
Itinerary
Print Itinerary- Pre-tour
Maui Pre-Tour Package
Arrive at Kahului Airport on Maui and make your way to our peaceful pre-night hotel located in the island’s verdant upcountry. Settle in, head to the beach for a swim, or watch a spectacular sunset with a cocktail in hand. If you wish, dine at Lumeria’s onsite restaurant. In the morning, your DuVine guides will meet you at the hotel to get the cycling adventure rolling. The amount listed is the starting price.
Inclusions: Hotel, Breakfast
Accommodations: Lumeria
Price per person in double occupancy: $500
Price in single occupancy: $965To reserve call +1 888 396 5383
- Day 1
Aloha, Maui!
After meeting your DuVine guides, jump right into a bike fitting while we sip on famous Hawaiian coffee. After a quick safety briefing, we set off out of Pai’a and ride up to the town of Makawao. Pause at a local bakery for some famous Hawaiian pastries before we continue pedaling along the slopes of Haleakalā, the island’s most dominant feature and best-known attraction. Aside from its majesty, Haleakalā’s volcanic soil has also nurtured the island’s agriculture, resulting in a diversification of crops like tea, flowers, coffee, and chocolate. Climb to a fresh picnic lunch on the volcano before embarking on the downhill descent that sends us soaring to our hotel. Tonight we enjoy a private dinner hosted by our friend and local chef at a wide-open upcountry farm.
Destinations: Makawao, Kula, Pukalani
Accomplished: 26 miles / 42 km, elevation gain: 3,214 feet / 980 meters
Longer Option: 35 miles / 57 km, elevation gain: 4,690 feet / 1,430 meters
Accommodations: Lumeria - Day 2
South Maui: A Step Back in Time
This morning we head to the sunny southern coast of Maui, where the climate is drier and the ocean views are incomparable. Gradually descend a blissfully traffic-free road to the coast, pedaling beside secluded bays until we reach a petroglyph site and village. Pause for a fantastic glimpse at ancient rock art, then transfer to a local farm for lunch. After a tour of the farm, we’ll feast on plenty of exotic tropical fruit and produce grown right here. This afternoon, choose to finish the ride on the wild coastal road or hop in the van for a transfer to our oceanfront resort located on the Road to Hana.
Meals: Breakfast / Lunch / Dinner
Destinations: Keokea, Kaupo, Hana
Accomplished: 27 miles / 43 km, elevation gain: 1,676 feet / 511 meters
Longer Option: 43 miles / 69 km, elevation gain: 3,264 feet / 995 meters
Accommodations: Hana-Maui Resort - Day 3
Flex Day
How you spend today is entirely up to you! Go surfing and canoeing on some of Hawaii’s most pristine beaches, followed by a traditional lunch. Take a hike to the top of a coastal ridge or keep collecting the miles on a ride through the jungle. And if you prefer, there’s always the option to spend the whole day on the beach. Your flexibility extends into the evening, with the freedom to find whatever restaurant calls to you for dinner in or around Paia.
Meals: Breakfast / Lunch
Destinations: Hana
Accomplished: Optional hiking or cycling
Accommodations: Hana-Maui Resort - Day 4
Road from Hana
Today we tackle Maui’s most famous route: the Road to Hana. Unlike everyone else on the Hana Highway, we’ll be riding in reverse—from Hana—to take advantage of the oceanside road and miss the tourist traffic. Curving along 40 miles of lush landscapes into Maui’s North Shore, this road offers all the tropical trappings: from waterfalls and lava tubes to golden-sand beaches and guava groves. Midway through the ride, we’ll visit a local chocolate producer and stop for a pick-me-up of incredible banana bread or a nutrient-dense smoothie. End the ride here if you wish, marveling at the whimsical rainbow eucalyptus, or challenge yourself and ride the remaining miles to Paia: we’ve cycled Maui’s entire eastern half in just two days! A relaxing night at our next beachside hotel and a seafood feast is just the ticket after our mid-week triumph.
Meals: Breakfast / Lunch / Dinner
Destinations: Hana, Wailua, Paia
Accomplished: 34 miles / 55 km, elevation gain: 4,005 feet / 1,221 meters
Longer Option: 45 miles / 72 km, elevation gain: 4,868 feet / 1,484 meters
Accommodations: The Inn at Mama’s Fish House - Day 5
West Maui
And we’re off! On our last day of riding, take a quick transfer right to one of our favorite coastal roads: the Kahekili Highway, named for an 18th-century Hawaiian noble. Begin along this narrow ribbon of pavement as it jogs through the Edenic countryside of Maui’s northern coastline and reveals a peaceful new bay around every bend in the road. At a roadside stand, we’ll fuel up with super-fresh coconut water and homemade banana bread. For lunch, it’s shrimp, poke bowls, and a view over the Pacific where all this fresh bounty was caught. Spend the afternoon exploring the timeless streets of Lahaina, Hawaii’s ancient capital, before heading back to our hotel—we may even catch glimpses of breaching humpback whales on our drive. Tonight we toast our accomplishments and bid farewell to this beautiful place at our hotel restaurant, a coveted island-dining destination.
Meals: Breakfast / Lunch / Dinner
Destinations: Waihee, Kahakuloa, Lahaina
Accomplished: 29 miles / 47 km, elevation gain: 4,412 feet / 1,345 meters
Longer Option: 41 miles / 66 km, elevation gain: 4,566 feet / 1,392 meters
Accommodations: The Inn at Mama’s Fish House - Day 6
A Hui Hou, Hawaii!
Enjoy one more relaxed morning on the island—you’ve earned it! Wake up with a swim or take a final sentimental stroll on the beach. Either way, we’ll transfer you back to the Maui airport around midday and see you off to your next destination.
Meals: Breakfast
Destinations: Paia
DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.
Arrival Details
Airport City: Kahului, Maui, Hawaii Pick-Up Location: Kahului Maui Airport or Lumeria Pick-Up Time: 8:45 or 9:30 am
Departure Details
Airport City: Kahului, Maui, Hawaii Drop-Off Location: Kahului Maui airport Drop-Off Time: 12:00 pm
Travelers Takes Note
For the hikes on this tour, we strongly recommend bringing hiking boots or trail shoes with good traction (not running shoes or sneakers). Moisture-wicking clothing or daypacks are also recommended, but not required.
Dates + Availability
- DatesPriceSpecial Events
- Dec 28 – Jan 2$7,695
Inclusions + Details

Accommodations
- Thoughtfully selected accommodations that reveal the true character of the region
- Luggage transfers
Meals
- Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
- 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
- Carefully selected local wine, beer, or spirits with every meal
Activities
- Wine tastings and activities as outlined in the tour itinerary
- Entrance fees to historic sites, museums, parks, and all other exclusive events
- Gratuities for baggage, porters, and hotel service
Gear
- Top-of-the-line bicycle selection
- Bike helmet
- Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
- GPS in most destinations
Support
- Expert bilingual guides with extensive local knowledge
- Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
- Pick-up and drop-off before and after your tour from predetermined meeting points
- Daily bike maintenance to ensure optimal performance