Looking for somewhere to travel during the months between November and April? Look no further than Hawaii and the island of Maui. It’s our favourite island for many reasons: it has reliably warm and sunny climate, great cycling, and plenty of other non-biking water sport activities to fill your days including surfing, stand-up paddle-boarding, and outrigger canoeing. You will see whales, loggerhead turtles, birdlife and more. We’ve designed this itinerary to have you stay in Kihei, on the Napili Coast in West Maui, and Pa’ai to give you access to the best riding (without requiring shuttles) and to allow you to experience the variety of this island.
Kihei, HI, United States
Napili Bay, Hawaii, USA
Paia, Hawaii, United States
What’s Included in the Cost of Your Trip?
INCLUDED IN REGULAR TRIP
6 nights hotels
All breakfasts and 1 dinner
Use of a high quality road bike and accessories
Detailed GPS, route instructions and maps
Personal meet & greet with our local Area Manager
Area Manager available on call throughout the tour
Custom trips also available and can start any day. Call or email for details.
ARRIVE / DEPART
Classic Accommodation: US $3,750
Single supplement: US $935
Luxe Accommodation: US $4,950
Single supplement: US $1,235
Arrival. Your hotel is included on this day and you check-in anytime after 2:00 pm. If you arrive in time, consider riding out to La Perouse Bay. Settle in, then hit the beach, swim and relax. If you are here between December and February, look for whales which can be often seen from shore. We recommend dinner at a local restaurant, Coconuts, that serves superb fish tacos in a casual setting, or if staying at the Mana Kai, the restaurant at the hotel has one of the best oceanfront settings in Maui.
Ride Distance: 23 km, 173 m gain.*
Optional early morning yoga class. For the second day of cycling, we recommend a ride from Kihei through upscale Wailea to Makena Beach to the Lava Flow and La Perouse Bay (Nature Area Reserve) and back or alternatively, out to Iao Valley State Park. Afterwards, you will have time for surfing, ocean kayaking (sit on top style) or stand-up paddle-boarding, where you will have a good chance to see loggerhead turtles.
Ride Distance: 23 km, 173 m gain or 55 km; 440 m gain.*
Start the day with yoga or a jog along a trail east of Wakapu Beach. Cycle north through Kihei reaching Lahaina for lunch. Stop and admire the banyon tree planted in 1873 whose branches extend over 200 feet from side to side. Lahaina is the oldest village on Maui and is filled with shops and galleries. Continue through Kanapali, and Hononowai to Napili Beach, stopping along the way where you please; there are pristine beaches all along this coast.
Ride Distance: 58 km, elevation gain 270 m.*
Your circumnavigation of West Maui will continue, following the coastal road past Kapanou Point and Kahului Bay, past Spreckelsville Beach, where windsurfers and kitesurfers entertain. Arrive to Pa’ia, the hippest village on Maui, filled with surfers (Laird Hamilton and Francisco Goya live here, among others). Paia is filled with great restaurants (Flatbread and Cafes des Amis are two of our favourites), coffee shops, yoga studios and surf stores and unique shops.
Ride Distance: 57 km, elevation gain 977 m.*
The road to Hana is an epic ride, and the scenery is spectacular the entire way. You’ll pass Hookipa, and Jaws, world-class surf beaches; turn around at Keanae (half-way) or descend all the way to Hana. Should you wish to return by helicopter (add cost-$200pp) this would make for a spectacular return trip!
Ride Distance: 70-100 km one way, elevation gain 1129-1374 m.*
Enjoy a ride up to the upcountry village of Makawao, where historic buildings, now filled with hip galleries and eclectic shops make for an ideal lunch stop and visit. Those wanting a real challenge can continue up to Haleakala Crater; it’s 10,000 ft and 38 mi from Paia to the top- it takes even strong riders several hours! An alternate ride is to take a shuttle up to Kula (we arrange; you can pay provider directly) and cycle from there along the Kula Highway as far as Nu’u Bay along a beautifully paved road with very little traffic. Back at your hotel, you may decide on a massage to reward your legs or swim at Baldwin Beach, reached easily on dedicated bike path from Paia.
Ride Distance: 52 km, elevation gain 2660 m.*
Depart at your leisure. The airport is a 15 minute taxi ride away and your hotel will help arrange.
*Distance and elevation gains may vary depending on hotels chosen for specific departure.
We’ve been staying here for years and think it is one of the best kept secrets on Maui. Recently renovated with contemporary décor, large pool this hotel is just meters from the ocean and a dramatic stretch of beach. We like the bar and restaurant on site also!
Alt: Maui Coast Hotel, Kihei
We love this hotel for its location and intimate number of rooms. Built in 1960, it has a nice swimming pool and you can walk to several excellent restaurants. Dramatic mesas, all beneath a vast desert sky, you’ve got yourself the ingredients for an unforgettable stay.
Nestled in a coconut grove in a secluded beach on Maui’s north shore, is Paia, Maui’s coolest town, with shopping, galleries, cafes, night-life and the island’s biggest and best organic grocery store. The Inn's beach is next door to famous Hookipa Beach, where international wind-surfing, kite-surfing and board-surfing competitions are held.
Adjacent to Ulua beaches and just steps from the shops at Wailea, this hotel has three excellent one-site restaurants, a beautiful swimming pool and relaxing spa facilities.
Set on 40 acres on Ka’anapali Beach, the completely-reimagined Hyatt Regency Maui Resort and Spa is a getaway in paradise. Enjoy Hawaiian hospitality with stargazing and a traditional nightly lu'au on-site, stay loose on the links with oceanfront golf, or unwind at our beachfront spa.
This hip hotel is right on the main street in Paia, in the heart of town. The rooms are smartly designed and the common rooms invite guests to socialize. Baldwin beach is a short walk away.