Hawaii 3 Island

Steve Powell
Price :
Surface :
Duration :
12 days
Support :
Inn to Inn
Difficulty :
Level 4

Maui, Molokai, and Lanai, three of Hawaii’s most beautiful islands and the setting for an unrivaled bicycle travel adventure. On Maui, we’ll ride along stunning coastal roads and make an epic climb from sea level to the top of the Haleakala volcano at 10,000 feet — the world’s longest paved climb! A small plane will take us and our bikes on the short 15-minute flight to Molokai for three days of unrivaled cycling on quiet roads with views of gorgeous valleys and the world’s tallest sea cliffs. A ferry will then take us out on the ocean, past migrating humpback whales, on our way to Lanai for a day of exploration by bike or shuttle van, or with snorkel and fins, before returning to Maui. 

This unique tour features a ferry and a small plane to bring together these three Hawaiian islands into a single bicycle tour. Our inn-to-inn format enables us to enjoy restaurant meals, overnight accommodations at unique hotels and inns, and riding lightly loaded bikes as we experience breathtaking roads in a tropical paradise. This is truly adventure cycling!

Photos by Steve Powell | Steve Powell | Steve Powell

Our 2022 departures have already taken place, check back for future dates.

"I think that the level of support for the price was outstanding compared to other tours I've done."


Day 1. Kahului, Hawaii, 0 miles

Today we’ll meet in the late afternoon for a group orientation meeting at the starting point hotel with beautiful oceanfront views, close to Maui’s main airport. Also nearby are several terrific restaurants with local Hawaiian food and a full-service bike shop. This will make it super convenient to get our bikes (and our bodies!) tuned up and ready for the adventure that awaits us on Maui, Molokai, and Lanai.

Day 2. Kahului to Kaunakakai, 25 miles

We’ll start the day with a short bike ride from our hotel to the commuter air terminal of Kahului airport. There we will simply roll our bikes onto a chartered cargo plane (no boxing or disassembly needed!), and then board our nearby nine-passenger planes for the short 15-minute flight to Molokai. What a terrific way to start a bike tour, with an aerial view of our forthcoming adventure!

Once on Molokai, we’ll head out on our bikes toward the stunning Kalaupapa Overlook on the north coast. Enroute we will enjoy the backroads of Molokai, with low traffic, beautiful views, and lots of off-bike enticements such as visiting a macadamia nut farm, coffee farm, or museum to learn about the culture of Molokai and the history of the sugar cane industry. Back on our bikes, we will reach the Kalaupapa Overlook that towers 1,700 feet above the Makanalua Peninsula and the famous town of Kalaupapa, founded as a leprosy colony in the 1800s. This unique location provides near total isolation since it is surrounded on three sides by the Pacific Ocean and the world’s highest sea cliffs on the fourth side. Thanks to modern medicine, the leprosy sufferers are no longer contagious, and tours of this historic site can be arranged for a fee. Access to Kalaupapa is via the steep Pali Trail, either by foot or possibly by mule, for those interested in this optional activity. Alternatively, there are hikes in the area for no additional charge and off-road bike trails with various surfaces. Everyone will enjoy the downhill ride on paved roads to Kaunakakai, where we will spend three nights at a comfortable oceanside hotel.

Day 3. Kaunakakai to Halawa and back, 52 miles

This morning we will start off the day with a great breakfast at a local café and bakery famous for its “hot breads” (more on that later!). We will ride east along a beautiful coastal route with stunning views both of the sea and of the towering mountains. The road gets quieter and narrower, with a posted speed limit of just 10 MPH, as we near the indescribably beautiful and lush Halawa Valley at the end of the road. With such amazing views of the valley and waterfalls, you may wonder whether you have stepped back in time to the Jurassic period. We will then reverse course to change our perspective and admire the not-so-distant views of both Maui and Lanai as we head back to Kaunakakai. Along the way we will have an opportunity to stop at several quiet beaches and coves for swimming and snorkeling.

