Meet your guides at the Kahului Airport on Maui, and take a quick transfer to our luxurious villa located on the island’s north coast. Settle in, head to the beach for a swim, or watch a spectacular sunset before our first dinner together prepared by our own private chef.

Begin the morning with a breakfast of locally grown tropical fruit and coffee. After a bike fitting and safety briefing, head out to tackle 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, then pedal back to our villa. 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. Dinner is served at our villa this evening: another satisfying spread from our private chef.

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

Set out from the coast today, or start riding from the town of Makawao where you’ll find the best Hawaiian pastries at a local bakery. Continue pedaling along the verdant 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 to the beach right after. Tonight we’ll leave the villa for dinner at a famous restaurant that’s considered a local institution.

Accomplished: 29 miles / 47 km, elevation gain: 4,412 feet / 1,345 meters

Longer Option: 33 miles / 54 km, elevation gain: 4,110 feet / 1,253 meters

How you spend today is entirely up to you! Go surfing or windsurfing on some of Paia’s most pristine beaches. 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. Rack up some extra miles with another bike ride into the uplands above Paia. And if you prefer, there’s always the option to spend the whole day on the beach. This evening, regroup for dinner together at the villa.

Accomplished: Optional hiking or cycling

Today we tackle Maui’s most famous route: the Road to Hana. 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 stop for a pick-me-up of incredible banana bread or a nutrient-dense smoothie. After a bit more climbing, we reach our lunch destination: a restaurant that attracts foodies from all around the island with culinary creations featuring ingredients from nearby farms. Later, cool off with a dip in the sea at the black sand beach, or take a closer look at Maui’s ancient history during a visit to a Polynesian temple. Return to the villa by transfer or take a helicopter ride for a bird’s eye view of the island—you may also choose to spend the night in Hana and close an impressive loop when we bike back to Paia tomorrow morning, cycling Maui’s entire eastern half in just two days.

Accomplished: 33 miles / 54 km, elevation gain: 3,533 feet / 1,077 meters

Longer Option: 41 miles / 66 km, elevation gain: 4,405 feet / 1,343 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 this 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 villa. This evening, you’re free to find whatever restaurant calls to you for dinner in or around Paia.

Accomplished: 29 miles / 47 km, elevation gain: 1,729 feet / 527 metersThis morning we head to the sunny southern coast of Maui, where the climate is drier and the ocean views are incomparable. Gradually descend this 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 villa. This evening, you’re free to find whatever restaurant calls to you for dinner in or around Paia. Accomplished: 29 miles / 47 km, elevation gain: 1,729 feet / 527 meters Longer Option: 73 miles / 117 km, elevation gain: 6,088 feet / 1,856meters Longer Option: 73 miles / 117 km, elevation gain: 6,088 feet / 1,856meters

There’s no better way to end the week than taking on the ultimate challenge: Haleakalā. We’ve ridden around this massive volcano all week, and now is your chance to climb the 10,000 feet from sea level to summit. Even though it’s a bucket-list ride for serious cyclists, the grade averages 5.4% for 35 miles—so there’s no shame in starting higher up the mountain and saving your energy for those eerily beautiful volcanic switchbacks, or even opting to conquer Haleakalā by hiking instead. Between the wild mountain weather and lunar landscapes of the crater, it promises to be an epic feat no matter how you approach it! Tonight, we toast to our accomplishments and bid farewell to this beautiful island with a private dinner at the villa

Accomplished: 21 miles / 34 km, elevation gain: 3,375 feet / 1,029 meters (or 2-3 hours hiking)

Longer Option: 35 miles / 57 km, elevation gain: 10,004 feet / 3,050 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.