for three days for a Paul McCartney concert. So excited!
Those trips sound awesome!!! You're going to have one hell of a summer
I loved Kauai – I was so fascinated by all the chickens (at least on the South side), and I'm so jealous you took the helicopter excursion! You got to spend more quality time with your boyfriend at some really great places – I tend to agree it's money well spent!
Hahaha…I was obsessed with all the chickens!!! There were a small bunch that clucked around our resort and I kept swiping extra bread to feed them with..so bad but so fun
The helicopter ride was incredible–definitely a bucket list item finally crossed off!
Ah well, sometimes we make errors and have to just go with the flow. Clearly the photos show how lovely the trip was and the stop at Napa must have been great! No travel plans here yet but we're planning to head to the UK next year with a trip to Spain, France, Italy and maybe Germany. We still have to plan it all but we want to try and get around to see all our family and friends.
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Wow, that sounds like a great euro tour–you guys are going to have such a great time!! If you get to Italy, don't miss San Gimignano in Tuscany. It's a tiny village surrounded by a giant earth wall that you can ride bikes/walk/run around the top of. It's a gorgeous town with incredible food that is a must-see
Wow, it seems you had an amazing time Jen. I wish I could visit some of the places that you went to! And lovely pictures btw.
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Thanks, Harry! Yes, it was a fantastic trip. I'm all about building memories and sharing experiences and this is the type of stuff that is the reason I work so hard all the time when not traveling
The trip does look incredible. I primarily travel work/business wise, so really have no desire to travel in my time off at all.
So keep saving and investing money. Perhaps one day the desire come around. I have two trips to western europe this month.
I think while you traveling there should be no regrets about expenses. The memories could not be bought. It is better do it while you young and get the most out of it.
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