17-Day Road Trip Itinerary: Rosarito, Mexico to Lakeside, Oregon with Stops in San Luis Obispo, Santa Cruz, Ashland, and Claremont

Day 1: Departure from Rosarito and Drive to San Luis Obispo

Morning: Depart early morning from Rosarito, Mexico, crossing the border and beginning the scenic drive north through California.

Afternoon: Arrive in San Luis Obispo by mid-afternoon. Explore the charming downtown and visit the historic Morro Bay.

Evening: Enjoy dinner in downtown San Luis Obispo and get a good night’s rest in preparation for the next day.

Day 2: San Luis Obispo Exploration

Morning: Visit the beautiful Bubblegum Alley and the San Luis Obispo Mission.

Afternoon: Head to Pismo Beach for some fun by the ocean and maybe spot some monarch butterflies at the nearby grove if in season.

Evening: Relax with a sunset walk along the beach and have dinner at a local seafood restaurant.

Day 3: San Luis Obispo to Santa Cruz Drive and Evening Arrival

Morning: Depart from San Luis Obispo and take the scenic Pacific Coast Highway (Highway 1) north.

Afternoon: Stop at Big Sur for breathtaking views and photos.

Evening: Arrive in Santa Cruz, check into your hotel, and have a relaxed dinner near the Santa Cruz Wharf.

Day 4: Santa Cruz Exploration

Morning: Visit the iconic Santa Cruz Beach Boardwalk and enjoy some rides and games.

Afternoon: Explore the Natural Bridges State Beach and walk around the Seymour Marine Discovery Center.

Evening: Have dinner downtown and enjoy an evening stroll on West Cliff Drive.

Day 5: Santa Cruz to Ashland, Oregon (Travel Day)

Morning: Begin the long drive north towards Ashland, Oregon. Pack snacks and prepare for highway stops.

Afternoon: Lunch and stretch breaks along the way; consider stopping near Redding, CA for a junior break.

Evening: Arrive in Ashland, check into your accommodation, and unwind after the drive.

Day 6: Ashland Exploration

Morning: Visit the Oregon Shakespeare Festival visitor center and explore Lithia Park.

Afternoon: Tour downtown Ashland’s shops, galleries, and cafes. Consider attending a matinee show if available.

Evening: Enjoy dinner in one of Ashland's cozy restaurants with local cuisine.

Day 7: Ashland to Lakeside, Oregon

Morning: Depart Ashland and head north towards Lakeside, Oregon along the scenic highway passing through the Rogue River area.

Afternoon: Arrive in Lakeside. Spend time settling in and visiting the Umpqua Lighthouse State Park.

Evening: Relax at your accommodation and enjoy a quiet evening by the lake.

Day 8-10: Lakeside and Surroundings

Morning: Explore local outdoor activities like hiking in Chase Park and boating on Cleone Lake.

Afternoon: Optional day trips to Coos Bay or the nearby Oregon Dunes National Recreation Area.

Evening: Enjoy lakeside dinners and stargazing in the clear Oregon skies.

Day 11: Lakeside to Claremont, CA (Begin Return Trip)

Morning: Depart early from Lakeside heading back south towards Claremont, California.

Afternoon: Stop along the way for lunch and break; consider a scenic stop in the Central Valley.

Evening: Arrive at Claremont and meet with friends. Relax and enjoy the evening catching up.

Day 12-13: Visiting Friends in Claremont

Morning: Spend quality time with your friends in Claremont.

Afternoon: Explore the Claremont Village shops and nearby Hillside Memorial Park.

Evening: Dine and socialize with your friends in the area.

Day 14: Claremont to Santa Cruz

Morning: Leave Claremont and make your way towards Santa Cruz for one last overnight stay.

Afternoon: Revisit favorite spots such as the Boardwalk or relax at the beach.

Evening: Enjoy a farewell dinner in Santa Cruz with ocean views.

Day 15: Santa Cruz to San Luis Obispo

Morning: Head south to San Luis Obispo.

Afternoon: Spend time shopping or visiting any missed attractions like the San Luis Obispo Museum of Art.

Evening: Rest for the night and prepare for the next travel day.

Day 16: San Luis Obispo to Rosarito

Morning: Set off on the final leg of the trip driving south to Rosarito.

Afternoon: Stop for breaks and lunch along the way, crossing the border back into Mexico.

Evening: Arrive home in Rosarito, concluding the trip.

Day 17: Rest and Reflect

Morning: Rest day at home, enjoying some downtime with your daughter.

Afternoon: Organize photos and souvenirs from the trip; perhaps plan a slideshow or scrapbook together.

Evening: Discuss highlights and memories, maybe plan the next adventure!

Time and Cost Estimates

• Border Crossing (Rosarito/San Diego): 1 hour, Free (may include minor fees if expedited)
• San Luis Obispo Exploration: 6 hours, $50 (meals and attractions)
• Big Sur Scenic Stop: 2 hours, Free
• Santa Cruz Boardwalk: 4 hours, $40 (rides and food)
• Natural Bridges State Beach: 2 hours, $10 (parking)
• Ashland Activities: 6 hours, $70 (museum, park, show tickets)
• Lakeside Outdoor Activities: 8 hours (over multiple days), $60 (boat rentals, park fees)
• Claremont Visit: 2 days, $30 (meals and outings)
• Travel Fuel (approx. 2500 miles): 40 hours driving total, $350 (gas estimate)

Total Estimated Cost: $660

Tips

For extending the trip, consider adding more days in Ashland to enjoy additional Oregon Shakespeare Festival performances or including nearby Crater Lake National Park. To shorten the itinerary, you could reduce stops by combining Santa Cruz and San Luis Obispo into a single day each, and limit the time spent in Lakeside.