Big Island Cycling Challenge

Big Island CyclingBig Island Cycling Challenge bicycle tour

A real challenge for the enthusiastic cyclist! Cycle around the Big Island in ONLY 4 days. Feel like a professional cyclist on this 250+ mile ride of grueling hill climbs, gorgeous descents, and rolling hills.

This adventure awaits the avid cyclist with a fitness level of 100 miles or more per week for the last several months. Discover why the Big Island is one of the best places in the world to ride your bike.

At Velissimo – Cycling Destinations, we do our utmost to provide you with the best Deluxe Cycling Vacations. Well-prepared routes, highest standards, deluxe accommodations, local dining experiences, and our all- inclusive service will make your cycling vacation with us special.

A minimum of 4 participants are required. Contact Us for custom pricing for smaller groups.

Day of Arrival

Upon your arrival you will check in to your hotel. In the afternoon there will be a welcome meeting where you will meet with your tour guide for an informative discussion on safety, the tour schedule, bicycle fitting, and routes for the following day.

Day 1

Let the challenge begin! The first day will cover approximately 74 miles of rolling terrain with a 13-mile uphill climb along Hawaii’s Gold Coast and the Kohala Mountain range. After reaching the top at 3500” we’ll descend for 6 miles into the quaint town of Kamuela, our first overnight stay.

Day 2

We start our day riding across part of the famous Parker Ranch, one of the largest privately owned cattle ranches in the USA. Along the way we’ll have great views of Mauna Kea with its 13796 feet. Descending into Hilo via the green headlands of the Hamakua Coast, stunning views of the ocean, tropical valleys, and waterfalls in giant river gulches will make this day special. Approx. 56 miles.

Day 3

Another challenging day in the saddle, today’s ride will start at sea level. Enjoy the steady climb up to 4200’ from Hilo into the town of Volcano, home of the most active volcano in the world, Kilauea.
Be rewarded with dramatic landscape changes and restore your energy on the long descent back to sea level. As we head back north we’ll pass the southernmost point of the USA, before we reach our well-deserved finish in the town of Ocean View. Approx. 76 miles.

Day 4

On this last day of riding, heading northward up the Kona Coast, the roads alternating between straight and winding take you across breathtaking sea cliffs, lava flow vistas, Ohia forest reserves, and world-famous Kona coffee farms. This incomparable variety of scenery is the compensation for gains and losses of elevation as you make your way to your hotel. Approx. 47 miles.


At the farewell breakfast you can reminisce about the past week and say, “Aloha” to all of the friends you’ve made during your tour. Then you are free to relax and prepare for your departure.

Included in your Big Island Cycling Challenge Package:

  • 5 nights accommodations
  • Performance bike
  • Experienced tour guides
  • 5 Breakfasts, snacks for lunch, energy nutrition, and drinks
  • 4 Dinners
  • Full support vehicle with luggage transport following the ride
  • Transfers from and to airport
  • Gratuities for hotel services, porters, and baggage

Not included:

  • Airfare
  • Lodging before or after the trip
  • Travel Insurance
  • Gratuities for your guides
  • Personal expenses such as laundry, telecommunications, mini bar, spa treatments, wine, and other alcoholic beverages