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Layover: San Francisco
Because of its location on a peninsula, San Francisco is confined within a space of about 7 miles wide by 7 miles long--which makes for an easy taxi-ride from San Francisco International Airport (13 miles south of San Francisco) to anywhere in town. But even if you have plenty of time to spare between flights, your best bet is the cheap and easy commuter train--BART (Bay Area Rapid Transit)--which you can pick up directly at SFO.
Longer layovers (4+ hours)
To make the most of your layover, take BART to either downtown or the Mission district. A ride to downtown (Embarcadero Station) takes 32 minutes, and costs $5.35 one-way, while a ride to the Mission district (24th Street Station) takes 23 minutes, and costs $5.20 one-way.
One option is to take BART to the Embarcadero Station, and spend some time in the Ferry Building Marketplace. If you're there on a Tuesday or Thursday (10:00 a.m. to 2:00 p.m.), or Saturday (8:00 a.m. to 2:00 p.m.), you'll find yourself at the best farmer's market in town. The shop and restaurant list truly is a composite of the best of the best in premium local and organic food, from Frog Hollow Farm to Cowgirl Creamery. The Slanted Door offers up grand views and Zagat-awarded Vietnamese food if you want a sit-down meal. Or, if you need to stretch those airplane-confined legs, you can take a walk along the Embarcadero--north for a view of Alcatraz, south for a view of the Bay Bridge and the "Cupid's Span" sculpture by Claes Oldenburg and Coosje van Bruggen, or west up Market Street--the Financial District's thoroughfare--for a little urban hustle-and-bustle.
Or try this itinerary for a good mix of shopping, views, meditation, food, and a good uphill climb to get your heart pumping. Get off BART at Powell Station, and follow the crowds north toward Union Square, the city's central shopping area. Then keep following the cable car line (but don't bother waiting in the long line for a ride) up Powell Street to Nob Hill, taking in the views of the Bay Bridge to your right. At the tip top, you'll find Grace Cathedral. Take a look at the grand, bronze doors (a replica of those from the Duomo in Florence, Italy), then walk one of its two labyrinths (indoor and outdoor). If you're up for a splurge, you could order a drink or bite while taking in a 360-degree views at the Top of the Mark. Otherwise, for a more ethnic experience, dim sum at Four Seas Restaurant in neighboring Chinatown is always good, too.
The Mission is another great area to meander if you've only got a few hours to sample San Francisco. Its Latino roots are on display along Mission Street, and its hipster side is a few blocks away along Valencia Street. Hop off BART at the 24th Street Station and stop at a taqueria that strikes your fancy. Or pick up a cone of Bi-Rite ice cream (it's organic, so that negates the calories) and take it across the street to people-watch at Dolores Park. (As one of the sunniest neighborhoods in foggy San Francisco, odds are in your favor.) Swing by Balmy Alley to check out the plethora of colorful murals, or pick up an eye patch at the city's only independent pirate supply store at 826 Valencia. If you're in the neighborhood at night, drop in for a play at The Marsh, live music at the Elbo Room, or the latest oddball event at The Make-out Room.
Shorter layovers (2 hours)
If you confined to the airport grounds, you don't have to rely solely on following changes on the arrival/departure board to pass the time. Try these out:
Roam the airport and find a piece of artwork from the SFO's collection that inspires you. You'll have plenty of opportunity throughout the terminals.
Need a massage or pedicure where you're heading next? Stop at XpresSpa. Its hours are friendly to early and late departures, too. The one in the International Terminal (Boarding Area G, near Gate 100, post-security) is open 7:00 a.m. to 11:00 p.m.; and the one in Terminal 3 (Boarding Area F near Gate 68, post-security) is open 8:00 a.m. to 11:00 p.m.
Restaurants are the usual lot, with the exception of a few standouts. Go to Boudin Bakery for San Francisco's famous sourdough bread--maybe as a bowl with clam chowder inside? (Terminal 3, Boarding Area F, food court at entrance to Gates 80-90, post-security) Grab a cup of the local's favorite brew, Peet's Coffee, which first started percolating in the area in 1966. (Several locations in Terminals 1 and 3) And for a different type of coffee altogether, head to Buena Vista Cafe. The cafe's original Fisherman's Wharf location is proud to have made the first Irish Coffee outside of Ireland in 1952. (Terminal 3, Boarding Area F near Gate 82, post-security)
And for the best shopping in SFO--hands down--head to the SFMOMA Store. You're the only one who has to know that the creative gifts from there were bought last-minute at the airport. (International Terminal, Main Hall, pre-security).