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23 Days in Hawaii: Our Slow Travel Fail

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Physician on FIRE has partnered with CardRatings for our coverage of credit card products. Physician on FIRE and CardRatings may receive a commission from card issuers.
Some or all of the card offers that appear on the website are from advertisers. Compensation may impact on how and where card products appear on the site. POF does not include all card companies or all available card offers. Credit Card Providers determine the underwriting criteria necessary for approval, you should review each Provider's terms and conditions to determine which card works for you and your personal financial situation.
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Living like a local for weeks at a time. That was the dream when I went part-time. Every day spent away would be sublime.

I promise the rest of this post won’t rhyme.

Our first lengthy family adventure was a complete success. The four of us spent three glorious weeks in Mexico. Our apartment overlooked the friendly and vibrant city of Guanajuato.

We woke up naturally to leisurely mornings. Our commute to school was a hike down the winding alleyways stairways. We explored our city, attended Spanish classes together, made new friends, and even made a habit of journaling and attempted guided meditation, actually getting our boys (and me) to sit still for minutes at a time!


Our Slow Travel Fail


I spied a four-day CME conference on Hawaii’s Big Island. We had visited Hawaii a couple times, but had never been to the Big Island, and our boys had never set foot on a single Hawaiian isle, so we made plans to go to Hawaii as a family.

If you’re going to fly all that way and cross four time zones, you might as well stay a while if you can. And we can. I don’t work that much these days, and our boys’ school is  lenient with our time away, so we planned a long trip. A 23-day long trip to be exact.

And if you’re going to fly all that way, and you have 23 days to spend there, you’ve got to visit multiple islands. We’d never been to Kauai either, and we had heard it was beautiful (it is), so we added that to the list. Oahu’s got a lot to see and do, especially for the kids, so we added Oahu to the itinerary.


Napali Coast hike
view from kauai’s kalalua trail


We booked one night at a luxury hotel in Waikiki the evening we flew in. I had more than enough SPG points to book The Royal Hawaiian from the welcome bonus on a Starwood Preferred Guest American Express Card (which has since been replaced by the Marriott Bonvoy Boundless card), and when we returned to Oahu, we stayed away from the hustle and bustle on the island’s west side.

The Big Island has a distinct division between the Kona side and the Hilo side, so we planned to spend at least a few days on each. And then we found a yurt in the south, not far from one of Earth’s four green sand beaches, so we booked a couple nights there, too.


love yurts
“Oooh Oooh, Love Yurts.” – Roy Orbison / Nazareth


Altogether, we stayed in six different places, rented three different cars on three different islands, which were reached with three different flights over 23 days.

So much for slow travel.


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Our 23 Day Hawaiian Vacation


We might as well call it what it was. A vacation. We like to say we don’t take vacations anymore, but when you’re sightseeing all day, enjoying happy hour every evening, and never in one place long enough to unpack the suitcase, you’re on vacation.

We flew out of Minneapolis early on Super Bowl Sunday, just ahead of the next-day rush, catching much of the big game live from the semi-comfort of the coach seat on our connecting flight to Honolulu.

Uber took us to The Royal Hawaiian, a grand coral colored throwback of a hotel right on the shores of Waikiki Beach. After a restful night and an early morning wakeup due to the four-hour time difference, we played on the beach before catching our flight to Lihue, Kauai.


boys in waikiki
life in the rainbow state


Not Slow Traveling on Kauai


Upon our arrival in Kauai, we picked up a sweet yellow convertible, crammed our gear into the little trunk, and headed off to the islands #1 most popular attraction: Costco. Honestly, I haven’t seen a retail store so crowded since the days when I actually partook in Black Friday sales at brick and mortar stores. Costco was similarly packed on the Big Island, but not so bad on Oahu.

With our provisions of food and beer to last a few days, we made our way up to Princeville, where our Airbnb ($40 off your first stay) apartment awaited us. It was actually a timeshare community at the Wyndham Bali Hai, which piqued my interest in this whole timeshare resale idea.

