Meet your guides at the Kahului Airport on Maui, and take a quick transfer to our peaceful hotel located in the island’s verdant upcountry. Settle in, head to the beach for a swim, or watch a spectacular sunset before our first dinner together to kick off the trip.

And we’re off! After our bike fitting, set out from the hotel on our first 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 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. We’ll stop at one such farm to pick vegetables and design our very own farm-to-table picnic. The best part about having lunch on the volcano? The big downhill that sends us soaring home right after.

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

Accomplished: 43 miles / 69 km, elevation gain: 3,447 feet / 1,051 meters

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 the region’s only general store. A visit here is like taking a step back in time: we’ll mingle with deep-rooted locals as we stock up for a picnic lunch, featuring exotic tropical fruit from nearby farms. After, a local guide will show us around a petroglyph site and village ruins for a fantastic glimpse at ancient rock art. 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—more on that tomorrow.

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

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. At the top of our longest climb, we’re treated to a Hawaiian barbecue lunch at a legendary roadside stand. Close an impressive loop as we ride into 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.

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

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 focus on food with visits to local producers of coffee, chocolate, and goat cheese. 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.

Accomplished: Optional hiking or cycling

First things first: begin the day with a breakfast spread of locally grown tropical fruit and coffee. Then it’s time for a transfer to one of our favorite coastal roads: the Kahekili Highway, named for an 18th-century Hawaiian noble. This narrow ribbon of pavement 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 with a great book on the beach—or pack in a little more adventure and head down to the water to try your hand at windsurfing. Tonight, we toast to our accomplishments and bid farewell to this beautiful island with a private dinner, hosted by our friend and local chef at a wide-open upcountry farm.

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

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.