By: Paula Wallis

Sitting in Vesuvio Bar, off Jack Kerouac Alley, sipping on a pint of Anchor Steam, one could almost believe they’ve traveled back in time and are sitting in the San Francisco of yesteryear. You expect to turn to the barstool next to you and see the man himself, Jack Kerouac, drinking off last night’s hangover, as some famous beat poet or another rails against humanity from the dimly lit corner of the room. To me, this bar truly felt like the San Francisco I had long imagined.

But it’s not just funky retro bars I came to see here, although San Francisco has more than it’s fair share of them. I wanted to see the whole city; tourist traps and local haunts alike. It would be easy to spend a week or two in San Francisco, enjoying that west coast vibe, but if you only have a weekend to spare, I’ve laid out just a few of the sights you should definitely check out while you’re here.

May through September is usually the best time to visit, when you’ll get the most sunshine and the warmest temperatures. However, I’ve gone during winter months as well and been happily surprised with the mild temperatures and clear, blue skies. Locals informed me that I’d lucked out with the weather. Taking in the sights around San Francisco can involve a lot of walking, if you’re so inclined, and it helps if the weather cooperates.

Fisherman’s Wharf

Yes, it’s definitely a tourist trap, but there’s a reason for that. It’s a great way to spend the day! Stroll around Pier 39, wandering in and out of art galleries, watching the street performers, sampling some fresh seafood or a bowl of hot seafood chowder (great on a rainy day), or just taking in the view across the bay towards Alcatraz. San Francisco Sea LionsThe absolute number one thing to do here though is to watch the sea lions. They showed up some 20 years ago and began colonizing the piers amongst the chowder and seafood shops. Experts speculate this influx was due to earthquake activity at the time, the Loma Prieta quake, which hit the Bay Area in 1989. With a population of 200-400 sea lions, it’s easy to spend a couple of hours just watching them bark, dive, play, or just lounge about on the docks, soaking up the sun. Following the mysterious influx of some 1500 sea lions in the fall of 2009, news coverage has shown an equally mysterious departure of the famed sea lions shortly after, but more recent reports have shown the slow return of San Francisco’s much loved sea lion population.

Alcatraz Island

AlcatrazOften referred to as The Rock, Alcatraz is the most famous tourist attraction in the San Francisco Bay Area. Located 1.5 miles off the mainland, Alcatraz Island began it’s history as a lighthouse, then a military fortification, a military prison, and finally a federal prison which housed such notorious prisoners as Al Capone, George “Machine Gun” Kelly, and Robert Franklin Stroud (the Birdman of Alcatraz). Between the years of 1969 and 1971 it was occupied by Indians of All Tribes, Inc, in what began as a symbolic occupation to awaken the American public to the need for Indian self-determination. This soon turned into a full scale occupation which eventually culminated in the forcible removal by armed marshals and FBI agents of the remaining occupants; five women, four children, and six unarmed men.

Today the prison remains open to flocks of tourists, arriving daily by ferry from Pier 33. If you want the full history as you explore the prison and its grounds, headsets are available which provide a running narrative from your starting point. Alcatraz is not only a fascinating place to explore American history; it also has somewhat of a seawall with some great views across the bay into the city and towards the Golden Gate Bridge. It makes a perfect spot to pack a picnic lunch and watch the ships roll in.

Pubcrawling on Columbus Street

The aforementioned Vesuvio Bar can be found on Columbus Street (across from arguably one of the best bookstores in the city, City Lights Bookstore), along with many other colorful and diverse pubs, clubs and cafes along the way. It helps to have a copy of San Francisco’s Best Dive Bars, by Todd Dayton, for this endeavor. It’s a guide which lists, by neighborhood, some of the seediest, grittiest, and most genuine hole-in-the-wall dives in the city. Mr. Bing’s Cocktail Lounge on Columbus Street is one that holds a special place in my heart, this is a true local haunt, and you’re guaranteed to meet some interesting characters in here. Start at the bottom of Columbus and make your way up, making sure to detour into any dead-end seeming alleyways that promise a drink around the corner. This is where you’ll find some of the most interesting little Irish snugs, stuffed to capacity with fascinating Americana and historic memorabilia.

Another great place to stop for a pint of Guinness and a pub lunch is Lefty O’Doul’s, located on Geary Street off Union Square. Simple fare and plenty of seating, along with countless T.V.’s playing any sport you can imagine, Lefty’s also boasts a great piano bar, which fills up pretty quickly with business clientele, coming in for a glass of wine and a sing along after a long day at the office, so get there early if you want a seat near the piano.

Ride the Cable Cars.

San Francisco Cable CarIt’s just not a trip to San Francisco unless you ride the cable cars. Preferably hanging off the side with one foot on the running boards, “just like in the movies,” as my husband put it. We insisted on doing just that, much to the annoyance of all the seated passengers who said we were blocking their view. Sorry folks, but it had to be done. A day pass, for $13.00, buys you riding privileges on the three separate routes, which gets you a pretty good tour of the city. Stops include Powell Market, Nob Hill, Fisherman’s Wharf, the financial district, Chinatown, Russian Hill, and Ghiradelli Square (Mmmm, chocolate). The Powell-Hyde cable car line has a stop at the top of Lombard Street, unless you want to do what we did – jump off at the closest stop at the bottom and hike up Lombard – whew! Lombard Street is billed as the “crookedest street” in the city, which, oddly enough, it isn’t. But it’s a beautiful street nonetheless, with steep switchbacks all the way down (or up, depending on your point of view) and is lined with lovely landscaping and Victorian mansions. Spend a half hour or so watching the carloads of people navigating the hairpin turns and screaming in mock terror at every corner.