With just four days on the island, we kept busy, visiting waterfalls like Opaeka’a, gawking at the “Grand Caynon of Hawaii” a.ka. Waimea Canyon, driving through the tunnel of trees en route to the Spouting Horn blowhole, and of course exploring its many beaches.


spouting horn blowhole, kauai
spouting horn blowhole, kauai


One of those beaches, Ke’e Beach, was at the base of the Kalalau Trail along the Nāpali Coast. It was there that I randomly chatted up a family physician who, like me, attended medical school at the University of Minnesota. He had been retired since his mid-fifties and strongly encouraged me to live below my means to follow a similar path. Preaching to the choir, doc!

We attempted the hike, but with the recent torrential rains (and continuing light rain that day), the steep, rocky terrain was tough and not all that safe for boys aged 7 & 9, so we headed back to the beach.

Another highlight on Kauai was the lighthouse and nature reserve at Kilauea Point. We watched whales breaching in the distance while albatrosses, frigate birds, and red-footed boobies soared just overhead. Having seen the blue-footed booby on the Galapagos Islands several years ago, we can now say we’ve seen both boobies.


Not Slow Traveling on the Big Island


Couldn’t hurt to stay in a yurt, am I right? Our first two nights were spend in a yurt high above the sea in an area appropriately named Ocean View. We also had a great sky view in this dimly lit, off-the-grid neighborhood. The boys loved our “glamping” experience, with one sleeping in the loft, one on the sofa, and my wife and I sharing the “master suite.”

We had solar electricity, propane-powered fireplace and hot water, and surprisingly reliable Wi-Fi, so I had no complaints, either. The terrain was other-worldly volcanic rock, as it is on much of the west and south of the island. Reminded me of Iceland. A very warm Iceland.

My CME fund footed the bill for our next four nights in a well-appointed condominium in Waikoloa Village north of Kona. I attended lectures while the rest of the family enjoyed time at the pool and the beach.


papakolea green sand beach
green sand, menacing t. rex


Speaking of beaches, we made our way down to Papakolea’s green sand beach at the southern tip of the island. We opted for the nearly six-mile round trip hike along the ocean, which was beautiful. The greenest sand, which comes from a volcanic rock called olivine, is actually found along the way, so if you hop in one of the trucks that will take you for $20, you’re missing out.


Olivine Green Sand
extreme close-up of olivine (green sand)


After the conference, we hit up the Hilo side, staying in a unique Japanese style home that was essentially a series of little buildings under one roof that wrapped around a center courtyard garden. You could call it a garden, but you could also call it a wildlife refuge; the hundreds of goldfish in the pond were occasionally dinner for the frogs, which were scared off by the chickens that ran under the house and into the inner refuge to raise a ruckus. As nightfall approached, all would seem calm until the shrill coqui frogs started hollering at the top of their little lungs.

The Winter Olympics were ongoing, and I did catch the men’s curling team capture the Gold Medal, but we mainly spent our evenings on the lanai enjoying good company (we were joined by a relative who flew all the way in from the mainland’s east coast), a cold beverage, and a good, loud show in the courtyard.

Other big island highlights included driving up Mauna Kea at night, sampling Mauna Loa macadamia nuts at the source, and of course, visiting Volcanoes National Park. We saw real live lava!

We also the pleasure of meeting up with a traveling troupe of physicians including Drs. Matt & Carrie Reynolds, the latter a pediatric gastroenterologist and the voice of The Hippocratic Hustle, the former a chill guy and surgeon.


kilauea is smokin’!


Not Slow Traveling On Oahu


By the time we got to Oahu, winter breaks were in full swing on the mainland, so we had a bit more competition for affordable housing. We found a reasonable spot in the Makaha valley in a condominium complex that gave us an ocean view and an unexpected level of seclusion, being on the top floor overlooking the thick canopy of trees.

On the property grounds were a hot tub, pool, and an absurd number of peacocks. Dozens and dozens of peacocks. Have you seen any of the Minions movies? It was like that, but thick with peacocks.

Once again, we found the beaches, but this time, we used of them a launch site for surfing lessons from The Military Guide’s Doug Nordman, a.k.a. Nords. I was able to catch my own waves, and the two of us spent several hours pushing my boys into waves of their own. Both were able to get up on the board and ride all the way into the sandy shore of White Plains Beach.

