top of page


a bespoke tour of the Hawaiian islands by Jess.Travel

"You never say goodbye to Hawai'i. It's always 'a hui hou.' Until we meet again."

custom hawaiian trip planner maui trip planner.png

An expertly curated, Hawaiian travel experience unlike anything you'll find elsewhere.

Endless potential experiences. All trips are custom and private.

> Less Tourists
> More Wonder
> More Authenticity
> More Culture
> More Affordable

Peruse below to narrow down some ideas.

I picked         ! What's next?

Jess Solo black.png
Hawaiian Trip planner

1. Interview

Hawaii Travel planner

2. Research

Private Hawaii itinerary

3. Book

jess hawaii travel planner.gif

4. Enjoy

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.

Maui custom travel planner.jpg
Jess Personal Travel Planning Fee.png

(per travel day)

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

Jess Hawaii custom travel planner.png


custom hawaiian travel planner
bottom of page