Putting TripIt.com to the Test

By Adam H. Graham
September 7, 2010
100915_tripit
Illustration by Nicole Wilkinson
For run-of-the-mill trips, it's a cool tool, but our intrepid traveler's itineraries proved too much for the reservation-tracking site.

Before My Trips
Nobody likes getting an e-mail with the word "problem" in the subject line. In the month after registering for tripit.com, a website designed to streamline your reservations and other travel information (with handy supplemental data like weather forecasts and hotel cancellation policies), I received five different e-mails with the same subject line: "Problem with your TripIt submission." Why? According to support@tripit.com, "We received your e-mail (Subject Line: Fwd: Azores confirmation) but had a problem processing it. This typically happens when your e-mail is not from one of our currently supported booking sites." So, which booking sites does it support? A lot, actually—over 1,000, including everything from well-known airline carriers like Cathay Pacific and JetBlue to obscure travel agencies like Horncastle Executive Travel and California Limousines. So for most people, and most trips, those "problem" e-mails are few and far between. But all it takes is using one site TripIt doesn't support to throw a wrench into the system—and to turn a time-saving tool into a hassle.

I was asked to rate tripit.com on three different levels based on my own personal trips. All of them—a Catskills road trip, a Croatia-to-Switzerland train journey, and a series of island-hopping flights and ferry rides through the Azores—were ultimately too complicated or off-the-beaten-path to maximize the tool.

On the Road
The best feature of tripit.com is the automated trip planner that allows users to forward their confirmation numbers to an e-mail address and voilá! The system automatically understands where you are and where you're going and stores all the addresses and phone numbers of your hotels and agencies. The site seems to cater to trips where you fly somewhere, rent a car, and stay at a nearby hotel. But if you're flying into JFK and then driving north a couple of hours to a cabin in the Catskills, the only way that TripIt can recognize your final destination is if you manually enter it into the system—its mobile app is not GPS-enabled and does not track your location in real time. My BlackBerry can determine my precise location in Google Maps using cellular triangulation technology, but for some reason, TripIt's app isn't able to do the same.

The verbiage in the "problem" e-mail illustrates two major kinks in the site. The first is the idea that anything is typical when it comes to travel. Airlines and airports have spent decades trying to streamline the language and codes of traveling. Tripit.com, launched in 2007, is a Johnny-come-lately to the game and doesn't exactly solve the puzzle. Not all languages are supported, and as a result, it failed to recognize foreign spelling of train stations in Italy. More significant, you can't change your itinerary on the mobile app, so if plans change—as they most likely will—you'll have to hunt down a computer to stay organized.

Another flaw: Tripit.com assumes that all reservations arrive via e-mail. But as is the case in many parts of the world, I had to buy my train tickets the analog way—at a train station in Croatia. Even if TripIt did recognize the codes, I'd have to manually add the various legs of the journey into the system: Trieste to Venice, Venice to Milan, Milan to Zurich. Since I couldn't set the record straight on my BlackBerry, the entire time I was in Croatia TripIt thought I was in Venice, my point of arrival, and kept giving me unhelpful Venice advice. I also could have used real-time train updates: My train from Venice to Milan was 20 minutes late (not surprisingly), but the Swiss train to Zurich was (uncharacteristically) late as well, so I needn't have sweated the connection—I was already sweating enough in the un-air-conditioned car.

The verdict
C+. When it works, TripIt provides helpful info. But when it doesn't, it requires you to manually add things yourself, which is a pain. I'll keep it, and continue to use it, but on a probation period. I'd like to see adjustments and upgrades made to the entire system—particularly to the mobile app.

PREVIOUS TEST LABS

Need a translator? These apps decode foreign languages...without WiFi!

Find out just how useful the iPad is as a travel tool.

Just how invincible is your travel gear? We put four popular items to the test.