I was proud of my boys, but what impressed me more were the volunteers and participants with Accessurf, who were out there giving the disabled and disadvantaged the opportunity to experience the joy of surfing.

We saw a young gal with a prosthetic leg surfing quite well; there was a wheelchair-bound man who caught waves on a larger tandem board with a lot of help from the volunteer crew. Nords let me know that it was one of his favorite charitable causes, and unbeknownst to him (at the time, at least), we decided to say Thank You for the lessons with a donation to Accessurf from our Donor Advised Fund.



Nords spent at least five hours giving private lessons to four of us; that’s worth $1,000 in my book, particularly when the money goes to a good cause.

Later that week, we returned to the same beach for a Bigger Pockets meetup with Brandon Turner, another graduate of The Nords School of Surfing. We were joined by Ty Roberts of Get Rick Quick’ish and CampFIRE Finance and his family of six, along with a couple dozen enthusiastic real estate investors. Great people and great food at the potluck picnic — I had my fill of delicious manapua and poke.


Monk Seal Oahu
monk seal at kaena point


A few years ago, my wife and I hiked from the north shore out to Kaena point, the northwesternmost point on the island, to see the monk seals and nesting albatrosses. On this trip, we hiked to the same point from the western shore. We saw one monk seal (from 50+ feet away — it’s illegal to get closer) and the Laysan albatrosses had hatched, so we saw the fuzzy little chicks. I highly recommend the hike from either direction if you find yourself on Oahu.


Laysan Albatross Chick
laysan albatross chick


Other highlights on Oahu include the Polynesian Cultural Center, a whale watching tour, the Dole Plantation — our boys loved the maze and we all loved the Dole Whip — and of course Pearl Harbor.



We flew to Hawaii for free. 3 round trips with travel rewards points, and one reimbursed from my CME fund.

Slow Travel versus Vacation


Slow Travel Ideal Morning: Wake up naturally, enjoy a home-cooked breakfast, and get a little schoolwork and blog work done before heading out for a few hours of family fun.

Actual Vacation Morning: The chickens started greeting the morning sun when it started rising in New York, we wake up to nature’s alarm clock and don’t bother showering since we’ll be covered in sunscreen, sand, and sweat in short order, and we head out for a full day of excitement, forgetting the sandwiches we had prepared the night before.


Kids Black Sand Beach


Slow Travel Ideal Afternoon: After a splendid three-mile hike in which we see the whales and dolphins frolicking off the coast under just the right mix of cloud cover, intermittent sun, and a cooling breeze off the ocean, we make it back to our abode and reflect on our day with gratitude.

Actual Vacation Afternoon: The rain altered our plans for the beach, mudslides have closed the nearby hiking trail, and we end up seeking shelter in a souvenir shop selling the same crappy tee shirts and shell-based kitsch you find at every tropical destination ever. We cruise home in bumper to bumper Hawaii traffic, arriving home to start making dinner about 30 minutes after the time we planned on eating dinner.


1868 lava flow


Slow Travel Ideal Evening: After dinner, we each read for an hour, the boys go to sleep without a fuss at 7:30 pm and maybe, just maybe, we enjoy an adult beverage or two together, but you don’t do that every night because this is not vacation. This is simply living away from home.

Actual Vacation Evening: “I said no Kindle if you can’t stop bickering, and you’ve been fighting since 11 a.m.!” The boys are finally ready for bed at 8:30 pm, and I crack the first of three strong beers because we’re only on this island for six nights and for some reason, I bought three six-packs on day one.


Friday Fireworks Waikiki
friday night lights in waikiki


I may be over-exaggerating a tad, but throughout the trip, we realized we bit off a wee bit more than we wanted to chew. It’s awfully easy and rewarding to set up residence in a far-flung location for a few weeks and enjoy the surroundings at a slower pace. It’s also quite fun to take an extended vacation while bouncing from place to place, but these are two entirely different kinds of trips.

I’m glad we booked this one, and while our days and nights were pretty action-packed, we did partake in many memorable experiences in an exotic land chock-full of natural beauty. If we make it back to Hawaii as a family, and I imagine we will eventually, I would plan to spend several weeks on each island, rather than several weeks for the whole frenzied whirlwind trip.



Have you been to Hawaii? What was your most memorable experience? Any other slow travelers or slow-traveler-wannabes out there?

