Harley Davidson Alaska and Hawaii Trip: How Three Riders Checked Off Their Toughest Coins
By Kristin Hughes, Travel Advisor | travelmorewithkristin.com
Some Challenges Require a Travel Advisor
Greg, Jesse, and David had a mission. Three buddies. One goal. Fifty states.
The Harley-Davidson 50 Rides, One Nation Challenge isn't a casual weekend trip.
It's a coin collection challenge where riders have to visit a specific landmark in each state and document it. These aren't easy stops. Many are remote. Some require rides across unforgiving terrain. And then there are the two that require giving up the bikes entirely: Hawaii and Alaska.
For three dedicated riders in their late 50s and 60s who've already tackled the majority of the 50 states, those two coins represented everything the challenge was about: determination, adventure, and not letting geography stop you from finishing what you started.
The problem: how do you plan a trip that covers two vastly different destinations, coordinates flights for three people, manages multiple hotel stays, secures the right rental car for Alaska terrain, books guided tours, and makes sure everything runs seamlessly so three guys can focus on the ride, not the logistics? That's where a travel advisor comes in.
Planning Your Harley Davidson Alaska and Hawaii Trip: Maui Coin, Alaska Coin, Done
The trip was straightforward on the surface: get Greg, Jesse, and David to Maui to hit the Road to Hana coin location. Then get them to Alaska to conquer Thompson Pass at elevation 2678 feet. Simple, right?
Except there's nothing simple about coordinating flights from Los Angeles (where they'd ridden their Harleys and left them with a Harley dealer for the week), flights to Maui, hotel stays, a full-day guided tour down the Road to Hana, rental car logistics in Alaska, multiple hotel stays across Anchorage and Valdez, navigation to Thompson Pass, and then everything in reverse to get back home.
These three weren't looking for luxury. They wanted functionality, authentic experiences, and guides who knew the terrain. They wanted to get the coins, see the country, and have stories to tell.
Maui: June 23-25, 2026
The Flight
Alaska Airlines nonstop from Los Angeles to Maui on June 22. Arrive 1:00 pm, giving them the afternoon and evening to check into their hotel and start to acclimate.
The Road to Hana
On June 23rd, a private guide picked them up at 7:00 am for the Small-Group Road to Hana Adventure Tour, an 8-hour drive that covers approximately 64 miles of one of the world's most scenic and challenging drives. Hairpin turns. Narrow bridges. Waterfalls. Black sand beaches. The Road to Hana is famous for a reason: it's stunning and unforgiving.
For three motorcyclists who'd spent the last year (or more) on the road, this was exactly their speed; real terrain, real challenge, real payoff. Halfway through the Hana Road sits the coin location, and by noon, they had their Maui photo in hand.
The rest of the day was time to enjoy the island — beach time, local food, recharging before the Alaska portion of the trip.
Downtime Matters
On June 24th, I'd pushed them to stay and actually enjoy Maui. Not every trip is about rushing from place to place. Sometimes the best part of a bucket list adventure is giving yourself permission to simply be somewhere beautiful. They took the day to relax, explore at their own pace, and mentally prepare for the Alaska push.
Alaska: June 25 — Early July, 2026
This is where the logistics required serious coordination.
Anchorage Base
On June 25th, they flew from Maui to Anchorage on an overnight/early morning flight. Upon arrival, they picked up a 4-wheel drive rental vehicle at the airport, essential for the terrain they'd be covering and the unpredictable weather Alaska could throw at them.
First night: Motel 6 Anchorage. Budget-friendly, functional, and close to the airport for a smooth start.
Into the Interior: Valdez
On June 26th, they began the drive south toward Valdez, stopping at The Best Western Valdez Harbor Inn (June 27-28), a perfectly situated hotel with views of the boat harbor and the snow-capped mountains in the distance. This location was strategic: it puts them close enough to Thompson Pass for the next day's run without an unnecessarily early morning start.
