Past Trips

Beachside comfort camping & active pursuits on the island of Maui, Hawaii!

Trip At A Glance

  • Trip type: Domestic
  • Category: Active
  • Dates: November 1-7, 2018
  • Duration: 7 days (6 nights)
  • Booking Deadline: July 23, 2018
  • Price: $1,488.00
  • Single Supplement: $652.00
  • Deposit: $446.40 (30.0%)
  • Group size: 10

Aloha fellow GenX-ers! Calling all nature lovers & adventure seekers - grab your sunscreen, hiking boots & backpack! Because this trip to the rustic side of Maui is made just for you!

We’re off to the Hawaiian island of Maui (the Valley Isle) to take some well-deserved time to unplug & connect while enjoying the remarkable hospitality of Hawaiian culture and the peaceful serenity of the natural beauty all around you.

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 coast of Maui 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. Southbound on the West Coast is Makena beach with great views of the islands of Molokini and Kahoolawe. We’ll adventure along the Road to Hana and hike into the craters & volcanoes of Haleakalā National Park. There is 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. Along the road to Hana, we’ll seek out the best fresh fish, shaved ice, barbecue and warm banana bread that Maui has to offer. Our camp meals will be delicious island fare catered by the popular and award-winning Three’s Catering Maui!


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

● Feel like a kid again while sleeping serenely in unique Tentalows right on Olawalu’s Coast. You'll be able to 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 “Rare & Sacred” landscape of Haleakalā National Park. This special place vibrates with stories of ancient and modern Hawaiian culture and protects the bond between the land and its people.

● Actively participate in an educational and delicious farm-to-table cuisine experience at O’O Farm. Tour and dine in the cool upcountry climate and panoramic bi-coastal views of the island. Enrich your soul with a connection to the land as you sit down to a gourmet lunch prepared in your presence with fresh natural products you just harvested.

● Delight in a snorkeling trip to the Molokini Crater located off of Maui’s Southern shore and Maluaka Beach. Snorkel inside the crater itself and experience its underwater sanctuary. Below the surface, see beautiful coral reefs, colorful fish and curious marine animals. During the 5-hour snorkeling adventure, we’ll be treated to breakfast & BBQ served on the boat.

● Experience the undisputed beauty that is the Road to Hana aka Heavenly Hana - aptly nicknamed for good reason! The amazing drive on Hana Highway hugs the coastline and is world famous for its stunning natural beauty, dramatic landscapes & towering waterfalls. With spectacular panaromic views in every direction, this is definitely a case in point where it's the journey not the destination! Along the way, we’ll also immerse ourselves in all the yummy, local delicacies unique to the East Coast of Maui.

● 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 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.

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 6-10 miles including some significant elevation gain. Everyone will need the proper gear including trail shoes and a daypack for hiking essentials.  (Note: There will be the option to stay back at camp and enjoy 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) between 12pm and 4pm
  • Day 2. Snorkeling Trip (South Maui)
  • Day 3. Road to Hana (East Maui)
  • Day 4. Hike Haleakalā National Park and Crater (Upcountry Maui)
  • Day 5. O’o Farm Tour (Upcountry Maui)
  • Day 6. Makena Beach and Sunset Cruise (South Maui)
  • Day 7. Departure Day to Maui International Airport - Travel home


Thu, Nov 1 Day 1. Arrive in Maui (OGG Airport) between 12pm and 4pm

Depart the continental US and arrive Kahului Airport (OGG). 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, and also an opportunity to stop at a food truck if you're hungry (early pick up only). 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]

Fri, Nov 2 Day 2. Snorkeling Trip (South Maui)