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58 thoughts on “23 Days in Hawaii: Our Slow Travel Fail”

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  6. Hello, Sounds like you had a great time! I wouldn’t look at your schedule being so busy as being negative. One of the things I have found is that its good to go explore a bunch of places so that you have a better idea where you’d like to hunker down on the following trip(s). We only get so many visits to Hawaii (or insert other awesome location), so best to get a flavor for a little bit of everything so you can maximize the fun/adventure on future visits.

  7. Great post and strategy! Getting the kids out school has always been one of the greatest challenges. It helps to be proactive with the leaders in the system.
    I am also very interested in how you and your practice designed a token system to devide the work in a fair an equitable way. You made a mention of it in another post. Any chance you could elaborate? Nights, weekends, holidays, etc? Thanks, DOAT

  8. Great post. I felt like I was back on Kauai. It’s hard to slow travel with CME. I feel guilty not going to at least some lectures. Then again, I’ve never slow traveled.

    I hiked every day on Kauai despite the mud. The hikes from Waimea canyon are epic, although very dangerous so probably not good for 7 and 9 year olds. Many die each year hiking in Hawaii. A young nurse got swept away in a flash flood on Oahu while we were there.

    I do dream of the 1 week per island type trip and that’s one reason why we are super savers now. I do however believe in segragation which is breaking up a pleasurable experience into smaller parts to extract maximum happiness. So my slow travel would be more like shift work. 1 week vacation mode, 1 week work/volunteer/learning mode and repeat and few times.

    Hawaii can be tough to get to and from, but we stopped in San Francisco for 2 days on the way back to avoid the overnight flight and that made all the difference. I guess that’s another benefit of slow travel is never having to take a crappy flight to make it there or back for some deadline.

    • Bummer that we didn’t connect while we were on the same small island. The conference got in the way, I guess. I’m like you. If someone’s paying for me to be there, the least I can do is show up.

      Your view on slow travel sounds like a winner. Love how you’re working through so many Hawaiian hikes. Beautiful place to get your boots muddy!


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  10. Glad you enjoyed your trip, Hawaii is fantastic to visit. However, as a local, living here is entirely different. I’ve heard it countless times, people (not you btw) visit the islands and think it’s some magical place, thinking their vacation mimics everyday life when it doesn’t. On your way to Makaha, I’m not sure if you saw the huge homeless camp near the boat harbor. Traffic is bad, housing is super expensive (possibly propped up by outside money), infrastructure is old, and so on. Tourism has gotten a lot worse over the years, a majority of people who move here leave within a few years for a variety of reasons, the population has decreased in recent years.

    Also, in regards to your costco experience, supposedly the busiest costco in the country is in Honolulu. I would also agree with Big Island being your favorite. However, I think it’s funny when people hype up Maui and Kauai as they are probably the most touristy and non-local islands. On a per-capita basis, they get more tourists than Oahu. Maui has kind of always been like that but Kauai has changed a lot in the past decade or so from a quiet local vibe to what it is now. Oahu gets a bad rep but can be great if you know where to look (unfortunately social media has made these areas more crowded with tourists) and it’s probably a better picture of how everyday locals live. Hilo is a bit old school Hawaii as well but that has changed somewhat too. I don’t blame you for not slow-traveling, there’s a lot to see and do and it can be exciting, but believe it or not it does get old or “normal” over time.

    • I agree wholeheartedly, JSA. Not exactly a local, having spent all of 5 weeks there in recent years, but we’ve noticed all the same problems. We even watched a short documentary (or possibly a portion of a longer documentary) on the hundreds of homeless in the camp near Makaha — right next to and across from the schools, no less.

      We’ve experienced slow and go traffic on every island, even Kauai, and it’s not like you can take an alternate route on mountainous islands. Tried to catch a Minnesota band playing at Kona Brewing, and there was a 90-minute wait for a table. No kids allowed at the bar — we found out the hard way and got kicked out (gently).

      Hawaii is a beautiful archipelago, and I could see us spending months there some winter, but I have no fantasy of a permanent move.


