hawaiin trip planner
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A personal travel experience by Jess.Travel

"I want to go back to my little grass shack in Hawaii. It won't be long 'til my ship will be sailing back."  

Jess Custom Hawaii Travel Planner
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An expertly curated, personal travel plan unlike anything you'll find elsewhere.

Hawaii's epic beauty and culture offers you endless potential experiences. All trips are custom and private.


Peruse below to narrow down some ideas.


The land of Pele and fire

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Honolulu & Waikiki

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Molokai, Lanai & More

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The Valley Isle & Haleakala

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Untamed Majesty

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I picked         ! What's next?

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Hawaiian Trip planner

1. Interview

Hawaii Travel planner

2. Research

Private Hawaii itinerary

3. Book

Custom hawaii itinerary plan

4. Enjoy

Let me take care of your booking after you approve your

I figure out what makes the perfect trip for you and your entourage.

I'll put together a custom travel plan keeping everyone in mind.

This is where you give the thumbs up and get excited. 

Just show up with your personal travel itinerary on your phone.

Other Destinations

Check out our main Jess.Travel Site for custom travel itineraries created for any destination.

"Psst...let me tell you a secret..."

I've taken my kids everywhere. You name it, and we've been there. Wine tastings, nice restaurants, etc.  How? 

Preplanning, going at the right times, having kids that have already had fun, and MORE planning! Traveling with kids is great if you do it correctly. 

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(per travel day)

How much is a trip planner?

Anyone can book a tour, pick a hotel, and read the list of "Hawaii must do's."  But, the unique travel experiences of walking to dinner on a beach, sharing a picnic of amazing Hawaiian food at an awesome overlook, or sipping coffee poolside with every family member considered, require foresight and attention to detail.


A #travellikeJess vacation itinerary includes:

  • Custom itinerary planning

  • COVID 19 Travel knowledge

  • Curating memorable travel experiences

  • Lodging options, including Airbnb/VRBO

  • Transportation booking

  • Restaurant reservations

  • Excursion planning

  • Travel Insurance offering

  • Sporting event booking

  • Dietary restrictions, disabilities & pets taken care of

  • App Download and PDF viewable custom trip plan

  • Detail to flow, no one in your party will be bored nor tired

your problems goodbye

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Travel Planner Hawaii
Whale watch in hawaii with a custom hawaiian travel plan
Custom Travel Planner Maui

Custom Hawaiian itineraries are a specialty of ours. Relax, have an adventure, or both. We have extensive knowledge of what Hawaii has to offer.

Using a Hawaiian travel planner like Jess will make sure you're experiencing the true Hawaii, and not just tourist traps.

Custom hawaiian trip planner
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My name is Jess and I love to travel. I'm a certified Nurse Anesthetist (CRNA) by trade, and a natural organizer. So, years ago, I started booking custom travel experiences for my friends and family, and decided to turn my passion into a business. Now, everyone gets to #travellikejess with a personal travel planner. 


I founded Jess.Travel to make sure the hassle of planning a custom travel itinerary would never become a barrier to seeing the world. I was born to create flexible, custom travel plans for people, and Jess.Travel/Hawaii is my newest focus. I have family who live in Hawaii, and it's one of my favorite places to be.

Jess.travel is not just a person. It's the idea that a custom travel itinerary should maximize your time by tying together "happy moments" in new places.  Your time is valuable. Let me handle all the details and organization. Have me create a personal travel itinerary for you today.

custom hawaiian travel planner