A Trendsetters and Trailblazers’ Best Places to Shop and Sip

Discover the unparalleled shopping experience in San Francisco, where diverse neighborhoods offer everything from upscale boutiques in Union Square to bohemian chic finds in Haight-Ashbury, ensuring there’s something to delight every shopper’s taste. And, if it were up to the local trendsetters and trailblazers no one would ever discover the hidden gems that are only 40-miles from San Francisco in the lovely Livermore Valley. The trendsetters would keep it to themselves that one of these awesome finds is San Francisco Premium Outlets® which is California’s largest outdoor outlet shopping mall. 

To help you get started, we’ve put together a list of some of the San Francisco shopping highlights. Take your pick!

Union Square

It’s real department store territory, where you’ll find all the major labels and some serious luxury items. Just a ten-minute walk away is the Westfield San Francisco Centre mall, famous for its huge Bloomingdale’s and a jaw-dropping range of other stores. 


It’s true that some of the stores here are decidedly touristy (although they’re still great for unusual souvenirs). Venture further into the markets and bazaars, however, and there are some really interesting items, from antique ornaments to Chinese tea and even furniture. There are some great bargains to be had, and as shopping experiences go, just visiting Chinatown is a pretty memorable experience. 

Mission District

Mission District brings out the arty side of San Francisco, with independent boutiques, cafés and restaurants dotted the length of Valencia Street. Let out your inner hipster at the many vintage clothing stores, or spend hours browsing the treasures hidden in the depths of the second-hand bookshops.

North Beach

North Beach is San Francisco’s very own ‘Little Italy’, and it’s perfect for visitors who want to get a little off the beaten track. The boutiques and vintage stores here are known as much for their impressive displays as their quality wares, so it’s a perfect spot for an afternoon of window shopping – and of course, you can pop inside if anything catches your eye!


The Embarcadero Centre is a shopping behemoth, with over 100 stores, bars, restaurants, cinemas and more all under one roof. Located in the financial district, it’s popular with tourists and San Francisco office workers alike, so it can get crowded, but you can be sure that the shopping won’t let you down.

San Francisco Premium Outlets®

What’s so great about this mall is that it’s home to discount factory outlets of well-known brands like Prada, Gucci, Versace, Coach, Kate Spade, DKNY, Clarins, and Burberry. Yes, brands that you rarely see on sale have whole stores dedicated to saving you money. Now you too can be a smart, savvy shopper who looks like a million but at a fraction of high-end retail prices!

Beyond the Shopping Scene

What the trailblazers don’t want you to know is that just a short distance from luxury discount shopping heaven is the Livermore Valley wine region. They don’t want you to know that Livermore Valley was the first winemaking region in California and Charles Wetmore’s Livermore Valley dry white wine put California on the world wine map by winning the Grand Prix at the International Paris Exposition in 1889. Yes, over 100 years ago.

The Trailblazers wouldn’t want you to find the 5000 acres of vineyards, or the 50 fantastic wineries tucked away between the rolling hills and picturesque canyons of Livermore. Unlike other wine regions of California, Livermore Valley has preserved its authentic charm and rural California spirit, so you can be sure that visiting these wineries will be personalized and intimate experience.

This special part of California has been a bit challenging for San Francisco visitors to see. There is no public transportation to the Livermore wine country and renting a car doesn’t make sense if you plan on wine tasting. Getting to the luxury outlets via public transit is a taxing experience and includes multiple bus rides and train stops. Who wants to deal with all that when carrying loads of shopping bags? And to experience both fantastic destinations in one day would be just impossible for most.

Lucky for us, Gray Line has created a brilliant new daylong tour that gives you a rare opportunity to visit both the outlets and the wine country all in one spectacular day. After your 9 am hotel pick up, you’ll have the chance to take photos while crossing the iconic Bay Bride with sweeping views of Alcatraz and Treasure Island. First stop is the San Francisco Premium Outlets where you have plenty of time (4 hours) to browse the 180 stores and grab a bite to eat at one of the 15 dining locations.

After a pleasant morning of shopping, your afternoon is spent enjoying a guided tour of Livermore Valley’s wine region and where you are encouraged to taste 3-5 different wines at two of the finest wineries in the area. At each winery, you will learn about the expert winemaking techniques put into each exquisite wine you taste and explore the grounds of the vineyards.

This is the first and only tour of its kind being offered to visitors staying in San Francisco.

What’s included:

  • Full-day trip from San Francisco to Livermore Valley Wineries and San Francisco Premium Outlets in Livermore
  • Drive over the San Francisco Bay Bridge for views of the Bay Area and Alcatraz Island
  • Free time for shopping and lunch at the San Francisco Premium Outlets
  • Wine tour and tasting at two wineries
  • Guided tour
  • Wine tasting
  • FREE Wi-Fi onboard tour vehicle
  • Hotel Pick-up and Drop-off for select SF hotels (must confirm at least 24 hrs prior)

Please Note

  • Winery locations and itinerary may change due to traffic or a previously booked special event at each site.
  • Buses are air-conditioned, and the size of the bus depends on the number of passengers booked for that particular day.
  • The minimum age for wine tasting is 21 years.