18 days in California Itinerary

18 days in California Itinerary

Created using Inspirock California trip itinerary planner

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Route & dates

18 days in California Itinerary

Start: Chicago
Fly + Drive:  8​h
1
Guerneville
— 2 nights
Drive:  30​min
2
Healdsburg
— 2 nights
bus:  30​min
3
Santa Rosa
— 2 nights
Drive:  1​h 15​min
4
San Francisco
— 3 nights
Drive:  3​h 30​min
5
Paso Robles
— 2 nights
Drive:  5​h 45​min
6
San Diego
— 2 nights
Fly:  4​h
7
Pacific Grove
— 3 nights
shuttle + Fly:  8​h 45​min
End: Chicago

2
nights
Guerneville

Guerneville ©
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 Inpirock 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 Outdoors Beaches

Side Trips

Bodega Bay, Sea Ranch Chapel, Sonoma Coast State Beach, Iron Horse Vineyards
Highlights from your plan
Armstrong Redwood State Reserve ©
Armstrong Redwood State Reserve
Sonoma Coast State Beach ©
Sonoma Coast State Beach
Korbel Champagne Cellars ©
Korbel Champagne Cellars

2
nights
Healdsburg

Healdsburg ©
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

Francis Ford Coppola Winery, Powell's Sweet Shoppe - Windsor
Highlights from your plan
Sapphire Hill Winery ©
Sapphire Hill Winery
Gracianna Winery ©
Gracianna Winery
Jordan Vineyard & Winery ©
Jordan Vineyard & Winery

2
nights
Santa Rosa

Santa Rosa ©
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, shop like a local with 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 traveler tips, photos, reviews, 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 Wildlife Parks

Side Trips

St. Helena, Castello di Amorosa, Mumm Napa
Highlights from your plan
Pride Mountain Vineyards ©
Pride Mountain Vineyards
Safari West ©
Safari West
Mumm Napa ©
Mumm Napa

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Visiting Alcatraz Island and Fort Funston National Park will get you outdoors. Do some cultural sightseeing at Golden Gate Bridge and Exploratorium. There's much more to do: take in the waterfront at Fisherman's Wharf, take some stellar pictures from Twin Peaks, kick back and relax at Baker Beach, and immerse yourself in nature at Marin Headlands.

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

You can drive from Santa Rosa to San Francisco in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Santa Rosa in December, expect somewhat warmer with lows of 45°F in San Francisco. Wrap up your sightseeing on the 1st (Wed) early enough to drive to Paso Robles.

Things to do in San Francisco

Parks Wildlife Nature

Side Trip

Marin Headlands
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Exploratorium ©
Exploratorium

2
nights
Paso Robles

Paso Robles ©
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 27th (Fri): examine the collection at Paso Robles Pioneer Museum, then look for all kinds of wild species at Elephant Seal Rookery, then take in the exciting artwork at Studios on the Park, and finally learn about winemaking at Tobin James Cellars. On the 28th (Sat), you'll have a packed day of sightseeing: learn about winemaking at JUSTIN Vineyards and Winery, stop by Pasolivo Olive Oil, and then tour the pleasant surroundings at Moonstone Beach.

To see where to stay, photos, maps, and more tourist information, read our Paso Robles trip itinerary planner.

Traveling by car from San Francisco to Paso Robles takes 3.5 hours. Alternatively, you can take a bus; or do a combination of flight and bus. Traveling from San Francisco in December, expect a bit cooler with lows of 33°F in Paso Robles. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to San Diego.

Things to do in Paso Robles

Parks Museums Wildlife

Side Trips

Elephant Seal Rookery, Moonstone Beach
Highlights from your plan
Elephant Seal Rookery ©
Elephant Seal Rookery
Moonstone Beach ©
Moonstone Beach
Tobin James Cellars ©
Tobin James Cellars

2
nights
San Diego

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.
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.

For traveler tips, other places to visit, and tourist information, go to the San Diego trip planner.

Getting from Paso Robles to San Diego by car takes about 6 hours. Other options: do a combination of train and flight; or do a combination of bus and flight. 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
Highlights from your plan
Torrey Pines State Natural Reserve ©
La Jolla Cove ©
La Jolla Cove
Gaslamp Quarter ©
Gaslamp Quarter

3
nights
Pacific Grove

Pacific Grove ©
Pacific Grove is a coastal city in Monterey County, California in the United States. Your day-by-day itinerary now includes Point Pinos Lighthouse. On the 6th (Mon), stroll through Asilomar State Beach, enjoy the sand and surf at Pacific Grove Shoreline Parkway Marine Refuge, enjoy the sea views from Point Pinos Lighthouse, then shop like a local with Gallery by the Sea Carmel, and finally stop by AiX. Here are some ideas for day two: get to know the fascinating history of Pacific Grove Oceanview Boulevard, identify plant and animal life at Monarch Grove Sanctuary, then look for all kinds of wild species at Point Lobos, and finally explore the world behind art at Casa Serrano, Historic Adobe.

For ratings, photos, and tourist information, go to the Pacific Grove trip builder site .

You can fly from San Diego to Pacific Grove in 4 hours. Other options are to do a combination of flight and shuttle; or drive. 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 Outdoors Beaches

Side Trips

Carmel, AiX, Casa Serrano, Historic Adobe
Highlights from your plan
Point Lobos ©
Point Lobos
Asilomar State Beach ©
Asilomar State Beach
Pacific Grove Oceanview Boulevard ©
Pacific Grove Oceanview Boulevard

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