Plan Your Next Getaway
Keep reading

Sweet Deals, Near and Far

Earlier this spring, my husband and I were invited to a backyard wedding outside of Paris. We embraced the chance to make a European summer vacation out of it—until we started searching for flights. After losing countless hours toggling between the pages of itasoftware.com and every online travel agency imaginable, I settled on a fare that we could stomach—albeit at the same price I paid to get to Tokyo a year earlier. Overpaying did have one pleasant side effect: It forced us to seek out good deals even more aggressively than we would have otherwise. Instead of a hotel, we rented an adorable apartment in the Marais through vrbo.com. We cooked each night, picking up warm baguettes from a local boulangerie. And we passed a pretty great afternoon snagging designer clothes for 50 percent off at the A.P.C. Surplus store (011-33/1-42-62-10-88, apc.fr). As rewarding as it was researching our own deals, sometimes it's awfully nice when someone else just tells you where to find them. In this issue, we've done just that. Our package of 40 affordable finds across Europe can serve as your guide and save you all sorts of money, not to mention time-consuming legwork. Even if Europe isn't on your to-do list (though the dollar won't be this strong forever!), I can guarantee you'll get value out of our fifth-annual Coolest Small Towns in America feature. This reader-generated list of 10 hometown escapes is a boisterous celebration of simple pleasures in small places. Ely, Minn.—2010's number one spot, which picked up 118,899 votes out of the nearly 440,000 overall—may not earn you a passport stamp, but there's no question that it'll be a memory no less exciting, and this one in our very own backyard.

