Experience Maui With Us

Welcome Roland Park Families!

We are excited for your middle schoolers to join us next summer on a specially designed 7-day adventure in Maui. Your kids will experience the natural beauty, culture, and spirit of the island while having tons of fun as they surf, snorkel, hike, and explore some of the highlights of Maui!

They will also giving back to the land through hands-on environmental service work, as we help with ongoing projects to protect the island. Take a look at the full itinerary below!

Trip Dates: May 31 - June 6, 2026

Tuition: $3550 (including flights up to $1000)

Trip Itinerary

Day 1: Arrival Day

Arrival in Kahului (OGG) where our leaders will be ready and waiting, before transferring to our campsite, setting up camp, and settling into our new home on the island of Maui.

Day 2 : Surfing the Waves and Coastal Exploring

We kick off our trip getting on the water to ride the famous Hawaiian waves. Our local surfing guide teaches us the basics of surfing techniques, how to read the waves, and gives us time to refine and develop our skills. After a relaxing picnic lunch on the beach, we continue to explore along the coastline hiking some nature trails and stopping off at iconic viewpoints.

Day 3: Boat Trip and Snorkeling Molokini Crater

We head off the coastline on a boat trip to experience another of Hawaii's impressive geological features. Molokini Crater is a crescent-shaped volcanic crater about 3 miles off Maui’s south shore, and is one of Maui’s most unique and beautiful places to snorkel. We spend time exploring the clear, warm waters of the crater.

Day 4: Haleakala National Park

We spend the day exploring Haleakala National Park. We hike along the various trails and explore other highlights of the National Park and surrounding areas.

Day 5: Service Work

Service day! Working with our local partner, we help with projects that could include tackling invasive species, planting native species, trail maintenance, beach clean-ups, erosion control projects, and other environmental conservation-based tasks. Service varies year to year depending on what the demands are at the time of the project. It will be geared around the age and ability of the group.

Day 6: The Iconic Road To Hana

Travel the iconic Road to Hana and visit waterfalls, ocean views, black and red sand beaches, flower farms, and quaint hiking trails. Choose between tasty Hawaiian BBQ, freshly baked banana bread, and homemade ice cream (or have them all!) at one of the locally owned and operated food trucks along the way. An iconic cultural trip in Maui full of surprises!

Day 7: Travel Day

We head home to Florida after an action-packed few days!

*Please note the itinerary listed below is the intended itinerary for this trip. No two trips are exactly the same. All itineraries are subject to change to ensure the best possible program experience. Weather, group dynamics, new opportunities, and the unpredictability of travel all shape the final trip itinerary - and it's all part of the adventure!

Hold Your Child’s Place

Space is limited on this trip, so complete the enrollment form below to secure your child’s place. Once we have this, our admissions team will reach out with more information for you.

See Previous Hawaii Trip Highlights

 
 

Additional Trip Information

WHAT IS INCLUDED AND EXCLUDED IN TRIP TUITION

The trip tuition listed above includes accommodations, activities, meals, group gear, and return flights from Tampa (TPA) to Kahului (OGG) (up to $1000). The tuition does not include personal gear and clothing, baggage, travel insurance and spending money.

ACCOMMODATIONS AND SHOWERING

Accommodations are tent camping for the full 7 days of the trip. Tents and camping gear are provided and we aim for it to be 2 participants in a 3-person tent or 3 participants in a 4-person tent with luggage, divided by gender. Bathrooms and showers are available at the campsite.

FOOD

Participants on this trip will plan, prepare, and eat meals as a group. Split up into smaller cook crews, each crew will have the chance to prepare a meal approximately once per day. This process is supervised by staff who offer advice on nutrition and menu planning, and ensure safe food storage, preparation, and handling. Meals are prepared on back-country-style camp stoves. Meals are nutritious and filling, but the nature of a camping program often necessitates a simpler menu than a restaurant or home cook might allow.

We are able to accommodate all dietary requirements and preferences.

TRAVEL

As part of the trip tuition, we will book return travel from Tampa (TPA) to Kahului (OGG) on your behalf. As part of the tuition, we have budgeted a reasonable amount for flight costs based on typical flights for this time of year on this route, and industry trends. In the event that flight costs rise significantly, we will communicate this with enrolled families, and the tuition is subject to change to reflect this.

TRAVEL INSURANCE RECOMMENDATIONS

The Road Less Traveled does not provide its own insurance nor do we require travel insurance for domestic trips. However, travel insurance can protect your investment in your participant's trip from the risk of unexpected expenses from last-minute cancellations or early trip departure.

About The Road Less Traveled

At The Road Less Traveled, we have been running student service and adventure trips for over 30 years. We are passionate about providing meaningful and impactful student travel, that allows teens to explore the world and grow in themselves.

You can learn more about RLT at the links below!