8 days in San Diego & Oregon Itinerary

8 days in San Diego & Oregon Itinerary

Created using Inspirock United States visit planner

Make it your trip
Fly
1
San Diego
— 2 nights
Fly
2
Portland
— 2 nights
Drive
3
Cannon Beach
— 2 nights
Drive
4
Timberline Lodge
— 1 night
Drive to Portland International Airport, Fly to Detroit

S M T W T F S
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San Diego

— 2 nights

America's Finest City

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.
Escape the urban bustle at La Jolla Cove and Black's Beach. The adventure continues: immerse yourself in nature at Torrey Pines State Natural Reserve, walk around Scripps Institute of Oceanography Coastal Reserve, tour the pleasant surroundings at Children's Pool, and get up close and personal with brilliant marine life at SeaWorld San Diego.

To find where to stay, reviews, photos, and more tourist information, read our San Diego tour planning tool.

Detroit to San Diego is an approximately 6-hour flight. You can also drive; or take a bus. Traveling from Detroit to San Diego, you'll gain 3 hours due to the time zone difference. Traveling from Detroit in July, expect nights in San Diego to be about the same, around 68°F, while days are little chillier, around 77°F. Finish your sightseeing early on the 12th (Mon) so you can fly to Portland.

Things to do in San Diego

Parks · Outdoors · Beaches · Zoos & Aquariums

Portland

— 2 nights

City of Roses

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.
Kick off your visit on the 13th (Tue): take a tour by water with Willamette Jetboat Excursions, get to know the fascinating history of Eastbank Esplanade, then look for gifts at Powell's City of Books, and finally hike along Forest Park. Here are some ideas for day two: steep yourself in history at Columbia River Highway, admire the sheer force of Multnomah Falls, and then whizz through the canopy at Pumpkin Ridge Zip Tour.

To find ratings, where to stay, other places to visit, and other tourist information, refer to the Portland day trip app.

Getting from San Diego to Portland by flight takes about 4 hours. Other options: drive; or take a bus. Traveling from San Diego in July, expect nights in Portland to be slightly colder, around 59°F, while days are somewhat warmer, around 83°F. Finish your sightseeing early on the 14th (Wed) so you can drive to Cannon Beach.

Things to do in Portland

Outdoors · Historic Sites · Tours · Parks

Side Trips

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 15th (Thu), admire the majestic nature at Ecola State Park, take in the dramatic natural features at Haystack Rock, and then tour the pleasant surroundings at Cannon Beach. Get ready for a full day of sightseeing on the 16th (Fri): kick back and relax at Hug Point State Recreation Site, hike along Cedar Wetlands Preserve, then kick back and relax at Manzanita Beach, and finally admire the majestic nature at Oswald West State Park.

To find traveler tips and tourist information, read Cannon Beach online driving holiday planner.

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. Traveling from Portland in July, you will find days in Cannon Beach are little chillier (69°F), and nights are about the same (55°F). Finish your sightseeing early on the 16th (Fri) so you can travel to Timberline Lodge.

Things to do in Cannon Beach

Parks · Outdoors · Beaches · Nature

Side Trips

Timberline Lodge

— 1 night
Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
Start off your visit on the 17th (Sat): take your sightseeing to a higher altitude at Timberline Lodge and Ski Area.

To find where to stay, photos, maps, and more tourist information, read Timberline Lodge trip maker tool.

Drive from Cannon Beach to Timberline Lodge in 3 hours. While traveling from Cannon Beach, expect a bit warmer days and about the same nights in Timberline Lodge, ranging from highs of 79°F to lows of 58°F. You'll have a few hours on the 17th (Sat) to wrap things up before traveling home.

Things to do in Timberline Lodge

Nature · Historic Sites · Winter Sports
Highlights from your trip

Oregon travel guide

4.4
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.