San Francisco

California | San Francisco | United States

San Francisco

A trip to the San Francisco Bay Area should of course, focus on the city itself. San Francisco is one of the prettiest cities in North America with its lovely Victorians, cable cars climbing up steep hills, expansive parks, and ocean surrounding it. While this itinerary takes you to our favorite must-see highlights of the city (with some excellent restaurants thrown in), with a few extra days you can see the redwood trees and enjoy the best wine tasting is anywhere in Napa.

Length: 3 – 5 days

Transportation: Car/cab/public transport. If you’re only visiting SF itself, there will be no need for a car. If you head to Napa and Muir woods, you’ll probably need one for a few days. Driving in SF can be a pain (have you paralleled parked at a 45 degree angle before?) and parking extremely expensive so opt in the city to walk, Muni, scooter, or lyft/uber/taxi. Rent a car on your way out for day trips.

Day 1 – 3 San Francisco

Day 1 – Heart of San Francisco Walk

Day 2 – Golden Gate Park, Lands End walk, and Museums

Day 3 – Fisherman’s Wharf & Alcatraz

Day 4 – Redwoods and Coast

Day 5 – Wine Country Less Traveled

With more time / other options:

San Francisco – there’s a lot more to see

Berkeley and Oakland

Consider a trip to the East Bay – the Oakland Museum does a great job with California history, take a stroll around UC Berkeley’s campus, grab a show at the Freight and Salvage or Berkeley Repertory Theater, visit the protest site of People’s Park, pop into Rasputin Music.

The East Bay has are great regional parks at Redwood, Tilden (steam trains, lake, Merry Go Round). Another great outdoorsy option is Mount Diablo State Park; the summit has great views on clear days, and there are interesting rock formations to explore at Rock City.

Point Reyes

Point Reyes National Seashore is another beautiful area. Our favorite hike leaves from near Bolinas, passes a couple of lakes and ends up at Alamere Falls, a waterfall that tumbles onto a wilderness beach.

Detailed Itinerary

Day 1 – 3 San Francisco

Day 1 – Heart of San Francisco Walk

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San Francisco City Walk

Welcome to San Francisco and get ready to leave your heart here! We’re from this city so think it and its surroundings are some of the best spots in the world. We hope you do too.

If you don’t plan to leave the city you won’t need a car. Parking in the city is very difficult and expensive. For a the two day trips with the extended itinerary, there are rental places in SF. From the airport, hop on BART to get you into the city. It’s incredibly easy (the train terminates at the airport so only goes one way), you can catch any train and then get off closest to your hotel (probably Powell Street station).

Consider a walking tour of the city. We’ll lead you through our favorite spots, but walking tours are always fun and you can pick the type you like here.

In terms of lodging, San Francisco is an expensive place to stay. If you can, try and stay near Union Square, Nob Hill, Russian Hill, or the Embarcadero. Do not stay in the tenderloin (it’s probably the least safe place in town) and we also recommend against the mission or outer Richmond because it’s a bit far. You could consider staying in Berkeley or Oakland (again be wary of parts of Oakland) and plan to take the local transit Bart in. However know that Bart’s last ride is 12:30 and you will be spending about 30 minutes commuting into the city. That said, it’s sometimes more affordable. Though part of the fun is being in the city and we’d recommend it if you can. This will be a 3 night stay.

Airbnb can be a decent choice. Some hotels we know and have had friends and family stay at include those in Union Square: Hotel Triton, The Westin St. Francis San Francisco, Sir Francis Drake Hotel, Hotel Zeppelin, Hotel des Arts, Hotel Zetta, Nob Hill: InterContinental Mark Hopkins San Francisco, Hotel Carlton, Stanford Court Hotel, Hotel G, and the Embarcadero: Hotel Griffon.

Begin your day by taking a walk through the city. This particular walk gives a great overview of some of the main tourist areas of the city as well as an exploration of some truly unique neighborhoods.

Start out at Union Square, shopping central for the city. If arriving on BART walk up from Westfield Shopping Center (where the BART stop is) up Powell Street past the cable car and you’ll run into Union Square. The cable cars you see were developed to deal with San Francisco’s famous hills and are a rolling historic monument (and also a pretty good way to get around the important tourist areas of the city).

The statue on the top of the columns in Union Square is supposed to be the goddess of victory but is actually Alma Spreckels – who started in poverty, worked as a nude model, successfully sued a miner for “personal defloweration” and ended up married to one of the richest men in the country. Heading west on Post Street leads to the Theater District. Around the Square are many of the main department stores and the square itself is a great place for people walking and turns into an ice skating rink in the winter.

