Maui DELUXE Sport Edition

First full week in February every year / 8 days and 7 nights
(Sunday through Sunday)   

This is our deluxe offering that features the "Maui Triple Challenge" and many non-cycling extras. 8 days, 7 nights in beachfront home/villas with full amenities. This tour also promises to include a few celebrity riders and presentations that will make the evening social hours at our roomy home villas all the more entertaining. A rental car is an option for those tour riders that want to explore more extensively on their own - but, of course, we offer airport pick-up and drop-off so that you don't have to worry about transportation if you don't want to.   

Maui BASIC Sport Edition

With the economic meltdown of the past few years, we decided that a more frugal travel option to Maui was needed (which is a challenge in itself because of the high lodging costs for the island).  Our "Basic" offering includes many of the same rides and activities of the Deluxe tour (including the "Triple Challenge"), but our accommodations are geared toward the more budget-minded traveler. 
Last full week in January every year (Sunday through Saturday)  7 days and 6 nights!

Here's what the Co-Motion website had to say about last year's Co-Motion Maui tour:

You might have a lot of preconceived notions about Hawaii, and riding your tandem or single bike on the islands. Rob has explored all the islands, searching out the ultimate island cycling vacation spot; one that offers warm breezes, exotic smells, and spectacularly scenic rides. Maui was the winner hands down. And if that doesn't sound like the best way to beat the winter blues, we don't know what is!

All rides and activities start and finish from our 'home base' - you only have to unpack once! And we can assure you that Rob is famous for finding great cycling routes that go out of their way to avoid cars and traffic.


Rob has reserved a special group of properties ("Deluxe Edition"). Your lodging for the week includes full-serve kitchen, large living room, and a host of entertainment options. We truly think you'll find your accommodations to be a second home - without all the 'bike hassles' typical of dealing with resort hotels. It's an easy walk or ride into town, and there are many great dining options available (when you're not taking advantage of the several barbeques offered or nightly social hours).

Rob also promises to line up a few surprise celebrity guest riders that are sure to entertain you nightly with some of their cycling exploits - and maybe even offer a few tips to improve your cycling skills during the group rides.


And we can't forgot to mention Rob's famous Maui Triple Challenge, if you're up for adventure (all those that complete the three epic rides during the 7 day stay will be awarded a special custom medal as a memento of their accomplishment). Of course, Second Summer Tours offers full sag support, so those that come to Maui with 'winter legs' can take full advantage of the scenery - when needed - from the luxury of the support van. And no worries about your 'significant other' having a great time if they're not as passionate about their cycling as you are .... Maui (and Second Summer Tours) offers plenty of non-cycling fun and relaxation for those that just want to 'hang out' - or hang ten.


All You Wanted to Know About 
Second Summer Tours Deluxe Sport Edition

Second Summer Tours "Maui Triple Challenge"  has proven to be a classic winner for cyclists hoping to escape the winter of North America.   Mark your calendar for one of our two trips for this epic cycling vacation.   We use central island lodging  to minimize time spent in a support van to reach the various attractions.   How about trying windsurfing for some non-cycling fun?   It’s a cycling vacation, but that doesn’t mean you can’t experience some of Maui’s other outstanding attractions.


Paia (Northshore) is the starting point of the famous Climb to the Sun highway, a stunning 10,000-foot ascent to the summit of Haleakala volcano. Coasting down the mountain has become popular with cruiser-bike tour companies, but we’ll take on the challenge of a roundtrip adventure to the top and back! More later on this climber’s delight


The town of Paia is also the jumping-off point for the Road to Hana, which meanders through lush, tropical terrain yet-unspoiled by the commercial development found on much of the Hawaiian islands. We’ll travel this road as part of our epic century ride around Haleakala volcano, but be warned: this route isn’t recommended if you’re attempting your first century. The road is so rough and isolated in spots, car rental agencies forbid you to drive on it (not a bad thing, as it helps keep tourist traffic in check).

All of our rides can be tackled on a standard road bike, but triple chainrings or “compact” gearing is strongly recommended, to make the steeper pitches more enjoyable. We also recommend leaving the lightweight race wheels at home—strong training wheels with wider road tires (at least 23 to 25mm) are better-suited for the rough stretches of pavement and occasional hard-packed dirt found on the more secluded, remote roads we’ll be on. Tandems—properly outfitted with heavier duty wheels and gearing—can tackle these challenges as well.

We’re here to assist with technical details like gearing and equipment, and if you're concerned about your fitness we’ve even devised a program to help you arrive on Maui in good riding condition. We’re here to maximize your fun factor, so call or e-mail if you need the help!


Home Sweet Home

f you loved the laid-back, feel-good groove of the 1960s, you’ll feel right at home in our Northshore and Kihei properties that we use for the 'Deluxe' edition of the Maui Triple Challenge. There’s a friendly ambiance to this part of the islands that recalls the true, ancient Hawaii of days gone by. You’ll be picked up at the airport by the Second Summer Tours van, and all rides begin and end at your doorstep. We’ll have a support vehicle with us for rest stops and emergencies on the longer rides, and transport will be provided for our planned non-cycling activities.

