Hawaii Three Islands Hopping

Experience the spectacular beauty of the Hawaiian Islands on this island-hopping journey around the 3 central islands of the archipelago, Maui, Lanai and Molokai.

Each with a vastly different character, look and feel, from the other-worldliness of Maui’s Haleakala Volcano and a lush paradise ride along the Garden of Eden that is the Road to Hana, to the alluring seclusion and arid splendor of Lanai, formerly the Pineapple Island now known as the Private Island, to the immense beauty and towering sea cliffs of Molokai, the tallest on the planet, you’ll wonder at the variety of the 50th State of the USA.

Each day includes some Hawaiian beach time during or at the end of the ride.


Day 1: Lahaina, Maui, Hawaii – Arrival

Arrive and transfer to Best Western Pioneer Inn.

Dinner and overnight: Pioneer Inn

Day 2: West Maui Loop, Hawaii – Total biking 29 km/18 miles

Breakfast, Bikes are delivered.

First day on the bikes takes you around the stunning West Maui Loop. With high sea cliffs and a single lane road this is island riding at some of its most spectacular.

Lunch included.

Dinner on your own, and overnight: BW Pioneer Inn Lahaina

Day 3: Lanai Island, Hawaii – Total biking 48 km/30 miles

The ride here is up or down with little flat land. The first stop is historic Lanai City, which has hints of the old south of mainland US with its pine trees, old wooden churches, and sleepy plantation atmosphere.

After a 3-mile van transfer out of Manele Bay, you will bike across the relatively flat mesa down to Shipwreck Beach, with a chance to ride or hike off road along the beach to see the shipwrecked tanker from WWII just offshore, and off-road the other direction to see the Hawaiian Church at Keomuku.

Afterwards we make a 6-mile ascent in the support van back to Lanai City and make a visit to the Lanai Culture and Heritage Center, followed by lunch (included) in Lanai City.

After lunch we have some time to visit the shops of Lanai City, before hopping on our bikes for a ride across the mesa. A long, steady descent takes us to the harbor at Manele Bay, where we’ll have a chance to finish with some beach time at Hulopo’E Beach. There are changing rooms, showers and great coral reefs so bring snorkeling equipment if you want to partake of the marine life and possibly swim with the dolphins.

Ferry from Lanai to Maui – 4:30 PM

Dinner on your own, and overnight: BW Pioneer Inn Lahaina

Day 4: Molokai Island, Hawaii – Total biking: 76 km/47 miles

Arrive Molokai by ferry and transfer to Halawa Valley.

Optional hike to Halawa Valley at additional cost.

Return guided biking from Halawa Valley to Kaunakakai; where we stop for lunch (included).

Continue after lunch to Pala’au State Park and Kalaupapa Overlook/Phallic Rock.

Ride bikes to airport and leave with guide/driver.

Return flight to Maui and transfer to Maui north shore hotel.

Dinner included tonight after check in.

Dinner and overnight: Maui North Shore hotel

Day 5: Day at leisure.


Lunch and dinner on your own.

Overnight at Maui North Shore hotel

Day 6: Maui Upcountry Ride – Total biking 55 km/34 miles

Breakfast and optional sunrise on Haleakala

3 AM departure for anyone doing optional sunrise tour to Haleakala (Additional costs).

We start with a visit to the town of Makawao.

Afterwards we ride a 700 foot climb from Makawao to Kula, with a stop at Kula Lodge to visit the gift shop and specialty grocery store.

We start descending afterwards down to Ulupalakua Ranch/Maui Winery where we stop for lunch (included) and a visit to the winery for some wine tasting if you wish.

Transfer by van afterwards to Kula Lavender Farm where we visit the farm and gift shop, and then start a long, beautiful descent from Kula Lavender Farm down to Kula, Makawao and then down from Makawao across endless sugar cane fields to the beach at lovely Paia, where we end our day’s ride and have a chance to swim, shop or have a drink at one of the many local establishments.

Dinner on your own, and overnight at Maui North Shore hotel

Day 7: The Road To Hana – Total biking: 63 km/39 miles

We saved the best ride to the end. The legendary Road To Hana is one of the great coastal roads anywhere. Located on the windward side of the island, this area is lush and green, full of thick forest, waterfalls and small water holes. You won’t forget this day of riding!

We start riding after breakfast at approx. 8 AM from Twin Falls on Hana Highway Mile 2

Stop for lunch (included) at mile 17 on the Kea’nae Peninsula

Afterwards, we transfer by van after lunch to mile 22, and have some time to visit waterfall and pools at mile 22, so bring swimsuits. Changing rooms available

We continue riding from mile 22 to Hana and stop at Nahiku Market to visit the shops and maybe grab a snack!

We finish the day with a ride through Hana and make a last biking stop to visit the historic Hasegawa General Store.

We finish the week’s ride with at beautiful Hamoa Beach and load up the bikes for a ride around Maui South Shore with stops at at famed aviator Charles Lindbergh’s Grave, and cross the spectacular lava fields of the South Shore of Maui.

We return to our hotel at approx 6 PM and a well deserved farewell dinner.

Farewell Dinner (Drinks not included).

Overnight at Maui North Shore hotel

Day 8: Kahului, Maui, Hawaii – End of bike tour



Option to try out kiteboarding down at the North Shore Beaches before catching your flight back home.


  • 3 nights at the historic Best Western Pioneer Inn, Lahaina, Hawaii, 2 per room
  • 4 nights at a comfortable North Shore hotel,Mauii, Hawaii, 2 per room
  • Flight from Molokai to Maui
  • 7 Breakfasts
  • 5 Lunches
  • 3 Dinners
  • Bicycle rental
  • Support van throughout except within the Haleakala National Park
  • Biking guide throughout with minimum of 6 people
  • Bike transport throughout
  • Ferry and bike transport to Lanai
  • Ferry transport to Molokai
  • Entrance Fees according to the itinerary

Not included

  • All extra personal expenses in hotels & during bike tours not mentioned in itinerary such as phone calls, laundry etc.
  • Drinks with meals
  • Trip Insurance
  • Airport/hotel transfers
  • Airfare to/from Hawaii
  • Lodging taxes and service charges
  • Ride Level: Intermediate – Expert:

Hawaii being a rather mountainous and therefore beautiful set of islands, presents us with many hills to contend with. Good news is that the road conditions are excellent throughout the islands we will be cycling on, we try to begin most days at the top of the hill for a long and thrilling downhill run, and we always have the support van to help you up whatever hills you’d rather not climb.

Number of Participants: Min. 2, Max. 12 participants

Note: The Support Vehicle is not allowed within the Haleakala National Park.