57 days in Boston & San Francisco Bay Area Itinerary

Created using Inspirock United States holiday maker
Make it your trip
Fly
1
Boston
— 20 nights
Fly
2
San Francisco
— 11 nights
Drive
3
Point Reyes National Seashore
— 4 nights
Drive
4
Healdsburg
— 7 nights
Drive
5
Napa
— 7 nights
Fly
6
Monterey
— 7 nights
Fly

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Boston — 20 nights

Beantown

Satisfy your inner culture vulture at Museum of Fine Arts and Newport Car Museum. Get outdoors at Windblown Cross Country Skiing and Snowshoeing and Dragonfly Sportfishing. You'll find plenty of places to visit near Boston: Chatham Lighthouse Beach (in Chatham), Concord (Louisa May Alcott's Orchard House & Walden Pond State Reservation) and Lincoln (Mount Misery & Mass Audubon Drumlin Farm Wildlife Sanctuary). There's lots more to do: explore the world behind art at Peabody Essex Museum, contemplate the long history of Otis House, surround yourself with nature on Barking Brook Sled Dog Adventures - Day Trips, and take in the awesome beauty at West Rattlesnake Mountain.

To find more things to do, where to stay, traveler tips, and tourist information, read our Boston trip itinerary planning website.

London, UK to Boston is an approximately 10.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from London to Boston. In February, Boston is little chillier than London - with highs of 4°C and lows of -5°C. Cap off your sightseeing on the 3rd (Sun) early enough to catch the flight to San Francisco.
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Parks · Museums · Wildlife · Outdoors
Side Trips

San Francisco — 11 nights

City by the Bay

Alcatraz Island and Golden Gate Bridge are good opportunities to explore the local culture. Visiting Ano Nuevo Elephant Seal Tours and Steep Ravine Environmental Campground will get you outdoors. Change things up with these side-trips from San Francisco: Skyline to the Sea Trail (in Saratoga), Fremont (Don Edwards San Francisco National Wildlife Refuge & Coyote Hills Regional Park) and Moss Beach (Fitzgerald J V Marine Reserve & Friends of Fitzgerald Marine Preserve). And it doesn't end there: visit Fisherman's Wharf, engage your brain at California Academy of Sciences, take your sightseeing to a higher altitude at Mount Tamalpais State Park, and wander the streets of SoMa.

To see traveler tips, reviews, photos, and more tourist information, read our San Francisco trip itinerary planner.

Fly from Boston to San Francisco in 7 hours. Alternatively, you can drive; or do a combination of bus, train, and subway. The time zone difference when traveling from Boston to San Francisco is minus 3 hours. In March, San Francisco is warmer than Boston - with highs of 21°C and lows of 11°C. Wrap up your sightseeing on the 14th (Thu) early enough to drive to Point Reyes National Seashore.
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Parks · Wildlife · Neighborhoods · Museums
Side Trips

Point Reyes National Seashore — 4 nights

Get in touch with nature at Point Reyes Safaris and Tomales Bay State Park. Satisfy your inner culture vulture at Point Reyes Lighthouse and Harvest Moon Winery. You'll find plenty of places to visit near Point Reyes National Seashore: Bolinas Lagoon (in Bolinas), Sonoma County Wildlife Rescue (in Petaluma) and Stinson Beach (Adubon Canyon Ranch & Martin Griffin Preserve).

Take the guesswork out of planning a Point Reyes National Seashore vacation by using our trip itinerary maker.

Traveling by car from San Francisco to Point Reyes National Seashore takes 2 hours. Alternatively, you can take a bus. Expect little chillier evenings in Point Reyes National Seashore when traveling from San Francisco in March, with lows around 7°C. Wrap up your sightseeing on the 18th (Mon) to allow time to drive to Healdsburg.
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Wildlife · Parks · Tours · Nature
Side Trips

Healdsburg — 7 nights

Visiting Fort Ross State Historic Park and Ace It Bike Tours will get you outdoors. Stephen & Walker Winery and Sapphire Hill Winery are good opportunities to explore the local culture. Venture out of the city with trips to Guerneville (Armstrong Redwood State Reserve & Guerneville 5 & 10), Sonoma Coast State Beach (in Bodega Bay) and Sharpsteen Museum (in Calistoga). It doesn't end there: learn about winemaking at Bella Vineyards and Wine Caves.

To find more things to do, photos, other places to visit, and tourist information, go to the Healdsburg online tour planner.

Traveling by car from Point Reyes National Seashore to Healdsburg takes 2 hours. Alternatively, you can drive; or do a combination of bus and train; or take a bus. In March, daytime highs in Healdsburg are 22°C, while nighttime lows are 6°C. Finish your sightseeing early on the 25th (Mon) so you can drive to Napa.
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Wineries · Parks · Nature · Historic Sites
Side Trips

Napa — 7 nights

America's Wine Country

Step out of the city life by going to Hagemann Ranch Trout Fishing and Ellis Creek Water Plant and Wetlands. Get a sense of the local culture at Wine Tours & Tastings and Hess Persson Estates. Venture out of the city with trips to Charles M. Schulz Museum (in Santa Rosa), Benziger Family Winery (in Glen Ellen) and St. Helena (Modus Operandi Cellars, Charles Krug Winery, &more). And it doesn't end there: do a tasting at Inglenook, get outside with Outdoor Activities, and explore the world behind art at Sonoma Valley Museum of Art.

To see more things to do, maps, traveler tips, and more tourist information, use the Napa day trip planning website.

Traveling by car from Healdsburg to Napa takes 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. Expect a daytime high around 22°C in March, and nighttime lows around 6°C. Cap off your sightseeing on the 1st (Mon) early enough to catch the flight to Monterey.
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Wineries · Tours · Parks · Museums
Side Trips

Monterey — 7 nights

Get a sense of the local culture at Pacific Grove Oceanview Boulevard and Casa Serrano, Historic Adobe. Take a break from the city and head to Point Lobos and 17-Mile Drive. You'll find plenty of places to visit near Monterey: Ano Nuevo State Reserve (in Pescadero) and Loch Lomond Recreation Area (in Felton).

For photos, ratings, and other tourist information, refer to the Monterey trip itinerary builder app.

You can fly from Napa to Monterey in 2.5 hours. Other options are to drive; or take a bus. When traveling from Napa in April, plan for slightly colder days in Monterey, with highs around 20°C, while nights are about the same with lows around 10°C. Wrap up your sightseeing on the 8th (Mon) to allow time to fly back home.
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Parks · Outdoors · Wildlife · Beaches
Side Trips