Get immersed in island life! Beachside comfort camping on Maui!

Trip At A Glance

  • Trip type: Domestic
  • Category: Active
  • Dates: October 26 - November 2, 2019
  • Duration: 8 days (7 nights)
  • Booking Deadline: June 30, 2019
  • Price: $1,692.00
  • Single Supplement: $760.00
  • Deposit: $507.60 (30.0%)
  • Group size: 10

Aloha, fellow Gen Xers! Calling all nature lovers & adventure seekers - grab your sunscreen, camera & backpack! Get ready to immerse yourself in the natural beauty of island life on this unique trip to the beautiful, rustic side of Maui! 

That's right, we’re off to the Hawaiian island of Maui (the Valley Isle) to unplug from the real world & take some well-deserved time to enjoy the remarkable hospitality of Hawaiian culture and the peaceful serenity of the natural beauty all around you.

We'll be traveling over Halloween week, so as a bonus, you'll be able to celebrate Halloween with the locals at the popular Annual Halloween Festival!

The Hawaiian Island of Maui is beloved for its incredible world-famous beaches, the super scenic Road to Hana, epic snorkeling with sea turtles, Haleakala’s magnificent volcano crater, and the island’s exotic ecosystems.

We’ll settle right into nature while comfort-camping at Camp Olawalu on the beautiful western coast of Maui. This sunny northwest coastal haven was once a retreat for Hawaiian royalty and the capital of the Hawaiian Kingdom. Just a few miles up the road is Lahaina. Once known as Lele, which means “relentless sun” in Hawaiian. Lahaina is a historic town that has been transformed into a Maui hotspot with dozens of art galleries and a variety of unique shops & restaurants. The southern portion on the West Coast is where you’ll find the gorgeous Makena Beach with panoramic views of the islands of Molokini and Kahoolawe.

We’ll also take a sightseeing air tour flying over the Road to Hana, the craters & volcanoes of Haleakalā National Park, the West Maui Mountains and the sea cliffs of Molokai (tallest in the World)! Wowza! There’s a lot to discover, so get ready for an active and explorative journey on Hawaii’s 2nd largest island!

Attention foodies… we have not forgotten you! We’ll sample and savor all of Maui’s tasty local cuisine! A unique island food experience begins in the misting forest of Waipoli in Upcountry Maui at O’o Farm. We’ll harvest our meal followed by a gourmet lunch prepared by a local chef. Prepare your tastebuds for the delicious local fish including Monchong, Mahi, Opah, Uhuh & Opakapaka prepared as poke, sashimi & fish tacos. Yum.

Trip Highlights

- Experience the real Maui in a very authentic way with lots of one on one time with Mother Nature, NOT doing the usual the tourist circuit being confined to the usual tourist bubble.

- Feel like a kid again while sleeping serenely in unique Tentalows right on Olawalu’s Coast! You'll maximize your time experiencing the natural beauty of the island by waking up to fresh air & beautiful mountain views (unlike hotel rooms), and saying goodbye to each wondrous day by enjoying epic sunsets.

- Hike the picturesque Waihe’e Ridge Trail with its incredible landscape in the Western Maui Mountains. This 4-mile moderate hike with a 1,604 ft. elevation features a waterfall, Maui’s unique plant life, and glorious views.

- Actively participate in an educational and delicious farm-to-table cuisine experience at the 8.5 acre sustainable O’O Farm. Relax while enjoying a tour and exclusive dining experience in the cool upcountry climate taking in the panoramic bi-coastal views of the island. Enrich your soul with a connection to the land as you sit down to a gourmet organic lunch prepared in your presence with fresh natural products you just harvested.

- Be dazzled in a 14-passenger Cessna as we take an unparalleled 1 hour 15 minute flying tour of Haleakala, Hana, the West Maui mountains & the seacliffs of Molokai (tallest in the world)! We’ll check out the spectacular sites of the Road to Hana through large viewing windows including Wai’anapanapa State Park, home to the unique, velvety smooth Black Sand Beach; and fly over the “Rare & Sacred” landscape of The Haleakala Volcano Crater, which vibrates with stories of ancient & modern Hawaiian culture and protects the bond between the land & its people.

- Enjoy a breathtaking sunset cruise on a luxury sailing catamaran called, The Ocean Spirit. We’ll set sail from historic Lahaina Harbor guided by a local marine naturalist. This is the perfect way to experience the essence of H’okipa (Hawaiian hospitality) as the crew pampers us with tropical cocktails and gourmet appetizers.

- Experience Halloween like you never have before - celebrate with the locals at the popular Anuual Halloween Festival where they close Main Street in Lahaina for the fun, festive Halloween revelers!


