Since I left home for my Great Escape, I’ve been doing monthly roundups of my adventures filled with anecdotes, private little moments, and thoughts that are found no where else on this blog. As this site is not just a resource for other travelers but also my own personal travel diary, I like to take some time to reflect on not just what I did, but how I felt. You can read my previous roundups here: Month 1, Month 2, Months 3 and 4, Month 5, Month 6, Month 7, Months 8 and 9, Month 10, Month 11, Month 12, Month 13, and Months 14 and 15.

When I started writing about Hawaii, I encountered a new problem — I just simply loved it too much. My love for Hawaii actually made it kind of difficult to write about — rather than putting my experiences into words, I just wanted to publish a post full of photos, excessive punctuation marks, and perhaps a caps locked adjective or two. But somehow I persevered beyond that Tourette-style blogging and managed to form actual sentences. And good thing — because those would be some really weird blog posts. Actually, I never expressed myself better than I did in my very first post about the islands, and one of my favorite pieces of travel writing I’ve done — a love letter to Hawaii.

Funny enough, Hawaii had never piqued my interest until my friends Wim and Dave moved there. Then I started counting up the family and friends I had spread across the state, and my trip to Oahu, The Big Island and Maui was born. Of course, as you may know, I ended up expanding my trip by length and area, tacking on Lanai and Kauai to my island count. And I had the absolute time of my life. I sprang awake after just six hours of sleep a night, I was active and full of energy, and I worked efficiently and signed off without guilt. I was on a perma-high, happier and more peaceful than I can ever remember being before.

Technically this trip was 40 days — let’s call it a generous month.

Oahu TravelOahu — an action packed first stop

Where I’ve Been

• 12 days on Oahu

• 7 days on The Big Island

• 5 days in Wailuku, Maui

• 7 days in Lahaina, Maui

• 5 days back in Wailuku, Maui

• 4 days on Kauai

The Big Island Travelthe beautiful The Big Island


• Hello — I went skydiving! Between that and my first helicopter ride over an active volcano, I feel like I had the aerial touring of Hawaii pretty much down. But really, I can’t think of the last time I did something that scared me as much as jumping out of a plane. I still get a little contact high just watching my video!

• While diving on Oahu and Lana’i was fantastic, nothing could possible top diving with the manta rays on The Big Island.

• So many firsts — surfing, skydiving, ATV riding, helicoptering — but without a doubt Stand Up Paddling is the one that will be with me for life now. I was so overjoyed to find a new water-based love!

• Putting together my Big Island video was so rewarding. It’s been a goal of mine to shoot more video as I travel, and I made it happen for once! This is the best footage I’ve ever shot — I feel really proud of it.

• Hawaii showed me I had a hidden passion for hiking! Between exploring a handful of hikes on Oahu, my conquering of Haleakala and taste of the Kalalau Trail, I found myself in love with another new hobby.

• For the most part, Hawaii has a pretty laid back party scene. But Heather and I found the exception and had so much fun going out in Oahu. If I lived in Honolulu I’d be in Chinatown every weekend!

• I really cherished getting to see the lesser-known sides of Hawaii, like the bohemian band of hippies on the Big Island. We got a good dose of it on a day spent in Puna, and an even better one getting to know Richard at Volcano Island Honey, who I was hoping would adopt me as a surrogate granddaughter.

Banana Bungalow — where to begin? This is an incredibly special place and I will always think back to my ten days here with a perma-smile on my face. Here, I remembered what I love about traveling solo — making friends! Already I’ve met up again with three different people I met here.

• It’s a funny favorite to have, but one of my best memories from Maui is the creepy and very unofficial tunnel I took on the Road to Hana! It involved swimming and treading water through pitch black underwater caves, and occasionally pushing through a crawl space and hoping there would be air on the other side! I confronted a lot of phobias that day and didn’t need a single therapy session to recover.

• This trip was all about people for me — the reunion of Cayman Islands crew Wim, Dave and Heather in Oahu, getting to know close family friends Warren and Claire on The Big Island, spending time with my Uncle Mark and Aunt Linda and tearing it up with Kyle and my Banana Bungalow buddies on Maui, and having an internet friendship come to life with Angie and Alex on Kaua’i. I feel blessed to have so many amazing people from past and present come into my life all at once!