We’ve sought out quiet and comfortable accommodations, with more local flavor than the typical high-zoot tourist resorts. These beach-front homes-villas (for the Deluxe tour) have all the features you might possibly desire after a long day in the saddle: large, fully-equipped modern kitchens, full laundry facilities, and huge living rooms (complete with cable television, DVD, and the most comfortable couches in Maui). And, of course, there's that spectacular setting. They're situated within easy walking distance to the beach, parks, and shops. All lodging is centrally located for ease of rider get-togethers and nightly social hours. The villas offer far more living space than a traditional luxury hotel room; it's not difficult to find your own 'private' spots in the villa or throughout the extensive--and spectacularly landscaped--grounds.


Whether on the Northshore or Kihei, you’ll experience the conveniences and treasures of small-town living. Both communities feature well-stocked health food markets, conventional markets, cafes, art galleries and more. Whether you join the group for meals, or venture out on your own, you’ll find plenty of outstanding fare—especially if you like fresh fish! We’ve made special arrangements with some of the local bistros, and their chefs have all been warned about cyclists’ tremendous appetites. Prepare to eat well! Several group dinners are included during your stay (including a traditional luau with all the accompanying festivities), as well as complimentary drinks and snacks during scheduled evening social hours, when you’re armchair racing with your newfound cycling friends. All our rental units have kitchens, if you prefer to dine in, and our van will make occasional supermarket runs, as well.

Your Maui vacation is a great opportunity to expand your cycling horizons, and rack up some epic miles in a tropical setting (average high/low temps for January and February are a near-perfect 78/62). Take advantage of our crew’s wealth of hard-won knowledge, and pick up some pointers that’ll make you a stronger, better cyclist. We’ll have several coaches to help lead the rides, and we’ll break into groups based on differing skill levels, where appropriate. This is a rare chance to advance your bike skills, while riding in paradise. Or, if you don’t want to push yourself, just put in some easy winter miles on our long, breathtakingly scenic routes.

Price of Admission


The fee for the “Deluxe Edition” stay in paradise is $2,475. The price has been reduced from previous years because we reduced by one day the length of the tour (to allow a bit more flexibility in rider's schedules for arriving/departing). Of course, if you wish to arrive early to Maui, and depart later, no problem; just let us know. Those booking early will be offered their choice of room (rooms vary in size and style) … so BOOK EARLY for best selection (this is the high season on the island)! IN ADDITION, ANY COUPLE THAT BOOKS A DELUXE TOUR BEFORE NOVEMBER 1 WILL RECEIVE AN ADDITIONAL $100 DISCOUNT OFF THEIR TRIP.

Our “Basic Edition” fee is $1,895; and also allows for extra days/nights if so desired.

Airfare is not included with any of our tours. We do offer the ability to schedule early arrival or late departure dates for those that one week just isn't enough time in paradise! Call or e-mail for details.

Single supplement is $450; however, we'll do our best to pair up singles with appropriate "roommates" where so desired. The home-villas in the 'deluxe' edition offer far more living space than a traditional luxury hotel room; it's not difficult to find your own "private" spots in the villa or throughout the extensive grounds.

Custom team clothing, support on the road for the longer "epic" days, several group dinners, post-ride socials, snorkeling boat trip (or other option depending on weather conditions), and more is included in both Maui tours! Custom cycling wear is by:

Tentative Itinerary
Maui Tripe Challenge

Detailed schedule will be sent before the tour. But like any of our tours, we maintain the right to be flexible when Mother Nature has other plans for our 'schedule'!

Day One

Arrive on day 1 in the afternoon/evening (unless you’ve opted for an early arrival). We will pick you up at the airport, and transport both you and your bike to 'home' for the week of riding fun.

We'll have a "Welcome to Maui" social hour over snacks, drinks and dinner, so you’ll get to know your week’s riding companions before we hit the bikes tomorrow morning.

Day Two

This will be your first real test to see how the winter layoff has treated your legs unless you took advantage of our pre-trip training service. We’ll meet at 10:00 a.m. for a loop through the western portion of Maui, approximately 75 miles on good to excellent pavement. We'll be starting a bit later today to allow for last-minute bike adjustments (or a little extra sleep for jet-lagged travelers). This route includes miles of spectacular scenery, but it’s a very narrow Second Summer Tours offers some great views!roadway that requires your undivided attention. (Rental car companies don’t allow their vehicles to be driven on these tricky, narrow roads, which is good news since it forces the few drivers to slow down to a cycling-friendly pace.) There are a few short (and steep!) stretches where you’ll be glad you’re packing triple chainrings or compact gearing. Expect a moderately paced ride, with frequent regroups and plenty of opportunity for picture taking. Of course, there’ll be an obligatory coffee-and-snack stop in Lahaina. (And Rob's got the tab, so have at it!) Today will be a great day for more casual cycling shoes (SPD sandals, MTB shoes or other more-walkable shoes), if you have a pair along. We’ll be in no hurry, and will have most of the day to stretch our legs. In the evening we’ll gather for a no-host social hour with complementary beer, soft drinks and snacks before we head out for dinner.  Make sure to bring a good appetite!

