17 days in San Diego & Portland Itinerary

17 days in San Diego & Portland Itinerary

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Route & dates

17 days in San Diego & Portland Itinerary

Start: New York City
Fly:  8​h
1
San Diego
— 9 nights
Fly:  4​h 30​min
2
Portland
— 7 nights
Fly + foot:  9​h
End: New York City

9
nights
San Diego

Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Discover out-of-the-way places like Del Mar City Beach and Windansea Beach. Your inner history buff will appreciate Mission Beach Boardwalk and San Diego Bay Walk. You'll find plenty of places to visit near San Diego: South Carlsbad State Beach (in Carlsbad), Lions, Tigers & Bears (in Alpine) and Moonlight State Beach (in Encinitas). Next up on the itinerary: take a stroll through Old Town Temecula, take a tour by water with Boat Tours & Water Sports, get up close to creatures of the deep with a dolphin and whale watching tour, and visit a coastal fixture at Old Point Loma Lighthouse.

To see more things to do, ratings, where to stay, and other tourist information, you can read our San Diego online trip itinerary builder .

New York City to San Diego is an approximately 8.5-hour combination of bus and flight. You can also fly; or drive. Traveling from New York City to San Diego, you'll gain 3 hours due to the time zone difference. Expect little chillier weather when traveling from New York City in July: highs in San Diego hover around 77°F, while lows dip to 68°F. Cap off your sightseeing on the 13th (Sat) early enough to travel to Portland.

Things to do in San Diego

Parks Outdoors Beaches

Side Trips

Mission San Juan Capistrano, San Clemente Pier, Del Mar City Beach, Coronado Beach, Moonlight State Beach
Highlights from your plan
Waterskiing & Jetskiing
Lions, Tigers & Bears ©
Lions, Tigers & Bears
Windansea Beach ©
Windansea Beach

7
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Popular historic sites such as Columbia River Highway and Pittock Mansion are in your itinerary. Eschew the tourist crowds and head to Columbia Gorge Discovery Center & Museum and Johnston Ridge Observatory. Get out of town with these interesting Portland side-trips: Cascade Locks (Starvation Creek State Park & Oneonta Gorge), WIndy Ridge Viewpoint (in Amboy) and Western Antique Aeroplane & Automobile Museum (in Hood River). The adventure continues: examine the collection at Flavel House Museum, delve into the lush surroundings at The Grotto - National Sanctuary of Our Sorrowful Mother, get engrossed in the history at Oregon Historical Society, and appreciate the views at Willamette Valley.

To find reviews, where to stay, photos, and more tourist information, go to the Portland trip planner .

Getting from San Diego to Portland by flight takes about 4.5 hours. Other options: drive; or take a bus. When traveling from San Diego in July, plan for somewhat warmer days and a bit cooler nights in Portland: temperatures range from 83°F by day to 59°F at night. On the 20th (Sat), you'll have the morning to explore before heading back home.

Things to do in Portland

Parks Nature Museums

Side Trips

Astoria, Cascade Locks, Johnston Ridge Observatory, Western Antique Aeroplane & Automobile Museum, Columbia Gorge Discovery Center & Museum
Highlights from your plan
Columbia River Highway ©
Columbia River Highway
Flavel House Museum ©
Flavel House Museum

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