Chicago: On tour with the Tate He's not joking. Sitting upright at the dinner table, contemplating works by Boltanski and Sherman, are two wide-eyed stuffed poodles, with cartoonish long lashes. A porcelain poodle stands beside the fireplace. Downstairs, in a room resembling the bedroom of a hyperactive 12-year-old girl, the shelves are thronged with scores of plastic poodle figurines and cuddly toy poodles, underneath cutesy signs that say things such as "Beware of Friendly Dog" and "Pardon My French Poodle." Poodles have even pawed their way into the bathrooms: as well as towels, mats and tissue-box covers embroidered with curly-haired canines, I spot a pink loo-seat decorated with two poodle silhouettes displayed like a picture on a wall. "When people come for dinner, they always bring a poodle," Jeff says, pausing in the kitchen beneath a shiny magenta maquette of one of Jeff Koons's famous Balloon Dog sculptures (what else?). Before we leave, Daryl shows me her subsidiary collections of kaleidoscopes and ornate hair clips. "Jeff's also got a load of aliens, but he keeps them in the basement," she says. I feel as though I have stumbled into one of Louis Theroux's Weird Weekends television documentaries. In fact, I am on a tour organised by Tate Travels - a new collaboration between the Tate gallery and the Ultimate Travel Company, offering high-end holidays designed "to promote enjoyment and understanding of art." One of several cultural events planned during my five-day trip, the visit to the Stokols was organised by Richard Hamilton, director of American Patrons of Tate, a charity. "The Tate can open doors," he tells me. It's amazing to see art in someone's home - it feels vibrant, very alive. This is unusual in that it's a very energetic collection. My first instinct upon meeting the Stokols was condescending: only in America, I thought, would you find such a colossal collision between high culture and kitsch. An hour and a half later, I had warmed to the couple, who have no children but used to own a black standard poodle called Anisette that died a few years ago. Art is often presented in galleries in a po-faced, reverential manner. Yet the atmosphere in their motley, clutter-ridden home was joyful and warm - closer in spirit to Willy Wonka's chocolate factory than to the white-cube austerity of an art gallery. "You should find humour or enjoyment in life where you can," Jeff says. Who would argue with that? Visiting the Stokols was a highlight of my trip to the Windy City. "Unforgettable" was the response from several members of the group I joined, who were predominantly over 50, well-travelled and thoroughly versed in art and culture. Barbara, who lives in Toronto, had a doctorate from Oxford on the Modernist poet Ezra Pound; Shields, a chartered accountant from Edinburgh with an artist daughter living in London, sits on the board of Scottish Opera. The Stokols were not to everybody's taste, though: some people were more bemused by the art than the poodles. Chicago is renowned for its bravura skyline, and much of the tour involved looking at landmark buildings. We were led by Bill Hinchliff, an enthusiastic Yale-educated architectural historian. "Chicago is the world's greatest museum of the skyscraper," he told us right away. No other city has the quality or variety where you can see so many different styles within three blocks - not even New York. The observation deck of the Sears Tower We started with the Water Tower, the oldest structure of note to survive the Great Fire that reduced a third of the city to ashes in 1871. Standing 154ft tall, the neo-Gothic tower, which Oscar Wilde castigated as "a castellated monstrosity," is now a toothpick compared with the gargantuan structures that surround it. With advances in metal-frame construction and fireproofing, as well as the advent of safe lifts, the multi-storey skyscraper became a possibility - and, thanks to architects such as Louis Sullivan (the "poet of the early skyscraper," according to Bill), it was born in Chicago. Early examples favoured a plain style. By the turn of the 20th century, though, decoration had become de rigueur, often imitating European architecture. The 36-storey Tribune Tower, completed in 1925, is typical: crowned by a limestone turret reminiscent of Rouen Cathedral, it looks as though it has a UFO in the shape of a Gothic structure, complete with flying buttresses, hovering above its roof. Walking down Michigan Avenue, with its buildings like English castles and Italian palazzos, I was reminded of the Las Vegas Strip, where mega-hotels pastiche the architecture of Paris, Venice, Egypt and ancient Rome. With unflagging energy, Bill whisked us through the chief architectural styles of the 20th century. He introduced us to the maverick genius Frank Lloyd Wright, whose Unity Temple, a proto-Brutalist, reinforced-concrete block west of the city in Oak Park, is astoundingly advanced for 1905-08. He rhapsodised about the distinctive sawtooth silhouette of the Art Deco Chicago Board of Trade Building. He elucidated the Modern style pioneered by Ludwig Mies van der Rohe - all streamlined, steel-and-glass purity, with minimal ornamentation. Mies van der Rohe came to Chicago from Germany in 1938. A decade later, he was commissioned to build two radical towers on Lake Shore Drive that Bill described as "the Adam and Eve of glass and steel." We drove past the 100-storey John Hancock Center, with its tapering profile and exterior cross-bracing like a stack of Xs. Clad in black aluminium, and with television and radio antennae sprouting from its roof like the horns of Beelzebub, it has a brooding, almost malevolent presence - it would make a good lair for an evil overlord in a comic book. Yet, more than four decades after it was built, it remains one of the city's best-loved structures. Not every skyscraper has been so successful. The blotchy façade of one tower prompted a member of the group to say, "It looks like it's got a disease." Bill gave short shrift to Chicago's third-tallest building: when the Carrara marble that once sheathed the 82-storey Aon Center (formerly the Standard Oil Building, or "Big Stan") began to buckle, the entire structure had to be re-clad in granite in the early Nineties. The Aon Center overlooks one of the city's most exhilarating recent architectural ventures: the 24.5-acre Millennium Park, which