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Visiting a big city with the family in tow can involve negotiations that put the United Nations to shame. What does junior want to do besides find a video arcade? how about his teenage sister, will she do anything other than shop? And where will this leave the parents, relegated to chaperone and banker? Some serious listening and advance planning is a good start toward creating a stimulating, and fun, big city vacation for everyone. Choosing the right city is also essential, as some are more family-friendly than others, in a variety of ways.

Our top five cities to visit with the kids have been chosen because of their charm, ease of navigation, broad range of attractions and activities and myriad options for both children and adults. While we're highlighting San Francisco, our top choice, Boston, Philadelphia, Seattle and Chicago are also worthy choices. Be sure to factor in rest breaks during the day for those who need it (city energy can be intense) as well as solo activities for each parent.

San Francisco Weekend, Day One

We check into the Hotel Monaco near downtown's Union Square. Our junior suite, like the rest of the place, is the sweetest eye candy. Widely striped, pastel-colored wallpaper is juxtaposed against dark red pinstriped curtains. The huge bed is covered in a soft white duvet topped with golden and lime green pillows. A mango-colored couch is velvety soft. Our two-year-old son, Steven, immediately jumps onto the bed and smiles in that Master-of-the-Universe sort of way.

Our plan on this misty morning, since our visit is during the holiday season, is to do some serious shopping around Union Square, the city's storied shopping district. We head two blocks east to the heart of the Square and are met by a stories-high Christmas tree, bedecked in colored orbs and what appear to be thousands of twinkling lights. Macy's is first on our list, since I'm looking for a navy blue tie for Steven. The children's department is so big that is takes us about fifteen minutes of walking around the fifth floor to locate the ties. Alas, the only ties are part of a complete ensemble and more than I want to spend. Seeing as how my husband, Fen, and Steven are already growing impatient with the (or is that my?) shopping adventure, we head back outdoors and decide to circle the square and check out the various holiday store windows.

Heading north to the far side of the square, we pass several chic European boutiques. Fen hustles me past them. As we approach Saks Fifth Avenue, we're sidetracked by the new Williams-Sonoma flagship store. The four floors of fantastical cookware look especially appealing since they're surrounded by rows of green garland and bright red bows. A clerk offers samples of peppermint bark and chewy chocolate brownies. Suddenly, my men are brightening. We load up on sweets and check out the terrific knife section on the second floor before checking out the windows at Saks. Once again, the kings of Fifth Avenue prevail thanks to their enchanting reenactment of "Sleeping Beauty" and we pronounce Saks' windows "best of Square."

Despite our sweet treat, we start to feel hungry and head for the Marriott Hotel across Market Street. I'm angling for a visit to the hotel's rooftop lounge and its panoramic 39th-floor view. As we arrive, however, the hotel concierge informs me that the rooftop lounge is closed during the day. Even the second-floor lounge isn't serving at this hour. This all turns out to be a lucky break as we happen onto the second-floor Garden Terrace Restaurant and what has to be one of the best buffet lunches in the city. The pork loin is tender and juicy and I nestle it against creamy garlic mashed potatoes. I also plop some crisp mixed greens on my plate and top them with dewy red tomatoes. Fen loads about ten different items on his plate, all of them delicious. Topping off our meal is one of the best bread puddings this side of New Orleans. Duly sated, Steven and I head back to the Monaco for a nap and Fen stays behind to visit the Cartoon Art Museum two blocks away. It's not kids-ville at this museum, rather a more serious study of cartoonists both whimsical and political. This is exactly the kind of candy store that Fen likes to visit.

As Fen returns and the sun sets, we head downstairs to the Monaco's "living room" for the nightly wine and cheese reception. The more-than-ample public space is a mix of jewel-toned couches and sink-into-me wing chairs. It's packed with hotel guests, most of who have met the night before at this very same soiree. A hotel staffer pours us a glass of red wine while Steven makes himself at home at the cheese and cracker spread.

"This reminds me of a dot-com party," Fen remarks.

He has a point. A pretty woman reads tarot cards for a hotel guest while a buff, black T-shirt clad young man dispenses head, neck and shoulder massages to an even prettier woman. People are exchanging business cards and everyone seems to be having a good time. Our good time had by all, we head to Millennium for dinner.

