Maui ( Hawaii)

Maui: Lifestyle at The Masters

After being constantly on the move for seven months traveling all over Southeast Asia, Barbie and I elected to slow things down, drop anchor, and settle in for a bit. We rented a killer condo for two months at The Masters on Kaanapali Hillside.

Let me tell you, after eating out three meals a day for seven consecutive months, it has been an absolute luxury to finally stand in our own kitchen and cook our own food. We’ve been on Maui for over a month now, and we haven’t gone out to a restaurant for a single meal. That’s the real flashpacker luxury right there—total control over your environment and your plate.

In years past, on all of our previous trips to the Hawaiian islands, we would just hop on a simple, painless five-to-six-hour flight from our old home base in Las Vegas. This time around, we departed from Fort Lauderdale, and that cross-country-plus-ocean transit is a completely different beast. It’s long, plain and simple.

From experience, I can tell you it takes a minimum of five days just to shake off the travel exhaustion, get into the rhythm of the island, and feel completely relaxed. Therefore, if you are making the trek all the way from the East Coast, I feel you need a bare minimum of two weeks on the ground to effectively assimilate into extreme chill mode. Anything less and you’re doing yourself a disservice.

Deciphering the Islands: Why Maui Has My Heart

We’ve spent extended time on three of the four major Hawaiian islands—Kauai, Maui, and the Big Island—and we genuinely love all three.

[The Big Doug Hawaiian Island Assessment]
* Kauai & Big Island ──> Absolute favorites, incredible nature.
* Maui              ──> Our designated home base; perfect balance of lifestyle & beaches.
* Oahu (South)      ──> Traffic, tourist congestion, Waikiki. Did not feel like Hawaii.
* Oahu (North)      ──> The exception? Supposedly a lot more appealing (jury is still out).

We’ve never really given Oahu a fair shot because our only exposure was a brief visit to the heavily touristed, overcrowded Honolulu and Waikiki area on the south side. We both absolutely hated it; it just didn’t feel like the real Hawaii. To be fair, I hear the North Shore of Oahu is a completely different animal and a lot more appealing, but the south side left a bad taste in our mouths.

Being able to spend months at a time out here lets you dig deep and experience island life like a local. By renting a residential condo on the hillside, we get to see Maui completely outside of the standard resort luaus, crowded hotel pools, and all the other touristy crap.

You might think all these islands would be identical, but they each have a totally distinct personality. I’ve never been to a place where nature is so aggressively in-your-face. Standing on the shoreline and watching giant winter waves beat the living shit out of the sand, the lava rocks, and me is a beautiful, humbling reminder that these islands are just a tiny piece of rock in a gigantic world of ocean.

Maui is heaven, but it’s not for everyone. If you come here expecting mega-resort coddling, you miss the point. But if you show up with the right expectations of low-key living, the right attitude, and the perfect balance of relaxation and curiosity, you will really dig it. Honestly, I have learned more about what actually matters in life here on this island than any other place on the planet. It is just such a cool place, and I could easily see it becoming our permanent home base in the future.

The Maui Beach Breakdown

We have been to just about all the highest-rated beaches across Southeast Asia, and I am telling you right now: the beaches on the Hawaiian islands remain my absolute favorites. The water here is a crystal-clear turquoise, the sand is perfectly golden, and best of all, the beaches are all public. Even if a beach sits directly in front of an ultra-exclusive resort, you can walk your ass right up, sit down, and enjoy the day.

There are around 80 distinct beaches on Maui alone, so if you think you’ve seen it all, trust me, you haven’t.

When we are on Maui, we always base ourselves on the West Side in the residential area of Kaanapali. The reason is simple: it has the largest concentration of the best beaches on the island. You can literally hop in the car, drive anywhere from one to ten minutes, and land on one of eight awesome beaches, each with a completely different vibe and surf.

Here is the Big Doug master list of Maui beaches, broken down by region:

🏖️ West Side (Big Doug Favorites, South to North)

Kaanapali: The classic, expansive stretch of golden sand with great swimming.
Airport Beach (Kahekili): Incredible coral reef right off the shore—perfect for a quick snorkel.
Napili Bay: A beautiful, crescent-shaped bay that’s incredibly scenic.
Kapalua Bay: Sheltered and calm
Honolua Bay: A rocky marine reserve with great snorkeling when the surf is calm.
DT Flemings: Great facilities and a popular spot for bodyboarding.
Slaughterhouse Beach: Stunning, cliff-framed cove.

🌴 Other West Side Options

Launiupoko Beach: local family spot with a protective reef wall. Just ok, in my opinion.
Hanakao’o Beach: Also known as Canoe Beach, right next to Kaanapali. Just ok, in my opinion.

☀️ The South Side

Makena (Oneloa) Big Beach: A massive, dramatic stretch of sand with powerful shorebreaks.
Little Beach: Tucked right next to Big Beach; famous for its wild Sunday afternoon drum circles and beach parties.
Kalepolepo Beach: Home to ancient Hawaiian fishponds and a great sunset view.
Kamaole Beaches (I, II, III): The classic Kihei beach parks with great park lawns.

💨 The Wild North Shore

Baldwin Beach Park: A massive, windy stretch near Paia.
Ho’okipa Beach: The undisputed world capital for windsurfing and high-energy ocean

🌀 The Lush East Side (Hana Highway)

Hamoa Beach: Regularly voted one of the most beautiful, raw beaches in the world.
Wai’anapanapa State Park: The famous black sand beach set against brilliant green jungle.
Red Sand Beach (Kaihalulu): A hidden, dramatic cinder cove that looks like another planet.

What’s Next on the Horizon

We will be soaking up the Maui sun until mid-July, and then it’s time for a major venue change. We’re heading straight to the East Coast to link up with my regular gang of degenerates at Saratoga Springs, NY, to wager on the ponies at “The August Place to Be.”

Once the race meet wraps up, it’s right back into full flashpacker mode as Barbie and I officially embark on Leg 2 (Year 2) of our round-the-world journey.