Celebrate Valentine's Day in Maui (Updated 2026)

Maui, USA
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Maui Activities

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Road To Hana: Maui Waterfall Hiking Tour in Private Jeep
Likely to Sell Out
Likely to Sell Out
4.9 (367)

Road To Hana: Maui Waterfall Hiking Tour in Private Jeep

This jeep, waterfall, bamboo forest, hiking tour on the Maui Hana Highway is unique because they are private! Yup, that's right. Just you and your...

8 hours • Hotel pickup offered
8 hours • Hotel pickup offered
8 hours • Hotel pickup offered
4.9 (367)
from
$349
Full-Circle "Reverse" - Luxury Road to Hana Tour from West Maui
4.8 (96)

Full-Circle "Reverse" - Luxury Road to Hana Tour from West Maui

#1 We go ALL THE WAY AROUND THE MOUNTAIN so you don't see the same thing twice! #2 We do it in REVERSE, the way...

8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
4.8 (96)
from
$349.99
Full-Circle "Reverse" - Luxury Road to Hana Tour from South Maui
4.8 (48)

Full-Circle "Reverse" - Luxury Road to Hana Tour from South Maui

#1 We go ALL THE WAY AROUND THE MOUNTAIN so you don't see the same thing twice! #2 We do it in REVERSE, the way...

8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
4.8 (48)
from
$349.99
Fun Mountain Bike riding on trails in Maui Hawaii!
4.7 (13)

Fun Mountain Bike riding on trails in Maui Hawaii!

Experience Maui Mountain Biking! Maui's finest singletrack adventure. Rides take place in a rarely seen part of Maui's Haleakala slopes. The location is a special,...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (13)
from
$350
Deluxe Halfway to Hana: Private Tour from Kahului
5.0 (199)

Deluxe Halfway to Hana: Private Tour from Kahului

This excursion is completely private! Just you and one of us! Receive undivided attention and the space for an intimate experience. Enrich the journey with...

7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
5.0 (199)
from
$359
Private Haleakala Summit & Stroll from Kahului
Likely to Sell Out
Likely to Sell Out
5.0 (69)

Private Haleakala Summit & Stroll from Kahului

Personalized tours ensure a relaxed and easeful day. Let us handle the logistics, you enjoy the ride. Our private setting supports an intimate experience and...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (69)
from
$359
Hana Rainforest and Haleakala Crater Helicopter Tour
4.9 (144)

Hana Rainforest and Haleakala Crater Helicopter Tour

Take off from the heliport to the North East rim of the Haleakala dormant Volcano Crater, fly over the East Maui rainforest to view the...

45 minutes • Free Cancellation
45 minutes • Free Cancellation
45 minutes • Free Cancellation
4.9 (144)
from
$368
West Maui and Molokai Special 45-Minute Helicopter Tour
4.9 (748)

West Maui and Molokai Special 45-Minute Helicopter Tour

Soar over majestic Maui and Molokai on exclusive 45-minute Maui helicopter tours. Enjoy the deep valleys and craggy ridges of the magnificent West Maui Mountains...

45 minutes • Free Cancellation
45 minutes • Free Cancellation
45 minutes • Free Cancellation
4.9 (748)
from
$368
Luxury Helicopter Experience with Hana Rainforest Landing
Likely to Sell Out
Likely to Sell Out
4.9 (323)

Luxury Helicopter Experience with Hana Rainforest Landing

During this 40-minute flight over the Hana Rainforest with exclusive landing within the Wailua Valley, see popular points of interest such as the Road to...

1 hour 15 minutes
1 hour 15 minutes
1 hour 15 minutes
4.9 (323)
from
$368.72
Private Standup Paddleboard Lesson for Beginners in Kihei
Likely to Sell Out
Likely to Sell Out
4.7 (9)

Private Standup Paddleboard Lesson for Beginners in Kihei

Learn one of the hottest water sports going, Stand Up Paddle Boarding (SUP) in one of the world's premier destinations, Maui . Maui offers unequaled...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (9)
from
$370
Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!
5.0 (587)

Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!

Maui’s ONLY *PRIVATE* Air Tour is Cool Hawaii #1 Ranked Outdoor Activity on Maui! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (587)
from
$380
Maui-PRIVATE-Air Tour: Volcano Lava & Jungle Waterfalls (2-5 Max)
4.9 (47)

Maui-PRIVATE-Air Tour: Volcano Lava & Jungle Waterfalls (2-5 Max)

Enjoy Maui's Only Private Air Tour Plane Made of Metal & with Non-Tinted Panoramic View Windows for Crystal Clear Clarity!  As Seen on HGTV's 'Hawaii Life':...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.9 (47)
from
$380
Small-Group Road to Hana Luxury Tour
Likely to Sell Out
Likely to Sell Out
4.8 (910)

Small-Group Road to Hana Luxury Tour

Travel the famously spectacular Road to Hana in comfort and style on this luxury small-group tour. With a maximum of just up to eight-passengers in...

10 hours • Hotel pickup offered • Free Cancellation
10 hours • Hotel pickup offered • Free Cancellation
10 hours • Hotel pickup offered • Free Cancellation
4.8 (910)
from
$385
Small-Group Luxury Tour: Road to Hana and Ka'eleku Cavern Day Trip
4.9 (91)

Small-Group Luxury Tour: Road to Hana and Ka'eleku Cavern Day Trip

Experience the highlights of the legendary Road to Hana on this small-group day trip. Travel by luxury Limo-Van along the breathtaking Pacific coast and through...

10 hours • Hotel pickup offered • Free Cancellation
10 hours • Hotel pickup offered • Free Cancellation
10 hours • Hotel pickup offered • Free Cancellation
4.9 (91)
from
$385
Deluxe Helicopter Tour of Molokai and Maui
4.9 (334)

Deluxe Helicopter Tour of Molokai and Maui

Discover the beauty of two of the Hawaiian Islands on this scenic helicopter tour from Kahului, Maui. After meeting your pilot, you’ll board the 7-passenger...

55 minutes
55 minutes
55 minutes
4.9 (334)
from
$375.64
2.5-Hour Private Kiteboarding Lessons at Kanaha Beach in Kahului
5.0 (6)

2.5-Hour Private Kiteboarding Lessons at Kanaha Beach in Kahului

Experience a 2.5-hour kiteboarding lesson in Maui by learning the basics from a professional Instructor. Learn how to set up a kite or fly a...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (6)
from
$394.96
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We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity starts.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Hawaii promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same activity, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Hawaii and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased activity into one or more parts sold separately.
  • Cool Hawaii reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Hawaii.

Sorting, ranking, and search results

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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