18 days in California Itinerary

18 days in California Itinerary

Created using Inspirock California trip itinerary planner

Make it your trip
Fly to San Francisco International Airport, Drive to Guerneville
1
Guerneville
— 2 nights
Drive
2
Healdsburg
— 2 nights
Drive
3
Santa Rosa
— 2 nights
Drive
4
San Francisco
— 3 nights
Drive
5
Paso Robles
— 2 nights
Fly
6
San Diego
— 2 nights
Fly
7
Pacific Grove
— 3 nights
Fly

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Guerneville

— 2 nights
Guerneville is an unincorporated community and census-designated place in the Russian River Valley of Sonoma County, California, United States. You've now added Armstrong Redwood State Reserve to your itinerary. On the 23rd (Mon), immerse yourself in nature at Armstrong Redwood State Reserve, then learn about winemaking at Iron Horse Vineyards, and then do a tasting at Korbel Champagne Cellars. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Sonoma Coast State Beach, then enjoy the sand and surf at Doran Beach, and then take in the spiritual surroundings of Sea Ranch Chapel.

Plan my Guerneville trip by asking Inspirock to come up with tips and suggestions.

Chicago to Guerneville is an approximately 8-hour combination of flight and car. You can also drive. The time zone changes from Central Standard Time (CST) to Pacific Standard Time (PST), which is usually a -2 hour difference. When traveling from Chicago in December, plan for much hotter days and a bit warmer nights in Guerneville: temperatures range from 60°F by day to 36°F at night. You will have some time to spend on the 25th (Wed) before leaving for Healdsburg.

Things to do in Guerneville

Parks · Beaches · Outdoors · Nature

Side Trips

Healdsburg

— 2 nights
The quaint city of Healdsburg is one of northern California's wine capitals, serving as the meeting point for three of Sonoma's most important wine-producing regions.
Your day by day itinerary now includes Stephen & Walker Winery. On the 25th (Wed), learn about winemaking at Sapphire Hill Winery, do a tasting at Ferrari-Carano Winery, then learn about winemaking at Dry Creek Vineyard, and finally do a tasting at Stephen & Walker Winery. Keep things going the next day: pause for some serene contemplation at St. John the Baptist Catholic Church, do a tasting at Gary Farrell Winery, then learn about winemaking at Gracianna Winery, then learn about winemaking at Jordan Vineyard & Winery, and finally learn about winemaking at Francis Ford Coppola Winery.

Plan trip to Healdsburg with our itinerary maker to find out where to go and what to do.

Healdsburg is very close to Guerneville. Expect a daytime high around 60°F in December, and nighttime lows around 36°F. On the 27th (Fri), you'll have the morning to explore before heading off to Santa Rosa.

Things to do in Healdsburg

Wineries · Shopping · Historic Sites

Side Trips

Santa Rosa

— 2 nights

Where Everything Comes Together

Located less than an hour's drive north of San Francisco, Santa Rosa serves as a convenient hub for travelers on their way to the world-famous Napa Valley wine country.
You've now added Safari West to your itinerary. On the 27th (Fri), identify plant and animal life at Safari West and then do a tasting at Siduri Wines. Here are some ideas for day two: learn about winemaking at Pride Mountain Vineyards, savor the flavors at Mumm Napa, then learn about winemaking at Castello di Amorosa, then see the interesting displays at Charles M. Schulz Museum, and finally view the masterpieces at Valley of the Moon Pottery & North Eagle Gallery.

To see reviews, ratings, and more tourist information, use the Santa Rosa trip planner.

Santa Rosa is very close to Healdsburg. Expect a daytime high around 60°F in December, and nighttime lows around 36°F. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow enough time to drive to San Francisco.

Things to do in Santa Rosa

Wineries · Parks · Wildlife · Museums

Side Trips

San Francisco

— 3 nights

City by the Bay

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Visiting Alcatraz Island and Marin Headlands will get you outdoors. Do some cultural sightseeing at Golden Gate Bridge and Fisherman's Wharf. There's much more to do: engage your brain at Exploratorium, take in the waterfront at The Embarcadero, kick back and relax at Fort Funston National Park, and take a stroll through Nob Hill.

To see more things to do, other places to visit, maps, and other tourist information, read San Francisco trip itinerary website.