Turn right on Post (head east) and then left on Grant and in a couple of blocks reach Cafe de la Presse which is a great little French cafe and a good place to stop for a coffee and/or breakfast. Just ahead is the Dragon Gate – the entry to Chinatown.

San Francisco’s Chinatown is one of the largest and is the oldest in North America. Americans of Chinese ancestry have been important contributors to California culture since the 1840’s. Walk down Grant and look into the various stores. Most stores on Grant are for tourists but still hold some interest and are fun to peruse. Pop into old St Mary’s Church, then turn left on Sacramento and walk one block up to Stockton. Here you reach a much more authentic part of town – be sure and check out the groceries and shops here. Turn right on Stockton and continue on to Broadway.

From here turn right on Broadway, which was / is the red light district of the city (note the signs) and end up at City Lights Bookstore, the epicenter for the Beat Poets, the nation’s most daring publisher of independent literature, and an epicentre for progressive thought. It was so important in its heyday it was declared a historic landmark. Right next door is Vesuvio Cafe, where beat poets imbibed after putting their books up for sale.

From here head up Columbus to Washington Square Park. Marilyn Monroe and Joe DiMaggio got married in the church you see across the Park. You’re probably hungry by this point, but even if you aren’t, pop into Mario’s Bohemian Cigar Store Cafe, a staple of North Beach for decades and one which serves fantastic paninis (the meatball is the best) and our favorite drink, the “house campari”. Alternatively grab the best pizza in town at Tony’s Pizza Napolatana.

Head up the hill to Coit Tower, built by a wealthy philanthropist to honor the firefighters and beautify the city. Be sure and go in to see the amazing WPA mural inside. You can take the elevator up for a view – great if few are around, but not worth a long wait.

From the tower walk down Coit Terrace. Turn right onto Montgomery St and left onto Filbert St. Descend the Filbert stairs. Being built on a series of hills there are stairs instead of streets scattered around town. These are some of the nicest because of a public garden started on the land around the stairs. Look for the famous parrots of Telegraph Hill – no one is quite sure where they came from. Half way down you reach the lovely Napier Lane – which is only reached by the stairs – imagine living here (and wonder how the moving companies deal with moving people here…) Then continue down.

At the bottom is Levi Plaza (home to the famous jeans – started for gold miners in the 1840’s), then reach the wide road and promenade along the bay called the Embarcadero. Cross the street to get to the wide pedestrian path, turn right and continue down to the Ferry Building. Back in the day all ferries (since 1898) crossing the bay came in here. When roads were built it lost importance as a transportation hub but has been converted into a really fantastic food hall – favorites tee include Cowgirl Creamery (for cheese) and FarWest Fungi but there are a lot of interesting vendors.

Wander outside from the Ferry Building and check out the view of the Bay Bridge (not as famous as the Golden Gate but still pretty and often lit up). Watch the sunset over the Bay with an oyster appetizer at Hog Island and then head to dinner at nearby La Mar or Kokkari.

Day 2 – Golden Gate Park, Lands End walk, and Museums

Today you’ll explore the western part of the City including Golden Gate Park, Lands End and some of the main museums.

Start with Dim Sum breakfast at Dragon Beaux or Begoni. If you don’t know what dim sum is, it’s sort of a Chinese brunch with small plates tapas-style which you either order or pick from carts that pass your table and share. In America it started in San Francisco. Either of these are our favorite options. Dragon Beaux is closer to the park (and parking) in the Richmond while Begoni is downtown in Chinatown so you would go first and then drive out. Both take reservations and it’s advisable to call ahead.

From here, head to the museums in Golden Gate Park. The park itself is one of the great urban parks of the world and was built on reclaimed sand dunes. If driving you can park in a garage under the DeYoung art museum or Academy of Sciences (same garage – connected).

The Academy of Sciences is an aquarium, natural history museum and planetarium all in one – with an albino alligator, live-action rainforest, and large “living” (growing turf) roof.

The De Young Museum offers art masterpieces and always has a great rotating exhibit. Head to the roof for amazing views of the city (free even if you don’t visit the museum).

Nearby (heading back east toward downtown) a fairly short walk takes you to the giant Victorian greenhouse of the Conservatory of Flowers which is a pretty place to pop in and explore. Back in the other direction just past the De Young museum are the lovely Japanese Tea Gardens.

