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Image by Drew Farwell

Honolulu to Maui

A two island hop sample


Editors Note: This is just a sample. An actual Jess.Travel itinerary contains much more detail specific to the trip.


This custom travel plan is designed to showcase the best of Hawaii, from bustling city life to serene natural beauty. Perfect for families and adventurous spirits alike, this itinerary balances relaxation with exploration, offering unforgettable experiences on the islands of Oahu and Maui.

If you love the idea of relaxing on beautiful beaches by day and exploring vibrant local culture by night, pack your bags for an incredible Hawaiian journey.

From the lively streets of Waikiki to the peaceful beaches of Maui, get ready to create lasting memories in paradise.


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Image by Fiona Smallwood

Your personal Hawaiian Vacation

 Day 1: Arrival in Paradise 

Welcome to Honolulu!

Upon arrival at Daniel K. Inouye International Airport, Honolulu, pick up your rental car from Enterprise (Confirmation #HNL2024). Drive to Leonard's Bakery for a famous malasada breakfast. Here's the [directions].

You are only 20 minutes from your hotel, The Modern Honolulu hotel (Confirmation #HON12345) [directions]. You picked this hotel for its prime location near Waikiki Beach and its luxurious amenities. Check-in is at 3:00 PM. Once you arrive, settle into vacation mode with a stroll on Waikiki Beach.

Tonight, explore the vibrant Waikiki area. Enjoy dinner at Duke's Waikiki, known for its beachfront views and delicious Hawaiian cuisine [directions]. After dinner, take a walk along Kalakaua Avenue, where you'll find shops, street performers, and lively nightlife.

Dinner Options:

  • Duke's Waikiki: Offers a family-friendly atmosphere with a diverse menu of Hawaiian and American dishes.

  • Roy's Waikiki: Renowned for its fusion of Hawaiian and Asian cuisine, perfect for a special night out.

  • Marukame Udon: A popular spot for casual dining, serving authentic Japanese udon noodles.

Cap off your night with a tropical cocktail at The Beach Bar at Moana Surfrider while enjoying live music and the ocean breeze. [directions]

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USS Arizona Memorial

The Bellagio fountain

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Sunset Cruise

 Day 2: Exploring honolulu 

Start your day with breakfast at Heavenly Island Lifestyle, known for its organic, locally-sourced ingredients. You chose this place for its healthy options and vibrant atmosphere. Here's the [directions from the hotel].

Spend the morning visiting Pearl Harbor to explore the USS Arizona Memorial and learn about the historical significance of the site. Your ticket were booked in advance. [Reservation here #123478]. You're going to spend several hours here watching the movies and seeing the exhibits.

Afterwards to wind down, head to Ala Moana Center for some shopping and the Shirokiya Japan Village Walk, a bustling food court with a variety of delicious afternoon snack options.

In the evening, enjoy your sunset dinner cruise on the Star of Honolulu along the coast of Waikiki. You chose this activity for its breathtaking views and romantic setting. Here's the [directions][Reservation #979043].

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North Shore, Oahu

Image by Amy Vosters

Dole Pineapples

 Day 3: North shore adventure

Check-out from The Modern Honolulu at 7:00 AM. Drive 1 hour to the famous North Shore [directions]. You picked this area for its world-renowned beaches and laid-back atmosphere.

Start your North Shore adventure with a visit to the Dole Plantation for a pineapple tour [Reservation #P7525]. Then, head to Waimea Bay Beach Park for a morning of sunbathing and swimming.

For lunch, try the shrimp trucks in Haleiwa, with Giovanni's Shrimp Truck being a popular choice [directions]. Spend the afternoon exploring Haleiwa Town's charming shops and art galleries.

Check-in at Turtle Bay Resort (Confirmation #NS56789) at 4:00 PM. You chose this resort for its stunning ocean views and variety of activities. Enjoy a relaxing evening at the resort, with dinner at their on-site restaurant, Lei Lei's Bar & Grill.

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Lanikai Beach


Byodo In Temple

 Day 4: beach day and culture 

Start your day with a visit to Lanikai Beach, often ranked among the most beautiful beaches in the world. Enjoy a morning of swimming and kayaking. If you decide to kayak, check out Kailua Beach Adventures. [directions]

For lunch, visit Kailua Town and try local favorites like Lanikai Juice for fresh smoothies and bowls. In the afternoon, visit the Byodo-In Temple, a serene and picturesque spot perfect for reflection and photos. [directions]

Return to Turtle Bay Resort for an evening of relaxation. Consider booking a spa treatment to unwind after a day of exploration.