reclaimed a railroad wasteland in the middle of Chicago, and was finished by 2005. The centrepiece is Cloud Gate, a 110-ton sculpture by the British artist Anish Kapoor. Sixty-five feet long, 32ft tall and made of highly polished and reflective stainless steel, it looks like a coagulating blob of mercury. It took a year to grind and polish the surface until the joins between all 168 welded sheets were entirely obliterated, turning Cloud Gate into a thing of flawless extraterrestrial beauty. Everyone loved the results: it was nicknamed the "jelly bean" before it had even arrived. If only the same could be said for the scarlet confusion of Orbit, the looping tower-cum-sculpture that Kapoor has built in London's Olympic Park. Nearby is the Frank Gehry-designed outdoor music pavilion, where we attended a free public concert one evening. Sirens inevitably intruded upon the performance of Mozart's Jupiter Symphony - yet the stainless-steel forms of Gehry's rampant design, which billows into the park like the visualisation of musical notes, compensate for any auditory loss. To the smiling attendant who showed us to our seats, Gehry's flamboyant metal ribbons resembled the eyelashes of Betty Boop. The day after the concert, I visited Chicago's impressive Art Institute to see a retrospective of the American Pop artist Roy Lichtenstein that will travel to Tate Modern next February. Tate Travels had organised a private tour with the show's curator, James Rondeau. "There is always a degree of levity about Lichtenstein's choice of subject matter, but he was extraordinarily serious about painting," Rondeau said in front of Look Mickey, the artist's first comic-book painting from 1961. This breakthrough picture feels like Athena sprung from the head of Zeus, because Roy already had a 10-year career as an artist and didn't make pictures that looked like this. What's so nice about looking at it in person is to see how handmade and improvised it is. You see these early attempts at dots - they are extraordinarily handmade. You really get a sense of the artist's brush. As with visiting the Stokols, the curator's tour offered a level of insight and access that I could not have enjoyed had I been travelling under my own steam. It was a pleasure to spend an hour chatting so informally with an expert. Tate Travels is being established at a difficult time, and its holidays aren't cheap (the Chicago trip cost £2,760 per person sharing for a week). While Ultimate Travel's delightful tour leader, Susie Orso, ran the trip efficiently, there were some teething problems: several members of the group were unimpressed by the Whitehall Hotel where we stayed - the fact that the lobby was being renovated didn't help, since there was only one working lift for the entire building. Moreover, there were elements of the trip that, though fascinating and enjoyable, were not exclusive to Tate: for instance, anyone could visit the permanent collection of the Art Institute, attend a concert in Millennium Park, or pay for an architectural tour of the city with a guide as good as Bill. You join a holiday of this kind because Tate, in the words of Richard Hamilton, opens doors. As one woman on the trip put it, Tate's brand "authenticates" the cultural content of the holiday - yet it's essential that the gallery bring something substantial to the concept of Tate Travels besides a name. On this occasion, Tate did. Take the Stokols: they're not your common-or-garden art collectors - and for that reason I felt glad to have met them. As future trips are fine-tuned - to Madrid, Oslo, Venice and elsewhere - I hope that the Tate's reputation will prise open a few more surprising doors. If it does, Tate Travels will have a winning formula on its hands. Other Tate tours St Ives: A Taste of Tate The trip begins with a preview of the winter exhibition at Tate St Ives, which examines the story of the district's artistic colony, with its curator, Sara Matson, ahead of the public opening the following day. A visit to Leach Pottery, which was founded in the 1920s, is led by its director, Julia Tomlow, and includes a demonstration by a resident potter. A guided trip to Porthmeor Studios, which are undergoing renovation, has been arranged, as well as a private tour of the Barbara Hepworth Museum and Sculpture Garden accompanied by Chris Greene, the head gardener, and Sara Matson. Studio visits and an optional drawing class at Newlyn School of Art are also scheduled. October 5-10, from £1,395pp. Barcelona: A Food Fiesta This trip includes guided tours of the Picasso Museum, the Mies van de Rohe Pavilion and Gaudí"s Casa Milà and his church of the Sagrada Familia; but it also has a culinary slant, with visits to traditional tapas bars, the Boqueria food market and specialist shops in the medieval streets such as one where hazelnuts and almonds are roasted on site. But the pièce de résistance is a visit to the home a Spanish sculptors, just outside the city, drinks and tapas included. November 29-December 2, from £1,573pp. Mexico: The Original Image The trip begins in Mexico City, with a visit to the studio museum of the late husband-and-wife artists Frida Kahlo and Diego Rivera, which was built in 1930 in a Modernist style. The Contemporary Art University Museum and a tour of an Aztec temple with an archaeologist are on the agenda before the group moves to San Miguel de Allende, home to the Sanctuary of Atotonilco, a masterpiece of Mexican Baroque. The final stop is the colonial city of Oaxaca, where the group will explore the Ethnobotanical Garden, set up by Francisco Toledo in 1993, and meet Angélica Vásquez, a distinguished local artist. Visits to private collections, wine tastings and cooking lessons are also on the programme. February 22-March 5, 2013, from £5,345pp. Australia: Living Art Experts in art, gardens, wildlife and wine will be on hand to guide this tour, which takes in collections of indigenous and contemporary art in Adelaide, Melbourne and Sydney, a performance at Sydney Opera House and a trip to the vineyards of the Barossa Valley, accompanied by Ben Glaetzer, a local wine-maker. Visits to the National Gallery of Victoria and to contemporary galleries in Melbourne will be led by Will Mackinnon, an artist who lives and works in the city. April 6-21, 2013, from £6,450pp. For full details, see Tate Travels (020 7386 4630; tatetravels.co.uk).