From the park head to nearby Haight Ashbury. The epicenter of the hippie movement and counterculture of the 1960s and the icon of the “summer of love” the area still houses lovely Victorian homes and while now incredibly expensive and gentrified, some of the shops still evoke the bohemian era of bygone times. You still see some unique souls wandering the street (often naked or only wearing a single clothing item, colorful costumes, etc) and you can imagine yourself back in the 1960s as you wander by the homes and shops of where the icons of the day lived, played, and worked. This self-guided walking tour gives a great overview. Look for the plaques denoting the buildings.

Sites include the Jefferson Airplane house, Hunter S. Thompson’s house, Janis Joplin’s homes, the Hell’s Angels house, the Grateful Dead house, Sid Vicious Party house, Patty Hearst Hideout, Charles Manson’s home, and the Full House house. The Alembic is a fun place for cocktails or food. Loved to Death is an incredibly weird store that you must stop in.

From the park head out to Lands End and the Lands End trail . This is best when it’s not foggy and offers some great Golden Gate bridge views. The walk begins at the historic Sutro Baths, a swimming place for San Franciscans at the turn of the century. Halfway along you come to one of the main art museums of San Francisco, the Palace of the Legion of Honor which is worth a visit. After completing your museum visit (if so inclined), finish your loop back to the start.

For dinner pick a SF restaurant from among our favorites in the city. After dinner grab drinks at The Big Four (if it’s reopened), an amazing bar in Nob Hill that evokes feelings of San Francisco in the 1920s. Otherwise we recommend True Laurel for after dinner drinks.

Day 3 – Fisherman’s Wharf & Alcatraz

Fisherman’s Wharf and Alcatraz

Today we’ll explore Alacatraz, the most famous prison in the world, and the San Francisco waterfront. Generally reserve at least a month in advance. We suggest starting with a morning tour – it’s less crowded and you won’t need to rush other activities to make sure you get to your tour time. The Ferry leaves from Pier 33. Alcatraz has a great audio tour of the penitentiary and offers fantastic views back to the city.

Next head a short distance south to the wonderful hands-on science museum – the Exploratorium. Expect to spend a couple of hours here playing with the experiments.

From here continue along the waterfront to Pier 39, a shopping center and tourist attraction. The main thing of interest here is the resident sea lion population, which moved in for unknown reasons shortly after the 1989 Loma Prieta earthquake and have been here ever since.

Continue west on the Embarcadero to Fisherman’s Wharf. Fisherman’s Wharf is very touristy. If you don’t want to be sandwiched into tourists, you might want to avoid this. However, it’s a decent place to get lunch – Boudin here is famous for its clam chowder in a bread bowl but there are tons of walk up seafood restaurants. If you don’t love seafood or the crowds are overwhelming, head to nearby Fog City Diner instead.

Keep walking along the Embarcadero until it stops on a park near Ghirardelli Square (you can’t miss the sign above the building) and enjoy an ice cream. You’ll get a view of the Golden Gate Bridge from this park.

If you still have time and energy tour the old ships at the Hyde Street Pier Maritime Museum.

Grab an Irish coffee made famous in SF in 1952 at the Buena Vista Cafe.

The Cable car stops here at Hyde Street and is a great way to get back to Union Square / Powell Street station. Pass the windy Lombard street on your way back (try and stand on the outside of the left of the cable car if you’re approaching it from behind for the best photo spot).

For dinner again pick a SF restaurant from among our favorites in the city

Cable Car

Day 4- Redwoods and Coast

Drive across the Golden Gate Bridge. Now is a great time to get those iconic pictures. There are parking areas on both the San Francisco and Marin sides and you can get out and walk on the bridge from either side but the Marin (north side) offers better views back to the city. From here it is a short drive to the spectacular Muir Woods (40 min drive). Muir Woods offer trails among the California’s old growth redwoods which is truly a spectacular site. Because of its popularity you will absolutely need to have a parking reservation to visit. There are lots in Mill Valley where you can park and ride a shuttle where reservations may not be required but it adds a lot of time – and probably best to even reserve that. In Muir Woods there is a lovely walk up through the old growth redwood forest along a stream.

From Muir woods head over to Stinson Beach. Another great hike (one of the best anywhere) is the Steep Ravine hike to Stinson Beach (16 min drive from Muir Woods). This requires some time and logistics as you will either need to walk back up the hill to your car or arrange transport. But we think it is worth it, offering spectacular views once you cross through redwood trees of the Pacific Ocean.

