Big Island of Hawai'i

Seven days of cycling reveal the full scale of Hawaiʻi Island, from lava-lined coasts and plantation towns to rainforest roads and active volcano landscapes. Along the way, ocean views, local food, and quiet backroads connect the island’s many distinct worlds.

7 days ✧ Guided ✧ 25 to 40 mi per day ✧ Boutique inns ✧ Support van
Start/finish: Kailua Kona ✧ Season: year round ✧ From: $5495

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Volcano Roads and Ocean Miles on Hawai'i Island

Hawai'i Island feels less like a single destination and more like a collection of landscapes stitched together by quiet coastal roads. Riding here reveals the island gradually, from lava-formed shores and plantation towns to rainforest valleys where the scent of the Pacific drifts inland on warm trade winds.

Hawai'i Island, often simply called the Big Island, carries a sense of scale that surprises many first-time visitors. Vast volcanic slopes rise above the ocean, tropical forests cloak the windward coast, and small towns still reflect the island's agricultural past. Traveling by bicycle offers one of the most rewarding ways to explore this varied landscape, where each stretch of road reveals another layer of Hawai'i's geography, culture, and history.

Mamalahoa Highway connecting Hawaiians since 1929 1929 date on old bridge The journey begins on the Kona coast, where sunshine and calm Pacific waters define the island's western shore. Riders spin along a portion of the famous Ironman World Championship course, a ribbon of pavement tracing the coastline with wide ocean views. The terrain rolls gently across black lava fields while waves break against the rocks below, a reminder that this island continues to be shaped by volcanic forces.

North of Kona the road leads toward the quiet villages of North Kohala. Historic Hawi, once a bustling sugar plantation town, now welcomes cyclists exploring the island's northern edge. Nearby the cliffs of Pololū Valley plunge dramatically toward the sea, revealing sweeping views of one of Hawai'i's most rugged coastlines.

From here the journey climbs into Hawai'i's ranching country along the scenic Kohala Mountain Road. While this stretch is enjoyed from the support vehicle rather than the saddle, the drive itself reveals a different side of the island, where wide pastures and rolling green hills overlook the distant Pacific. In Waimea, riders return to their bikes and begin a memorable descent along the historic Mamalahoa Highway toward the Hamakua Coast.

Private dinner at old plantation house Pedalers group at private dinner The eastern side of the island tells a different story. Moist trade winds feed lush rainforest along the Hamakua Coast, creating one of the most scenic stretches of riding on the island. Here the route follows sections of the historic Old Mamalahoa Highway, a narrow road that once served as the primary connection between coastal communities. Today it winds through dense forest, past waterfalls and remnants of old sugar plantations, offering glimpses of Hawai'i's agricultural past.

The town of Hilo provides a lively contrast to the quiet roads of the Hamakua Coast. Farmers markets overflow with tropical fruit, cafés serve fresh fish and island favorites, and the steady rhythm of rainfall nourishes the surrounding rainforest. From here the journey continues toward one of the island's most remarkable landscapes: Hawai'i Volcanoes National Park.

Within the park the land reveals the volcanic forces that created the island itself. Lava flows stretch across the terrain in dark rippling fields while steam rises from vents scattered across the landscape. Even a simple exploration of the park's roads and viewpoints reveals the scale of this active environment where the island continues to grow from beneath the earth.

Pūloʻuloʻu at Pu'ukohala Heiau (do not enter symbols) kapu poles at Pu'ukohala Heiau One of the most exhilarating rides of the tour follows as the road descends from the volcanic highlands toward the southern coast. Riders pass through the stark beauty of the Ka'ū Desert before reaching the black sand shoreline of Punalu'u Beach, where green sea turtles often rest along the sand beside the surf.

Along the way the journey reveals another essential part of island life: food. Simple roadside cafés serve Hawaiian favorites like kalua pork and plate lunches, while coastal restaurants highlight fish caught that same day in nearby waters. Kona coffee, macadamia nuts, and tropical fruit appear regularly at markets and roadside stands.

