Maui & Lanai Family Multi-Adventure Tour – Older Teens & 20s


A Two-Island Adventure in Hawaii

From $4,298 - $6,198 pp dbl. occ. | 5 days / 4 nights

(+$1,260 to $2,060 for sgl. occ.)

Slow down and embrace island living. Let sea turtles set the pace as you snorkel alongside them. Relax on a beach under palm trees. The only rush is the one you'll get from seeing a pod of dolphins from your kayak. Or from feeling the wind on your face as you bike coastal roads. There's no need to hurry on Maui and Lanai, but your family will want to dive right in.   

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Start Kaanapali, Maui / End Lanai, Lahaina or Kahului, Maui

Maui and Lanai multisport tour map


  • Pedal along the west coast and through the up-country, passing charming villages with incredible ocean views
  • Hike stunning coastal trails on Lanai and learn about ancient Hawaiian traditions, many of which carry on today
  • Paddle and snorkel in Makena Bay, looking for sea turtles, sea urchins and schools of colorful fish
  • Experience the beauty and diversity of two dynamic and dramatically beautiful islands by land and sea

Start Kaanapali, Maui / End Lanai, Lahaina or Kahului, Maui

Maui and Lanai multisport tour map


Days 1-2 Bike to Nakalele Point and watch for the impressive “blowhole” created by the combination of high tide and powerful surf beneath the rocks | Enjoy fresh fruit under palm trees by the beach | Pedal along the coast of West Maui, keeping your eyes open for whales | Spin along routes with stunning views of the West Maui Mountains and coastline | Explore the villages of Makawao and Paia | Savor fresh local flavors with farm-to-table fare.

Day 3 Watch for dolphins as you kayak through the pristine waters of Makena Bay | Snorkel with parrot fish and sea turtles near a colorful reef | Visit Lahaina, a charming island town with great shops and delicious shaved ice | Ferry to Lanai, the smallest inhabited island in Hawaii | Options abound at our splendid hotel—swim or snorkel at Hulopoe Beach, treat yourself at the spa or luxuriate poolside.

Days 4-5 Walk on the blissful Koloiki Ridge Trail amid guava and eucalyptus trees as you enjoy panoramic vistas of Maui, Molokai and the Pacific Ocean | Delve into the ancient traditions and plantation-era history at the Lanai Culture & Heritage Center | On our last morning, sleep in or greet the day with a scenic walk along the coast.

The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.

Please click on a date below for specific pricing and possible itinerary variations.

  • Available
    to Book
  • Going
  • Contact
  • Private Trip
    – Reserved

F Family Dates - Older Teens & 20s

2019 June
2019 July

View Private Dates

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities. You can pick from a large selection of dates for your group of 8 or more. Call us for date availability. If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

2018 Private Trip Pricing
  • 10 or more guests: from $4,298 pp dbl occ
  • 8 - 9 guests: from $4,798 pp dbl occ
2019 Private Trip Pricing
  • 10 or more guests: from $4,298 pp dbl occ
  • 8 - 9 guests: from $4,798 pp dbl occ
  • 6 - 7 guests: from $6,998 pp dbl occ
  • 4 - 5 guests: from $8,498 pp dbl occ
  • 2 - 3 guests: from $9,398 pp dbl occ

Please click on a date below for specific pricing and possible itinerary variations.

Don't see your ideal travel date? Make a Date

    for 8 or more guests
    for 16 or more guests
  • Reserved

F Family Tours - Older Teens & 20s

2018 December
2019 June
2019 July

View Scheduled Dates

The sky’s the limit! Tell us what your dream trip would be and we'll make it happen! Whether you're looking for a honeymoon trip for 2, a 30-person family reunion or a 100-person corporate trip, we can do it all. A dedicated Custom Trip Consultant will work closely with you to bring your dreams to reality. Call us at 800-462-2848 to speak with your Custom Trip Consultant or click on the button below.



F Family Tours - Older Teens & 20s


From $4,298 - $6,198 pp dbl. occ.
5 days / 4 nights

(+$1,260 to $2,060 for sgl. occ.)

Traveling with Kids

Premiere Hotels

Hotel Wailea
Hotel Wailea

Wailea (2 nights)

Four Seasons Resort at Manele Bay
Four Seasons Resort Lanai

Manele Bay (2 nights)

Activity Level

This trip is rated Levels 1-3

What's Included

Services and equipment are included.

Why Backroads

Why Travel with Backroads in

More On This Trip

Reviews by Power Reviews ®

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Premiere Hotels

Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the View Scheduled Dates or Private Dates tabs.

Hotel Wailea

Hotel Wailea

Wailea (2 nights)

Savor panoramic views of islands and ocean at this intimate luxurious hotel, nestled on 15 acres of Zen-inspired grounds with tropical gardens and waterfalls.  A Relais & Châteaux member. (pool)

Four Seasons Resort at Manele Bay

Four Seasons Resort Lanai

Manele Bay (2 nights)

This sumptuous resort is set on the south coast of Lanai overlooking gorgeous Hulopoe Beach and surrounded by lush gardens, koi-filled ponds, waterfalls and exquisite Polynesian artifacts. (pool, spa)

This Trip Is Rated Levels 1-3

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.

Daily Route Options (drag to see full )

Daily Route Options
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 Biking 7* 700 15* 1200 31* 1700
2 Biking 15* 500 25 700
3 Walking/Hiking 3 600
Kayaking Makena Bay Paddle & Snorkel (2.5 Hours)
4 Walking/Hiking 3* 500 5* 1000
Other Optional Afternoon Activities (golf, paddleboarding, snorkeling)
5 Walking/Hiking 3 200

Note: The hiking terrain includes forest trails, coastal paths of lava rock and sand and unpaved country roads. The biking routes follow rolling paved country and coastal roads.

* Includes shuttle.

Learn more about how we determine our activity level and fully support a range of abilities and interests.

Please note that our distance and elevation figures come from Ride with GPS. Other sources (such as Map My Ride and Garmin devices) may give differing elevation figures due to different GPS and mapping technologies. Readings from a Garmin or a smart phone are influenced by other factors such as air pressure.


All breakfasts, 3 lunches, 3 dinners

Available Bike Options

The key to a stellar day’s ride is a bike that’s perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Read on for your available bike options for this trip.

Backroads Titanium Bikes (Included in your trip price)

Our custom-built titanium bikes are specially designed for you—and we offer different models for varied terrain so your bike is ideally suited to the region. Our custom-made bikes are included in your trip price.

Touring Bike (Included)

Burley Kazoo trailer bike (Included in your trip price)

The Burley Kazoo trailer bike, for children up to 85 pounds, attaches to an adult bike with your child providing some of the pedal power for a real team effort! It's ideal for kids who may be comfortable pedaling around the neighborhood but aren't yet ready for bike touring.

Burley Kazoo trailer bike

Burley Cub trailer (Included)

Burley Cub trailer (Included in your trip price)

The Burley Cub trailer, for one or two children 60 pounds and under, is sturdy carrier that attaches to our bikes. It provides a comfortable and safe ride in the spacious interior with inner pockets for snacks and drinks, a reclining seat with a secure five point padded harness system and an adjustable sunscreen.

Burley Cub trailer

Burley Cub trailer

Also Included

  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Get the Straight Talk about This Trip

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.