14 days in United States Itinerary

14 days in United States Itinerary

Created using Inspirock California tour planner

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Route & dates

14 days in United States Itinerary

Start: Boston
Fly:  7​h 15​min
1
San Francisco
— 2 nights
Drive:  2​h 15​min
2
Monterey
— 2 nights
Drive:  15​min
3
Pebble Beach
— Few hours
Drive:  4​h
4
Santa Barbara
— 1 night
Drive:  4​h 45​min
5
Alpine
— 3 nights
Drive:  45​min
6
San Diego
— 4 nights
Fly:  6​h 45​min
End: Boston

2
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Your day-by-day itinerary now includes Ghirardelli Square, Fisherman's Wharf and The Speakeasy. Start off your visit on the 30th (Mon): take a leisurely stroll along Fisherman's Wharf and then browse the different shops at Ghirardelli Square. On the next day, steep yourself in history at Golden Gate Bridge, take a peaceful walk through Muir Woods National Monument, and then enjoy some classic entertainment at The Speakeasy.

To see other places to visit, ratings, traveler tips, and tourist information, you can read our San Francisco day trip planning tool .

Boston to San Francisco is an approximately 7.5-hour flight. You can also do a combination of flight and train; or drive. Due to the time zone difference, you'll gain 3 hours traveling from Boston to San Francisco. In September in San Francisco, expect temperatures between 76°F during the day and 58°F at night. You will leave for Monterey on the 2nd (Wed).

Things to do in San Francisco

Nature Historic Sites Parks

Side Trip

Muir Woods National Monument
Highlights from your plan
Golden Gate Bridge ©
Golden Gate Bridge
Muir Woods National Monument ©
Muir Woods National Monument
Fisherman's Wharf ©
Fisherman's Wharf

2
nights
Monterey

Monterey ©
Monterey is a city in the U.S. Your day-by-day itinerary now includes A Taste of Monterey-Wine Market & Bistro as well as 17-Mile Drive. Kick off your visit on the 2nd (Wed): take a memorable drive along 17-Mile Drive, then get to know the fascinating history of Pacific Grove Oceanview Boulevard, and then learn about winemaking at A Taste of Monterey-Wine Market & Bistro.

To see traveler tips, more things to do, photos, and more tourist information, use the Monterey trip builder site .

You can drive from San Francisco to Monterey in 2.5 hours. Other options are to fly; or do a combination of train and bus. Expect a daytime high around 70°F in October, and nighttime lows around 52°F. On the 3rd (Thu), you're off toPebble Beach.

Things to do in Monterey

Outdoors Scenic Drive Shopping

Side Trip

Pacific Grove Oceanview Boulevard
Highlights from your plan
Pacific Grove Oceanview Boulevard ©
17-Mile Drive ©
17-Mile Drive

few
hours
Pebble Beach

Pebble Beach
Pebble Beach is an unincorporated community on the Monterey Peninsula in Monterey County, California. On the 4th (Fri), contemplate in the serene atmosphere at Carmel Mission and then admire the architecture and history at San Carlos Borromeo de Carmelo Mission. Keep things going the next day: hike along Partington Cove, admire the majestic nature at Pfeiffer Big Sur State Park, then take in the views from Rocky Creek Bridge, then take in the exciting artwork at Carmel Art Association, and finally make a trip to Bird Rock Vista Point.

Ask Inspirock to suggest an itinerary and make planning a trip to Pebble Beach fast, fun, and easy.

Pebble Beach is just a short distance from Monterey. October in Pebble Beach sees daily highs of 70°F and lows of 52°F at night. Wrap up your sightseeing on the 6th (Sun) early enough to travel to Santa Barbara.

Things to do in Pebble Beach

Outdoors Parks Tours

1
night
Santa Barbara

Santa Barbara ©
Nestled between the Pacific Ocean and the Santa Ynez Mountains, Santa Barbara is a solid vacation destination with its wide beaches, renowned wineries, and some of California's finest shopping and dining options.
Kick off your visit on the 4th (Fri): enjoy the sand and surf at Thousand Steps Beach, then look for all kinds of wild species at Douglas Family Preserve, then walk around Arroyo Burro County Beach Park, and finally take a stroll through State Street Underpass.

To see reviews and more tourist information, read Santa Barbara online trip planner .

Getting from Pebble Beach to Santa Barbara by car takes about 4.5 hours. Other options: do a combination of car and flight. While traveling from Pebble Beach, expect somewhat warmer days and about the same nights in Santa Barbara, ranging from highs of 77°F to lows of 53°F. Finish up your sightseeing early on the 4th (Fri) so you can travel to Alpine.

Things to do in Santa Barbara

Outdoors Parks Beaches
Highlights from your plan
Arroyo Burro County Beach Park ©
Arroyo Burro County Beach Park
Douglas Family Preserve ©
Douglas Family Preserve

3
nights
Alpine

Alpine ©
Alpine is a census-designated place (CDP) in the Cuyamaca Mountains of San Diego County, California. You've now added Lions, Tigers & Bears to your itinerary. Start off your visit on the 5th (Sat): stop by The Bird Watcher, then get outside with Wright's Field in Alpine, and then look for all kinds of wild species at Lions, Tigers & Bears. On the 6th (Sun), you'll have a packed day of sightseeing: grab your bike and head to Goodan Ranch Sycamore Canyon Preserve, do a tasting at Principe di Tricase Winery, then do a tasting at Chuparosa Vineyards, and finally learn about winemaking at Ramona Ranch Vineyard & Winery.

To find more things to do, photos, other places to visit, and other tourist information, you can read our Alpine trip planner .

Traveling by car from Santa Barbara to Alpine takes 4 hours. Alternatively, you can do a combination of car and flight. Traveling from Santa Barbara in October, expect nights in Alpine to be about the same, around 57°F, while days are a bit warmer, around 84°F. You'll set off for San Diego on the 7th (Mon).

Things to do in Alpine

Outdoors Wildlife Parks

Side Trips

Ramona, Goodan Ranch Sycamore Canyon Preserve, The Bird Watcher
Highlights from your plan
Lions, Tigers & Bears ©
Lions, Tigers & Bears
Chuparosa Vineyards ©
Chuparosa Vineyards
Ramona Ranch Vineyard & Winery ©
Ramona Ranch Vineyard & Winery

4
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.
Your list of things to see and do now includes Old Town San Diego, Balboa Park, Old Town Temecula, and other attractions. Do some cultural sightseeing at Fort Rosecrans Cemetery and USS Midway Museum. Step out of the city life by going to South Carlsbad State Beach and Torrey Pines State Natural Reserve. Take a break from San Diego with a short trip to Moonlight State Beach in Encinitas, about 36 minutes away. There's still lots to do: tour the pleasant surroundings at Coronado Beach, don't miss a visit to Mt. Soledad National Veterans Memorial, kick back and relax at Pacific Beach, and see the interesting displays at San Diego Air & Space Museum.

For reviews, where to stay, more things to do, and tourist information, use the San Diego online trip builder .

Getting from Alpine to San Diego by car takes about an hour. When traveling from Alpine in October, plan for a bit cooler days in San Diego, with highs around 78°F, while nights are a bit warmer with lows around 64°F. Finish up your sightseeing early on the 11th (Fri) so you can travel back home.

Things to do in San Diego

Parks Outdoors Beaches

Side Trips

Moonlight State Beach, Coronado Beach, South Carlsbad State Beach, Old Town Temecula
Highlights from your plan
La Jolla Shores Park ©
La Jolla Shores Park
Coronado Beach ©
Coronado Beach
South Carlsbad State Beach ©
South Carlsbad State Beach

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