By the time riders return to Kona for a final evening beside the Pacific, the island feels both vast and personal. Traveling by bicycle reveals Hawai'i Island in a way few visitors experience. The miles unfold at a human pace, villages appear unexpectedly around bends in the road, and each day deepens the connection to the land and culture of this remarkable island.

Your Journey, Day by Day

Day 1: Kona's Charm & Coastal Delights

  • Arrive in Kailua Kona and settle into your accommodations.
  • Explore the charming town of Kailua Kona at your leisure.
  • Enjoy a sunset dinner with local food and craft beer.

Our Island Dream begins in Kailua Kona, where we'll greet you at the airport. Settle in, relax by the pool, and soak up the island vibes. As the sun begins to dip below the horizon, we'll gather for an orientation and then head to a local café for a taste of Hawaiian "grinds" (food) and a selection of refreshing island microbrews.

Relax: Free time until dinner
Eat: Dinner
Sleep: Royal Kona Resort

Day 2: Ironman Inspiration & Coastal Cruising

  • Explore the historic Pu'ukohala and Lapakahi State Parks.
  • Cycle along the iconic Ironman course with breathtaking coastal views.

After a leisurely morning, we'll shuttle to Waikoloa Village for bike fittings. Then, it's time to channel your inner Ironman as we cycle along the famous Ironman course. We'll explore Pu'ukohala National Park, a site of great historical significance, and visit the Lapakahi State Historical Park, an ancient village. We'll continue past the Ironman turnaround point to admire the King Kamehameha statue and the stunning Pololu Valley before returning to the eclectic town of Hawi.

Ride: 32 mi / 52 km, Land: flat
Eat: Breakfast, Lunch, Dinner
Sleep: Kohala Village Inn

Day 3: Kohala Mountain Vistas & Waipio Valley Wonders

  • Enjoy scenic views along the Kohala Mountain Road.
  • Cycle down the historic Old Mamalahoa Highway.
  • Visit the breathtaking Waipio Valley overlook.

This morning, we'll drive along the scenic Kohala Mountain Road, taking in its panoramic vistas. While cycling is unfortunately prohibited on this stretch, the drive itself is a treat. We'll hop on our bikes in trendy Waimea and enjoy a winding descent along the historic Old Mamalahoa Highway. This road, once a Hawaiian footpath, offers a glimpse into the island's past. We'll visit the Waipio Valley overlook, a place said to be where the Polynesians first settled. Tonight, we'll enjoy a private chef-prepared dinner at our charming B&B, a 1930s-era home.

Ride: 25 mi / 41 km, Land: downhill & flat
Eat: Breakfast, Lunch, Dinner
Sleep: Waipio Wayside B&B

Day 4: Hamakua Coast History & Hilo's Delights

  • Cycle along the scenic Hamakua Coast.
  • Stop for a refreshing smoothie at What's Shakin'.
  • Explore the historic town of Hilo at your leisure.

Today, we'll cycle towards Hilo, the Big Island's largest town, along the Hamakua Coast. This area, once a thriving sugar cane region, is now a landscape of charming villages, lush forests, and rolling fields. We'll follow the Old Mamalahoa Highway, meandering along the volcanic contours of the island. Don't miss a smoothie at the famed What's Shakin' along Onomea Bay Road! The afternoon and evening are yours to explore Hilo's historic downtown and its delightful cafes.

Ride: 26 mi / 42 km, Land: flat and small hills
Eat: Breakfast, Lunch
Sleep: Hilo Hawaiian Hotel

Day 5: Volcanic Wonders & Rainforest Adventures

  • Explore the fascinating Kaumana Caves.
  • Hike through Volcanoes National Park and witness volcanic landscapes.
  • Discover the unique Nahuku lava tube.