  11. Sounds like you had a great time! I wouldn’t look at your schedule being so busy as being a negative. One of the things I have found is that its good to go explore a bunch of places so that you have a better idea where you’d like to hunker down on the following trip(s). We only get so many visits to Hawaii (or insert other awesome location), so best to get a flavor for a little bit of everything so you can maximize fun/adventure on future visits.

    My philosophy is “how do you know where the best places are until you’ve been to all the places?” There are going to be some duds along the way, but most of the time you’ll discover something pretty special.

  12. Great “slow vacation” post PoF! We’ve spent a lot of time in Hawaii, so I know exactly how wonderful a “vacation” like that is, even if it isn’t “slow travel”

    I like your definition of slow travel though … “if you don’t fully unpack your bag its a vacation.”


  13. We love Hawaii! It’s our home away from home. We go every other year and stay for about a week. Currently, we spend our time on Oahu since our kids are younger. We’ve gotten to a point where we’ve seen most things on Oahu, so we spend a lot of time lounging around at the hotel with some sightseeing sprinkled into our days. Dole Plantation is always a must when we go, for the Dole Whip and the maze and/or train ride. Once the kids are older, we will definitely explore other islands. We’ve found that while other islands are beautiful (we’ve been to Maui), some of the activities are not compatible with having younger children. When we retire, we would definitely love to spend more time island hopping and maybe spending about a month there. Thanks for sharing your experience. Although it may not have been the expected slow travel, it seems like your trip was very well planned out with lots of memorable activities.

    As for your timeshare interest, we love our timeshares! I think if you are able to buy resale at a reputable place (not sure if ebay is one), there should be no issue. Also, I would make sure you buy at a relatively nice hotel/chain. I have heard many stories about people who bought timeshares at a random hotel, only to have the quality of the timeshare go downhill and the timeshare is pretty much worthless. Also, even if you buy with a bigger chain, make sure they are consistent in quality especially if you think about trading. Rule of thumb is to make sure you are happy staying at the timeshare you’ve bought at. Sure you can always exchange, but you may not get the location you want. We bought at Marriott and Disney, both resale. We love them. The only thing with Marriott is that we cannot trade easily unless we want to go to a different site and pay more to do so. Lucky for us, we love our Marriott timeshare. We also have the option of breaking up our 2 bedroom into a one bedroom and a studio for two consecutive weeks, which we’ll likely do when we retire. With Disney, we can stay at other resorts as long as they have availability. With both, we know the quality we are getting, which is always top-notched. Sure, we can probably stay somewhere cheaper for the cost of the maintenance dues (~$1800 a year for both), but who doesn’t love a guaranteed ocean view 2 bedroom at the Marriott in Hawaii and staying at a deluxe Disney resort when you are at Disney World.

  14. Sounds like a fantastic trip, even if it was jam-packed! Since my parents retired they have spent 4-5 weeks in Hawaii every winter (they must have been there at the same time as you as they also mentioned the torrential rains this year). Since they’ve done it so many times they fully embrace slow travel and only ever go to one island on each visit. I would do the same thing as you though and max them out if I had the time. From my limited memories of Hawaii (I haven’t been for years), each of the islands is so unique and has its own character.

  15. We were just in Maui for 13 days. Stayed at the same place and definitely SLOW traveled. A few days we just spent the entire day on the beach. We thought about island hop but glad we didn’t do that.

    • Good for you! Our only time on Maui was about 16 months ago for a week, much of which was spent at an anesthesia conference in Kaanapali. We took the road to Hana, saw Chuck Lindbergh’s gravesite, and continued around to complete the island loop in direct violation of the rental car agreement.

      It became clear why they didn’t want us there in our Nissan Ultima, but the car survived, and so did we.


  16. As soon as you started adding islands, I knew your slow travel trip was not anymore. 🙂

    I’ve done that before – didn’t regret it exactly but I truly love slow travel when we can do it, so I make an effort not to overbook ourselves as much as I can now until we have the leisure to travel for a month at a time. As an official homebody, more than a month is probably too much.

    I’m trying to decide if I should try to meet up with any bloggers when we get out to Hawaii ourselves since we can only get away for a week.

    • Most of the folks I met up with were just passing through, too, so it might depend on the timing more than anything. Of course, there are bloggers based there, as well. Either way, I’m sure you’ll have a great time.

