Expedia Road Trip: Dad's Guide to Hawaii with Travel Blogger Matt Villano

Meet Matt Villano.  Travel Blogger.  Dad.  Hawaii aficionado.  Check out his guide to all things Hawaii.  From farms, to road trips, to the tough decision of where to stay with the family, Matt has you covered. 


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Hawaii Island Home on the Range

By Matt Villano


It’s no secret that the trifecta of suntan lotion, beaches and maitais is an integral part of the typical vacation in Hawaii. But after years of infinity pools and room service and cabana boys on the island archipelago, this summer my wife and I decided that our next Hawaiian adventure with the kids had to be something different.


So we stayed in a clapboard cabin. On a farm. In the middle of nowhere on Hawaii Island.


I know, I know—for tried-and-true resort rats, the whole thing sounds totally un-Hawaii. But that was precisely the point. Wewanted our two daughters to experience a real working ranch, complete with cattle and a bunkhouse.


Our oasis: Puakea Ranch, a 35-acre farm situated two miles south of Hawi, on Hawaii’s northwest tip.

Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano  

The place is dripping with history: All four of the structures on the property date back to the 1940s or earlier, vestiges of the place’s former life as a pig ranch and a sugar plantation as part of the communal Kohala Field system. (My wife, children and I stayed in the oldest home at the ranch, a long bungalow built by working families at the turn of the last century. It was called “Cowboy House.”)


Puakea also offers luxury: When the owners purchased the place in 2006, they spent three years gutting the structures and retrofitting them with modern kitchens and luxurious (standalone) bathhouses, turning what was once a ramshackle farm into a high-end-yet-farm-flavored retreat.


Most important, Puakea is a haven for little ones learning about the world. Animals on the ranch outnumber humans by a count of nine or 10 to one. Storms come in from the east like gangbusters and move through just as quickly, leaving nothing but rainbows (sometimes double-rainbows) in their path. On clear nights, thanks to zero light pollution, the night sky reveals a bazillion stars.


Our girls—ages 3.5 and 1—loved interacting with all of this wonder. Every morning, my toddler and I fetched eggs from the chicken coop across the lawn and plucked papayas from trees out back. During afternoons, the four of us tromped up the hill to watch the horses graze. In the evenings, my wife sauntered into the garden to snip herbs for pasta and other dishes. On aimless walks around the property, I’d take the baby to watch the switchgrass wave in the whipping wind and play spot-the-wayward-cows-and-goats.

Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano   Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano  

Even rainstorms were enjoyable; when we weren’t trying to catch drops in our open mouths, we huddled on the lanai and watch geckos darting to and fro.


We did leave the ranch—to explore the sleepy town of Hawi, to hit the state beaches on the Kohala Coast and to hike the mile-long, quad-burning trail down into the Pololu Valley at the end of the road. Still, our favorite moments of the trip were the ones we spent at Puakea.


All told, we stayed in this wonderland for 11 days—the best part of a month we ended up splitting between Maui and Hawaii Island.


No matter how much we appreciate a good resort stay, there’s no question we’ll be back.




Hawaii:  Exploring the ‘Back Road’ to Hana

B Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano y Matt Villano


Maui rental car companies and the local convention and visitor’s bureau will tell you that there’s only one way to Hana—the 36-mile Hana Highway that starts in Paia and hugs the twisty-turvy northeast coast from there.


But there’s another route to Maui’s most secluded spot: the Pi’ilani Highway that encompasses highways 31 and 330, and stretches from outside of Kula for 45 miles along the south coast.


Many refer to this thoroughfare as “the back road.” For years—basically since the road opened in 1937—locals were the only ones driving it. In recent years, as a preponderance of tour busses has made traffic on the Hana Highway intolerable, a growing number of tourists are ignoring warnings from local rental car companies and giving the Pi’ilani a try.


To be fair, these warnings aren’t for naught; one section of the road traverses a dry river bed, a few sections are unpaved, and a few other sections are so poorly paved they might as well just be dirt. Still, a drive on the Pi’ilani introduces visitors to a Maui many never see. For this reason, it’s worth the time.


The drive begins in Keokea, a tiny town on the southeast shoulder of Mount Haleakala. Here, at Grandma’s Coffee House, stop for a char siu (barbecued pork) omelet and a cup of house-grown coffee. Portions at this Greasy Spoon bakery are so large you won’t need to eat again until Hana, especially if you buy a home-baked cookie for the drive.


After Ulupalakua Ranch—home to Maui’s only winery —the topography changes dramatically. Green trees disappear. Volcanic desert takes over. Five miles out and you’re not sure whether you’re still on Maui or you’ve been transported to Wadi Rum.


(Thankfully, the Pokowai sea arch and blossoming wiliwili trees remind you this is not the desert.)

Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano  

Next up is Kaupo, one of the oldest settlements on Maui. Here, leave time to stop and marvel at St. Joseph’s Church, a stone chapel that has been standing in the same spot since 1860. Another step back in time: The Kaupo Store, a family-run grocery that sells snacks and cold beer by the bottle, and displays a number of antique cameras which date back to when the place opened in 1925.

Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano  

Unpaved and poorly-paved stretches of road (which, at some points, narrow to one lane) connect Kaupo to the southeast corner of the island, where lush tropical forests return. This region, dubbed Kipahulu, is home to Palapala Ho’omau Church, burial site of Charles Lindbergh (yes, that Charles Lindbergh), and a section of Haleakala National Parkthat includes a cascading waterfall known for its seven pools. It’s also where you’ll find the organic Laulima Farm; volunteers lead tours here every Monday morning, and a farmstand (that used to boast a bicycle-powered blender now) sells everything from jackfruit to fresh arugula.


Hana is another 30 minutes from here—a winding drive that curls past more waterfalls, more beaches and thousands upon thousands of guava trees. Celebrate your arrival with a maitai in the bar at Travassa Hana; while all of the other daytrippers hurry to beat return traffic on the Hana Highway, you can linger to the sounds of live ukulele music, knowing that on the Back Road, it’ll be smooth sailing all the way home.




Hotel vs. Condo: Which is Best for Family Travel?

By Matt Villano


You’ve blocked out days off, booked the airplane tickets and reserved the rental car. The only remaining aspect of planning that next family trip is locking down accommodations. The big question: Do you opt for a hotel or a condo?


To help you find the option that best suits your family, we’ve analyzed both choices as they relate to four important travel considerations: Budget, spaciousness, amenities and variety.


Here’s what we found.



In most destinations, condos and vacation rentals are cheaper than hotels across the board. According to the Maui Convention and Visitors Bureau, a three-star hotel in Maui, costs an average of $329 per night, while a week at a condo of similar stature runs from $1,200 to $1,500 per week (a savings of approximately $500 per week). Condos lead to savings in other areas; when you stay in a place with a kitchen, you can hit the grocery store or farmers’ markets and prepare meals instead of eating out—a savings of up to $100 per family per day. Also, most condos don’t charge for parking, while hotels do (this can save you up to $30 per day).



With standard hotel rooms measuring between 500 and 700 square feet, it’s safe to say that many condos offer more space for a family to spread out. Granted, some vacation rentals are smaller than others, but most condos start around 1,000 square feet and go up from there. In warm-weather climates such as Hawaii, condos generally have large patios, too. Still, the grounds of most condo complexes are relatively small; luxury hotels and resorts usually exist on large parcels of land that provide plenty of room for travelers to spread out. In most cases, this open space makes individual accommodations seem less claustrophobic.



While condos generally comprise nothing but accommodations and laundry facilities, hotels—especially luxury hotels—boast a veritable smorgasbord of on-site amenities and other entertainment options. Swimming pools, tennis courts, whirlpools, private beaches, fitness centers and restaurants are among the value-added options that are common at hotels. Throw in room service, concierge desks and formalized daycare programs and the number of on-site family-friendly perks at hotels in a particular market greatly outweighs the number of benefits at condos and vacation rentals in the same market.



Options abound for those looking to book accommodations on the next family trip. With hotels, these choices usually range from standard rooms to suites and cabanas. With condos, the possibilities are virtually limitless, from stationary RVs to attached apartment units, one-room cabins to multi-room homes. Families who opt for condos or vacation rentals also have a broader variety of locations from which to choose; most hotels usually are clustered in tourist-oriented resort districts, while condos are spread across a destination, sometimes in residential areas with no other tourist infrastructure at all.


In booking accommodations for your next family trip, it’s important to remember that needs change over time; what worked for your clan on the last big vacation may not work for you all the next time around. Another caveat: Consider other travelers. If you’re traveling with a little baby who is still screaming through the night, a more secluded spot—i.e., a vacation rental—might work best.


Finally, be sure to do your homework. Accommodations comprise an integral part of every family vacation, and choosing the right place can turn a good trip into a memory that will last forever.


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Sidebar: What to look for when you book

If you opt for a condo or vacation rentals on your next family trip, it’s important to keep the following tips in mind:


  • Note the amenities. Most rentals include linens, towels and kitchen accoutrements. Some, however, do not. It pays to ask before you book so you know what you’ll need to bring.
  • Mind your pets. Many vacation rentals allow pets, but require visitors to sign and submit to a series of rules and regulations regarding where the animal sleeps and spends most of its time. If you’re traveling with a companion of this sort, expect some extra paperwork.
  • Embrace payment plans. Because rentals are owned by individuals, most require at least half of the full payment up-front. Many use PayPal (or require cashier’s checks). Preparing for this transaction can save you time and money on the back end.
  • Double-check the rental’s cleaning policy. Some contracts require renters to do some of the cleaning; others have refundable cleaning deposits to pay for a crew to clean after your stay.


– M.V.



About Matt Villano

Expedia Road Trip:  Dad's Guide to Hawaii with Travel Blogger Matt Villano Matt Villano is a freelance writer, editor and copywriter based in Healdsburg, Calif. In more than 15 years as a free agent, he has had articles published in publications including TIME, The New York Times, The Wall Street Journal, National Geographic Traveler, Sunset, Islands, Coastal Living, Entrepreneur and more. He currently writes the family travel blog for Parenting magazine, and covered adventure travel for SeeAmerica.com, the official website of the U.S. Travel Association. In addition to travel, Villano’s areas of expertise include business, technology and gambling (yes, gambling). When he’s not working at his stand-up desk, Villano is chasing after his two daughters, both of whom are future New York Yankees fans.