Six-Day Adventure in San Diego, California

Advisor - Brit Healey
Curated By

Brit Healey

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  • USA

  • California

  • San Diego

  • Beaches

  • Domestic Travel

  • Slow Travel

  • Coastal

  • Downtown

  • Outdoors

Road winding along a cliff in San Diego, California
Curator’s statement

There are many great places to eat, shop and explore all across San Diego! Whether you're a first-timer to this coastal town or just seeking a new adventure, hop in your car and check out the spots featured in this guide, vetted by yours truly.

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Where to stay

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Kimpton Hotel Palomar San Diego

Urban-chic boutique hotel in located in the heart of downtown within walking distance of all of San Diego's hot spots.

Fora Perks
  • $50 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

The Guild Hotel, San Diego, a Tribute Portfolio Hotel

Historic hotel revived for the modern traveler with design-forward interiors.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenities

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Andaz San Diego

Contemporary space in San Diego that channels chill Californian vibes.

Fora Perks
  • $50 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Advisor - Brit Healey

Unlock perks by contacting Brit to book your trip.

Day 1: Check In & Dinner in Hillcrest

Hillcrest sign in San Diego, California

After picking up your rental car and checking into your hotel, I recommend doing the following:

Grabbing a scallop burrito from El Zarape.

Build your own meat and/or cheese plate at highly-rated Barrel & Board in Hillcrest. Another spot to go to is La Bonne Table for award-winning traditional French cuisine. Hillcrest is the Greenwich Village of San Diego (i.e. LGBTQ+ mecca) and a must-see for anyone visiting the city!

Afterwards, make your way to Realm Of The 52 Remedies for super creative drinks in a Chinese-inspired speakeasy. Advance reservations are a must!

Day 2: Food, Shopping & Ocean Beach

Communal Coffee in San Diego, California

Start your day with a coffee at one of San Diego's trendy coffee shops! You can find a handful of cool spots in the North Park neighborhood such as: Holsem Coffee and Communal Coffee.

Donut lovers need to visit Nomad Donuts. While in the neighborhood, stop by these cute shops for unique souvenirs/gifts: ARTELEXIA, Hunt and Gather, Pigment, Gold Dust Collective, and HOME + HOUND.

This afternoon, cruise on over to Ocean Beach! Coordinate visiting on a Wednesday so you can hit up the Ocean Beach Certified Farmers’ Market and Wednesday Night Out from 4-7pm. Walk around and soak up the vibes! Next, head over to the infamous Sunset Cliffs to watch the sunset amongst other travelers and locals.

For dinner, the is Liberty Public Market is an awesome choice. If you want something a bit fancier, the Italian trattoria Cesarina never disappoints. Craving seafood? Mitch's Seafood is legit. All 3 spots are relatively close to each other en route back to your hotel.

Day 3: Morning Hike & Mezcal Tasting

Person sitting on Potato Chip Rock on a sunny day in San Diego, California

No trip to San Diego is complete without doing at least one hike! Cowles Mountain Trail is a great moderate option (3 miles out and back). For those who want a more challenging experience, do the Potato Chip Rock Hike which is 7 miles round trip. Heads up, Potato Chip Rock Hike is more of a climb than hike but the views are truly iconic!

Look for relaxing way to spend your afternoon? Buy tickets to a movie showing at Rooftop Cinema Club Embarcadero.

This evening, I recommend going to Wolf in the Woods for an otherworldly New Mexican-inspired dinner or Wormwood, followed by mezcal tasting at Tahona Bar. Once again, advance reservations are a must!

Day 4: Coronado & Pacific Beach

Hotel del Coronado in San Diego, California

Start your morning off with a matcha latte at Holy Matcha.

Afterwards, drive or take the ferry to Coronado. Walk around town, walk down the beach, marvel at Hotel del Coronado. You can even rent bikes and bike the Silver Strand!

Secret tip: A great spot to see San Diego's skyline at night is Bayview Park in Coronado.

You'll want to check out Pacific Beach on a Friday night for chill bonfires, people watching, and a happening nightlife. Grab dinner at Swagyu Chop Shop & Burger. If you are up for it, you can also go to neighboring Mission Beach which has a similar vibe.

Day 5: Little Italy & Balboa Park

Tower in Balboa Park on sunny day in San Diego

Head over to the Little Italy Mercato Farmers' Market (Saturdays) bright and early with an empty stomach and plenty of cash to splash! While in the neighborhood, check out Little Italy. Love & Aesthetics is a super cute shop to check out. If you wind up getting hungry, Morning Glory has a fun weekend brunch or you can go to Ironside Fish & Oyster for a proper raw bar. Continue exploring into the Gaslamp Quarter while you are in the area.

Another classic thing to do is walking around and chilling out in Balboa Park. Once you get hungry, you can grab a bite to eat at KINDRED, an eclectic spot for vegan eats and death metal music.

Make a visit to Wild Island Collective to see the most amazing Instagrammable plant nursery. They also host workshops and events for plant lovers.

A cool spot to eat ramen for dinner at Underbelly. If more in the mood for American fare, The Lion's Share.

Day 6: Encinitas, Torrey Pines & La Jolla

Seal relaxing on a rock on the beach in La Jolla

Cruise up the coast today! The first stop is Four Moons Spa in Encinitas. Hammam Scrub, Infrared Sauna, and Four Moons Custom Massage anyone? While in Encinitas, you can also go shopping at Salt Culture.

Go shopping at Cedros Avenue Design District in Solana (which also hosts a farmer's market on Sundays). 

Hungry? Grab food at Del Mar Skydeck – home to nine restaurants, one central bar, and three tap stations over two levels.

Drive to Torrey Pines State Natural Reserve and spend a few hours hiking.

Next stop is grabbing some food in picturesque La Jolla. Top spots are Shorehouse Kitchen, Trilogy Sanctuary and El Pescador. Don't forget about experiencing La Jolla Cove where groups of seals and sea lions tend to hang out.

Walk around La Jolla and take pictures of the awesome street art. Scripps Pier, Ellen Browning Scripps Park and Windansea Beach in La Jolla are great spots to take photos.

Conclude your final day in San Diego by watching the sunset at Mount Soledad!

Advisor - Brit Healey

Travel Advisor

Brit Healey

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