Napa Valley Wine Train

Sample a taste of the luxurious Napa Valley lifestyle. If you book at least one day in advance, you can ferry over to Vallejo from San Francisco, where a shuttle will pick you up and transport you to the Wine Train. There are several different packages you can choose from; lunch, dinner, weekend getaways, or even weddings. Several offer winery tours as part of the packages, which I recommend you take them up on, as admission can get pretty pricey at some of the wineries when not part of a package ($60.00 and up). Top notch service and a glass dome roof riding car make this an unforgettable experience.

Some wineries worth mention include the recently renovated Francis Ford Copolla winery, where wine lovers and movie buffs alike can get their fix, touring through the winery, which is interspersed with sets from some of his movies. The Clos du Val Winery is another one worth stopping by – I found a wine merchant in Vancouver that carries a select few of their reds, much to my delight! For a perfect day, start at V.Sattui Winery; take a browse through their market place, picking out fresh deli meats, cheeses, and breads, then pick up a bottle of their crisp strawberry Gamay Rouge and picnic on their two and a half acres of shaded grounds outside the gorgeous stone winery building. Some other wineries of note include Sterling Vineyards. Perched atop a hill with sweeping views all around, Sterling’s architecture is somewhat reminiscent of the Greek Island of Santorini. And finally, Castello di Amorosa, where the winery itself is a castle built from stone brought over from Italy for this specific purpose. But I’ll let you discover the rest on your own, there are so many award winning wineries in Napa and the surrounding area, both large and small, and everyone seems to have a different favorite.

Dine Out.

With restaurants like Harry Denton’s Starlight Room, Wolfgang Puck’s Postrio, and Jardiniere, it hardly needs to be said that San Francisco has a dining scene rivaling that of New York City. So I won’t spend a huge amount of time listing all the fabulous restaurants this city has on offer. I will, however, point out a few of my favorites that are definitely worth a try while you’re there. The Tonga Room at the Fairmont Hotel is an absolutely amazing tiki-themed restaurant that must be seen to be believed. Tables are situated around an indoor lagoon, upon which floats a barge with a lively Calypso band to entertain you while you dine on Pacific Rim menu options. Occasional tropical storms pass through the room, complete with thunder, lightening, and rain, but not to worry; you’ll stay dry under your thatched umbrellas. If you’re in the mood for a little dancing after dinner, take a spin on the dance floor built from the remains of the S.S. Forester.

You’ll probably recognize The Fog City Diner from television or movie sets, as it’s used frequently when the script calls for a scene in a typical American style diner. With checkered tile floors, stainless steel décor, and a decidedly 1930’ish feel, it perfectly fits the bill. The food here, however, is not your typical American diner fare. A little on the pricey side, this is a restaurant where you can dress down but still enjoy an upscale dining experience.

Located on Powell Street, Lori’s Diner is a nostalgic throwback to the fabulous 50’s. Simple menu choices; burgers, shakes, malts, fries, etc, make this a great place for families to dine, with reasonable prices to match. No fine dining here, it’s just fast-paced fun. Classic oldies add to the upbeat atmosphere (there’s even a jukebox), and there’s plenty of memorabilia to wander around and admire as you wait for your meal.

The Haight

Famed for its role in the 1960’s hippie culture, the Haight-Ashbury district still retains much of the laid back, peace loving mentality it became known for, if peppered here and there with trendy clothing stores and nightspots these days. It’s still worth a wander through here if you’re hoping to find some relics from the Summer of Love. The well maintained Victorian homes in the neighborhood, known as “Painted Ladies” are absolutely gorgeous and make for some great photos. The Haight-Ashbury Street Fair is held on the second Sunday in June every year, and can get quite busy, as it is a tourist destination in itself. Much of the street is only open to pedestrian traffic for this, with live bands playing outdoors.

The Castro

For gay, lesbian, bisexual, and transgender visitors, this is The district to check out. It is known as the world’s first gay community and has become a symbol of pride and acceptance throughout the years. This is where Harvey Milk lived, worked and began his political career as a gay activist. Everyone is welcome here, and some of the Pride Festival events outdo any carnival anywhere else in the world. If you have the opportunity to attend the Pride Parade, don’t pass it up, it’s incredible.

These are just a few of the attractions on offer in San Francisco, one of my favorite cities in the world, and I haven’t even touched on the live music scene, Chinatown, Sausalito, shopping in Union Square…. It’s no wonder there’s over 1000 songs written about this city, and still more yet to be written, I’m sure.

Author’s note: Props to my wine-genius friend, Corey Barlow, who was good enough to take my sorry, broke self in after I returned from traipsing around SE Asia. Corey lives and works in Napa Valley, firmly entrenched in the wine industry. He was also kind enough to tour me around some of Napa’s amazing wineries, of which my memory, is, not surprisingly, a little fuzzy. Thanks Corey, for everything, but also for supplying the names of wineries that were just on the tip of my tongue, and for suggesting a few new ones I’ve yet to explore. But I will. Soon.

About the author:

Paula Wallis makes her home in beautiful British Columbia in the Best City in The World, Vancouver. She spends her spare time seeking out the best beaches in the world and is a huge fan of hammocks. Follow her on