A scant block away, Millennium is a temple of haute vegetarian cuisine. Or so I thought - our waiter clues me in to the fact that the food is of the stricter vegan variety, meaning that no dairy or egg products are used in the preparation. The beauty of Millennium, aside from the warm pumpkin-colored room and knowledgeable and attentive wait staff, is that the food is as good as at the best meat-and-potatoes houses in the city. Probably better. Our winter citrus salad is topped with mandarin oranges and grapefruit sections and flecked with fresh dill and candied hazelnuts. The salad tastes incredibly fresh and the flavors are utterly clean. A grilled pear and chicory salad is cool, crunchy and lightly drizzled with a pear-vanilla balsamic dressing. Each flavor, and we can really taste every one, is mild, sweet and unique. We find an Indian-spiced three-lentil soup with a young coconut mandarin chutney to be subtle and lovely. It's the stuffed winter squash, however, that brings us the most original collection of flavors: nutty, warm, sweet and buttery all at the same time. Our half a squash has been roasted and then stuffed with a wild rice, parsnip and root vegetable risotto. Chunks of maple-roasted tempeh, plump Brussels sprouts and bits of caramelized onion either rest on a pomegranate reduction or sidle next to a cashew cream. Just as warming is a dish of winter squash and chestnut ravioli, paired with an Idaho pink bean-root vegetable ragout, sauteed greens and caramelized persimmon. If this all sounds too good to be true, let's just say I've barely done it justice. And here Fen and I thought the only time to visit a vegetarian restaurant was during the summer - wrong! We're also delighted that Steven has found most dishes, especially those featuring squash, to his liking. We pad back to the Monaco and promptly fall asleep.

Day Two

"This hotel reminds me of a big birthday party," says Fen, as we awaken to blue skies.

After a quick eggs-and-potatoes breakfast at Lori's Diner a block up and around the corner from our hotel, we make a run for the Powell-Hyde cable car. In operation since 1873, the cable cars are an only-in-S.F. experience since there are no others left in the world. Our car goes left and right and up and down, depositing us at the corner of Hyde and Bay and a few blocks from the Hyde Street Pier, part of the San Francisco Maritime National Historical Park. We've come here to see the collection of old ships, tramps and steamers, guessing that this attraction will be far less kitschy than the rest of its neighbors along Fisherman's Wharf. Much of our time is spent playing a delightful game of hide and seek with Steven on the ferryboat Eureka, an inland passenger vessel that chopped through the waters of San Francisco Bay at the end of the nineteenth century. Game over, we stroll up the street to The Cannery, a three-story collection of shops and restaurants housed in what used to be the world's largest peach cannery. Not to be missed in ye olde brick warehouse is Lark in the Morning, a musical instruments store. Think maracas, harmonicas, jingle bells and assorted other things you'd love to shake, rattle and roll. Oh, and about a hundred flutes. We leave the bells and whistles behind, tote our purchases and walk a few blocks more in order to catch a dressed-up-for-the-holidays Powell-Mason cable car, with the Cable Car Museum our destination. This free museum, a lightly visited attraction if our visit was any indication, is utterly unique. We enter and walk downstairs first in order to see the giant wheels, formally known as "sheaves," that pull huge lengths of wire cable, thereby making the operation of the city's cable cars possible. The almost melodic quality of this simple process entrances us. Upstairs, we observe more spinning wheels and take a few pictures next to car number one, bearing the original "Clay Street Hill Railroad Company" moniker. Fen snaps more pictures of Steven and me on board the back end of a now-retired cross-town cable car.

We walk a handful of blocks to get to the edge of Chinatown and Yuet Lee Seafood, an oft-touted Chinese restaurant housed in a rectangular, bare-boned room. The word on Yuet Lee is that it's also unique, an original. Our mussels in black bean sauce may not be all that, but we eat them all. Ditto the prawns and fresh greens. The salty nature of the food, however, leaves us hankering for something sweet so we walk some more and get to Caffe Trieste in North Beach. This fabled café was a favorite stomping ground of the beat poets of the 1950s, who surely knew a thing or two about a strong cup of coffee. My caffe mocha is topped with homemade whipped cream and not too sweet, which seems just right.

