Choose Your Own Cycling Adventure

Blur the lines of vacation and training with one of these epic, brag-worthy bicycling trips.

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Get The Pro Treatment In The Desert

Tucson, Ariz.

Since 28-year-old Owen Gue started The Cycling House in 2005, he and his staff of enthusiastic athletes have refined every detail to create an ideal training environment. Gue, who used to race bikes as a junior and still has an incredible passion for all things cycling, exudes the patience of a kindergarten teacher as he helps participants improve their riding. (TCH also hosts camps in Mallorca, Spain; Colorado; Wisconsin; and Gue’s home state of Montana.) Everyone on staff appears to operate on two main goals: to make you a better cyclist and to ensure you have a good time doing it.

The sprawling mansion in Tucson seems built for this exact purpose, with a massive kitchen (including a top-notch espresso machine), a stretching room stocked with yoga mats and foam rollers, an outdoor TRX training station, a huge garage that houses sports nutrition and endless bike tools, and a pool and hot tub for post-ride dips. Every morning a healthy breakfast is ready when you wake up, your tires are pumped and the SAG van is stocked. All you have to do is pedal.

One of the week’s highlights is the famous 21-mile climb of Mount Lemmon (or 27 miles for the longer version). It’s not uncommon to catch pro cyclists like Tom Danielson passing you on the way to the top. One of the camp guides will snap high-quality photos along the way — which you’ll receive on a thumb drive at the end of the week — so your ascent is fully documented. Reaching the top is satisfying, but the reward of the swooping descent is even sweeter.

Throughout the year, pro Brendan Halpin hosts regular camps, and pro Ironman triathletes Linsey Corbin and Ben Hoffman serve as guest guides. TCH also offers camps leading up to specific races, such as Ironman Arizona. If you’re in hardcore training mode, the mountain-view Oro Valley public pool is a mile away, so you can add a swim workout before or after riding.

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TCH creates the perfect opportunity to get a jump-start on the upcoming season, especially for athletes stuck indoors all winter. You can bring your own bike or rent one from the company’s fleet of Cannondale SuperSix carbon road bikes. You’ll make plenty of new friends, eat incredibly well and leave with much stronger cycling legs than when you arrived.

Who it’s for: Triathletes looking for a cycling fitness boost

Brag factor: “I climbed Mount Lemmon.”

Rider level: Comfortable riding three-plus hours at a time, rides at least three days a week

Length: 6 days, 5 nights

Sample day: After waking up to a full gourmet breakfast from the house chef, go for a swim at the nearby outdoor pool or just take your time and saddle up for one of Tucson’s best routes — a typical ride is around 60-70 miles.

Cost: $1,495-$1,995 covers accommodations, guides and meals for the week (the higher range includes bike rental)

Ride The California Coast

San Francisco To Santa Barbara

You’ve undoubtedly seen pictures of the California coastline (or even driven on it) but nothing compares to cruising by those rugged cliffs and turquoise waters while on two wheels. Thousands of cyclists make the trek down Highway 1 every year, so it’s easy to find an organized trip that suits you based on how much distance you want to cover per day or how hands-off you want to be in regard to logistics.

A middle ground between complete DIY and a full-on guided tour is to hire SAG Monkey, a “personal bike concierge” business that handles everything from transporting your gear to the next hotel to providing delicious ride nutrition (gluten-free chocolate chip cookie bars or sweet potato rice cakes!). Chef Nick Nicastro provides impressive all-you-can-eat dinners made from his elaborate 22-foot kitchen trailer parked right outside the hotel for each night.

Day one takes you from San Francisco to Seaside, a 130-mile route with about 5,500 feet of climbing. Start by crossing the iconic Golden Gate Bridge and enjoy stunning views of the city. After you emerge from the fog, the epic sights continue through redwood forests before the sandy surfing beaches begin. If you’re lucky, you’ll get a powerful tailwind, which makes the triple-digit miles fly. Make a lunch stop at Whale City Bakery Bar and Grill, just north of Santa Cruz in Davenport, Calif., for delicious baked goods or a hearty sandwich to fuel the rest of the day.

