How to Plan a Cycling Vacation

Rob Annis

For me, the only thing better than visiting a new place is seeing it for the first time from a bike saddle.

As a cycling fanatic, most of my trips involve a bicycle in one way or another. Whenever I’m heading to a new place, the first place I try to hit is a bike shop, whether it’s to rent a bike or just get recommendations for local routes. For the past few years, my bicycle has been a central part of my travel plans, whether it’s traveling to a far away city for a massive charity bike tour or renting a house and pedaling in every direction for a week.

Every travel website claims the journey is often as important as the destination, and that’s even more true on a bicycle. You’re traveling at slower speeds, and exposed to the elements and your surroundings much more than if you were in a car. In my opinion, there’s no better way to travel.

In San Antonio, a wrong turn led my wife and I down a maze of residential streets. As we attempted to find our way back to our hotel, we stumbled across a beautifully decorated gazebo, where moments before a deliriously happy couple had gotten married. As the mariachi band serenaded the crowd, we watched from afar, not wanting to intrude on the scene. The scene reminded us of our own wedding years before, and quickly eased any frustration that was building inside me after I got us lost.

So what’s the right bike tour for you? If you’re a first timer, going with an established tour company or tagging along with a more experienced friend will be your best bet. Bike travel has its own unique set of challenges – equipment failures, gear options and unforeseen physical limitations – that novice riders might not be ready for. The Adventure Cycling Association is an incredible resource for finding a bike tour or planning your own epic journey.

The one-day or weekend tour

Probably the most common bike tour is a short-term tour. Organized rides typically have multiple distance options, so you can ride 100 miles while your significant other does 30 at their own pace. Organizers will usually have support stations between every 15-20 miles, so you’ll be able to stop, refill your water bottles and grab a quick snack. Some of the better one-day rides have mechanics at most stops to quickly adjust your brakes or solve the mystery squeak coming from your bottom bracket.

If you’re looking for quiet and solitude in nature, this type of tour is not for you. The Hilly Hundred, a two-day autumn ride through the rolling hills and foliage of Southern Indiana, boasts more than 5,000 riders, so you’re never truly alone on the roads.

Guided group tours

Go to the back of almost any cycling magazine and you’ll see offers from multiple companies offering to lead you and a group of other riders in winding tours through gorgeous roads or trails here in America or abroad. Groups tend to be on the small side – expect about a dozen or so riders, depending on the operator – with a follow van filled with drinks, food and repair tools. Depending on the tour, riders will either camp or stay in hotels or inns along the way. Guides typically are extremely knowledgeable about the areas they ride, so be sure to spend some time pedaling next to them.

Be sure to study the routes and mileage before signing up for this type of tour and be honest about your skill level. There are few things worse than signing up for an expensive tour and spending large portions of it in the van because the route is more mountainous than you can handle.

Romantic couple pedal

This is definitely high on my list of to-do trips with my wife. Several tour operators specialize in scenic inn-to-inn trips through Vermont or other states. Each morning you depart from a different bed-and-breakfast, outfitted with a map and a snack. While you and your better half casually pedal to the next inn on your itinerary, your luggage is transported via van. Many of the tours offer different routes to make it as easy or as challenging as you want.

These are great tours, but make sure you know some basic bike repair skills, like changing a flat tire, before you go. Depending on the tour, the operator might not offer roadside assistance.

Self-supported bike packing

For riders interested in riding at their own pace and roughing it a bit, this is a great option. Your only limit is your imagination; some friends and I are currently planning a 3-5 day tour hitting Midwest microbreweries. If you want to camp at night, ultralight gear and food can be towed behind you in a trailer. Or you can try credit-card touring, where you stay at a hotel each night and carry extra clothing and gear in panniers strapped to your bike.

Try to pick friends who are roughly at the same cycling level and temperament as you. If you’re planning on riding mostly back roads, make sure at least one of your group members has the needed mechanical skills to do roadside repair work, like fixing a broken chain or spoke.

Fantasy camp for racers

In July, I’ll be riding part of the Tour de France with Sports Tours International, along with a dozen or more other cycling enthusiasts. For about nine days, we’ll be riding the same roads as the pros – albeit a lot slower. For amateur racers like me, the trip will be the closest I’ll ever come to the WorldTour peleton. During the ride, we’ll leave before the pros, stop for a bit to eat and watch as the real racers rocket past. Afterward, we’ll pedal our way back to the hotel. Most professional races, including the Amgen Tour of California and the US Pro Cycling Challenge in Colorado, have similar tours. For other pro cyclist wannabes, there’s the La Vuelta Puerto Rico, a three-day, 375-mile “pro-like experience,” according to the website.

Many of these trips are typically for more advanced and fit riders. Scan the tour operator’s website to get an idea of what to expect before typing in your credit card information.