I drop Fen and Steven off at the hotel for a bit of rest and head to the Kabuki Springs Spa for some rest of my own. Nestled in the heart of Japantown, this city-center spa is true to the spirit and substance of a Japanese bathhouse. The spa's large communal bath is spacious and softly lit, with dark wood accents and potted greens adding a touch of elegance. I begin my ritual with a contemplative seated shower and a visit to the spa's large steam room. After a short break on one of the many chaise lounges, I take a dip, make that a very quick dip, in the bracing cold pool. This is followed by a soak in the hot pool, which feels merely warm, yet wonderful, at this point. I repeat this ritual several times over a two-hour period and get myself back to the hotel in time for dinner. We make it easy on ourselves this evening and dine at the hotel's restaurant, the Grand Café. Housed in a turn-of-the-century art nouveau ballroom, the Grand Café is one of those places that puts you in a celebratory mood by the sheer force of its grandeur - you can't help but feel special being here. We play along and prance through three courses, all of them satisfying.

Our last piece of business on this San Francisco day is to revisit the holiday tree at Union Square by night. The tree does not disappoint, and I swear I see visions of sugarplums dancing in Steven's head. Or maybe it's the wine.

Day Three

We hop on the subway a few blocks away from the Monaco and head for the Mission District, the city's Latin Quarter. Our mission is to find the best Mexican breakfast in the city and we are not disappointed. At La Quinta Restaurant, near the corner of Mission and 20th Street, we feast on huge plates of huevos rancheros, over easy eggs topped with a mild red sauce, and huevos Mexicana, eggs scrambled with onions, bell peppers and spicy jalapenos. Both dishes are served with creamy refried beans and perfectly cooked rice, and the coffee provides just the right jolt. Best of all, the staff couldn't be friendlier. A full-filling end to our delightful San Francisco weekend.

Details

Hotel Monaco, 501 Geary Street (415) 292-0100 or toll free (866) 622-5284 monaco-sf.com. Doubles from $215, junior suites from $255; package rates and Internet specials available; adjoining rooms available.

Garden Terrace Restaurant, San Francisco Marriott, 55 Fourth Street (415) 896-1600 marriott.com. Buffet lunch for two around $38.

Cartoon Art Museum, 655 Mission Street, (415) CARTOON cartoonart.org. Tues-Sat 11 AM-5 PM. $6 adults, $4 students and seniors, $2 children ages 6-12, free for kids 5 and under.

Millennium, 580 Geary Street (415) 345-3900 millenniumrestaurant.com. The chef's five course tasting menu is $60 per person.

Lori's Diner, 336 Mason Street (415) 392-8646. Breakfast for two averages $18.

Hyde Street Pier, at the foot of Hyde Street at Jefferson Street. Open daily 9:30 AM-5 PM. Adults $5, children 17 and under free.

The Cannery, 2801 Leavenworth Street (415) 771.3112 thecannery.com. Shops open daily at 10 AM, Sunday at 11 AM.

Cable Car Museum, 1201 Mason Street (415) 474-1887 cablecarmuseum.com. Open daily 10 AM-6 PM, closes at 5 PM during the winter months; admission is free.

Yuet Lee Seafood, 1300 Stockton Street (415) 982-6020. Open daily except Tuesday 11 AM-3 AM. Lunch for two about $20; cash only.

Caffe Trieste, 609 Vallejo Street (415) 982-2605 caffetrieste.com. Open daily 6:30 AM-11:30 PM; till 12 AM on Friday and Saturday. Coffee and pastry for two around $8; cash only.

Kabuki Springs Spa, 1750 Geary Boulevard (415) 922-6000 kabukisprings.com. Open daily 10 AM-9:45 PM. Communal baths open to women on Sunday, Wednesday and Friday, for men on Monday, Thursday and Saturday; Tuesdays are co-ed (clothing required). $15 facility fee before 5 PM Monday-Friday; $18 after 5 PM and on weekends.

Grand Café, Hotel Monaco, 501 Geary Street (415) 292-0101 monaco-sf.com. Open for breakfast, lunch and dinner Monday-Saturday, brunch and dinner on Sunday. Dinner for two about $90.

La Quinta Restaurant, 2425 Mission Street (415) 647-9000 laquintarestauranta.com. Open 7 AM-6:30 PM seven days a week. Breakfast for two around $15; lunch for two averages $18.

Elaine Sosa is a food and travel writer based in San Francisco, California. When she's not busy as a domestic goddess she's out traveling with husband Fen and three-year-old son Steven. She hopes to be the next Charles Kuralt.