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Day two is known as the most beautiful but also the most challenging, as you climb more than 8,300 feet (over about 125 miles) on your way from Seaside to Morro Bay. There are seemingly endless awe-inspiring views, especially through Big Sur, and those who have done this route in January often spot whales and dolphins. Before you get to your destination for the night, stop in Cayucos, Calif., for a hand-rolled Brown Butter Sea Salt Cookie at Brown Butter Cookie Company. Day three takes you slightly inland from Morro Bay to Santa Barbara (115 miles, 5,100 feet of climbing), traversing through farmland and wine country before shooting you back out to the coast.

The coast ride is all about options — because the appeal truly is in the journey, you can hammer away for hours or simply spin at your leisure.

Who it’s for: The experienced rider looking for base miles set against the backdrop of America’s most remarkable views

Brag factor: “I rode more than 350 miles on the California coast in three days. What’d you do this weekend?”

Rider level: Comfortable riding more than 80 miles at a time and regularly rides three-plus times per week

Length: Entirely up to you, but this itinerary is three days at an average of 120 miles per day.

Sample day: Grab a quick breakfast and roll out early, tackling the first half of the ride before a long lunch break in a town along the way. Continue on and return just in time for dinner. Sleep and repeat.

Cost: For SAG Monkey services, prices vary, but $175-$250 per day for full ride support, mobile bike repair, post-ride dinner and beverages for a minimum group of eight. Does not include nightly accommodations.

Savor The Tuscan Countryside

Tuscany, Italy

If you love exploring a new place via bike but are slightly overwhelmed by the logistics of doing so in a foreign country, one of Trek Travel’s vacations is the way to go. The company’s Tuscany Explorer trip is perfect if you crave a mix of challenging riding, small-village exploring and, of course, copious amounts of Chianti and bruschetta.

Once you’re in the hands of your two friendly and knowledgeable guides, you barely have to think about anything. Every morning starts with a continental breakfast in an elegant hotel — you stay in two towns during the week — before guides debrief you on the route options. You see a new part of Tuscany every day at your own pace, guided by clear, turn-by-turn directions you can affix to your handlebars. There’s never pressure to rush, as part of the fun of this adventure is documenting the scenery along the way.

At a glance, the rides don’t seem too high in mileage (they top out around 60 miles) because the root of the difficulty lies in the climbing-to-miles ratio. You’ll pass by vineyards, medieval cities and charming farmhouses on some of the most butter-smooth roads you’ll find anywhere. Your steed for the week, the Trek Domane, feels luxurious yet agile, capable of handling Tuscany’s technical, exhilarating descents.

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The tourism features on this bucket-list-worthy trip are half the appeal. You’ll do private wine and olive oil tastings, experience the Roman ruins during a walking tour of Volterra, and gorge on an elaborate mid-ride homemade picnic — think spicy wild boar salami, juicy tomatoes, freshly baked bread — on a vineyard and horse rescue farm. Some nights include group dinners and others are on your own so you can do a fair amount of exploring.

You’ll leave Tuscany with a belly full of the best local foods and a true sense of the rich culture and beauty of the area. And all your hills at home will definitely feel a lot easier!

Who it’s for: Cycling gourmands who are as enthusiastic about riding through vineyards as they are about tasting the wine that comes from them

Brag factor: “I spent a week riding my bike through Tuscany” has a nice ring to it, doesn’t it?

Rider level: Comfortable riding at least 45 miles at a time, bikes on a regular weekly basis

Length: Six days, five nights

Sample day: Options range from 20 miles (1,500 feet of climbing) up to 60 miles (3,800 feet), broken up by an al fresco lunch in a local village. You can hop in the van at any time, sans judgment.

Cost: $2,599 covers accommodations, two full-time guides and SAG support, luggage transport, use of a Trek Domane carbon road bike (with electronic Di2 shifting and a cycling computer included).

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