8 Fall-Foliage Cruises

Casco Bay, Maine Operating out of South Freeport, Maine—home to the L.L. Bean flagship store—Atlantic Seal Cruises offers passengers the chance to see more than just the changing maple trees. On the nearly three-hour-long outings through Casco Bay, passengers often spot cruisers often spot photo-worthy wildlife like seals basking on the shore, and the crew occasionally hauls up lobster traps along the route to demonstrate how to measure and band the tasty crustaceans. atlanticsealcruises.com, Sept. 15–Oct. 31, $35. Timing Tip: Check up on how the leaves are changing at the state's official fall foliage site, which starts publishing reports Sept. 15. Atlantic Ocean, New England and Canada Talk about making a splash. With 12 departures this fall, MSC Cruises' full-scale ocean voyages cover some of North America's most spectacular leaf-peeping territory. For it's inaugural stateside season, the Europe-based company is sending the 2,550-passenger MSC Poesia between New York and Quebec, with ports of call at Prince Edward Island; Halifax, Nova Scotia; Newport, R.I.; Boston; and Bar Harbor, Maine, to name a few. Not quite ready to kiss warm weather good-bye? MSC's October 23 cruise, Autumn Leaves to Palm Trees, drops travelers at Fort Lauderdale for one last beach fling. atlanticsealcruises.com, select departures in Sept. and Oct., from $599 (price is for a six-night cruise and includes meals). msccruises-us.com. Timing Tip: For updates on foliage around New England, visit Yankee Magazine's fall foliage chronicles. Hudson River, N.Y. Times Square, the Empire State Building¿world-class fall foliage? One of the Big Apple's best-kept secrets comes to life each year north of Manhattan. Circle Line Downtown's five-hour cruises depart from the city's South Street Seaport select Saturdays at 11a.m., bound for the Hudson River Valley, where they sail past a handful of well-groomed state parks and historic small towns like Sleepy Hollow. With an open sundeck and two enclosed lower decks, there's plenty to do on board: continental breakfast and lunch, a complimentary wine tasting, and college football games broadcast on satellite TV. But once the boat passes Bear Mountain Bridge, all eyes turn to the banks. Watching the pops of red, burnt orange, and yellow on either side of the 400-passenger catamaran, you'll feel like New York City is worlds away. Book and arrive early—there's no reserved seating. circlelinedowntown.com, Saturdays Oct. 23–Nov. 6, $120 (includes meals). Connecticut River, Conn. It's only been operating for about 40 years, but the Essex Steam Train and Riverboat package transports passengers straight back to the 19th century. After boarding a vintage railcar at the 1892 Essex Station in Essex, Conn., riders sip warm apple cider as the coal-powered train chugs up to Deep River Landing, about four miles north. There, the three-level, 220-passenger Becky Thatcher riverboat waits to take sightseers on a 90-minute cruise from Deep River to East Haddam, providing a spectacular survey of birch, dogwood, sumac, and maple trees—plus the state's trademark white oaks—along the way. Reserve tickets ahead for weekend trips, which often sell out; typically, colors are at their peak for two to three weeks following Columbus Day (this year that means October 8 to 24). essexsteamtrain.com, Thursdays through Mondays Sept. 30–Oct. 25, $26. Timing Tip: Before the "all-aboard!" peruse the state's foliage reports. Tennessee River, Ala. What other afternoon cruise claims a hospitality director as part of its crew? On the Pickwick Belle, that's just one part of its old-school Southern charm. Other genteel touches on the old-fashioned, 149-passenger paddlewheeler: plenty of upper-deck benches for relaxing through a 90-minute ride, and lunches in the lower dining room for longer trips. Bonus¿the state's warmer climate means the trees (mainly poplar, dogwood, maple and hickory) don't hit peak color until late October, so you have more time to plan your departure. Cruises depart from Florence Harbor Marina in Alabama or Pickwick Landing State Park in Tennessee. pickwickbelle.com, select Tuesday, Thursday, and Saturday departures starting Oct. 9, $22. Timing Tip: Check out the Alabama Tourism Department's official website for more details on foliage. Illinois River, Ill. Consider it a vote of confidence that most of the Spirit of Peoria's two- and three-night itineraries from Peoria, Ill. to St. Louis are already sold out. Luckily, latecomers can still book the 487-passenger paddleboat's overnight trip, which combines a 70-mile journey through vibrant sycamores, maples, and oaks with a one-night stay at Starved Rock Lodge, in Utica, Ill. The package provides onboard entertainment like live banjo and ragtime piano music and covers all meals, drinks, lodging, and a guided hike through Starved Rock State Park in the afternoon. Owner and captain Alex Grieves—who goes on nearly every Spirit of Peoria excursion—says his favorite (read: the best) weekend is usually in mid to late October. This year, he's looking forward to the Oct. 18 to 19 cruise for optimal colors. spiritofpeoria.com, select Monday–Tuesday cruises through Oct. 25, from $279 (includes ticket, overnight at Starved Rock Lodge, guided hikes, and all meals and drinks). Lake Taneycomo, Branson, Mo. After an unseasonably wet summer, Missouri is primed for a rare explosion of fall colors. And Lake Taneycomo, just northeast of Branson, is a perfect place to revel in it. Branson Landing Cruises' two boats, the elegant Lake Queen paddleboat and the tricked-out, 100-foot,luxury yacht Landing Princess cover five different options, including lunch cruises, dinner cruises, and no-frills sightseeing itineraries that depart each morning and afternoon. Because the Ozarks are home to a wider range of trees than many Northeast forests—and they all turn colors in different time frames—it pays to be aware of when your favorites will be in top form. (Sassafras and sumac trees typically go earlier, while oaks, hickories, and others continue to turn well into October.) Whenever you go, there's another sight worth keeping an eye out for: the memorable morning show of eagles and herons drying the day's dew from their wings. bransonlandingcruises.com, select departures in Sept. and Oct., $16 for sightseeing cruises, $26 for lunch cruises, $40 for dinner cruises. Timing Tip: Check Missouri's fall color guide for more details on foliage. Columbia and Snake Rivers, Ore./Wash. What Oregon lacks in autumnal Technicolor splendor it makes up for in pure ruggedness. On one of 13 cruises sailing this fall from Cruise West, leaf peepers can take in the picturesque Multnomah Falls, the 4,000-foot-deep Columbia gorges, and the snowcapped Cascades while tracing nearly 1,000 miles of Lewis and Clark's famous route. (Also featured on the weeklong round-trip cruises sailing out of Portland: stops at wineries in Walla Walla, Wash.) The trips are made exclusively by the Spirit of Discovery and Spirit of '98, two small-scale coastal steamers that max out at about 100 passengers. If your travel dates are flexible, sign up for Cruise West's Stowaway option—you'll get 25% off to take any slot within a 30-day travel window. cruisewest.com, Sept. and Oct. departures for eight-day cruises, from $3,299 (includes everything except alcohol). Timing Tip: For more on the area's colors, check up on foliage reports online or call Oregon's Fall Foliage Hotline (800/547-5445).