Steep Ravine Trail

Continue driving to have a fantastic meal outside on the water at Hog Island Oysters (43 min from Stinson Beach). You will definitely need reservations here for the cafe. Make sure you order the BBQ’d oysters with chipotle butter sauce.

Hog Island Oysters

From Hog Island Oysters head to Point Reyes Station (16min drive from Hog Island), where you can stop and sample some great (and somewhat famous) cheeses at Cowgirl Creamery. From here it is not far to the beautiful Point Reyes National Seashore – which has spectacular beaches, and miles of hiking trails. Stop by the historic lighthouse when you arrive. It’s really worth a day of its own so you might be limited in what you can do – but it’s worth even a brief stop and a walk on the beach.

For pre-dinner drinks go to Heidrun Meadery where you can sample mead (made from honey) in a beautiful garden setting. Grab dinner in Point Reyes at the Station House Cafe.

Drive to your lodging in Sonoma or Healdsburg. In Sonoma we like Andrea’s Hidden Cottage, Fairmont Sonoma Mission Inn and Spa, Gaigehouse and Dryokan, Inn at Sonoma, Oleana, and Cinnamon Bear Creekside Inn. In Healdsburg we recommend Hotel Healdsburg or Boon.

Day 5 – Wine Country Less Traveled

A trip to the wine country just north of San Francisco is a must do on any Northern California itinerary. It’s a beautiful area but unfortunately has benefitted a little from its own popularity. We have been visiting for years and have chosen some of our favorite distinctly less touristy places that generally provide a better value and an enjoyable day.

Napa Valley

Napa is of course the famous valley but the Sonoma Valley to the west and Healdsburg to the North have equally lovely scenery and wineries (usually cheaper) as well. Honestly we don’t Napa. It’s overrun with tourists and has gotten incredibly expensive ($60 for a tasting). We tend to venture to Healdsburg or Sonoma instead (or other places in the state but that’s for another itinerary).

With one day you can pretty much choose one area. Please get a designated drive or seriously limit yourself. Safety first. With more time add another day in another one of these places.

Sonoma:

Begin your day at the historic Sonoma Plaza where you can grab breakfast at Sunflower Caffe or The Girl and the Fig and wander a bit. Great options here for tasting include Anaba Wines, Schug Carneros Estate Winery, Imagery Estate Winery, Kunde, and Schermeister (more or less in that order of driving). For dinner (if you end with Schermeister) we recommend the very good Glen Ellen Star right next door. Otherwise return to Sonoma Plaza and eat at The Girl and the Fig, LaSalette, or slightly further away, HopMonk Tavern.

Napa:

Begin your day with brunch at Oxbow Public Market, an artisan food market that’s wonderfully fun to poke around in or for a seated option head to Mustard’s Grill. There are a lot of famous, expensive, (some not all that great) and now highly touristed wineries in this beautiful valley. It would take decades to sample them all. We first suggest a stop at Grgich Hills Estate. Founded by the winemaker whose California wines stunned the world by beating out hundreds of French wines at the “Judgement of Paris”, it’s a great place, though increasingly expensive (have we gotten that across – Napa is expensive!). Other options include Rombauer Winery, a California staple for its chardonnay. Other ones we like include Clos Pegase Winery, Krupp Brothers Winery and Estate, Matthiasson, and ZD Winery. If you want a very laid back experience where the wine maker sits at your table with you, head to Elyse (also probably the most affordable of the bunch). If you visit Napa, you should make your way up to St. Helena and Calistoga for that Napa scenic beauty. These are extremely pretty Napa valley towns and offer artisan shops and places to eat. If wine tasting isn’t your thing but you still want to see Napa Valley, take a hike at Bothe-Napa Valley State Park or head to the spa at Calistoga. For dinner head to Calistoga Inn, Solbar – Solage, Evangeline, Gott’s roadside, Mustards Grill, The French Laundry, Bouchon Bistro, or La Calenda. For The French Laundry you must make reservations far in advance.

Healdsburg:

Healdsburg is lovely and beautiful but slightly further. Stop at Troubadour or Summer’s Market and Deli for a bite to eat first. Our favorite spot is De La Montanya where you can taste and explore their beautiful garden. Other options we like include Mill Creek Vineyards, Mauritson, MacRostie, Mounts, Bella, Wilson, Medlock Ames, and Reeve Wines. For dinner check out Valette, Spoonbar (great cocktails), Barndiva, Chalkboard, and Dry Creek Kitchen (which is very splurgy and requires advanced reservations).

If you’re spending the night before a flight, drive back to San Francisco and crash one final night.

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