#OnTheRoad On Instagram: The Chesapeake Bay And Eastern Shore

Did you know June is National Great Outdoors Month? I’m celebrating by hopping in a car with some friends and taking a road trip through the Chesapeake Bay, the largest estuary in the United States, and other parts of the Eastern Shore and surrounding area. We’ll start with a trip to the beach and then some camping on Assateague Island National Seashore, famous for its wild horses. So long as the weather (and my cellphone) keeps up, we plan to crisscross the border between Maryland and Virginia to explore some small towns, paddle through the bay on kayaks and eat plenty of crabs and oysters. Then, we’ll round the trip out by hitting up Baltimore and Washington, D.C. I’ll be chronicling it all through the @GadlingTravel Instagram feed, so if you’re not already following along it’s a great time to start.

Four Down Two Across: Homer, Alaska


Saturday morning, at the Ocean Shores motel in Homer, I was sitting at the desk peering out the big window at the water. I saw splashing in the distance. I asked Robert, “Is that a whale?”

Indeed it was. In fact, it was one of four whales, swimming up the sound, their backs visible in the water. Over the next hour or so we saw probably 20 whales altogether. A beautiful start for the day.

After breakfast at McDonald’s, we drove to Soldotna, a town of 5,000 about 90 minutes north, to play with the Soldotna Table Tennis Club. During the academic year the club plays at a school, then breaks for the summer. Since school was now closed, and we still wanted to play, special arrangements were made at the Soldotna Elks Club, which has two tables in a gym in the basement. Most of the club members were away, but six of us (including two teens) showed up, playing from noon to 2:30. We had a good time and a great workout.

Back on the road, Robert and I stopped for lunch again at Suzie’s Cafe in Sterling. Robert had his favorite, a chickenburger, while I tried the hot open turkey sandwich with mashed potatoes and corn on the cob. This is the very definition of “comfort food.”A little after 6 pm we arrived in Eagle River, just north of Anchorage, at the home of Boyd and Shirley Bennett. Boyd, 84, is many-time table tennis champion of Alaska, the first table tennis champion of the Arctic International Games, the coach of many younger Alaskan players, and the first inductee (in 2005) into the Alaska Table Tennis Hall of Fame.

Now with a couple of titanium rods in his back, Boyd doesn’t play anymore, but he’s still enthusiastic about the game. Boyd and Shirley built a wing on their house to hold two table tennis tables. The lighting, flooring, and overall conditions are professional. An Eagle River Table Tennis Club used to play here. After dinner Robert and I played a best-of-seven match, with Boyd and Shirley watching from the side. Robert spotted me 8 points per 11-point game. I ended up winning 4 games to 2, but as the score suggests, it wasn’t easy. Conversation about table tennis and lots more ran late into the evening.

Regarding yesterday’s puzzle, my answer was HORSESHOER.

Here’s a new challenge: Take the word EAGLE. Change one letter in it and rearrange the result to make a new word. Then change one letter in that and rearrange the result to make another word. And so on. How many steps does it take to change EAGLE into RIVER? Only common, uncapitalized words are allowed.

Follow Will and Robert’s Trip across Alaska through next week at “Four Down Two Across.”

America’s Most Beautiful Bike Ride? Maybe

As I round the final switchback of the climb, the road grade tilts upward yet again. My fingers nudge my shifter, trying to retreat to a lower gear, but I’m already on my final cog; it’s up to just my legs now to get me to my first destination of the day.

About 30 hard pedal strokes later, I coast into the Emerald Bay scenic vista, my reward for hundreds of feet of climbing that cool spring morning. I lean my bike against a sign and stare down upon the beautiful blue lake below. Had I seen this same image on a travel brochure, I’d swear it was photoshopped, but it’s here in front of me, in living color brighter than any Kodachrome image I’ve ever seen.

If you’re calling a bike ride “America’s Most Beautiful,” the scenery had better deliver. Luckily for the organizers of this 100-mile jaunt around Lake Tahoe and the surrounding countryside, it does … and then some. I’ve ridden these roads multiple times over the past three years, and the lake continues to take my breath away nearly every time I see it.Two Lake Tahoe centuries are offered by ride promoters each year – America’s Most Beautiful Bike Ride in June and the Tour de Tahoe in September – but it’s simple enough to create your own epic ride. Although the lake’s circumference is only 72 miles, a 28-mile out-and-back excursion on Highway 89 to the nearby town of Truckee will give you the mileage you need to crack 100 miles on your cyclocomputer.

To ride the 72-mile loop, just keep the lake on your right side and pedal. There are more than a few convenience stores offering Gatorade and granola bars along the route, as well as plenty of mom-and-pop diners, delis and bakeries to grab lunch during the ride. Be sure to stop in Tahoe House Bakery & Gourmet, which bakes the best coconut macaroons my buddy Ross has ever tasted. I’m partial to the Denver omelet at the Driftwood Café, and I’ve also heard great things about Café Fiore in South Lake Tahoe.

