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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?

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Corporate Travel Planner

1. Interview

Custom group travel itinerary

2. Research

Company travel planner Jess.Travel

3. Book

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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 Hawaii itinerary on each phone.

and the custom Hawaiian trip

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Dive into the heart of paradise with Jess.Travel's bespoke Hawaiian travel itineraries, designed for families and groups yearning for an experience as unique as the islands themselves. Whether you're dreaming of navigating the lush trails of Kauai, witnessing the majestic volcanoes of the Big Island, or simply soaking in the vibrant culture and sun-drenched beaches of Maui and Oahu, Jess's personalized travel planning services bring your ideal Hawaiian adventure to life.

Embrace the spirit of aloha with Jess as your guide, freeing you from the hassle of endless research and planning. Let us transport you beyond the ordinary, where the rhythm of the waves matches the beat of your heart, and every moment is infused with the magic of the islands. From luxurious beachfront resorts to hidden gems only known by locals, your Hawaiian journey will be crafted with an attention to detail and a passion for creating unforgettable memories.

Say aloha to a stress-free vacation, where every aspect of your trip is meticulously organized to suit your tastes and interests. With Jess.Travel, your dream of a perfect Hawaiian escape is not just a possibility—it's a promise. Let us take you on a journey where the beauty of Hawaii blends seamlessly with the excellence of our custom travel planning, ensuring your adventure is as breathtaking as the islands themselves.

Other Destinations

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

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Jess Personal Travel Planning Fee

(per travel day planned)

How much is a Hawaiian trip planner?

Anyone can book a tour, pick a hotel, and read the list of "Hawaii must do's." But, for the unique travel experiences of dining on a beach at sunset, sharing a picnic of delectable Hawaiian cuisine at a stunning overlook, or sipping coffee poolside with every family member's preferences considered, you need foresight and meticulous planning.

A #travellikeJess custom Hawaiian travel itinerary includes:

  • Custom Hawaii itinerary planning

  • Curating memorable and authentic Hawaiian travel experiences

  • Premium lodging options, including luxurious Airbnb/VRBO stays

  • Transportation booking for seamless island travel

  • Exclusive restaurant reservations for the best local cuisine

  • Excursion planning to uncover hidden gems, such as snorkeling in Molokini Crater or hiking the Na Pali Coast

  • Comprehensive travel insurance offering

  • Sporting event bookings, including surfing competitions

  • Luau reservations for an authentic cultural experience

  • Volcano tours on the Big Island

  • Whale watching tours during migration season

  • Catering to dietary restrictions, disabilities & pets

  • App download and PDF viewable custom trip plan

    Experience the magic of Hawaii with Jess.Travel, where every detail is crafted to provide you with an unforgettable tropical adventure.

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My name is Jess, and travel is my calling. What started as arranging trips for friends and family has blossomed into Jess.Travel, a service dedicated to removing the hassle of travel planning. With my background as a certified Nurse Anesthetist (CRNA) and a natural organizer, I've turned my passion into a thriving business that brings joy to our clients.

Jess.Travel/Hawaii represents not just a new venture but a personal invitation to explore the islands' magic. With family ties in Hawaii, my connection goes deeper than mere visits—I share with you an insider's love and knowledge of the place. Here’s why Jess.Travel should be your first choice:

  • Deep Local Insights: Having family in Hawaii means we offer not just travel itineraries but journeys enriched with local wisdom and hidden gems that only insiders know about.

  • Hassle-Free Planning: Leave the stress of researching flights and booking hotels, and activities to me. We ensure a seamless vacation plan, so all you need to do is look forward to the experience.

Choosing Jess.Travel means entrusting your custom Hawaiian adventure to someone who sees beyond the tourist trails and offers a gateway to genuine experiences, backed by a personal connection and a passion for creating unforgettable memories. Let us guide you to a Hawaii that’s closer to the heart, rich in culture, and full of undiscovered wonders.

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