Traveling by car from Santa Rosa to San Francisco takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Santa Rosa in December, expect a bit warmer with lows of 45°F in San Francisco. Cap off your sightseeing on the 1st (Wed) early enough to go by car to Paso Robles.

Things to do in San Francisco

Parks · Wildlife · Beaches · Nature

Side Trip

Paso Robles

— 2 nights

Paso

A town of hot springs and wine, Paso Robles (or "Pass of the Oaks") feels like a desert paradise to those who travel here.
Your day by day itinerary now includes Paso Robles Pioneer Museum as well as Studios on the Park. Kick off your visit on the 2nd (Thu): see the interesting displays at Paso Robles Pioneer Museum, identify plant and animal life at Friends of the Elephant Seal Visitor Center and Gift Shop, then gain insight at Studios on the Park, and finally learn about winemaking at Tobin James Cellars. On the 3rd (Fri), you'll have a packed day of sightseeing: do a tasting at JUSTIN Vineyards & Winery, stop by Pasolivo Olive Oil, and then stroll through Moonstone Beach.

To find maps, ratings, reviews, and tourist information, use the Paso Robles attractions planner.

Traveling by car from San Francisco to Paso Robles takes 4 hours. Alternatively, you can take a bus; or fly. Traveling from San Francisco in January, Paso Robles is slightly colder at night with lows of 37°F. Cap off your sightseeing on the 3rd (Fri) early enough to travel to San Diego.

Things to do in Paso Robles

Parks · Museums · Beaches · Outdoors

Side Trips

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.
Kick off your visit on the 4th (Sat): get a taste of the local shopping with Gaslamp Quarter, admire the majestic nature at Torrey Pines State Natural Reserve, and then pause for some serene contemplation at Mary, Star of the Sea Catholic Church. Get ready for a full day of sightseeing on the next day: kick back and relax at La Jolla Cove.

To find other places to visit, where to stay, and tourist information, go to the San Diego trip planner.

Getting from Paso Robles to San Diego by flight takes about 5.5 hours. Other options: drive; or take a train. Traveling from Paso Robles in January, San Diego is somewhat warmer at night with lows of 51°F. Wrap up your sightseeing by early afternoon on the 5th (Sun) to allow enough time to travel to Pacific Grove.

Things to do in San Diego

Outdoors · Parks · Beaches · Shopping

Pacific Grove

— 3 nights
Pacific Grove is a coastal city in Monterey County, California in the United States. Your day by day itinerary now includes Point Pinos Lighthouse. Start off your visit on the 6th (Mon): enjoy the sand and surf at Asilomar State Beach, kick back and relax at Pacific Grove Shoreline Parkway Marine Refuge, enjoy the sea views from Point Pinos Lighthouse, then get a taste of the local shopping with Gallery by the Sea Carmel, and finally look for gifts at AiX. Keep things going the next day: appreciate the extensive heritage of Pacific Grove Oceanview Boulevard, look for all kinds of wild species at Monarch Grove Sanctuary, then admire the majestic nature at Point Lobos, and finally explore the world behind art at Casa Serrano, Historic Adobe.

For where to stay, other places to visit, more things to do, and more tourist information, read Pacific Grove route planning app.

You can fly from San Diego to Pacific Grove in 4 hours. Other options are to drive; or take a bus. In January, Pacific Grove is slightly colder than San Diego - with highs of 62°F and lows of 44°F. Wrap up your sightseeing by early afternoon on the 8th (Wed) to allow time for travel back home.

Things to do in Pacific Grove

Parks · Beaches · Outdoors · Nature

Side Trips

California travel guide

4.1
Specialty Museums · Wineries & Vineyards · Beaches
The Golden State
The country's most populous state, California includes landscapes that range from the forested northern coast to harsh southern deserts. Sandwiched right in the middle of the state is a fertile valley, home to farms, vineyards, and orchards. California's cities offer diverse attractions, from amusement parks and upscale shops to award-winning restaurants and innovative art galleries. Outside the state's big urban centers, places to visit include some of the nation's most rugged national parks, ancient forests, towering mountain peaks, and ski resorts. More than just a surfing destination famous for its beaches and winding coastal roads, California also boasts one of the world's largest economies, bolstered by the booming tech industries.