Thompson Pass: The Coin
On June 28th, the main event. Thompson Pass sits at elevation 2678 feet on the Richardson Highway between Valdez and Anchorage. It's remote. It's stunning. And it's a completely different landscape from Maui's tropical Road to Hana.
They drove to the pass, took the coin photo at the iconic Thompson Pass sign with the mountains and snow as their backdrop, and checked off one of the most challenging coins on their list.
The Chena River Lodge & The Northern Route Back
For the return journey, I'd booked them at The Best Western Chena River Lodge (June 28-29) near Fairbanks, a beautiful property that sits right along the Chena River. This gave them the opportunity to explore the northern reaches of Alaska and see a completely different side of the state on the drive back south.
The return route followed the Parks Highway south through the interior, giving them views of the Alaska wilderness, smaller towns, and landscapes most tourists never see.
Why This Trip Needed a Travel Advisor
On the surface, this Harley Davidson Alaska Hawaii Trip sounds manageable: flights, hotels, tours, done. But what actually happened was:
✈️Flight Coordination: One continuous itinerary across multiple airlines and time zones, coordinating three people, luggage, timing around a full-day guided tour, and matching flights to hotel check-in times so they didn't lose hours to airport logistics.
🏨Four Different Hotels Across Two States: Each with different check-in needs, each strategically placed for the next day's mission. One wrong booking could mean an extra 2-3 hours of driving.
🌸The Road to Hana Tour: This required advance booking through a tour operator, confirming 3 adults, specifying pickup location and time, and ensuring the tour included the specific coin location without wasting the group's time.
🚙Alaska 4WD Rental: Not all car rental companies have the same 4WD availability. I sourced the right vehicle, arranged airport pickup, ensured insurance was appropriate for off-road terrain, and confirmed it was ready on arrival.
🧭Navigation & Route Planning: Thompson Pass requires driving in and out with no room for error. The northern route back required knowledge of road conditions, seasonal considerations, and timing to make sure they weren't on unfamiliar terrain after dark.
🏍️Three People, Different Preferences: Coordinating hotel choices that worked for all three, managing group dynamics on tour bookings, and ensuring each person felt the itinerary respected their time and budget.
☮️The Unspoken Factor: Peace of Mind
Here's what I provided that isn't on an itinerary: they didn't have to worry. They rode their bikes to LA, flew on confirmed reservations, arrived at each hotel knowing it was paid and waiting, knew exactly what time their tour picked them up, knew their rental car would be ready, and knew that if anything went wrong along the way, they had someone coordinating it all that they could call. That peace of mind is worth more than the cost of booking it right.
The Clients' Perspective
By the end of the trip, Greg, Jesse, and David had:
✓ Ridden their Harleys to Los Angeles ✓ Flown to Maui and experienced the iconic Road to Hana ✓ Collected the Hawaii coin (one of the two toughest) ✓ Experienced Maui's beaches and culture ✓ Flown to Alaska and rented the right vehicle ✓ Explored two completely different regions of Alaska ✓ Reached Thompson Pass and collected the Alaska coin (the other toughest) ✓ Driven back through the Alaskan interior ✓ Returned to Los Angeles ready to continue their quest.
They checked off their most difficult coins. They didn't have to manage any of the logistics themselves. They focused on the ride, the mission, and the experience.
That's the power of a travel advisor for bucket list trips.
Ready for Your Own Bucket List Adventure
Whether it's three Harley riders conquering the 50 Rides, One Nation challenge, or a couple celebrating a milestone anniversary, or a group of friends finally taking the trip you've been talking about for years, the trips worth taking are the ones worth planning right.
I specialize in exactly this: bespoke, multi-destination, logistically complex trips for people who have the means and the mission but need someone to handle the details so they can focus on the experience.
You don't have to be motorcycle enthusiasts. You don't have to have a coin collection challenge (though I love that kind of goal). You just have to be ready to stop talking about it and start doing it.
