5 Day Itinerary for San Francisco and Big Sur

Here’s a confession: I love creating itineraries. It’s a sickness. Trust me, you don’t want to see the “Travel” folder in my Google Drive. So. Many. Itineraries. 

In my past life, I bet I hit it big as the World’s Best Cruise Director because planning is my jam.

Here in my current life, I’ve yet to make a career out of being an Itinerary Planner Extraordinaire.

That doesn’t stop me from searching Google, TripAdvisor, and Pinterest for other people’s itineraries when I’m attempting to come up with my own. I like to see how other travelers grouped together various activities, what places they visited and when, and what they recommend doing.

This puzzle-like process helps me figure out how I can make my trip plan the best it can be.

Type A much?

Digital Itinerary Planning

 

Given my fervor for developing itineraries, I’ve gained quite the reputation among my friends and colleagues for this, er, hobby. When people ask me to share past trip plans with them, it gives me a chance to dig back into past travels, and my itineraries allow me to reflect on memories from past experiences.

This will be my first post in a new series that focuses ONLY on itineraries— no recaps or stories (I’ll link to any that I write about, of course!), just a list of what I did and where I went to help anyone who might be planning a similar trip.

Earlier this month, I traveled to San Francisco with my boyfriend to visit my best friend. Since we’ve both been to SF a couple of times, we weren’t overly concerned with doing all the tourist activities in the city. We spent a lot more time wandering around that I’d do if I were visiting for the first time. But, if you’ve been to San Francisco before, here’s an idea on how to get another look at this beautiful city.

Our 5 Day San Francisco and Big Sur Itinerary

DAY 1: TAMPA > SAN FRANCISCO: LOWER HAIGHT, PRESIDIO, MARINA

  • Arrive SF around 11 AM
  • Lunch at Palmyra Mediterranean Cafe in the Lower Haight
  • Walk to Alamo Square to see the Painted Ladies of Full House fame
  • Take Uber to the Presidio: LucasFilms Studio & the Yoda Fountain, Palace of Fine Arts
  • Walk to Pier 39 via Fort Mason (this was a bit of a walk, about 2.5 miles;  if you’re not feeling up for a lengthy trek, I recommend catching the free Presidigo shuttle!)
  • Take Uber to Ferry Building Marketplace: my favorites are Blue Bottle Coffee, cheese at Cowgirl Creamery, ice cream from Humphry Slocombe
  • Dinner at Umami Sushi in the Marina
  • Overnight at a friend’s place in the Lower Haight

Palace of Fine Arts Presidio San Francisco

DAY 2: SAN FRANCISCO: 16th AVENUE MOSAIC STAIRS, BAKER BEACH, NORTH BEACH

  • 5 mile run in Golden Gate Park
  • Coffee and breakfast at The Grind on Haight St.
  • Bus from Lower Haight to Moraga St. to see 16th Avenue Tiled Steps
  • Climb all the stairs to Grand View Park (this is an intense climb; I was huffing & puffing by the end!)
  • Take an Uber to Baker Beach near the Presidio
  • Dinner at Original Joe’s in North Beach (even though this is an Italian restaurant, I had the best and biggest burger I’ve ever had here)
  • Overnight at a friend’s place in the Lower Haight

View of Golden Gate Bridge from Baker Beach San Francisco

Grand View Park San Francisco

DAY 3: SF > MONTEREY: PACIFIC GROVE, 17 MILE DRIVE, CARMEL 

  • Breakfast in the Marina District of SF at the adorable Rose’s Cafe
  • Uber to SFO airport to pick up rental car
  • Drive to Airbnb in Pacific Grove (I highly recommend this Airbnb that we stayed in during our trip! It’s perfect for 3-4 adults, is well-decorated with an outdoor patio, and is within walking distance to the Monterey Bay Recreation Trail and the Monterey Aquarium)
  • Do 17 Mile Drive (there’s a $10 entry fee, but it’s so worth it!)
  • Stop in Carmel for dinner at Flying Fish (Please make a reservation and eat here. This is the best seafood I’ve ever had, and I grew up in Florida. I’m still dreaming about the ginger salsa appetizer and almond-encrusted sea bass weeks later!)

DAY 4: BIG SUR 

DAY 5: MONTEREY > SF: MONTEREY AQUARIUM, SANTA CRUZ, SAN FRANCISCO

  • 3 mile run on the Monterey Bay Recreation Trail because I couldn’t get enough of these views the day before
  • Breakfast at First Awakenings near the Monterey Aquarium
  • Monterey Aquarium (our Airbnb came with 2 free passes, which made this a worthwhile 2-hour adventure)
  • Coffee & shopping at Bright Coffee on our way out of Monterey
  • Drive from Monterey to Santa Cruz
  • Late lunch in downtown Santa Cruz
  • Drop rental car off at airport
  • Redeye flight back to Tampa

Monterey Bay Aquarium Jelly Fish

Are San Francisco and Big Sur on your travel bucket list? Have you been before and have recommendations to share in the comments?

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Meg Roberts
Meg Roberts is an avid runner, travel fiend, and content strategist based in Tampa, Florida. She enjoys exploring new places on foot, mile by mile. Follow along as she writes about making time to run, travel, and dabble with other hobbies, all while holding down a full-time office job that she loves.

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