Today, we'll explore the power of volcanoes! We'll begin at Kaumana Caves, walking through massive lava tubes. Then, it's off to Volcanoes National Park for a scenic picnic and a three-mile hike along the Halema'uma'u Trail. We'll descend into the caldera, shaped by recent eruptions, and witness stunning lava flow views. We'll also explore the surreal lava landscapes of Mauna Ulu, trek through a lush rainforest to the Nahuku lava tube, and finish the day at our historic lodge in Volcano Village.

Walk: 5 mi, Land: hilly
Eat: Breakfast, Lunch, Dinner
Sleep: Kilauea Lodge

Day 6: Downhill Thrills & Turtle Time

  • Enjoy a thrilling downhill bike ride.
  • Visit the black sand beach at Punalu'u and see sea turtles.
  • Explore the southernmost towns in the US and the historic Monkey Pod tree.

Get ready for an exhilarating downhill ride! After breakfast, we'll descend from the volcano's heights to sea level. We'll cycle through the stark landscapes of the Ka'u Desert, past macadamia groves, and down to the black sand beach at Punalu'u, a favorite spot for sea turtles. From there, we'll climb slightly to the southernmost towns in the US: Na'alehu, home of the famous Punalu'u Bakery, and Wai'ohinu, with its 150-year-old Monkey Pod tree planted by Mark Twain. From Wai'ohinu, we'll shuttle back to Kailua Kona for our last night and a farewell dinner at the historic Kona Inn.

Ride: 40 mi / 65 km, Land: downhill, one small climb
Eat: Breakfast, Lunch, Dinner
Sleep: Royal Kona Resort

Day 7: Farewell, Hawaii!

  • Enjoy a final breakfast overlooking the Pacific.

All good things must come to an end. We'll provide shuttles to Kailua Kona Airport, leaving you with incredible memories of your Hawaiian cycling adventure. A hui hou kakou (until we meet again)!

Travel: Shuttle to airport
Eat: Breakfast

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The cool inns where you will sleep!


  • photo of Royal Kona Resort

    Royal Kona Resort

    Situated along Kailua Kona's picturesque coastline, this resort offers comfortable rooms with ocean views, a refreshing pool, and easy access to local shops and restaurants.

  • photo of Kohala Village Inn

    Kohala Village Inn

    Located in the historic town of Hawi, this inn provides cozy accommodations, a welcoming atmosphere, and proximity to local art galleries and eateries.

  • photo of Waipio Wayside Bed & Breakfast

    Waipio Wayside Bed & Breakfast

    Step back in time at this historic 1932 sugar plantation home, offering five charming guest rooms, organic breakfasts, and a serene gazebo with ocean views near the sacred Waipio Valley.

  • photo of Hilo Hawaiian Hotel

    Hilo Hawaiian Hotel

    Overlooking Hilo Bay, this hotel features spacious rooms with breathtaking views, an on-site restaurant and lounge, and easy access to Hilo’s farmers market and natural wonders.

  • photo of Kilauea Lodge

    Kilauea Lodge

    Nestled near Hawaii Volcanoes National Park, this historic lodge offers rustic rooms, lush gardens, and a chance to experience the island's volcanic landscape up close.

Note: Hotels shown are our preferred choices but may not be available for all dates. Alternates will be of similar style and quality.

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11 - 17 Oct 2026 $5395 7 days sorry 😢 sold out
single occupancy from +$1075deposit $800prices per person in US Dollars
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15 - 21 Mar 2027 $5495 7 days Book Now available
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single occupancy from +$1075deposit $800prices per person in US Dollars
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13 - 19 Mar 2028 $5595 7 days Book Now available
15 - 21 May 2028 $5595 7 days Book Now available
11 - 17 Sep 2028 $5595 7 days Book Now available
29 Oct - 4 Nov 2028 $5595 7 days Book Now available
single occupancy from +$1075deposit $800prices per person in US Dollars
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All the little details!

Getting to the Fun!

The Big Island of Hawaii Bike Tour meets and ends at Ellison Onizuka Kona International Airport in Keahole, Hawaii. Guides will meet arriving flights, between 9:00 and 15:00

Guests should plan their flights to arrive in Kona before 15:00 (3 pm) on Day 1 of the tour and their departing flights after 10:00 (10 am) on Day 7.