Trip type & Activity level: This trip is considered active adventure tourism with some cultural sightseeing. Active pursuits include walking & general touring, hiking, and water sports including sailing & snorkeling (optional). Our travelers should be in good health & able to walk 4-5 miles including elevation gain. Everyone will need the proper gear including trail shoes and a daypack for hiking essentials.  (Note: On our hiking day, there will be the option to stay back at camp and enjoy the beach.)

To understand what to expect when you click "Book Now," please see our Booking Process page.

Forget the standard hotel experience, we'll be staying in unique tentalows at Camp Olawalu!

Tentalow camp pano

Our camp is a short walk to the beach on Maui’s beautiful Western Coast! Visiting this nature retreat is like visiting Hawaii the way it used to be – a peaceful and fun tropical paradise. Enjoy breathtaking sunsets and experience some of the best whale watching, snorkeling, and kayaking Maui has to offer right off our beachfront and mountain-view property. Hike multiple nearby trails and discover the feeling of ancient Hawaii. 

Maui camp olawalu 1

What is a Tentalow? A tentalow is perfect fusion between the simplicity of camping and the luxury of a good night sleep. Enjoy your own private outdoor hot/cold shower with rainfall shower head, a pedestal sink with mirror, your own porch with seating, solar lighting, and lots of space to hang and store things. Fruit trees, tropical vegetation and lots of green grass surround you and invite you to stretch out and relax.

Tentalow outside              Tentalow beds smaller


  Tentalow sink smaller          Tentalow toilet sink

Our mountain-view tentalow offers the following amenities:

• Adirondack chairs

• Private outdoor hot/cold shower

• Pedestal sink, mirror & dressing area

• Interior solar lights

• Twin beds (two beds make 1 king) each with pillow, mattress & mattress protector

• Complete set of linens for each bed / cot (includes: fitted and flat sheets, pillow case, blanket, 2 hand and 2 bath towels)

• Cooler with ice available

Campground amenities include:

• Twelve bathrooms, each with toilet, sink, mirror, hand soap & paper towels

• Picnic benches, BBQ grills

• Outdoor dishwashing station with deep sink

• Internet hotspot at check-in window

• Trash & recycling bins


  • Day 1. Arrive in Maui (OGG Airport)
  • Day 2. Makena Beach State Park
  • Day 3. Maui Flight Experience
  • Day 4. Hike The Waihe’e Ridge Trail (Western Maui Mountains)
  • Day 5. O’o Farm Tour (Upcountry Maui)
  • Day 6. Camp Day at Olowalu Water Sports & Halloween Festival Lahaina
  • Day 7. Free 1/2 Day & Sunset Cruise (departs Lahaina Harbor)
  • Day 8. Departure Day to Maui International Airport & Travel home


Sat, Oct 26 Day 1. Arrive in Maui (OGG Airport)

Depart the continental US and arrive Kahului Airport (OGG) between 12:00pm and 4:00pm. Our Trip Leaders will be at the airport to pick you up (there will be two designated pick up times, see below under Flight info). You'll be transported back to Camp with a quick stop to pick up any provisions you may like to have during the week in your Tentalow. Once our group is settled in and comfortable at Camp Olawalu, we'll gather around the fire for a catered meal of delicious local fare and some cold beverages. [D]

Sun, Oct 27 Day 2. Makena Beach State Park

Let’s take a day to chill on one of the most gorgeous and captivating beaches in the world! Makena State Beach is a beach goer’s dream! We can rent snorkeling gear and check out the turtles & other charming sea creatures. We’ll grab snacks from the food trucks lined up on the road and pack a cooler of beverages. We’ll stop for dinner on the way back to Camp. [B]

Mon, Oct 28 Day 3. Maui Flight Experience

Today we'll be dazzled as we embark on a super scenic 1 hour and 15 minute panoramic flight over the island! Take off and soar like a bird through Maui's Central Valley and learn about the Sugar Cane Plantation history. We'll fly over the Molikini Crater and then South East over the iconic Makena State Beaches. We continue onto the lava fields and hear about the eruption a mere 300 years ago. The adventure continues as we venture around the circumference of the Haleakala Crater with its red sand dunes resembling the Planet Mars. A large percentage of Maui cannot be seen from the ground and our pilot will give us a private tour from the air over breathtaking scenery! Next up are the waterfall outside of Hana, the Town of Hana, red sand beach and the entire Northern Coast over the Famous Road to Hana. This will be a fun and spectacular ‘hands-on’ experience in a 4 seater plane with incredible photography opportunities! After landing we will make our way back to camp and enjoy more delicious Hawain cuisine at a local restaurant of our choosing. [B]