      In the past, I’ve wanted to squeeze as much as possible out of every day. I’m doing my best to change that, but this trip was not indicative of my efforts at all.


  17. Vicarious fun! A quick question – off all the places you guys stayed at, which one had the fastest, most reliable Internet? I am always looking for places like that because it helps us extend our vacations.

    • To be honest, the internet was fine everywhere except in Paradise Park south of Hilo where we had DSL. That was a bit slower and spotty. But the yurt had regular high-speed internet with no interruption.


  18. Can you elaborate on how you balance slow travel with your kids vs time away from school? Do they do online assignments? Are they in public vs private? Seems like it would be great to take extra time during non peak seasons but the hard part is getting stuck with the schools vacation schedule

    • They’re in 2nd and 3rd grade in a public school. We do the math sheets and reading that they would be doing in class, and when they return, they present to their class on a topic related to our travels. For example, they’ve put together a Google Slides presentation on the formation of the Hawaiian Islands and the Mummies of Guanajuato.

      We met with the school principal last year, told him our tentative plans, and he loved the idea of us getting our boys away to see more of the world. I realize not every school will be as open-minded, but I’m sure they’d rather have the tax dollars allotted per pupil than to lose them to homeschooling.


  19. Long time reader, first time commenter here. Glad to hear you had such a great time in Hawaii, PoF! I had the privilege of three trips there during medical school, as my best friend was stationed with the Army on Oahu. Used it as an excuse to travel there with free lodging! I hope to go several times more after residency is done.

    I’ve experienced every island except Kauai, which sounds amazing from everyone who has gone. My favorite islands are a tie so far, between Maui and the Big Island. The rural beauty and the welcoming natives on the Big Island will always stick with me. We had a taxi driver who literally took us on a tour of the island pro bono just because (we tipped heavily haha). Maui is that perfect blend of touristy but also authentic Hawaiian. Not nearly as crowded as Oahu, and the Road to Hana is one of the most incredible drives I’ve ever taken. Also played some ridiculous golf courses in Maui as well.

    Also, it’s cool to hear you met up with Brandon of BiggerPockets while you were there. I listened to one of his podcasts while he was there; made me jealous! Small world here in the personal finance realm!

  20. When our son was two we took him to the big island for two weeks and did a circuit around the island. Enjoyable if a bit stressful with kids. On our honeymoons we went to Maui and Maui. Hiked to the end of the Kalalau trail and camped there. I will note you don’t want to do all 11 miles each direction in one day. Most people at the beach looked at us as if we were nuts for going in one day and out the next. But sleeping in a tent way out there was cool. My wife swears given the considition of the trail she won’t do it again:(

  21. Hardly the unmitigated disaster that I was expecting from the title, but a good lesson on the nature of travel.

    A few years ago, a younger colleague, embarking on a road trip with her young family, posted a blog on “family trips vs. vacations”.


    We were both heading to Michigan the same time, and I texted her a photo of our “vacation lunch”, which included a hard blueberry cider, IIRC, and the analogous “trip lunch” with high chairs, crayons and Mac and cheese at the table next to ours.

  22. I absolutely love Hawaii. I think it’s the most beautiful and unique place on earth. And that is why I plan on moving there as soon as possible after my residency. Not great for my portfolio, but absolutely crucial for my wellbeing 🙂

  23. My question is what beer did you drink while out there? Gotta visit Maui sometime braddah, which I thought you did. They renovated the Maui Brewing Company headquarters. Surprised y’all went this time, as it is kind of a wet season. I’ve been lucky with my trips to Maui: March 2013 (honeymoon) and Sept 2017 (fam vacation).

  24. Looks like you had fun. I advise people going to Hawaii to spend one week in one spot on one island. Don’t hop around. You waste too much of your vacation at the airport and packing to go to the airport and unpacking when you arrive. Next trip (or week) you can do another island.

    My favorite Hawaii activity was riding bikes down the volcano on Maui. That was a blast. No prior experience needed.

    I just got back from a 31 day cruise to the Amazon and will be posting that on my blog soon. Now I’m ready for a 4 month world cruise.

    Looking forward to “slow travelling” with you to Cuba in September.