Ellison Onizuka Kona Airport code: KOA     Local Time: GMT-10

  Travel Tip:   Sometimes better fares can be found to Honolulu, with a separate inter-island flight to KOA. But do leave sufficient time between flights (3 hours suggested).

Whatcha gonna getExceptional Stays & Comfort
  • Charming boutique lodges, inns & resorts
Delicious Local Flavors
  • Flavorful dinners with local specialties
  • Hearty breakfasts, café-style lunches
Adventure & Exploration
  • Free use of top-quality bicycles
  • Expert guides with insider knowledge
  • Detailed route maps & easy-to-follow instructions
Hassle-Free Support
  • Support van for luggage & easy lifts
  • Hassle-free airport pickup & drop-off
  • Daily baggage transfers between hotels
Your papers, please

U.S. citizens do not need a passport for our U.S. tours, but you will need a REAL ID-compliant driver's license or another TSA-accepted form of identification for domestic flights.

Non-U.S. citizens need a valid passport to enter the United States. Depending on nationality, foreign travelers will need either an approved ESTA under the Visa Waiver Program or a visitor visa. ESTA applications should be made only through the official U.S. government site: https://esta.cbp.dhs.gov/. For visa questions, contact your nearest U.S. Embassy or Consulate.

What are the road conditions like on the Big Island?

The roads are nicely paved, with good shoulders on many of the main riding sections. The historic Mamalahoa Highway has little or no shoulder in places, but it also has very little traffic, which is why it remains such a favorite stretch of the route.

Is the riding mostly coastal or inland on the Big Island?

Much of the riding follows the shoulders of the volcano, often 500 to 1,000 feet above the ocean rather than directly beside the waves. The Big Island is geologically young, with fewer long beach roads than some of the other Hawaiian islands.

Instead of a simple oceanfront boulevard, the route mixes coastal views, green hillsides, old roads, lava landscapes, and broad Pacific panoramas.

What is the food like on the Big Island?

Food on our Hawai'i trip ranges from local-style favorites to fresh seafood dinners. Along the way, we introduce you to island staples such as loco moco, kalbi ribs, fresh ahi poke, and coconut-crusted mahi mahi.

It is a chance to taste the local side of Hawai'i, from casual roadside meals to ocean-fresh fish after a day of riding.

How hot and humid will it be on the Big Island?

Hawai'i is moderated by the surrounding Pacific, so temperatures rarely become extreme. Days are warm and tropical, but the ocean helps keep both heat and humidity more comfortable than many guests expect.

The bigger surprise is often the opposite: it can feel genuinely cool at night near Volcano, so a light layer is useful even in Hawai'i.

What should I pack for the changing elevations on the Big Island?

Most of the trip calls for warm-weather cycling clothes, but the night near Volcano can be chilly. A light sweater or fleece is useful, along with a long-sleeve jersey or arm warmers for the morning descent.

Think tropical riding by day, with one cool mountain evening in the mix.

Are there strong winds on the Big Island?

The trade winds frequently blow across the island, but our direction of travel helps reduce their impact. Much of the time we ride with the winds or at an angle to them rather than fighting straight into them all day.

Winds can be stronger around the east and west ends of the island, but those sections are usually only a short part of the day's ride.

What makes cycling Hawai'i different from riding on the mainland?

Hawai'i surrounds you with greenery as you circle the island, with towering volcanoes rising on one side and the deep blue Pacific dropping away on the other. Flowers bloom year-round along the roads, and small roadside stands sell fresh fruit or tuna caught that morning.

The ride feels tropical, local, and wonderfully far from the mainland, even when the cycling itself is relaxed and approachable.

How difficult are the climbs on the Big Island cycling tour?

There are no major climbs of consequence on this tour. The riding includes some long, gradual inclines along the coast and the lower slopes of the volcano, but nothing like a sustained mountain pass.

The terrain is more about steady, scenic riding than steep climbing.

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