Day Three

A day on your own in paradise! We will also offer an informal ride that will depart at 10 a.m. for the upcountry town of Makawao - where a touch of cowboy culture meets the surfing crowd. In the afternoon we'll offer an easy hike (walk actually) to the world-famous Iao Needle.

Day Four

Weather permitting, today is our day to attack the climb to Haleakala’s summit. It’s a 40-mile-long ascent, so we’ll be off to an early start. The first group will meet at 7:00 a.m. and depart at 7:15 a.m.; a second group will depart at 7:30 a.m. We’ll already have your permits and passes for the National Park, and we’ll have extra gear and clothing should you need it along the way. The long climb means drastic climate changes, as you progress from the tropical beachfront setting at the start to the mountain's 10,000-foot summit.
More great views along the way

This is only an 80-mile day, but the first 40 miles are all uphill—10,000 feet up! Thankfully, the road surface is excellent. A number of bike touring companies shuttle people to the top and let them coast down the volcano, so tourists and locals alike are used to seeing cyclists on the road. Chances are, we’ll be the only ones riding up this road to the sun. The best racers make the climb in less than three hours; we’re expecting a bit slower pace, around five to six hours. Reaching the summit will be one of the highlights of the week, and for your efforts you’ll be treated to some of the most beautiful, strangely alien scenery this side of Mars. After absorbing the view, snapping a few photos, and maybe even placing a cell phone call home from your unusual location, get ready for 40 miles of almost zero-pedaling descent. Figure on maybe an hour to coast off the mountain and arrive back at our beachside digs.

Day Five

Recovery day! The collapsed, submerged crater off the coast of Lahaina offers some of the finest snorkeling in the world. This is something you won’t want to miss, even if you’re not into ocean sports. We’ve contracted with one of the leading boating/charter services for a fun morning of swimming, snorkeling and exploring Maui’s spectacular, underwater world. There’ll be an on-the-boat barbecue, so we’ll be able to fuel up for the next day’s riding while we play on the water. There’ll be an optional ride out to the dock and back, for those who’d like to spin their legs out after the previous day's climb—it’s about 10 miles each way.    If Mother Nature doesn't cooperate with good boating conditions, we'll line up another island option to check out.

You’re on your own tonight, for socializing and dinner. Rest up—or not—for the final leg of your Maui Triple. With loops around both ends of the island and the hill-climb, we promise the upcoming Haleakala Century will be like no other you’ve done before.

Day Six


Haleakala Century Elevation PDF

The morning of day 6 will come all too early for most of us, as the first group will depart at 6:45 a.m. sharp, the second group at 7:00 a.m. We’re guessing most of you will want to complete the Maui Triple Challenge start to finish, but if your legs are still feeling the ride after the 10,000 foot climb of Haleakala, we’ll do our best to provide shuttle service to the halfway point for all who request it (early trip registrants have priority). It’s going to be a long, hot one, so two large water bottles are the minimum today (and that’s taking our mid-ride support stop into account).

This tough 100-miler is actually three rides in one — you’ll tour lush tropics, semi-arid desert and Maui’s beautiful upland country. There’s not much opportunity to rest because of the challenging road surfaces and narrow lanes. If the climbing
  doesn’t put some hurt and lactic acid in your legs, there’s also 15 miles of rough—very rough—pavement that, while not as bad as Paris-Roubaix cobbles, it might make you think you're competing in your own Hell of the Pacific. This is the ride where you’ll really appreciate those wider, more comfortable tires. You’ll look forward to the short dirt stretch at the end—it’s smooth! Epic scenery, and a pass through quaint and historic Hana, makes the effort worthwhile. This is guaranteed to be a long, hard day in the saddle, but if you complete the century you can take pride in a well-earned triple for the week.

You’re on your own for dinner, to better-accommodate the likely range of finishing times. (Hey, you might be too tired to raise a fork to your mouth anyhow.)

Day Seven

Time to say good-bye to new friends, and let your legs enjoy a break from the bike. Pack up, check out, and head home (unless you opted for an extended stay). Many of our riders have `red-eye' flights out of Maui for the last day (typically around 10 p.m.), but you don't have to worry about storing your gear or “checking out” early from our lodging - this nice Second Summer Tours perk is included as part of your tour package (so you can get some last-minute fun in).

I'll start by saying this trip (Maui) was unforgettable. Great people, great weather, great riding, and great support...I am especially grateful to Rob and the Penseyres, but appreciate all that everyone did to make this a truly memorable trip. The accommodations were first rate.

Paul (and Dianne) Duncan 
Eugene OR