Day 4. Kaunakakai to Kepuhi and back, 49 miles

Today we will explore the central and western portions of Molokai, transitioning from the wetter mountainous region to the drier open expanses in the west. We will reach the west coast of Molokai at Kepuhi, a favorite spot for surfers, and nearby one of Hawaii’s longest white sand beaches, the beautiful Papohaku Beach. On a clear day, you can see all the way to the neighboring island of Oahu, about 27 miles. On our return trip, we have an option to take a short spur road uphill to the small town of Maunaloa, with great views of the surrounding area, and an opportunity for refreshments. We’ll spend the night back in Kaunakakai and have a chance to see more of the town at dinnertime. And after dinner, we can check out those “hot breads” baked fresh each evening, with your choice of toppings. But you’ll have to go around back, through a dark alley, to the night window of the bakery, so bring a light with you. It’s a little bit spooky but well worth it!

Day 5. Kaunakakai to Lahaina, 24 miles

Today we will take an early morning shuttle to the Molokai airport where we will board our short flight back to Maui, rolling our bikes into the cargo aircraft exactly as we did previously. We’ll be back on Maui well before noon and then head out of the hustle and bustle of Kahului, across the center of Maui, passing the Maui Ocean Center (with a terrific aquarium), Lookout Point (a great vantage point for seeing migrating whales), and a pie shop that beckons, all enroute to Lahaina, once the capital of the Kingdom of Hawaii. We’ll spend two nights in Lahaina at a hotel near great seafood restaurants and directly adjacent to the harbor, where we’ll pick up the ferry to Lanai tomorrow morning.

Day 6. Lahaina to Lanai and back, 0-46 miles

After four days of robust riding, today is a well-deserved rest day, but there are so many on-bike and off-bike options to choose from! Most options start with a ferry ride across the Auau Channel (approximately one hour) from Lahaina to Manele Harbor on Lanai, and the ferry is included in our tour. (Note: There are great land-based options available today near Lahaina, such as whale watching, or a bike ride to a vantage point with great coastal views, for anyone who would rather not take the ferry ride, which could get a bit choppy). For those on the ferry, we’re likely to see the humpback whales that ply these waters from January to April. Once on Lanai you can explore the island by bike, shuttle van, or walk to nearby Hulopoe Beach well known for its terrific snorkeling, or hike to Puu Pehe (Sweetheart Rock).

There are three paved roads on Lanai that all lead uphill from the coast to the center of the island and quaint Lanai City. It’s refreshing to know that you’ll probably encounter only a handful of cars if you choose to explore Lanai by bike. In the mood for some mountain biking, but didn’t bring a mountain bike? Electric mountain bike rentals are available in Lanai City for some off-road adventures before boarding the ferry for the return trip to Maui. We will spend the night back in Lahaina.

Day 7. Lahaina to Makawao, 51 miles

We’ll set out this morning from Lahaina, and ride along the coast of West Maui, with beautiful views of Lanai and Molokai, as we pass the resort areas of Kaanapali and Kapalua. We’ll say goodbye to most of the vehicle traffic as we take the coastal Kahekili Highway for some of the most challenging and beautiful bike riding of the entire trip. This epic road twists and turns and narrows to not much more than a single lane, with several steep climbs and fun descents, and endless Pacific Ocean views. We’ll pass through a handful of small towns and undoubtedly be tempted to stop at one of the banana bread or shave ice stands. Civilization will return as we briefly pass by our start point hotel in Kahului, but we then turn inland and head “Upcountry” to the small town of Makawao on the slope of the Haleakala volcano. Our accommodations for tonight and the next two nights will be at a small establishment with cute cottages and a swimming pool and hot tub. Besides offering stunning views of the valley below, Makawao is perfectly located for tomorrow’s climb up Haleakala.