• Number Eighteen on my Happiness at Twenty Three post. And that’s all I’m going to say on the subject.

• This month I adopted two new Hawaii obsessions — shave ice and Hawaiian reggae. Shave ice speaks for itself — I’m a sugar addict. The music stayed with me and in my iPod rotation long after the trip ended — check out Common Kings, Irie Love, Josh WaWa White, Kimie for a little taste of what plays all day every day on island radio.

Maui Travelrelaxation and friendship on Maui


• My trip started out on a very dramatic foot when I almost missed my flight! In an effort to save money, I took the Airtran to JFK. I’ve always taken the Airtran from the airport but never to it — I’m always paranoid about something trapping me underground. And GUESS WHAT? It did. Somewhere under Atlantic Avenue, a man has a heart attack and all trains were stopped, leaving me clawing at the windows like a caged animal. I made it to JFK at 9:20 for a 10:00am departure — when I arrived panting, sweating and disheveled at check-in they shook their heads and told me half the plane had already boarded. With some well-placed tears their minds were changed and I found myself sailing through security with a personal escort. I was the last person to board the plane — with just a few bonus gray hairs.

• Not that there is ever a really great time to have your website hacked, but it certainly felt extra cruel to spend any of my precious time on the islands dealing with it.

• While the Big Island was filled with highlights, there were also some lowlights. First, we had a nightmare with our car rental. It’s a boring story, but suffice it to say it was not the best way to kick off our stay on the island. Then, the weather was somewhat surprising — we were met with gray skies and rain more mornings than not, and we ended up with a bum sunset at Mauna Kea. Also, I really did not factor in the enormous distances between locations. As much as we loved our cherry red jeep and enjoyed having the freedom to come and go as we pleased, we spent a little too much time in that car. And as I had been the one planning that entire leg of the trip, I felt inevitable planning guilt! Putting together the video I link to above was really therapeutic for me — it reminded me that despite these minor annoyances I was able to see almost a lifetime of natural beauty in less than a week.

• I had a touch of professional drama on Maui — an awkward situation that left me feeling my only true low of the entire trip. I hate to vague-blog, but I can’t say more — you’ll have to wait for my book!

• I lost my favorite bikini and my new sunglasses! And yes — I completely realize that if  something this trivial ends up on the lowlights list, it was a pretty amazing month.

Roundup 16Kauai, my bonus island


Unfortunately I didn’t keep track of my budget in Hawaii the way I had hoped I would — and honestly, it wouldn’t have been representative of a typical travelers situation. But let’s just say I never would have expected Hawaii to be within my financial grasp — then I booked a free flight using credit card points, and didn’t pay for a single night’s accommodation thanks to crashing with family and friends and a work assignment.

Going through my Mint statements, I calculate that I spent roughly $3,500. That number is in NO way precise — I was often traveling with friends so things got complicated with bill splitting, and I have no idea how much cash I walked in or out of Hawaii with. But it’s a good rough estimate, and it works out to about $87 a day.

So if I didn’t spend anything on my flight to Hawaii or accommodation, where did all that cash go? I splurged majorly on activities like skydiving ($350), ATV riding ($105), and diving with the manta rays ($165) and spent a small fortune on inter-island flights and baggage fees ($484), a decent chunk but well-spent chunk on flight change fees ($180).

Family and Friendsjust a few of the hosts who showed me so much aloha


This is a new category for my monthly roundups! Since I wrote this post, I’ve made a commitment to staying fit on the road, and so it seems appropriate. I didn’t track my daily workouts on this trip the way I’m doing currently, but I did pretty well at keeping up on this trip. I slipped a bit on The Big Island, simply due to the fact that we were in the car most of the day, every day. But in Oahu we hiked often and Heather and I went for runs together around the Hawaii Kai suburb. This was the first time I ever felt confident enough to run with another person — I used to be embarrassed I’d be too slow or not be able to run long or fast enough — but I absolutely loved it! Now whenever I’m home my friend Michelle and I are running buddies.

