Big Island Itinerary Planning for First-Time Visitors

Personalized itinerary reviews, trip planning, and video consults

Planning a Big Island trip sounds fun until you start trying to piece it all together.

Suddenly you’re juggling maps, restaurant lists, tour options, beach recommendations, coffee farms, and conflicting advice from Redditors.

Maybe you already have a rough itinerary and just want reassurance that it’ll work. Maybe you want someone to build the trip for you from scratch. Or maybe you simply want the chance to talk things through with someone who knows the island well before you finalize your plans.

That’s where I come in!

🙋‍♀️ Aloha, I’m Tabitha, your Big Island Expert!

People are more and more having AI create travel itineraries for themselves and when I see the crap it comes up with, I’m sad for those people who are going to have a confusing and difficult time (ie, having you unnecessarily backtrack out of the way for lunch or suggesting a stop that’s been closed for 5 years).

I’ve lived on the Big Island and still visit regularly and stay up-to-date on island happenings, which means I understand not just what there is to do but how the island actually functions.

I also used to be a travel agent, so I know how to plan trips that save time and money while making every day count.

I help thoughtful planners like you:

✅ Decide what’s truly worth your time and money

✅ Create days that feel full but not exhausting

✅ Avoid common unnecessary hassles many first-timers run into

No matter where you’re at in the planning process, I’m here to help make your Big Island trip feel less overwhelming and get you excited to pack your bags.

What Service Do You Need?

Itinerary Review

Does this sound like you:

• You’ve built a solid draft itinerary but want reassurance that it’ll work
• You need help filling in blank spaces in your days
• You want help with logistical headaches and minimizing unnecessary extra driving
• You’d like clarity on which things are worth doing and which ones you can probably skip

Have you already mapped out a rough Big Island itinerary with activities, restaurants, and places you want to see, but want someone experienced to look it over and make sure it all realistically works?

Perhaps you’re worried about trying to cram too much into one day or the opposite, you have gaps in your itinerary and aren’t sure what to fill them with.

Either way, I’ll help you make sense of it all.

Send me your current itinerary, no matter how complete or incomplete it is, and I will look it over with a fresh set of expert eyes. I’ll point out what works, what may need adjusting, sprinkle in insider tips and suggestions you may not know about, and send it back polished up and ready for your trip.

What You Get:

✅ Itinerary review — A detailed review of your itinerary to make sure your days flow smoothly and make sense
✅ Expert suggestions and tips – Honest recommendations and “secrets” to help make your trip smoother, more memorable, and less stressful
✅ Updated itinerary – Your itinerary sent back with personalized adjustments, suggestions, and notes so you can confidently follow it once you arrive on the island

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Trip Planning

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Travel Consult

Does this sound like you:

• You’ve got your Big Island itinerary planned (or mostly planned) but want help refining it
• You have a lot of questions about your Big Island itinerary and would rather talk things through face-to-face instead of emailing back and forth
• You process information better by having an actual conversation
• You want expert feedback and reassurance before finalizing your plans

Have you already got your Big Island itinerary mostly planned out, but want the chance to talk it through with someone experienced before finalizing everything?

Do you simply process information better through conversation and want the ability to ask questions, brainstorm ideas, and get immediate feedback in real time?

Instead of going back and forth over email, we’ll hop on a one-on-one video call and work through your trip together. It’ll be like meeting a friend over coffee.

We’ll talk through your itinerary ideas, questions, priorities, must-dos, and concerns, and I’ll help refine your plans, offer suggestions, point out anything that may need adjusting, and help make your trip feel smoother, more manageable, and more exciting before you even step on the plane.

Travel consult pricing is $60 for a 30 minutes or $100 for a 60 minutes.

What You Get:

✅ One-on-one video call – A face-to-face conversation where we talk through your itinerary, questions, ideas, and concerns in real time. We’ll refine your current plans or build out your trip from scratch based on your interests and how you like to travel
✅ Shareable video link – Travel companions can use your meeting link to join in the conversation
✅ Expert suggestions and tips – Honest recommendations and “secrets” to help make your trip smoother, more memorable, and less stressful
✅ Follow-up notes – A written summary of everything we discussed, including recommendations, suggestions, and itinerary adjustments so you can easily reference it later

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😃 I can’t wait to work with you!