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San Diego

5 day itinerary for San Diego

Personalized with:

Work 9am-5pm

Cigar smoking

Live music

Scenic views

Local food

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Itinerary

San Diego is a fantastic city with so much to offer, and I’m excited to help you craft an ideal 5-day itinerary that fits your work schedule and interests. Let’s dive in!

Day 1: Arrival and Scenic Views

Morning:

  • Start your day with a quick breakfast at in La Jolla. Their French toast is a must-try!
  • After breakfast, take a stroll along the for some stunning ocean views. You might even spot some sea lions!

Work:

  • 9 AM - 5 PM: Work time!

Evening:

  • After work, head to for a scenic sunset at . The views of the Pacific Ocean and the San Diego skyline are breathtaking!
  • For dinner, try for some fresh local seafood.
  • End your night at for a laid-back vibe and some live music. They often have local bands playing, and you can enjoy a cigar on their rooftop deck!

Day 2: Culture and

Morning:

  • Grab a quick breakfast at in the . Their farm-to-table approach is delightful!

Work:

  • 9 AM - 5 PM: Work time!

Evening:

  • After work, visit . Take a leisurely walk through the gardens and enjoy the beautiful architecture.
  • For dinner, check out in for a taste of local cuisine.
  • Post-dinner, head to in the . It’s a cozy spot where you can enjoy a fine cigar and maybe even catch some live jazz music!

Day 3: Beach Day and Local Eats

Morning:

  • Start your day with breakfast at in Pacific Beach. Their breakfast burritos are legendary!

Work:

  • 9 AM - 5 PM: Work time!

Evening:

  • After work, head to . Take a walk along the boardwalk and enjoy the ocean breeze.
  • For dinner, grab a bite at in Pacific Beach, known for its fresh catch and local flavors.
  • End your night at for some live music and a relaxed atmosphere. Don’t forget to enjoy a cigar on their patio!

Day 4: Exploring Downtown and Live Music

Morning:

  • Enjoy breakfast at in . Their chilaquiles are a crowd favorite!

Work:

  • 9 AM - 5 PM: Work time!

Evening:

  • After work, explore the . It’s vibrant and full of life!
  • For dinner, try , a modern steakhouse with a fantastic ambiance.
  • After dinner, catch a live music show at . They often have great acts, and you can enjoy a cigar outside before or after the show!

Day 5: Relaxation and Farewell

Morning:

  • Have a leisurely breakfast at in Hillcrest. Their maple bacon doughnuts are to die for!

Work:

  • 9 AM - 5 PM: Work time!

Evening:

  • After work, take a scenic drive to . Enjoy the breathtaking views of the cliffs and ocean.
  • For your farewell dinner, indulge in some local cuisine at in La Jolla. The rooftop terrace offers stunning views!
  • End your trip with a relaxing cigar at in La Jolla, where you can reflect on your wonderful time in San Diego.

And there you have it! A perfect blend of work, scenic views, local food, and live music, all while enjoying your cigars. Enjoy your trip to San Diego! 🌞✈️

Places of interest

The Cottage San Diego

The Cottage

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La Jolla Cove San Diego

La Jolla Cove

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Point Loma San Diego

Point Loma

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Cabrillo National Monument San Diego

Cabrillo National Monument

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Point Loma Seafoods San Diego

Point Loma Seafoods

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The Pearl Hotel San Diego

The Pearl Hotel

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Café 21 San Diego

Café 21

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Balboa Park San Diego

Balboa Park

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The Prado San Diego

The Prado

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Cigar Lounge San Diego

Cigar Lounge

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Breakfast Republic San Diego

Breakfast Republic

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Mission Beach San Diego

Mission Beach

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The Fishery San Diego

The Fishery

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The Beachcomber San Diego

The Beachcomber

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The Mission San Diego

The Mission

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Gaslamp Quarter San Diego

Gaslamp Quarter

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Born and Raised San Diego

Born and Raised

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House of Blues San Diego

House of Blues

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Great Maple San Diego

Great Maple

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Torrey Pines State Natural Reserve San Diego

Torrey Pines State Natural Reserve

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George’s at the Cove San Diego

George’s at the Cove

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The Cigar Shop San Diego

The Cigar Shop

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