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21 Days Road Trip from San Diego to Portland

21 Days Road Trip from San Diego to Portland Itinerary

Last updated: 2024 Jun 14

Exploring San Diego

Morning
Start your day with a delicious breakfast at Snooze an A.M. Eatery. Then, embark on a Solana Beach E-Bike Tour to Torrey Pines or North Coast Solana Beach E-Bike Tour to Torrey Pines or North Coast to enjoy the coastal views and nature.
Afternoon
For lunch, head to The Crack Shack for a unique dining experience. In the afternoon, explore the San Diego Maritime Museum San Diego Maritime Museum of San Diego Admission and enjoy a San Diego Luxury Sailing Experience San Diego Luxury Sailing Experience on the bay.
Evening
Indulge in a delightful dinner at Juniper & Ivy known for its innovative cuisine. End the day with a San Diego Gaslamp Quarter Food Tour San Diego Gaslamp Quarter Food Tour to experience the local culinary scene.
Bedtime
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Solana Beach E-Bike Tour to Torrey Pines or North Coast

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San Diego Maritime Museum of San Diego Admission

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San Diego Luxury Sailing Experience

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San Diego Gaslamp Quarter Food Tour

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Coastal Beauty of San Diego

Morning
Enjoy a morning stroll at Mission Beach Mission Beach and have breakfast at The Cottage La Jolla. Then, join a San Diego La Jolla City and Coast Guided Sightseeing Tour San Diego La Jolla City and Coast Guided Sightseeing Tour to explore the stunning coastline.
Afternoon
For lunch, savor delicious dishes at Puesto. Spend the afternoon snorkeling at San Diego La Jolla Cove San Diego La Jolla Cove Guided Snorkeling Tour and visiting Birch Aquarium at Scripps Birch Aquarium at Scripps to learn about marine life.
Evening
Dine at the iconic George's at the Cove for dinner with ocean views. End the day with a San Diego Bay Eco Pedal Boat Rentals San Diego Bay Eco Pedal Boat Rentals to enjoy the sunset on the water.
Bedtime
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Mission Beach

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San Diego La Jolla City and Coast Guided Sightseeing Tour

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San Diego La Jolla Cove Guided Snorkeling Tour

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Birch Aquarium at Scripps

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San Diego Bay Eco Pedal Boat Rentals

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Historic San Diego

Morning
Start your day with breakfast at The Cottage. Explore the historic Balboa Park with a guided walking tour San Diego Balboa Park Guided Sightseeing Walking Tour to admire the architecture and gardens.
Afternoon
For lunch, try the delicious offerings at The Fish Market. Visit the USS Midway Museum San Diego USS Midway Museum Entry Ticket in the afternoon to learn about naval history and enjoy a San Diego Old Town Tales, Tacos, and Tequila Walking Tour San Diego Old Town Tales, Tacos, and Tequila Walking Tour for a cultural experience.
Evening
Indulge in a fine dining experience at The Marine Room known for its oceanfront setting. End the day with a San Diego Gaslamp Quarter Walking Tour San Diego Gaslamp Quarter Walking Tour to discover the historic district.
Bedtime
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San Diego Balboa Park Guided Sightseeing Walking Tour

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San Diego USS Midway Museum Entry Ticket

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San Diego Old Town Tales, Tacos, and Tequila Walking Tour

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San Diego Gaslamp Quarter Walking Tour

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Culinary Delights in San Diego

Morning
Start your day with a hearty breakfast at The Friendly. Embark on a San Diego Barrio Logan Food and Art Guided Walking Tour San Diego Barrio Logan Food and Art Guided Walking Tour to explore the vibrant neighborhood.
Afternoon
For lunch, enjoy the flavors at Cafe 21. In the afternoon, take a San Diego Sidecar Wine Tasting Tour San Diego Sidecar Wine Tasting Tour to experience local wines and scenery.
Evening
Dine at the elegant Herb & Wood for dinner. End the day with a San Diego Night Date Glow Pedal Boat with Downtown Views San Diego Night Date Glow Pedal Boat with Downtown Views for a romantic evening on the water.
Bedtime
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San Diego Barrio Logan Food and Art Guided Walking Tour

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San Diego Sidecar Wine Tasting Tour

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San Diego Night Date Glow Pedal Boat with Downtown Views

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Adventure in San Diego

Morning
Have breakfast at The Hake Kitchen & Bar. Start your day with a thrilling experience on the Patriot Jet Boat Thrill Ride San Diego Patriot Jet Boat Thrill Ride for an adrenaline rush.
Afternoon
For lunch, try the seafood at Truluck's Seafood, Steak and Crab House. In the afternoon, explore the Torrey Pines State Natural Reserve Torrey Pines State Natural Reserve for a hike with scenic views.
Evening
Enjoy a seafood dinner at Water Grill. End the day with a San Diego Gaslamp Quarter Historic True Crime Walking Tour San Diego Gaslamp Quarter Historic True Crime Walking Tour for an intriguing evening.
Bedtime
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San Diego Patriot Jet Boat Thrill Ride

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Torrey Pines State Natural Reserve

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San Diego Gaslamp Quarter Historic True Crime Walking Tour

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Relaxation in San Diego

Morning
Start your day with breakfast at The Lot. Enjoy a leisurely morning at The Med The Med for a relaxing beach experience.
Afternoon
For lunch, savor the flavors at The Smoking Goat. Spend the afternoon at Children's Pool Beach Children's Pool Beach for some sun and sea.
Evening
Dine at The Oceanaire Seafood Room for a seafood dinner. End the day with a San Diego Day or Sunset Sailing Excursion with Drinks San Diego Day or Sunset Sailing Excursion with Drinks for a scenic cruise.
Bedtime
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Children's Pool Beach

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San Diego Day or Sunset Sailing Excursion with Drinks

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Exploring Portland

Morning
Travel from San Diego to Portland. Start your day in Portland with a delicious breakfast at Tasty n Alder. Explore the city with a Guided Walking Tour of Downtown Portland Guided Walking Tour of Downtown Portland, Oregon to discover the local landmarks.
Afternoon
For lunch, try the unique dishes at Le Pigeon. Visit the Pittock Mansion Pittock Mansion in the afternoon for panoramic views of the city.
Evening
Dine at Andina for a taste of Peruvian cuisine. End the day with a Portland Downtown Scavenger Hunt & Self-Guided Walking Tour Portland Downtown Scavenger Hunt & Self-Guided Walking Tour for a fun evening adventure.
Bedtime
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Guided Walking Tour of Downtown Portland, Oregon

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Pittock Mansion

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Portland Downtown Scavenger Hunt & Self-Guided Walking Tour

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Adjacent Cities

Yosemite National ParkSequoia National ParkGrand Canyon National ParkFlagstaffDallas

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