Total Days: 5 Days | Accommodations: Recommend the Washington Square Inn or a hotel in Nob Hill | Transportation: Lots of walking and urban hiking, Uber and a car rental for 36 hours | Traveled With: Sister and brother in law | Type of Trip: A whirlwind of walking to the best landmarks and excellent food/drinks | Highlights: Alcatraz, Wine Tasting, Land’s End Hike
DAY 1
At a glimpse: Downtown hills and water views
Travel agenda: Get situated at your accommodation. Start your SF adventure by taking an Uber to the top of Crooked Lombard Street. Walk 30 mins down admiring the engineering of eight tight switchbacks, well-kept gardens and multi-million dollar homes!
Head southeast 10 minutes to the largest Chinatown in the country. Wander around and look for Chinatown Gate that leads to Grant Street with kitschy stores and produce and herbal shops. Stop at Vital Tea Leaf for a tea tasting or The Golden Gate Fortune Cookie Factory in Ross Alley for authentic and freshly baked fortune cookies. For lunch, go to China Live and order the pan-fried pork dumplings!
Urban hike 15 minutes to Coit Tower in Telegraph Hill. At the top, catch your breath and admire a 360 panoramic view. Walk down the Filbert Street Steps, a unique perspective of houses and vegetation nestled among a very steep hill, and then keep walking to the water until you hit the the tourist-driven Embarcadero. Don’t stay long but stop at Pier 39 to take a peek at the seals and experience the madness. The Ferry Building is closer to the Bay Bridge and worth browsing through! To rest your legs, stop for a cocktail at the Slanted Door or one of the many small bar counters. From there it’s a 10 minute walk to dinner at Wayfare Tavern, a cozy spot for authentic American dishes. It’s been a long day so the Deviled Eggs and Fried Chicken will do the trick!
DAY 2
At a glimpse: Morning at Alcatraz and exploring Golden Gate Park
Travel agenda: Start the day with breakfast/brunch and coffee at the SF institution Mama’s on Washington. From there, walk 15 minutes to Pier 33, where the ferry to Alcatraz takes off. Plan on 3-4 hours of touring and exploring “The Rock.”
Tip: Alcatraz should be booked in advance. If you need convincing, click here.
Once back on the mainland, rent a car downtown for 36 hours. Drive to Golden Gate Park and explore the 1,017 acres of gardens, lakes and attractions (where buffalo roam!). Spend time at the Academy of Sciences famous for housing a swamp, aquarium, planetarium, rainforest AND a living roof. This is also a good day to drive to the Mission and stop at Dolores Park. Cap off the day with dinner at Lazy Bear, a Michelin star dinner party experience.
Tip: Lazy Bear will have to be booked two months ahead of time, though putting your name on the waitlist can also yield good results. Great alternatives are Rich Table, The Progress and Foreign Cinema among so many others!
DAY 3
At a glimpse: Wine Country
Travel agenda: Grab a kouign amann and/or chocolate banana almond croissant and coffee for breakfast at B. Pattisserie. Then head over the Golden Gate Bridge and drive to wine country (and designate a D.D.!)
Tip: If you’re a Full House fan, the original house for the tv series is located just a couple blocks away from B. Pattisserie on 1709 Broderick St.
Kick off your day with a tasting at Ram’s Gate Winery, one of the first vineyards in Sonoma. Don’t let the location fool you, the setting is beautiful and the Chardonnay and Pinot Noir will be an excellent start. Next head 30 minutes to Chateau St. Jean, a picture-perfect ambiance with several different tasting options available, including a classic tasting, a charcuterie pairing, breakfast pairing and even an escape room challenge (although you may not want to leave!). Then drive 20 minutes to the quaint town of Sonoma. Peruse the shops and enjoy lunch at the Girl and the Fig.
Finally, drive 10 minutes for the final tasting at Scribe, a mellow, hip vineyard that prides itself on not being too fancy. Drive back to the city to regroup and detox. On the way, stop at the Golden Gate Bridge Vista Point in Marin for some epic photos. Return the car and rest up for activities tomorrow!
Tip: Reservations aren’t required at some wineries but as a rule of thumb, always call beforehand to ask about tasting reservations and options.
DAY 4
At a glimpse: Walking, hiking, biking and food rewards along the way
Travel Agenda: Don your sneakers and head to coffee and toast in the Outer Sunset at Trouble. From there, walk 10 minutes to Ocean Beach, a white sandy escape and surfer’s paradise, and then north to the Cliff House. From there, take the incredible Land’s End path (1.5 miles) that ends in the beautiful town of Sea Cliff.
Tip: Don’t miss the labyrinth 1/3 of the way through!
After, Uber to lunch at Souvla in the Marina. Souvla has wonderful rotisserie naturally-raised meats that can be added to salads or pitas for a perfectly health(ish) meal. Then pick up bikes around the corner at Golden Gate Bridge Bike Rentals on Lombard street. Bike first to the Palace of the Fine Arts in the Marina, then pedal along the waterfront and up the hill to the Golden Gate Bridge and follow the map to Sausalito. Don’t be afraid to stop and enjoy the views from both sides!
Bike to Bar Bocce, a fun hangout spot with firepits, bocce courts, marina views and fantastic flatbread pizza for dinner. After, the ferry terminal is just down the street and you can return the bike with Sausalito Bike Return. Take the ferry, ideally the Blue & Gold Fleet to Pier 41, back to SF and grab dessert at Ghirardelli Square while watching the sunset along the Aquatic Park Pier.
DAY 5
At a glimpse: Walking the fabulous side of the city
Travel agenda: Start the morning by walking up the Lyon Street Steps, 332 steps with Bay views along the way, to Pacific Heights. Walk along “Billionaire’s Broadway” with incredible residences that range from modern homes with living roofs to historic mansions. When it’s time for lunch, walk 15 minutes to Spruce for the best burger of your life.
After head to Fillmore Street and then down the marina (a true SF hill!) and have a drink at the Balboa Cafe, a staple in the Marina, to toast to your SF trip.
If it’s not your first time in SF, check out these alternative destinations!