The Weirdest Travel Gear

A bib that puts you in the driver's seat If your road trip is too fast-paced for sit-down dining, strap on a BeltzBib and don't think twice about dribbling drive-through delicacies all over your clothes. The bib—modeled here by BT staffer Nicholas DeRenzo—hooks over the shoulder, and any food that falls short of your mouth should wind up in a four-inch pouch that's waterproof and, we assume, ketchup- and mustard-proof, too. dans-products.com, $8. When every drop counts A full six feet wide, the tandem-like Dualbrella should adequately keep two people from getting wet while exploring a new city. Unfortunately, while the jumbo shield doubles your coverage from the rain, it also doubles your dorkiness as tourists. hammacher.com, $40. A guilt-free way to let loose If the person sitting next to you on a flight plops down a GasBGon "flatulence filter seat cushion," should you make a stink and ask to switch seats—or be thankful your gassy neighbor was considerate enough to come prepared? Tough call, especially if the cushion in question is the "Tush Down" model, covered in football-patterned fabric. The seat's carbon filter—designed to muffle the sound and absorb the smell of breaking wind—is supposed to be replaced every three to six months for most users...but more frequently for tailgaters who consume lots of beer. gasbgon.com, $25. See 8 of the world's weirdest hotels. A sorta-portable hardware store Versatility is the big selling point for Swiss Army tools, but this Giant Knife—which weighs two pounds, serves 141 functions, and costs a whopping $1,400—is ridiculous. And it's not only the price that's impractical. Just imagine the trauma of watching it get tossed into the confiscated bin at a TSA checkpoint. wengerna.com, $1,400. Ooh la la: A travel bidet If you're one of the eight or nine Americans who's accustomed to using a bidet at home, you'll definitely want to know about the battery-powered Renaissance Premium Travel Bidet, which enables you to wash up down below at hotels and restrooms that haven't yet embraced this European hygiene fixture. It comes with two nozzles, two AA batteries, and a sleek gray travel bag. sanicare.com, $40. Sit back, relax, and slip on a Slanket Not every flight has a blanket for every passenger and—come to think of it—no flights have blankets with sleeves. But fear not! A petite, travel-size Slanket conquers both of those conundrums and costs $8 less than the original Slanket, which is intended primarily for couch use. theslanket.com, $25. Check out the world's weirdest restaurants. Bedbugs beware Available in two-ounce bottles easily taken on the go, Rest Easy's all-natural pesticide kills bedbugs and bed mites. But we have to raise the issue: If you think you're going to need to use this on your vacation, perhaps you should be staying at a different hotel. resteasy4bedbugs.com, $6 for two 2-ounce bottles. Peal protection Bruised produce can be a bummer, but don't let that stop you from traveling with your favorite delicate fruit. The plastic BananaBunker—available in five colors and in one unmistakable shape—safeguards snacks from getting banged around in your bag. Flexible and extendable, it can accommodate all but the largest bananas. bananabunker.com, $7.