Tue, Oct 29 Day 4. Hike The Waihe’e Ridge Trail (Western Maui Mountains)

We'll stop and pick up a packed lunch. Then continuing driving towards the Western Maui Mountains while enjoying the majestic scenery along the Northwest Coast into the base of the mountains. The Waihe’e Ridge Trail is a moderate 4 mile hike with 1,604 feet of elevation. This hike in the West Maui Forest Reserve promises lush scenery, amazing valley views and some dramatic ridge-line hiking. Elevation gains are clean switch-backs and stairs spaced apart by spots of flat terrain. The trail is moderately exposed so bring lots of water and sunscreen & a hat! We will reward ourselves with a picnic lunch at the top to take advantage of the views and photo opps! [B]

Wed, Oct 30 Day 5. O’o Farm Tour (Upcountry Maui)

A truly unique island experience begins in the misting forest of Waipoli in Upcountry Maui where you will find O’o Farm. Our informational and interactive tour of this sustainable farm includes harvesting your meal followed by a gourmet organic lunch prepared by Chef Daniel Eskelsen. You can simply just relax into the afternoon and maybe opt to sip some fresh roasted Maui coffee. BYOB. After an incrediblly delicious lunch, we'll take a drive to the nearby Maui Wines and enjoy their beautiful setting while tasting some of their fabulous wine…with a hint of pineapple notes. [B,L]

Thu, Oct 31 Day 6. Camp Day at Olowalu Water Sports & Halloween Festival Lahaina

Let’s go back in time and experience a day at Camp! Wake up at Camp Olowalu, enjoy breakfast and then your activity choices are unlimited! You can opt for a guided kayaking trip (or go alone), snorkel along the Olowalu beach, relax with a guided yoga class with Judy, fall asleep in a hammock, take a walk, float in a tube, read a good book, or if you want, make a craft. :) Today is the day to just chill and enjoy all of the fun Camp Olowalu has to offer. Later in the day, we'll dress in costume (or not) and join the locals in Lahaina for the Annual Halloween Festival! The Main Street in Lahaina is closed for the Halloween Revelers. Festivities go late into the evening. Maybe we can come up with a group themed costume! We can grab dinner in Lahaina at the yummy Paia Fish Market. [B]

Fri, Nov 1 Day 7. Free 1/2 Day & Sunset Cruise (departs Lahaina Harbor)

Sleep in after the Halloween Festivities and enjoy the first part of the day at camp. Later in the day, we'll depart for Lahaina, catch up on any last minute souvenir shopping and then head to the Lahaina Harbor for a wonderful Sunset Cruise. This relaxing cruise is aboard Maui’s newest luxury sailing catamaran, Ocean Spirit, and departs from historic Lahaina Harbor. It’s the perfect way to enjoy a Maui sunset! And a great opportunity to experience the essence of hoʻokipa (hospitality) as the crew pampers us an array of premium appetizers & eats along with tropical cocktails, champagne, wine and other refreshing beverages. What a great way to wrap up an amazing week with new friends! [B,D]

Sat, Nov 2 Day 8. Departure Day to Maui International Airport & Travel home

Breakfast at Leoda’s Kitchen and Pie Shop. And then its unfortunately goodbye. :( You’ll have a group transport group to Kahului Airport (OGG) for your flight home. [B]

*Not ready to go home (particularly for east coasters)? Want some ideas to add onto your Maui vacation? Let us know & we’ll be happy to provide you with some fun options either before or after your time with us! We have ferry information, destination spas and unique experiences to suggest for anyone who is continuing their stay in Hawaii.

*Please note that we will do our best to stick with this planned itinerary, but some activities are weather permitting. Other activities & tours will be substituted as necessary.


Ground transportation roundtrip from Kahului Airport (OGG) to camp and to all excursions 

Tentalow accommodations for 7 nights (double occupancy) 

6 excursions:

  - Flight Sight Seeing Experience

  - Road to Hana day trip

  - Hiking Western Maui Mountains

  -O’o Farm Tour and Luncheon

  -Makena Beach outing

  -Sunset Sailing Cruise

7 Breakfast vouchers for Leoda’s

1 Lunch

2 Dinners

NOLS Certified Hiking leader

Park entrance fees

Extra snacks, refreshments, paper products & cups



Any meals or beverages not mentioned above



Early Bird Pricing (double occupancy): $1,692 (plus airfare) - book by May 30, 2019

Regular Pricing (double occupancy): $1,792 (plus airfare) - book by July 12, 2019

Single Supplement: $760

Deposit: 30% ($507.60) due upon booking

Final Balance: due 90 days before departure

Cancellation policy: Only 100% refundable within two weeks of paying your deposit. We recommend a premium Trip Insurance policy via a reputable company like TravelSafe; which can be booked easily from our trip booking website.

