Custom travel itineraries

Planning your dream California vacation has never been easier


Bespoke California travel itineraries, without hours of research

Struggling to plan your California vacation? Let me simplify things for you with a personalized, day-by-day travel itinerary tailored to your interests and style. I’m a local Californian, and travel industry insider, so I'll guide you to the best-kept secrets that only an insider could uncover—from charming boutique hotels along the coast to up-and-coming culinary stars.

Spend less time on boring logistics, more time enjoy a seamless California trip tailored just for you.

What’s included

Full Day-by-Day Itinerary

Receive a detailed plan for each day, with hotel recommendations, activities, and restaurants, along with helpful tips, like how to get to each place or a can’t miss dish on the menu.

Pre-Departure Checklist

A customized “to-do list” with

✓ Direct booking link for hotels
✓ Activities and restaurants to reserve in advance
✓ Additional reminders, like renting a car

Custom Google Map List

This will allow you to see all planned destinations, activities, hotels, and restaurants directly in your Google Map app for easy, on-the-go navigation.

customer testimonials

  • Jessie knows so much about California and some of the highlights of our trip were areas we never would have discovered without her expertise.

    Jon L.

  • I hate planning trips, but working with Jessie meant I didn't have to do any of that. It was like joining a trip with a friend who had already done all the work.

    Jenny T.

  • It's like showing up for a group tour and following what they had planned for the day, just without the group. Perfect for my husband and I's anniversary getaway!

    Angie C.

Hey, I’m Jessie!

Let me plan your trip

I’ve lived in California for over 10 years, and been a travel industry insider for just as long. I’ve spent countless hours exploring all the things this amazing state has to offer, including outdoor adventures like hiking and cycling, wine tasting throughout the state, food, and beautiful hotels and resorts. Whether you want to see California’s most iconic spots or discover something new, I’ve got you covered.

How it works

Tell me about your trip, travel style, and what you want to see.

01 // Fill out a questionnaire

02 // Let me create your itinerary

Sit back and relax as I craft a personalized itinerary just for you.

I’ll work with you to make any necessary changes until it's perfect.

03 // Review and give feedback

04 // Final delivery

Receive your finalized itinerary and get ready to go!

Pricing

Package Duration Price
One Perfect Day 1 day + 1 night $120
Weekend Getaway 2-3 day trips $220
A Little More 4-5 day trips $400
Let’s Stay Awhile 6-7 day trips $540

Example

Weekend in Sea Ranch

Located on California’s Sonoma Coast, this historic vacation community is an artful blend of architecture and nature. This weekend getaway itinerary was developed for a couple who loves learning about history, is interested in some easy to moderate hiking, and birding.

  • Once you submit your questionnaire and payment, expect your itinerary within 3 business days. The final trip plan will be delivered 24 hours after receiving your feedback.

  • No, but I will provide an easy-to-follow list of all activities, hotels, and restaurants you need to book.

  • I will check availability for your dates before adding anything to your itinerary, but if you’re unable to get a reservation or a hotel, restaurant, or activity I will provide an alternative free of charge.

  • Please reach out directly. I respond to all customer requests and am happy to consider a refund or re-do, depending on your situation.

  • Many travel advisors earn commission from bookings made by clients, and will only work with clients who have a minimum budget. I work with clients of all budgets and, since you pay upfront for my services, I have no incentive to push you towards a particular product in order to earn more commission.

  • For now, yes. I believe the best travel advice comes from the locals who live here—which is why I focus on my home state of California :)

FAQs

Got questions? Get answers.