Great American Drives

VERMONT ROUTE 100 Stamford, Vt. to Newport, Vt., 216 miles Snaking through the center of Vermont all the way from the Massachusetts border to Canada, Route 100 feels less like a state highway than one long, rambling backcountry path. A strict billboard ban preserves every vista as the road winds between the peaks of Green Mountain National Forest and passes through quaint valley towns like Hyde Park and Weston, population 631. With only farm stands, country stores, and covered bridges breaking up the landscape, you'll consistently feel 200 miles from the 21st century. Don't miss: The seven-mile stretch through Granville Gulf State Reservation, a favorite for leaf peepers, is also home to the multitiered, 35-foot Moss Glen Falls, which can be seen from the road. Trip tip: The Vermont Curiosities guidebook ($16) goes beyond foliage, introducing travelers to little-known gems around the state, from roadside barbecue joints to hole-in-the-wall museums. GREAT LAKES SEAWAY TRAIL Massena, N.Y. to West Springfield, Pa., 518 miles Consider this scenic waterfront byway an inland version of California's Route 1—minus the traffic. Among the highlights of the 500-plus-mile drive: the St. Lawrence Seaway's imposing Eisenhower Lock, the 28 historic lighthouses skirting the shores of the Niagara and St. Lawrence rivers, and Lakes Ontario and Erie, and the country's ultimate aquatic spectacle, Niagara Falls. Forty state parks along the way supply ample spots for camping, as well as opportunities for everything from bird-watching to shipwreck diving. Don't miss: Presque Isle State Park, a sandy, 3,200-acre peninsula near Erie, Pa., has miles of untouched beaches to explore. Trip tip: Ditch the tired car games in favor of the Seaway Trail's new geocaching trail: a high-tech treasure hunt where you use a GPS unit to locate natural and historic landmarks. Supplies are available at the Seaway Trail Discovery Center's online gift shop. BLUE RIDGE PARKWAY Waynesboro, Va. to Cherokee, N.C., 469 miles One of the New Deal's most ambitious endeavors, this curvaceous "park to park highway" links Virginia's Shenandoah National Park with North Carolina's Great Smoky Mountains via dozens of hairpin turns and 26 tunnels cut through Appalachian granite. Spot a 19th-century farm or postage-stamp-size town at the bottom of a verdant mountainside and you'll realize how seemingly unchanged the road remains since its inception in 1935. Don't Miss: Concerts of traditional Appalachian banjo and fiddle music start at 10 a.m. Sunday through Thursday at the Blue Ridge Music Center, located in Galax, Va. Trip Tip: Banjo music is the ideal soundtrack for this drive. Get in the mood with Drive Time: Blue Ridge Parkway($8), a CD compilation of Appalachian music with songs by Aaron Copland and John Williams. FLORIDA'S OVERSEAS HIGHWAY Key Largo to Key West, 113 miles Spanning more than 100 miles of the Florida Bay, the Gulf of Mexico, and the Atlantic Ocean, this one-of-a-kind road is actually the largest segmented bridge in the world, crossing the water in 42 places as it hops across the 1,700 islands of the Florida Keys. At dozens of spots along the route, side streets let drivers tackle a stretch on foot or bicycle, or break for snorkeling through a shipwreck at San Pedro Underwater Archaeological Preserve State Park and sunbathing at Bahia Honda State Park. Don't miss: The Seven Mile Bridge—only a slight exaggeration, at 6.79 miles long—connects the Middle and Lower Keys and rises 65 feet above the water, high enough to gain unobstructed 360-degree visibility. Trip tip: Read Ernest Hemingway's To Have and Have Not, which is set in Key West; then visit the eccentric author's home, now a museum at the end of the highway. HISTORIC ROUTE 66 Chicago to Los Angeles, 2,448 miles First immortalized by John Steinbeck in The Grapes of Wrath, this original mega-highway has long personified the American dream of escaping hard times and making it big out West. Although you won't find the 84-year-old road on maps anymore (it's been replaced by segments of the Interstate Highway System), you can still follow the classic drive from the small towns of the Midwest and Great Plains through the deserts of the Southwest and on to Los Angeles. Don't miss: The 400-mile-long Oklahoma portion best embodies the retro spirit most 66 