Frequently Asked Questions
What is the Harley-Davidson 50 Rides, One Nation Challenge?
The 50 Rides, One Nation challenge is a Harley-Davidson program where riders visit a designated location in each of the 50 states, document it with a photo, and collect a commemorative coin for each state. It's designed to encourage riders to explore America on their bikes. The challenge isn't about speed — it's about the mission, the journey, and the camaraderie of fellow riders pursuing the same goal.
How long does the 50 Rides Challenge typically take?
It varies widely depending on the rider. Some riders tackle it over a few years, completing multiple states in extended riding seasons. Others take 5+ years because they pursue it casually, fitting rides in between family and work. The most committed riders can complete it in 2-3 years if they dedicate multiple long trips per year. For Greg, Jesse, and David, completing Hawaii and Alaska represented the final significant challenge — they'd already tackled most of the continental US.
Why do Hawaii and Alaska require flying instead of riding?
Well, you cannot physically ride a motorcycle across the ocean to Hawaii. 🤣 So there's that. Alaska can technically be reached by motorcycle, but the route requires extensive preparation, backcountry navigation, and weather considerations that are extreme even for experienced riders. For most riders pursuing the 50 Rides challenge, flying to these states and renting bikes/vehicles makes far more sense than attempting the alternatives.
What is Thompson Pass and why is it significant?
Thompson Pass is a mountain pass in Alaska at elevation 2,678 feet on the Richardson Highway between Valdez and Anchorage. It's designated as one of the snowiest places in Alaska and is a spectacular landmark. For the Harley 50 Rides challenge, Thompson Pass is the designated Alaska coin location, making it a must-visit for anyone pursuing the complete 50-state collection.
Is the Road to Hana dangerous?
The Road to Hana is famous for its challenging terrain: narrow lanes, tight hairpin turns, blind corners, and elevation changes. For regular car drivers, it's an exciting (sometimes hair-raising) drive. For motorcyclists, it's manageable with proper attention and caution. For someone in a guided tour with an experienced driver handling the vehicle, it's spectacular and safe. The road is well-maintained and thousands of tourists drive it every year without incident.
Can you plan complex multi-state trips like this?
Absolutely. This is exactly the kind of trip I specialize in. If you have a specific goal (collecting coins, celebrating a milestone, pursuing an adventure), multiple destinations, and logistics that require coordination, I can help. I handle flights, hotel coordination, rental vehicles, guided tours, timing, contingencies, and everything in between so you can focus on the experience, not the details.
How should I prepare for driving in Alaska?
If you're renting a vehicle in Alaska, confirm that it's appropriate for the terrain you'll be covering. In summer (when most visitors come), standard rental cars work fine for highways and main routes. For more remote areas or winter driving, 4WD is essential. Check weather and road condition reports before departing each day. Bring appropriate clothing — Alaska weather changes quickly. Download offline maps in case cell service is spotty. And don't underestimate distances; it's a BIG state.
What's the best time to visit Alaska if you're pursuing the 50 Rides Challenge?
June through August is peak season and offers the best weather, longest daylight hours, and most accessible roads. Winter driving in Alaska is serious business and requires specialized tires, chains, and experience. For someone collecting the coin, summer travel is the safer and smarter choice.
What should I expect for hotel options in Alaska?
Alaska has everything from luxury lodges to budget chains like Best Western and Motel 6. In Anchorage and larger towns, you'll find better variety. In smaller towns along remote highways, options are more limited: Best Western, Motel 6, and some local properties are common. Booking in advance is essential, especially during peak summer season.
Greg, Jesse, and David traveled to Hawaii and Alaska in June 2026 as part of their ongoing Harley-Davidson 50 Rides, One Nation Challenge. Their trip was coordinated and booked by Travel More with Kristin.
Ready to plan your adventure? Get in touch here.
— Kristin Hughes Travel More with Kristin