You don’t need to be a super-fit rider to finish the route, nor do you need an expensive $6,000 racing bike. I passed several folks who were stretching the limits of their XL cycling jerseys, but still managed to make it up every hill and mountain. Throughout the ride, I came across several riders who earned my admiration and respect – a New Jersey cyclist riding a heavy steel single-speed, a woman on a tiny folding bike with 20-inch wheels and multiple riders atop heavy old-school mountain bikes.

That said, be ready for between 3,500 and 4,000 feet of climbing on the route. There are two major climbs – the 800-foot climb up to the 6,900-foot Emerald Bay summit, which features multiple switchbacks and a steep kicker toward the end, and the 7,100-foot Spooner Lake summit climb, which rises 1,000 vertical feet over eight miles. After Spooner, just when you think the climbing’s over, you’re faced with seven demoralizing rolling hills. More than a few riders say those climbs are the toughest of the day.

My Cannondale Supersix was armed with a standard Ultegra crank and an 11-28 rear cassette, and I never felt in jeopardy of going backwards on a climb. For the less-vertically inclined, a compact or triple chainring will allow you to spend more time in the saddle rather than standing on the pedals.

Dedicated bike lanes and wide shoulders for most of the route allow more nervous riders an extra degree of security. Because Tahoe is a popular destination for road cyclists, local motorists are used to riders and typically give them a wide berth. Nevada’s new 3-foot passing law helps as well.

You can ride in either direction, but I’d recommend most riders stick to navigating the roads in a clockwise direction; going counter-clockwise, you’re stuck pedaling up Spooner on a busy multiple-lane highway for nearly 8 miles. Better to safely descend on that same road, where your speed will nearly match the automobile traffic. Because of the occasionally twisty nature of the highway, stick to the center of the right-hand lane; the shoulder is too narrow to safely navigate at speed.

But the biggest dangers to cyclists aren’t drivers, but themselves. The route offers at least two screaming downhills, and less experienced riders must resist the temptation to break the sound barrier descending. During my most recent trip, I rounded a blind corner to come across two ambulances in the center of the road tending to injured cyclists. I squeezed my brakes, causing my rear wheel to fishtail slightly as I came to a stop. Had I been going faster, I might have joined the riders on the pavement.

Being a popular tourist destination means plenty of lodging options around the lake. I usually use Harvey’s, a casino hotel straddling the edge of California and Nevada as my base of operations, although there are literally hundreds of other options nearby.

Ironically, visitors will see photos of the area’s immense natural beauty throughout the casino, but many won’t venture outside the gambling parlors. In the early-morning hours before day one of riding, I stumble out of bed and find myself in the casino. On my way to breakfast, I’m forced to weave through hordes of heavy-lidded gamblers wearing last night’s party clothes. Walking toward the escalator to the restaurant, I noticed a man nursing a half-empty Corona at the bar, holding a cigarette burned down nearly to the filter with one hand and sullenly punching the buttons of a video poker machine with the other. Forty minutes later – and nearly as many cups of coffee later — I saw him again, in the same spot, holding his head in his hands.

Beware the mountainous region’s notoriously unpredictable weather – three years ago organizers of the Amgen Tour of California canceled two stages of the race after a heavy blizzard made the roads nearly impassable. A week later, I rode the route and was pelted by rain and hail as the mercury struggled to pass 45 degrees for most of the day. When the temperatures rose, so did the condensation — as the water on the roads evaporated, the roads were blanketed with a thick vapor making it nearly impossible to see more than 10 feet in front of you. However the last two years have been nearly perfect, with the chilly morning temperatures in the upper 40s giving way to highs in the 70s later in the day.

I’ve ridden all over the U.S., in some of the most incredibly scenic places that human eyes have come across. Are the roads surrounding Lake Tahoe truly America’s Most Beautiful? That’s hard to say, but I can promise you won’t be disappointed.

Video: 102-Year-Old Woman Makes First BASE Jump

In celebration of her impending milestone birthday, Dorothy Custer wanted to do something a little different this year. So, on the day she turned 102 she decided to make a tandem BASE jump off the Perrine Bridge in Twin Falls, Idaho. That’s a leap of 486 feet and as you can tell from the video below, Dorothy enjoyed ever second of the experience, which also gave her the record as the oldest person to ever make such a jump.

This is a far-cry of last year, when she marked her 101st birthday by ziplining over the Snake River Canyon. We should all be so adventurous and outgoing when we reach 100. Oh, who am I kidding! Most of us will just be happy to reach 100, let alone still enjoying experiences like these.