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Bryce Canyon

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 Day 5: Cultural immersion and hiking

Begin with breakfast at Kono's North Shore, famous for its breakfast bombers. Here's the [directions].

Head to Waimea Valley to explore the lush botanical gardens and swim at the waterfall. This location offers a beautiful mix of culture and nature. [directions]

For lunch, visit Haleiwa Beach House for delicious Hawaiian cuisine and ocean views. Spend the afternoon hiking the Ehukai Pillbox Hike for breathtaking views of the North Shore. [directions]

Enjoy dinner at Pa'akai in Turtle Bay Resort, which features farm-to-table dining with local ingredients.

Capitol Reef National Park Travel Planner
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Capitol Reef

 Day 6: Capitol Reef National Park: the hidden gem 

Check-out from Capitol Reef Resort at 7:00 AM. Drive to Capitol Reef National Park. You chose this park for its less crowded trails and diverse geological features. Here's the [directions].


Then, head on your way to Hanksville [directions from CNP] for your tour. You'll drive the 8 miles through stunning red and orange Capitol Reef National Park and also pass by the pioneer town of Fruita where you can pick fruit from an original orchard created in 1880!


Get ready for some fun as you experience canyoneering in Robber's Roost [directions] and then a 4x4 ride along not for the faint of heart! Today is all about challenging yourself kissed with the reward of great views and a great dinner in hipster Moab.


Drive  1.5 hours to check-in at Moab Springs Ranch [directions from Hanksville] (Confirmation #232425) at 4:00 PM. You chose this place for its close proximity to the adventure activities in Moab. Spend the day mountain biking and relaxing at the resort. Remember to wear a helmet and other necessary safety gear while biking.

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Moab mountain biking

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Don't break your face

 Day 6: Mountain bike Moab 

Moab and mountain go together like peanut butter and jelly.  This town was made for adventure!


Meet your guide, get fitted to your bike, and get on the trail!  There are tons of options for all levels and any of them have views for days.  You'll work up an appetite and earn the right for a yummy local lunch.  

Back in Moab, you've got your pick of local haunts.  Gastropubs, breweries, BBQ, and Thai abound here.  And, leave room for the spectacle of Nitro ice cream at The Garage. 


Then, hang at your resort pool and soak those bones in the hot've earned it! 

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Arches NP

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Tired mommy

 Day 7: Drive to Salt Lake City 


Check-out from Moab Springs Ranch at 8:00 AM. Drive 6 minutes to Arches National Park (Reservation #189943HG)You picked this park for its iconic Delicate Arch and other unique rock formations. Here's the [directions]


Arches National Park is a stunner! So, grab your map and head to the back of the park to escape the crowds. 


On the way, you'll navigate yourself to these awesome roadside arches so get your camera ready!

- Skyline arch

- Sand Dune arch

- Balanced Rock arch


When it's time for lunch, head to Windows arch parking lot and take your pick of 3 short hikes to 3 separate's the most bang for your buck! Lunch in any shade you find and enjoy these anomalies.


After all the scenery you've experienced, the highway drive 3.5 hours to Salt Lake City will bore you to tears! Put on some good music, grab some fancy coffee for the road, and remember all the fun you've had. [directions from Arches to hotel]


Check-in at Hilton Salt Lake City Center (Confirmation #293031) at 6:00 PM. You chose this hotel for its central location and comfortable rooms. Once there, head out on foot for a 15-minute walk to the Utah State Capitol building and grounds and then to Temple Square to see the Mormon headquarters before dinner. Both of these are beautiful to poke around and explore. Here are the [directions].


Good food is abundant in Salt Lake City. You can opt to go commercial or go to the gritty underground bar scene. I'd do both. Pretty Bird has the best chicken sandwiches. If whiskey is your thing, Whiskey Street will pour you a nice one to toast the end of a phenomenal trip.


Check-out from Hilton Salt Lake City Center at 11:00 AM. Drive 11 minutes to Salt Lake City International Airport. Drop off your rental car (Confirmation #78910). Here are the [directions to the airport]. Your return flight, Delta DL 4321, departs at 2:00 PM.

Exhale! We hope you had an unforgettable adventure and made lots of wonderful memories. Rest up, and when you're ready for your next adventure, we'll be here to help plan it!

Jess custom travel planner sample itiner

Congrats! You survived family vacation!

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