    Dr. Cory S. Fawcett
    Prescription for Financial Success

    • You’re doing semi-retirement, or the repurposed life you’ve got, exactly right! Best to embark on these adventures when you know you’ve got your health and the energy to enjoy them to the fullest. You may still have it in 20 years, but there are no guarantees.


  25. We absolutely love Hawaii. My sister lived there for a bit, so we made as much of it as we could.

    As for the whole slow travel thing. We’ve done both, and after time we realized we’d much rather miss a few things and take it slow than rush rush rush everywhere. Plus then you always have a reason to go back!

    • Awww man, I’ve never had a sister living in Hawaii. Not fair! I’ve never even had a sister!

      I don’t love everything about Hawaii — the traffic, even on the lesser populated islands, can be a nightmare — but it’s got enough awesomeness to keep us coming back in spite of what we’ve been telling ourselves.

      Living on the left coast, as you do, makes it a bit easier to get there. Compared to Miss Bonnie in Phlly, you’re already halfway there.


      • Yeah well, unfortunately they have since moved. The joys of the military. We haven’t been back since. We will at some point I’m sure.

  26. Sounds like a great time. Love reading in rhyme. The islands are lush, no one’s in a rush. Next time I get back I’ll have to take a crack, at glamping in a yurt on volcanic rock, not dirt. Glad we got a chance to meet you and the whole PoF crew.

    • You’re a poet and you know it!

      Great to meet the entire GRQ clan, as well. I’m glad our paths crossed.


  27. Thanks for this post! Our boys are dying to go to Hawaii, but it’s sounds like the best idea is to pick an island and explore it, rather than flying back answerable forth. It does sound like you made the most of your time, with blogger meet ups and paid-for accommodations and flights! The pics are great. Looking forward to taking these longer trips more than once per year!

    • It’s tough, Laurie, because there is so much to see and do. We prefer a slower paced travel, but you don’t go to Disney World and spend every day at Epcot. If you’re spending the money and going all that way, you want to see all the attractions. As we’ve both figured out, the best of both worlds would be to spend an entire winter (or longer) in Hawaii, so you’d have weeks on each island and not be in a hurry on any particular day.


  28. I strongly prefer slow travel to vacationing, it’s probably what most interested in FIRE. Two separate three month international internships in college kind of ruined me for quick stops in distant places.

    I may be going to Hawaii in November for the first time. I’ll be sure to reference this before planning my trip!

    • It’s funny how we can be “ruined” by great experiences. It’s sort of a corollary to the hedonic treadmill. Once you’ve been exposed to a better way of living, it’s hard to go back!


  29. I have dreams of our family taking 3-4 week trips in the future, so I’m going to keep these tips in mind. Sadly we didn’t get to do the green sand beach (only had a week and had our 3YO with us – hopefully next time). My favorites on Hawaii were probably the hot springs outside of Pahoa, the newborn monk seal pup, and all the fantastic farmers markets we got to.

    • Great tip, Angela! We found the hot spring / “king’s bath” at Ahalanui / Pahoa on one of our last days on the big island. Seemed well known by the locals, and not so busy with tourists. What a great spot to spend an hour or two.

      I regret that we didn’t do more hiking; I think that will be easier when our boys are at least a few years older.


  30. Love the slow travel ideal vs. actual comparison. Just like the ideal budget vs. actual 🙂 This was a great write-up as my wife and I are 22 hours away from our flight and first trip to Hawaii, one week on the Big Island (most excited) and one week on Oahu.

    • Mahalo, Jason. Enjoy your trip! The Big Island was our favorite. So varied with plenty of unique and natural attractions. Some that I didn’t mention for brevity’s sake are the petroglyphs and King’s road in Waikoloa, breweries in Kona (there’s one in Hilo, too, but we didn’t get there), the ruins from King Kamehameha’s settlement north of there, black sand beaches, … I could go on and on. No wonder we couldn’t slow travel.

      One thing I’d like to do, but we didn’t as it’s not recommended for kids (and it was late) was to drive to the top of Mauna Kea where the mountain is snow capped. We did come home to a couple feet of fresh snow, so I did have that fun greeting.


  31. Sounds similar to Dr. Carrie Reynold’s Hawaii trip – not slow enough! We try to make it out to Hawaii semi-regularly. Planning on a CME trip early 2019.

