Services

Windsurfing Rentals
  1. Limited Edition Windsurfing Rental Package

    We offer the Limited Edition Rental Package for discerning sailors who want to ride only the best! Enjoy the best conditions in the world on the best rental gear in the world!

    Ride the latest 2014 Limited Edition Fanatic or RRD boards, the latest Maui Sail or Ezzy sail on a full carbon boom and mast. You'd have to be a pro windsurfer to get gear this good! The best gear on Maui at the best rates!

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    Limited Edition Windsurfing Rental Package

    Starting From $70.00

  2. Premium Windsurfing Rental Package
    We offer the Premium Rental Package for sailors who want great gear that performs like they want and can hold up to any of Maui's rough conditions, at an affordable rate. Ride the latest 2014 X-Tech RRD or Fanatic FSW boards, the latest Maui Sail or Ezzy sail on a full carbon mast and aluminum boom. The best gear on Maui at the best rates! Learn More

    Premium Windsurfing Rental Package

    Starting From $55.00

  3. Racing Gear Package
    We are the first shop on Maui that rents full racing gear! Adrenaline junkies get in line! Ride the latest 2014 Limited Edition RRD boards, the latest Maui Sail TR-X or TR-9 on a full carbon boom and mast. You'd have to be a pro racer to get gear this good! Reserve on-line and receive our special pre-book discounted rate. The best gear on Maui at the best rates! Learn More

    Racing Gear Package

    Starting From $85.00

Kiteboarding Rentals
  1. Kiteboard Wave Package
    Are you ready to test your wave riding skills on the best waves on Maui? Then use the best gear on Maui! Rent our 2014 North Rebel, Dice or Neo or 2014 Ozone Reo , or all new for 2014 Ben Wilson Surf kites. Match with a North WAM or Jimmy Lewis Shack wave board, and start ripping! Includes one kite and board - unlimited exchanges. Rip it up! Learn More

    Kiteboard Wave Package

    Starting From $85.00

  2. Kiteboard Freestyle Package
    Ride some of the best big air, big trick freestyle gear on the market today! Ride the 2014 North Vegas or 2014 Ozone Catalyst kite, in conjunction with a North or Underground twin-tip board and have the time of your life! Rate includes one kite - with unlimited exchanges - plus board and harness. Learn More

    Kiteboard Freestyle Package

    Starting From $85.00

SUP Rentals
  1. Surfing Stand-Up Paddleboard Rentals
    When on Maui why not try a day or more of the newest sport to hit the water - stand-up paddling! Try one of our super easy Elua Makani Big Mac boards, or go tear up the surf on an Elua Makani Surf Swallow. Rate includes 24 hour rental with board and paddle, plus roof racks (if needed). Learn More

    Surfing Stand-Up Paddleboard Rentals

    Starting From $35.00

  2. S.I.C. Raceboard Rentals
    Try the latest sports sensation on Maui - the downwind SUP run from Maliko Gulch to Kahului Harbor - on the boards that were built just for the fastest, most exciting runs imaginable. Feel the glide on the S.I.C. Bullet Series boards as you fly down the coast as many times as you can in one day. TheF-16 and F-17 boards require some skill because of the ASS (adjustable steering system) rudder, but these boards do it better than anything else on the water. Or try the easier F-14 without ASS if you just want to cruise! Book early, especially for weekends and race days, as these are a favorites with Maui locals and racers alike. Learn More

    S.I.C. Raceboard Rentals

    Starting From $55.00

Surfing Rentals
  1. Shortboard Rentals
    We have a great selection of Elua Makani and Surftech shortboards available to rent on a daily or weekly basis. Unlimited exchanges, so try a different board any day as conditions change. Great selection of great boards! Roof rack included (if needed). Learn More

    Shortboard Rentals

    Starting From $20.00

  2. Longboard Rentals
    We also have a great selection of longboards from Elua Makani and Surftech. Whether you're riding big Kanaha, or heading to the south shore, we have the ideal board for you! Learn More

    Longboard Rentals

    Starting From $25.00

Lessons
  1. Windsurfing Lessons
    Whether you are a beginner learning for the first time, or an expert wanting to fine-tune your skills, we have an instructor and lesson plan ready for you! Choose any of our lesson plans and become the windsurfer you always wanted to be tomorrow! Learn More

    Windsurfing Lessons

    Starting From $89.00

  2. Kiteboarding Lessons
    Learn to kite in Maui's beautiful warm waters and steady winds. Whether you are a first-time beginner or an advanced rider looking to sharpen your skills, we have an instructor and lesson package that will help you kite your best! Learn on the best North gear, or rent our gear at special rates to round out the perfect lesson! Learn More

    Kiteboarding Lessons

    Starting From $89.00

  3. Surfing Lessons Maui
    Learning to surf is one of the best ways to enjoy Maui's beautiful ocean waters! What could be better than some fun in the sun and exercise while learning the sport of Hawaiian royalty! Learn to surf on Maui! Learn More

    Surfing Lessons

    Starting From $89.00

  4. Stand Up Paddle Lessons Maui | Maui Stand Up Paddle Board Lesson
    Learning to stand-up paddle is easy - but, anything is easier and safer with proper instruction, so we do recommend stand-up paddling lessons for beginners, or if you are going into the surf for the first time. We do also recommend an instructor to accompany you if you are doing the Maliko-Kahului coast run for the first time. Learn to SUP with Maui's best instructors! Learn More

    Stand-Up Paddling Lessons

    Starting From $89.00

Vacations
  1. Maui Vacation Packages

    We can make all your travel plans for you in one all-inclusive package that can include accommodations in some of Maui's most beautiful homes, with vehicle appropriate for your needs, and gear rental. We can even book special events like weddings or promotional events. Book any or all your vacation needs with one call or e-mail to Second Wind today!

    We can also book other Maui activities - whale watches, zip lines, cycling, horseback riding - anything you want as part of your all-inclusive package. The perfect Maui vacation is only one phone call away!

    Book and all-inclusive accommodation/car/gear package and receive our VIP card for 10% off everything in our store!


    Please visit our vacation rental agency:
    ** MAUI CONNECTIONS

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    Vacation Packages

    Starting From $0.00