Molikini Sail & Snorkel. We’ll embark on a 55-foot glass bottom catamaran and take a scenic cruise to Molokini crater from Maalaea Harbor. While on board, enjoy a continental breakfast of fresh bagels with cream cheese, jams, tropical fruits, Kona coffee and juices. Admire spectacular views from your boat including stunning white sandy beaches that stretch for miles and sparkling turquoise ocean water. Learn about the fascinating history, culture and marine life of Maui from your naturalist expert guide. A barbeque lunch and beverages also will be served on board this exciting five hour adventure. I hope we’re luckier than the castaway of Gilligan’s Island! We’ll return to camp for hot showers and a light dinner catered just for us before resting up for another big day. [B,L,D]

Sat, Nov 3 Day 3. Road to Hana (East Maui)

We'll combine the best highlights on the Road to Hana with its spectacular panoramic views. This super scenic, winding drive is also referred to as Heavenly Hana - aptly nicknamed for good reason! Hana Highway brims with an estimated 600 curves & 54 bridges, epic ocean views, towering cliffs & waterfalls, lush valleys, a unique black sand beach, the beautiful Pipiwai Trail (bamboo forest hike), and the picturesque & peaceful Oheo Gulch also known as the Seven Sacred Pools. Along the way, we’ll discover some of the best foodie stops in all of Maui including Aunt Sandy’s warm banana bread and shaved ice. Don’t worry, we’ll burn those calories with a 2-mile hike to 200-foot Waimoku Falls! So many options for cuisine and hikes along the way! This will be an all-day excursion with many stops including dinner. (No meals included in price this day as we’ll be eating our way back to Camp wherever we feel like). This will be a longer day on the road, returning to camp in the evening for rest and relaxation.

Sun, Nov 4 Day 4. Hike Haleakalā National Park and Crater (Upcountry Maui)

Hiking Haleakala National Park and Crater. We’ll head out for Haleakala National Park around 7:00am. This National Park is considered a rare and sacred landscape - some say it looks like Mars! We’ll take the Trail called Sliding Sands into the Haleakala Crater. It’s a 12-mile hike with strenuous elevation, but we can shorten it based on the group's fitness level. Start increasing your stair climber level now. :) At a minimum, we’ll be hiking 6 miles of the trail. You will need several layers of clothing for temps ranging between 40-85 degrees, daypack, hydration with capacity of 3-4 liters, comfortable hiking shoes, and the “10 essentials” for each hiker. This will be another jam packed day of super fun adventure arriving back to camp late with dinner catered by Three’s Catering Food Truck. [L,D]

Mon, Nov 5 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 the farm includes harvesting your meal followed by a gourmet lunch prepared by Chef Daniel Eskelsen. We welcome you to relax into the afternoon and sip some fresh roasted Maui coffee with us. BYOB. After an amazing lunch we will hit the shops of Lahaina. We’ll end the day with some more tasty eats in town - perhaps a fish shack or other yummy stop. [B,L]

Tue, Nov 6 Day 6. Makena Beach and Sunset Cruise (South Maui)

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 top off the evening and the week with a 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 our 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]

Wed, Nov 7 Day 7. 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.

*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 (double occupancy)

● 6 excursions

-Snorkeling excursion including continental breakfast & BBQ

-Road to Hana day trip

-Hiking Haleakala National Park & Crater

-O’o Farm Tour and Luncheon

-Makena Beach outing

-Sunset Sailing Cruise

● 4 Continental breakfast meal at camp Olawalu

● 3 Lunches

● 4 Dinners includes heavy appetizers during sunset cruise

● NOLS Certified Hiking leader

● Park entrance fees

● Extra snacks, refreshments, ice, paper products & cups


● Airfare

● Any meals or beverages not mentioned above

● Gratuities/Tips

● Souvenirs

Early Bird Pricing (double occupancy): $1,488 (plus airfare) - book by May 31, 2018

Regular Pricing (double occupancy): $1,588 (plus airfare) - book by July 23, 2018

Single Supplement: $652

Deposit: 30% ($446.40) 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: November 1-7 2018

Total Days: 6 nights / 7 days

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


Travel Days: November 1 and November 7

Arrival Day: Afternoon/evening on Thursday November 1st.

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 7th.

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!"