travelers are looking for, with ghost towns like Texola and Americana-rich sights such as the 66-foot-tall soda bottle marking Pops restaurant in Arcadia. Trip tip: Find (and stay on) the historic route with Here It Is! Route 66 The Map Series (historic66.com, $12), eight foldout maps with full driving directions and recommendations for the most worthwhile stops. MONUMENT VALLEY Kayenta, Ariz. to Mexican Hat, Utah, 43 miles Nothing about dusty U.S. 163 in northeastern Arizona prepares you for the otherworldly structures that rise out of the desert floor just a few miles north of Kayenta. Along the Utah/Arizona border, Monument Valley is a dreamlike panorama of giant red mesas, sandstone buttes, and freestanding rock formations soaring as high as 1,000 feet. When the highway leads north into Utah, the earth seems to invert, and the towering red rocks give way to the ancient, deep-set canyons carved by the San Juan River. The drive is short, but it might take you hours, thanks to the sheer number of compelling photo ops. Don't miss: The 17-mile dirt road looping through Monument Valley Navajo Tribal Park is postcard-perfect, especially when the sun sets over natural rock statues like the 450-foot Totem Pole spire and the rounded pinnacle known as The Thumb. Trip tip: It's nearly impossible to watch any of the seven westerns director John Ford filmed in Monument Valley—including Stagecoach, The Searchers, and Fort Apache—and not want to see this environment firsthand. GOING-TO-THE-SUN ROAD Glacier National Park, Mont., 50 miles Here's one case where the name of the route actually does justice to its grandeur. The only drivable passage through Glacier National Park, Going-to-the-Sun Road has segments that hug the side of the Rocky Mountains, providing jaw-dropping views of the park's dense cedar forests, glacial lakes, and, of course, slowly diminishing glaciers: Only 25 glacial fields (ones larger than 25 acres) remain, a sixth of what existed in 1850. Sightings of wildlife like grizzly bears, bald eagles, and moose are common; drive slowly to (safely) take it all in. Don't Miss: At Logan Pass, elevation 6,446 feet, you can hike even higher into the mountains, where some of the crags stay snowy all summer. Trip Tip: Rent and watch the opening scene of The Shining; the overhead driving shots show Jack Nicholson and family navigating Going-to-the-Sun Road's dramatic twists and turns. MOUNT EVANS SCENIC BYWAY Idaho Springs, Colo. to Mount Evans Summit, Colo., 28 miles This drive is all about superlatives: In addition to being the shortest trip to make our list, it's also North America's highest paved road, inclining some 7,000 feet in less than 30 miles. And it also has one of the shortest driving seasons: Memorial Day to Labor Day, weather permitting, which, lucky for us, is the best time to take in its yellow wildflowers, bighorn sheep, and a dizzying survey of the Rocky Mountains and Continental Divide at the 14,230-foot summit. Don't miss: Five miles before the byway's end, pull over for a sky-high picnic along the glassy, glacier-fed lake at Summit Lake Park. Trip tip: The weather on the Alpine tundra can change quickly; you could see rain, snow, 80-degree sunshine, or all three—in one day. An all-weather jacket such as Marmot's lightweight Essence ($160) will serve you well—it's waterproof, nylon-lined, and has integrated cooling vents. CALIFORNIA ROUTE 1 Orange County, Calif. to Mendocino County, Calif. 655 miles The Pacific Coast Highway shows off the country's widest range of wow-inducing waterfront scenery, from the pristine beaches of Malibu to the cliffs of Big Sur, over the Golden Gate Bridge, and through the colossal redwoods of Humboldt County. More than 400 miles of the route run within sight of the ocean; drive south-to-north if you want a little distance from the road's edge, or north-to-south to feel the sea spray on your skin. Don't miss: Destined to be replaced by a tunnel in 2011, the landslide-prone pass 500 feet above the ocean known as Devil's Slide is this year's biggest last-chance thrill for adventurous drivers across America. Trip tip: The California Coastal Access Guide is the Golden State road-tripper's bible, with full-color maps and abundant details on where to swim, camp, hike, fish, and pull over for the best ocean sunsets—nearly 900 public points in all.