    • Two of our three Hawaiian getaways have involved CME. It’s obviously a popular destination for that. I think we’re good for awhile — it’s so far away and there are many tropical places we haven’t yet seen. From the east coast, you could be on the beaches of the French or Spanish Riviera more quickly, not to mention the Caribbean.

      Our next beach trip is next month, already. A week on Honduras’ Roatan island before a medical mission trip on the mainland.


      • Long time reader, but rarely one to comment. For what it’s worth, I don’t care for Roatan – the sand flies are really annoying. My favorite experience in Honduras was a trip through a tropical rain forest known as “La Moskitia” – I used this company and did the 7-day overland adventure – I plan to return with my son in a few more years as I think it will be a great experience for him: http://www.larutamoskitia.com/

  32. I love the slow travel vs actual comparisons! They’re so funny and super true to what happens on every single trip.

    I remember our first morning in Bali, where we planned to ride to the beach on our little scooters but instead wasted a few hours getting stopped by the (corrupt) police who wanted a bribe for one of us not wearing a helmet. It was literally down the road and the scooter was crazy slow.

    I also like the yurts! So fun and unexpected. Did you ever consider listening to a time share for some free nights :)?

    • Corrupt cops, huh? What fun!

      The day we left the Wyndham Bali Hai, we had time to kill before hitting the airport, so we signed up for their on-site presentation. I learned a lot and kind of enjoyed it, actually. I also enjoyed the $150 AmEx card they gave us.


      • So fun! I didn’t want to give him the bribe out of the principle of it. Why does a police officer get a better standard of living because he gets bribes? What about all the other hard working citizens of Bali?

        In the end, going to court and paying for the ticket was more expensive so we just paid the $6 USD. Apparently we could’ve just paid him $1-$2.

        Haha, someone should write a blog post called “How I got paid $3k to go to Hawaii” -> by listening to a different time share every day. I feel like I’d get worn down after a week or so maybe though 😛

        Looking forward to your next post in May about the orphanage help 🙂

  33. Great information, Doc! I’m so happy that at least one of has seen both boobies now. Did you get any side shots? A-hem…

    Hawaii sounds amazing, even if you did cram too much into your itinerary. No one reading your post is going to feel sorry for you, I can assure you of THAT, my Minnesota brother.

    Curious about the Bigger Pockets gathering — did you take away any golden nuggets of wisdom, or was the value mainly in the networking (and of course, meeting up with stellar kids like Ty and Brandon?)

  34. Sounded amazing! It’s hard to not want to just take it all in while you are there.
    We are following your footsteps but at a slower timetable. We want to do one extended trip a year. We are headed to Iceland in a few months and then Norway. I wanted to go to Paris but we got vetoed by a geography obsessed 7 year old and so it is. None of us have been to Norway and my husband and I have both been to Paris, so we let him win. Where are you headed to next? In your next life you could be a travel writer.

    • You let a 7 year old veto your international travel plans??? That’s just wrong.

      Course, growing up I was lucky to travel by car 16 hours to see friggin’ Boston/Salem.

      • Yes. Yes I did.

        When that seven year old knows more geography than you and your husband combined, you just learn to give in.

  35. Hawaii is so beautiful! I’ve been there 3 nights and one day (the joy of time travel). I would absolutely love a longer stay to explore more of the islands sine I was pretty much limited to Waikiki.

  36. My sister was born in Hawaii, but I’ve never been (I am the youngest in my family). I’ve always heard it was beautiful and wanted to go. Just haven’t had the chance yet. It sounds like there is so much to see!

    A lot of the stuff I read on wellness/happiness suggests that the less stressful your travel is the more joy you derive from a trip. It sounds like you guys traveled a lot. Was it pretty straight forward jumping from island to island? Or was that a stressful experience picking up your suitcase and jumping ship to a different place every few nights?

    The trip sounds like a blast even if it wasn’t “slow travelling.” I am sure your boys enjoyed it and that you’ll have good memories to talk about for years to come!

    Also, you must be very proud to say you’ve seen both boobies now. (What a hilarious comment, I literally laughed out loud. Wasn’t expecting that).


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