In Maui I also kept up with my running, and on my short time in Kauai I went for an epic hike and had a good SUP workout. Throughout the trip I tried to keep up my daily routine of pushups, crunches, and tricep dips. In terms of eating healthy, I did fairly well. I packed a month’s worth of oatmeal packets which helped me start every day on the right foot, though I admit that I was often derailed by my insatiable shave ice addiction. While I didn’t step foot in a gym the entire forty days, I think this was one of my most successful trips ever in terms of keeping healthy on the road.


Tucker was a little bitter about being left behind

What’s Next

Post Hawaii I spent two months back in New York, with trips to Vegas and Florida keeping my wanderlust at bay until I could leave for my next big trip — Southeast Asia!

As always readers, thank you so much for coming along for the ride! I can’t express how much I loved sharing this trip with you.


  • Amy
    January 29 2013

    I never really considered Hawaii as a feasible backpacking destination but all your recent posts have convinced me otherwise. I particularly loved your post on the Banana Bungalow – I can’t believe such a place exists in such an ‘expensive’ destination. My bf and I have added it to our travel wish-list!

    • Alex
      January 30 2013

      I’m SO glad to hear that Amy…. basically the best compliment you can give a travel blogger! Let me know when you get to Hawaii 🙂

  • Kathryn Allen
    January 29 2013

    “… just wanted to publish a post full of photos, excessive punctuation marks, and perhaps a caps locked adjective or two. But somehow I persevered beyond that Tourette-style blogging and managed to form actual sentences.

    I wish I’d written this sentence.

    What a “caps-locked adjective or two” 40 days!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

    • Alex
      January 30 2013

      You know what’s funny? I wrote that sentence in my first post about Hawaii (months ago I think!) and saved it for this post!

  • Dani
    January 29 2013

    I looked up what #18 on your Happiness list was and now of course I am dying to find out more 😉 What an amazing time you had – totally jealous!!

    • Alex
      January 30 2013

      We need to meet in person so I can spill all my secrets 🙂 After very raw-blogging my big breakup, I’ve decided to be more discreet about future romantic relationships until they become very serious…

  • Alexa
    January 29 2013

    I really have been enjoying your posts about Hawaii. My goal is to visit each Island (I have been to Maui, Big Island, and Oahu). I recently am having a nightmare with my car rental in Maui. I’m hoping that Amex might help me with deductible (some cards offer rental car insurance!). Thank you so much for these posts.

    • Alex
      January 30 2013

      What happened with the car rental? We had a nightmare with ours in The Big Island…. ugh.

  • dana
    January 29 2013

    omg no more vague blogging please! i always get so curious and frustrated when people only tell half a story.

    • Alex
      January 30 2013

      Hey Dana, I’m sorry! I hesitated over even writing those two things because it irritates me with other bloggers too. But as well as being entertainment and tips for other travelers, this is also my own personal diary in a way, and I want to be able to remember all the highs and lows years from now when I look back 🙂 I’m pretty much an open book anyway, I only hold back when other people’s privacy is at stake.

  • Wow girlfriend what a month!!!!!!!! Your life is just so freaking fabulous! You’ve made me miss Hawaii so so so much.

    • Alex
      January 30 2013

      I most certainly cannot complain! Actually writing these posts made me miss it too… I’ll have to return sooner rather than later!

  • Alexa
    January 30 2013

    Ugh, when I returned the car there was a black scratch on the driver’s side door. 🙁 I did not do this, I think it might have occurred when I had to valet at the hotel. I think AMEX can help with the charges so I’m looking into. No fun!

    • Alex
      February 1 2013

      Yikes! That’s why car rentals make me so nervous. Fingers crossed for ya!

  • Arienne Parzei
    February 1 2013

    Wow, what an awesome roundup! When I was travelling back to Canada from New Zealand I worked out an extending stop over in Honolulu for 2 nights and 3 days. Best decision ever! I too fell in love with Hawaii, and we’re talking only getting to see a little sliver of the place. I can wait to go back to visit Hawaii “properly”, especially after reading this post!

    • Alex
      February 2 2013

      Believe me… I’m scheming ways to get back to Hawaii as well 🙂 What an amazing place!

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