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.
Only Great Explorations:
· Small groups, extraordinary guides, and authentic experiences
· Order off the menu at restaurants you won’t find in guidebooks
· Distinctive, charming hotels too small for larger groups
· We design and operate our own trips so there are only good surprises
Maui is a popular destination for road cyclists including pro racers who love the variety, challenging options and climate. Given the popularity of the island, there is some inevitable traffic on some of the routes, but there are good shoulders on many of the roads and frequent signs reminding motorists to give cyclists space. Winds (attracting kite surfers), high mid-day temperatures and sometimes rain are factors in our ride planning. Maui is certainly a dream destination and for avid cyclists in particular, a superb place to ride. Add in the opportunity to outrigger paddle, SUP, surf and relax on stunning beaches and it’s without equal in North America.
Straight Talk
Kihei, HI, United States
Day 1+2
Napili Surf Beach Resort, Napili Place, Lahaina, HI, United States
Day 3
Paia, Hawaii, United States
Day 4-7
| 2026 | 2027 |
|---|---|
| Jan 3-9 | Jan 2-8 |
| Jan 17-23 | Jan 16-22 |
| Feb 7-13 | Feb 6-12 |
| Feb 21-27 | Feb 20-26 |
| Mar 7-13 | Mar 6-12 |
| Oct 17-23 | Oct 16-22 |
| Nov 7-13 | Nov 6-12 |
| Nov 21-27 | Nov 20-26 |
| Dec 5-11 | Dec 4-10 |
| Dec 19-25 | Dec 18-24 |
Trip can start at any date. Self-guided and custom trips also available. Call or email for details.
Trip Size
Total Days
Arrive/Depart
Activity LevelModerate
40-100 km (options) daily
Van supported
TerrainModerate with some rewarding climbs
CostLand Cost
US $4,950
Includes 6B/2L/5D
Single Supplement
US $1,250
Bike Rentals
Hybrid Bikes: US $320
Racing Bikes: US $420
E-bikes*: US $480
*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.
Getting There
The principal airport on Maui is in Kahaluli. We will meet at the first hotel between 4-6 p.m. so you will want to plan your flight accordingly.
Kihei
Your hotel is included on this day and you check-in anytime after 2 p.m. Settle in, then hit the beach, swim and relax. Between December and February, look for whales which can be often seen from shore. We will dine at a local restaurant that serves superb fish tacos in a casual setting.
Kihei
Optional early morning yoga class. Meet your bike. For the first day of cycling, we will ride from Kihei through upscale Wailea to Makena Beach to the Lava Flow and La Perouse Bay (Nature Area Reserve) and back. 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.
Distance: 23 km; 173 m gain
Napili Beach
Start the day with yoga or a jog along a trail east of Wakapu Beach. Cycle south 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.
Distance: 58 km; 270 m gain
Pa’ai
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). You may also bump into pro cyclist Ryder Hesjedal who lives and trains here off-season. Paia is filled with great restaurants (Flatbread and Cafes des Amis are two of our favourites), coffee shops (Anthony’s is our ‘go to’ for java), yoga studios and surf stores and unique shops. There are no chain stores allowed here (yeah)!
Distance: 57 km; 977 m gain
Pa’ai
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!
Distance: 71 km; 1,374 m gain or 123 km; gain 2,503 m gain
Pa’ai
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) 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.
Distance: 52 km; 2,660 m gain or 115 km; 3,069 m gain
Depart
Enjoy a morning yoga session and then depart at your leisure.
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!
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.
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.
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