Day 8. Makawao to Haleakala and back, 58 miles

Today may very well prove to be the most memorable day of the bike tour, and perhaps the most memorable day of bicycling ever for everyone on the tour. Rising early, we will enter Haleakala National Park and make the epic climb of 8,600 feet to the top of the Haleakala volcano at 10,023 feet above sea level. This challenging climb covers 29 miles at an average grade of just under 6 percent. Our bikes will be lightly loaded but carrying enough cold-weather clothing for the well-deserved descent. The view from the top should be amazing, with all of the surrounding Hawaiian islands visible on a clear day. We will also be able to view inside of the Haleakala Crater, which some people say looks like Mars. After gliding 29 miles (all downhill!) back to our cottages, we’ll enjoy a well-deserved dinner at a restaurant in Makawao. (Note: For anyone not wanting to attempt the climb up Haleakala, an alternative ride with stunning views around Maui Upcountry is described for the following day, and is a perfectly acceptable option for today.)

Day 9. Layover day in Makawao, 0 or 21 miles

Today is a rest day to let us recover from yesterday’s challenging climb up Haleakala. This is a great location to explore the town of Makawao, within walking distance, and other nearby Upcountry locales such as Kula, with beautiful views of the valley below. Looking for a new challenge? You can try ziplining on the slopes of Haleakala. Or better yet, just chill out by the pool and hot tub near our cottages.

For anyone looking to do more riding and exploring today, or as an alternative to the Haleakala climb on the previous day, we have put together a beautiful loop ride around Upcountry. This bike ride passes a large botanical garden, a cute farm stand, a country store, and a small café that features locally sourced food, all on a ride with stunning views of Central and West Maui.

Day 10. Makawao to Hana, 56 miles

From Makawao, we will ride counterclockwise to the easternmost portion of Maui, exploring what is called the backside of Haleakala. We will transition through several climatic zones, from dry lava fields to lush tropical rain forests, as we head toward the small town of Hana. Along the way, we will be challenged with several miles of dirt or gravel on a lightly traveled section of roadway, but entertained by absolutely stunning coastal vistas. There will be an opportunity to visit the very remote gravesite of famed aviator Charles Lindbergh and the nearby Pools of ’Ohe’o and waterfalls in Kipahulu. We will spend two nights in Hana at comfortable oceanside accommodations.

Day 11. Hana Layover, 0 miles

Today is a well-deserved rest day after working so hard to ride around the backside of the massive Haleakala volcano, to get to remotely located Hana. The focus for today can be the ocean, with one beautiful beach within walking distance and several more beaches, including a unique black sand beach, just a short bike ride away. Looking for additional stimulation? Take advantage of Hana's unique rainforest location by touring a tropical botanical garden and a lava tube, both within an easy bike ride.

Day 12. Hana Kahului, 50 miles

After watching the sunrise and enjoying a great final breakfast, we will head west along the famous Hana Highway, with over 600 switchbacks and spectacular ocean and mountain views. Today’s destination is Kahului where our adventure began 12 days ago. Leaving early from Hana will let us avoid most of the traffic coming later in the day from the more populous sections of Maui. Just before returning to Kahului, we will pass Hookipa Lookout and Beach, very popular with both surfers and turtles, who love to sunbathe on the rocks. You can swim and snorkel nearby and then hop on the bike path that begins just past the town of Paia and winds quietly around Kahului airport and past several more beaches back to our starting point hotel. We'll enjoy a final night together at the hotel, and celebrate with a grand dinner and comfortable overnight accommodations. This will make for an enjoyable and memorable way to end our adventure of three beautiful Hawaiian islands.


Additional Details
Start Location:
Kahului, HI
End Location:
Kahului, HI
Kahului Airport (OGG)
Total Days:
Riding Days:
Layover Days:
Average Daily Mileage:
Indoor (Inn to Inn)
Indoor Dining
Level 4
Very Hilly
Elevation Alert:
High Point: 9,990'
Restricted Bike Type:
Tandem, Trike, eBike, eTrike
Single Supplement

Know before you go

A note about eBikes:

Unfortunately, transporting non-standard bikes and eBikes between islands on this tour is extremely difficult due to our interisland transportation. Renting eBikes on the different islands may be possible, but is not guaranteed.

A note about accommodations:

Due to the location and availability of some of the accommodations, some overnights may have more than two people in a room and/or shared common areas/bathrooms. Single Supplements are available, but may require a shared bathroom in select locations.