57 days in San Francisco Bay Area, Chicago and Beyond & Boston Itinerary

Get some cultural insight at Wine Tours & Tastings and Pride Mountain Vineyards. Get outdoors at Ellis Creek Water Plant and Wetlands and Sonoma Valley Regional Park. You'll find plenty of places to visit near Napa: Petaluma Seed Bank (in Petaluma), Glen Ellen (Arrowood Vineyard & Winery & Benziger Family Winery) and St. Helena (Corison Winery, Charles Krug Winery, &more). There's lots more to do: admire the masterpieces at Hess Persson Estates, do a tasting at O'Brien Estate Winery, examine the collection at Charles M. Schulz Museum, and contemplate the long history of Lachryma Montis.

To find ratings, maps, where to stay, and tourist information, go to the Napa trip planner.

London, UK to Napa is an approximately 14.5-hour flight. Due to the time zone difference, you'll gain 8 hours traveling from London to Napa. Traveling from London in February, expect nights in Napa to be about the same, around 4°C, while days are a bit warmer, around 20°C. Finish up your sightseeing early on the 18th (Sun) so you can go by car to Healdsburg.

Do some cultural sightseeing at Stephen & Walker Winery and Ace It Bike Tours. Visiting Fort Ross State Historic Park and Sonoma Coast State Beach will get you outdoors. Change things up with these side-trips from Healdsburg: Armstrong Redwood State Reserve (in Guerneville) and Sharpsteen Museum (in Calistoga). There's more to do: do a tasting at Bella Vineyards and Wine Caves.

To see reviews, ratings, and other tourist information, go to the Healdsburg road trip app.

Drive from Napa to Healdsburg in 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. In February, daily temperatures in Healdsburg can reach 21°C, while at night they dip to 5°C. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to Point Reyes National Seashore.

Visiting Point Reyes Safaris and Tomales Bay State Park will get you outdoors. Your cultural itinerary includes sights like Point Reyes Lighthouse and Harvest Moon Winery. Explore the numerous day-trip ideas around Point Reyes National Seashore: Bolinas Lagoon (in Bolinas), Sonoma County Wildlife Rescue (in Petaluma) and Stinson Beach (Adubon Canyon Ranch & Martin Griffin Preserve).

Quickly create a custom-made itinerary for Point Reyes National Seashore using our trip planner.

Traveling by car from Healdsburg to Point Reyes National Seashore takes 2 hours. Alternatively, you can drive; or do a combination of train and bus; or take a bus. In February, daily temperatures in Point Reyes National Seashore can reach 20°C, while at night they dip to 5°C. Finish up your sightseeing early on the 28th (Wed) so you can go by car to Pescadero.

Visiting Ano Nuevo Elephant Seal Tours and Pescadero Marsh Natural Preserve will get you outdoors. Change things up with these side-trips from Pescadero: Windy Hill Open Space Preserve (in Los Altos) and Loch Lomond Recreation Area (in Felton).

To see traveler tips, photos, other places to visit, and other tourist information, you can read our Pescadero itinerary planner.

Drive from Point Reyes National Seashore to Pescadero in 3 hours. Alternatively, you can drive. In February, daytime highs in Pescadero are 19°C, while nighttime lows are 9°C. Wrap up your sightseeing on the 2nd (Sat) early enough to drive to San Francisco.

Satisfy your inner culture vulture at Alcatraz Island and Fisherman's Wharf. Escape the urban bustle at Friends of Fitzgerald Marine Preserve and Richardson Bay Audubon Center. Change things up with these side-trips from San Francisco: Don Castro Regional Recreation Area (in Hayward), Steep Ravine Environmental Campground (in Mill Valley) and Green Gulch Farm (in Muir Beach). There's much more to do: take in the views from Golden Gate Bridge, look for all kinds of wild species at Don Edwards San Francisco National Wildlife Refuge, engage your brain at California Academy of Sciences, and see the interesting displays at Exploratorium.

For maps, reviews, and other tourist information, you can read our San Francisco online road trip planner.

Traveling by car from Pescadero to San Francisco takes 1.5 hours. Expect a daytime high around 21°C in March, and nighttime lows around 11°C. Finish your sightseeing early on the 13th (Wed) so you can fly to Chicago.

Take a break from the city and head to Angler Charters and North Park Village Nature Center. The Art Institute of Chicago and Field Museum are good opportunities to explore the local culture. Get out of town with these interesting Chicago side-trips: Lynfred Winery (in Roselle), Fort Sheridan Forest Preserve (in Lake Forest) and Prairie Wolf Slough (in Highland Park). There's lots more to do: meet the residents at Shedd Aquarium, see the interesting displays at Medieval Torture Museum, take a stroll through The Magnificent Mile, and get to know the resident critters at Lincoln Park Zoo.

To find reviews, more things to do, traveler tips, and tourist information, you can read our Chicago travel itinerary planner.

You can fly from San Francisco to Chicago in 6 hours. Other options are to drive; or do a combination of subway and train. Due to the time zone difference, you'll lose 2 hours traveling from San Francisco to Chicago. In March, Chicago is colder than San Francisco - with highs of 8°C and lows of -1°C. Cap off your sightseeing on the 23rd (Sat) early enough to catch the flight to Boston.

Your cultural itinerary includes sights like Museum of Fine Arts and Newport Car Museum. Visiting Windblown Cross Country Skiing and Snowshoeing and Chatham Lighthouse Beach will get you outdoors. Venture out of the city with trips to New Hampshire State Liquor Store & Safety Rest Stop (in Hooksett), Sheiling Forest (in Peterborough) and World's End (in Hingham). Next up on the itinerary: admire the masterpieces at Peabody Essex Museum, head outdoors with Dragonfly Sportfishing, explore the landscape on two wheels at Shining Sea Bikeway, and explore the galleries of Isabella Stewart Gardner Museum.

For where to stay, traveler tips, photos, and other tourist information, you can read our Boston vacation maker website.

Getting from Chicago to Boston by flight takes about 4 hours. Other options: drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. March in Boston sees daily highs of 7°C and lows of -1°C at night. Finish up your sightseeing early on the 8th (Mon) so you can catch the flight back home.