Dates: October 26 - November 2 2019 (Spend Halloween on the island of Maui!)

Total Days: 7 nights / 8 days

Total Group Size: Ten travelers (plus two trip leaders) 


Travel Days: October 26 and November 2

Arrival Day: Afternoon/evening on Saurday October 26th.

Sample Flight from East Coast US to Maui:

Alaska direct to LAX from Baltimore-Washington International Airport (BWI)

Depart BWI at 7:39 a.m., arrive LAX at 10:30 a.m.

Depart LAX on United at 2;48 PM, arrive Kahului Airport (OGG) at 5:34 PM

Approximate cost: $725

Sample Flight from West Coast US to Maui:

Delta Los Angeles International (LAX) direct to Kahului (OGG)

Depart LAX at 8:34 a.m., arrive (OGG) at 11:25 a.m.

Approximate cost: $425

Arrival transfer times - OGG Airport to camp

*Travelers will have the option of a 1:00pm and 5:00pm pickup at Kahului (OGG) to take advantage of our free group transportation to Camp Olawalu.

If arriving at another time, transportation is available through Uber for an estimated fare of $85-$100. Gen-X Travel Club is not responsible for providing alternative transportation.

Departure transfer times - OGG Airport to camp

*Travelers must depart Kahului Airport (OGG) no earlier than 1PM on our departure day of November 2nd.

If you book an earlier departure flight you will be responsible for providing yourself alternative transportation which could cost as much as $120.

Transportation around Maui

Our trip leaders will be providing our Maui driving transportation to and from camp and to each daily excursion. We will have two 7 passenger vans - each accommodates 6 passengers including the driver.


We always recommend trip insurance & suggest TravelSafe insurance - a reputable company with competitive pricing and great coverage options.

Here are a few reasons to get trip insurance:

● Reimbursement for cancellation penalties (which can be 100% of your investment) in the event of an unforeseeable illness, injury or death of you, your travel companion or a family member.

● Reimbursement for cancellation penalties if you are called for jury duty, your home is damaged due to fire, windstorm, flood or vandalism or military leave cancelled.

● Reimbursement for unused portion of your trip if it is interrupted.

● Medical evacuation/repatriation expenses to an appropriate medical facility or back home in the event of a serious illness or injury while traveling.

● 24-hour help line for any travel emergency, such as medical, lost tickets, lost passports, and other travel documents.

Note: The 'Cancel for Any Reason' premium policy must be purchased within two weeks of your initial trip deposit.

JUDY:  Travel Planner / Trip Leader / SoCal Chapter Meetup organizer / VP of Road-Trip Affairs

Judy bio pic

I picked up my love of off the beaten path travel from my parents. In the 70s, we packed up our family's wood paneled Chevy station wagon and coordinating olive green pop-up camper for a 5-week trip from Delaware to San Francisco. (No, I am not a Griswold.) Some of my favorite stops included The Badlands, Wyoming, and the Redwood forest. I passed the travel bug onto my kids by taking them on an 8-week, 3000 mile trek across Europe staying with friends and at campgrounds in 8 countries. Highlights included; London, Berlin, South of France, Norway and Switzerland.

In 2014, we relocated from the East Coast to California. I have spent the last few years continuing to build my travel expertise by refining my backpacking skills, orienteering know-how, & obtaining my Wilderness First Aid & Safety certification from The National Outdoor Leadership School. A few of my recent trips include a 40-hr trek solo on the Amtrak Coast Starlight in coach from LA to Portland, a 4-day backpacking trip climbing Mt. Whitney, and hiking and exploring Bryce, Yosemite The Grand Canyon, Mt. Hood and Zion National Parks. 

My favorite hobbies include real estate (also my "real job") pickleball, yoga, decorating, reading & of course, my passion for travel! Favorite song: "I Heard it Through the Grapevine" it takes me back... because I played "The Big Chill" soundtrack non-stop in 1985. My favorite kind of pizza is Buffalo Chicken pizza...and I recently stepped up my adult beverage game from Michelob Ultra to craft beer. Yes… East Coaster at heart!

I have lived in 6 states, resided in 20 homes, and have driven enough miles to be an excellent long-haul truck driver. Given those stats, I follow the mantra, “And so the adventure begins!"