line The Very Best Wailea Vacation line

With a lot of long hours in the field (our job is rough), we have put together a list of what we consider to be the very best of the experiences to be had on Maui. The list is ever-expanding though, so let us know if there is something new you’d like to try!

Maui Kitesurfing


From the shoreline, it is an elegant dance of vibrantly colored kites over the water. From the water, it’s the feeling of the wind pulling you across the open ocean with all the speed of wake-boarding and all the freedom of paragliding.

For the memories of a lifetime, Hotel Wailea has brought kiteboarding to your doorstep with its own accredited academy. Through one-on-one instruction, our passionate instructors will unlock the secrets of this exhilarating sport and help you fine-tune your skills to harness the power of the wind and glide gracefully across Maui waters.

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What we like:

  • Instructors are extremely knowledgeable and are able pinpoint exactly what technique(s) and specific detail(s) to correct in order to get you riding.
  • One-on-one instruction allows you to learn at your own pace
  • Instructors translate their passion and keep you improving and advancing.
  • Learn with the best and latest equipment.

What to wear:

  • Swim suit, rash guard and board shorts
  • Sunscreen
  • Sunglasses recommended – best with a strap so you don’t lose them in the water


Meet at Kiteboarding School of Maui, Inc. located at Adventure Sports Maui.

400 Hana Highway
Kahalui, HI 96732

One-on-one lesson with your instructor will take place at Kanaha Beach, also known as Kite Beach.


  • Washrooms available at meeting location
  • Porta potties at Kanaha Beach

Know Before You Go:

  • With the many complexities involved in kiteboarding, proper instruction and practice are essential in order to become an independent rider and always remain safe.
  • Upon arrival at the beach, your instructor will outfit you with all proper gear including harness, life-vest and a helmet.
  • To get the most fulfilling experience it is best to plan for several days of lessons.
  • Instructors are usually booked two weeks in advance, so to ensure a spot, it’s best to plan ahead.
  • Most desirable weather conditions on Maui generally occur April through October.

Rates/Additional Choices:
Starting at $80/hr
Pricing for lessons is dependent on length and level of lessons. Build your package you way you want it.

For skilled kiteboarders: KSMaui offers advanced lessons, and has a variety of top brand equipment available to rent or purchase.

Hotel Wailea Experiences


The X’s are marked and the map to Maui’s best hidden beaches is in your hands. Seek out the most pristine waters, optimum snorkeling, colorful sunsets, extreme kiteboarders, beaching turtles and more.

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Included in your package:

  • Curated map of Maui’s most interesting beaches
  • Gourmet picnic basket lunch
  • Hotel Wailea sarong

How to book:

You are welcome to add the Island Beach Safari to your stay at any time. We do ask that you let us know by 5pm the day before you’d like to safari, so that we can prepare your picnic lunch.

By Email: guestservices@hotelwailea.com
By Phone: 1-808-874-0500



Kai Kanani Hotel Wailea Cocktail Cruise


Pull your toes from the sand (only temporarily of course) and place them upon the deck of the Kai Kanani for an unforgettable evening experience.

Toast the sunset with a glass of champagne or cheers with a Mai Tai, local beer or your favorite selection from the premium open bar.

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What we like:

  • An authentic nautical experience, the boat sets sail directly from the beach. Shoes are left on the sand (in the expert care of Kai Kanani staff) and the cruise is all barefoot luxury.
  • During the sail, your choice is to mingle…or not to mingle, but definitely nibble. Enjoy a wide array of fresh and local appetizers.
  • There is plenty of space and time to move around the catamaran and enjoy the views from inside the cabin or on the breezy deck.
  • There is a good chance of whale sightings during the winter season December to April.
  • The Kai Kanani staff is very charming and cater to your every need, leaving you to simply relax and enjoy the food, the drink and the setting sun.

What to wear:

  • Your favorite sailing attire or beach wear that can get wet up to your knees or lower thighs.
  • Short, flowy dresses are not recommended for ladies since it often is windy while sailing.
  • A light cover-up is recommended if you get chilly.


The Kai Kanani departs from the beach fronting Makena Beach & Gold Resort Wailea, Maui.

5400 Makena Alanui, Makena, Maui.

  • Complimentary valet parking is available
  • Kai Kanani Mercedes Shuttle service is available to & from Hotel Wailea. Please make sure to reserve your spot in advance at (808) 879-7218 since seating is limited.

Know Before You Go:

  • Space is limited, so each sailing is not overly crowded.
  • In the case of inclement weather, your sailing may be rescheduled.
  • A camera is a must!

Rates/Additional Choices:

Starting at $90.00/adult

Ask about the Capische? dining experience on the Kai Kanani (dates vary).

Hawaiian Outrigger Canoe Experience at Hotel Wailea


Among our favorite Maui activities, relive a part of Hawaiian history and walk in the footsteps of the Ali’i in this traditional Hawaiian Outrigger Canoe tour.

Your journey departs beautiful Wailea Beach in South Maui. Wailea in ancient Hawaii meant “Waters of Sacred Happiness”. Come join us for an authentic Hawaiian experience.

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Participate in traditional Hawaiian chants (oli) as you paddle your canoe (hoe wa’a) along the South Coast of Maui, taking in breathtaking views of Haleakala, West Maui Mountains, Lana’i, Kanaloa (Kaho’olawe) and Molokini. Come see the honu and honu’ea (Hawaiian Green Sea & Hawksbill turtles) and learn about the Polynesian Voyagers who sailed the Polynesian Triangle (New Zealand to Rapa Nui to Hawaii) using only celestial wayfinding. In honoring the wisdom and knowledge passed on by generations from our ancestors…we are inspired to share the values and traditions that have sustained our Hawaiian Culture in the past.

When: Every Wednesday, from 8am-9am

Where: Meet at Wailea Beach (Hotel Wailea Beach Club) by 7:50am.

Maximum capacity: 6 people

Reservations: Please be sure to sign-up at the front desk by Tuesday evening at the very latest. Availability is on a first-come-first-served basis.

Cost: Complimentary for Hotel Wailea guests

*If you would like to arrange a separate private tour, our concierge would be happy to arrange it for you. Cost is $60/person.



Let us custom tailor a yoga experience for you in one of Maui’s incredible settings. Whether it is a sunrise session in our tropical gardens or sunset salutations on the beach, practice in your choice of place and time with personal guidance from our talented instructor. Accessible to all skill levels, this is bound to be an unforgettable experience…

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Private Session Rates:

$80 per 1 hour
$105 per 1½ hours
$150 per 2 hours

Group Session Rates (2-4 people):

$110 per 1 hour
$150 per 1 1/2 hour
$200 per 2 hours

Meet your instructor:

Aloha, welcome to yoga at Hotel Wailea!

My name is Erika and I am really looking forward to meeting you on the mat. I have been so fortunate to have been studying the art of yoga since 1998 and hope to share with you how wonderful and uplifting this practice is.

All skill levels are welcome. If this is your first session ever, don’t worry. Your practice will be designed for you whether you are a raw beginner or a skilled practitioner. Take the opportunity to either get back to some basics or move into variations that suit your personal needs. There is something so very wonderful about practicing yoga on this sacred island of Maui, I know you will love it!

Learn more about Erika at: www.lettucedoyoga.com