Lahaina Sailing Tours | Things To Do

Sailing

West Maui Sailing Tours

If you love spending time on Maui’s beautiful waters, there’s no better excursion than one of the Lahaina sailing tours. Whether you opt for a sunset sail, trade wind sail, or adventure sail (like whale watching or snorkeling), catamaran excursions are a great way to experience thrill and excitement during your stay in our Napili Bay accommodations.

Sailing Maui

Sailing Maui is home to two of Maui’s favorite sailing catamarans, the Hula Girl and the Shangri-La. With daily excursions and custom charters, this company offers many options for the perfect adventure.

Teralani Sailing Adventures

Teralani has options for snorkel trips, sunset sails, whale watching, private charters and many additional on-the-water activities, with catamarans departing nearby right in Whalers Village on Kaanapali Beach.

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What our guests are saying…

					We recently spent a wonderful six days at Hale Napili on Napili Bay in Maui, and from the moment we arrived, we knew we had found our new "happy place." We stayed in a comfortable one-bedroom, upper-floor condo that offered a magnificent sunset view from our beautiful balcony.

The location is a hidden gem. The apartment is perfectly situated within a protected, calm bay, which made our dream of being able to swim at any time of day come true—exactly what we had hoped for on our first trip to Hawaii. The lawn is manicured and lined with palm trees, a serene spot just steps from the sandy beach where we spent hours chilling and watching the whales from our front yard and balcony. A major bonus was seeing sea turtles swimming peacefully around the coral reefs!

The condo itself was very comfortable and well-equipped, with clean, new kitchen amenities. We truly appreciated the complimentary beach gear (towels, chairs, umbrella, floats, and noodles), which added significant value to our stay.

The small, private nature of Hale Napili is a major draw. With fewer than 20 rooms and an elevated lawn area, it feels exclusive, ensuring a lounge chair is always available. The digital key access made everything seamless, and the manager, Jamie, was incredibly kind and accommodating, ensuring all our needs were met—her excellent service instantly made us repeat customers. We quickly realized why every other guest we met had been returning for years: Hale Napili truly is the best-kept secret in all of Maui.

We loved the peaceful atmosphere and the politeness of the other guests. We plan to return to Hale Napili at every opportunity!				
Esra B.
1/21/2026
					We've stayed at Hale Napili three years in a row and love it.  And, we are still newbies - some of our neighbors during our visits have been coming for 15 years and more.  That in itself is almost enough to know about Hale Napili.  However.....some further detail:



This is a boutique 18 unit condo/resort.  Its a fantastic setting with its front lawn elevated privacy and fantastic ocean views while merely a set of stairs down to the Napili Bay beach.  Napili Bay is somthing out of a 1950's movie setting - not a high rise in sight.



The facility, grounds and staff service are something out of a Ritz or Four Seasons but small and intimate.  Jamie, a third generation part of the team manages Hale Napili with huge Hawaiian aloha.



A 2 minute walk takes you to the terrific Island Vibes cafe for breakfasts and lunches.  We have learned to get by without a rental car.  A seven minute public bus takes you to the Island Center Market and their fresh made, daily Poke takeout selection.



Hale Napili is a place to relax, chill and unwind without failing to mention fantastic sunsets.  Highly recommend.				
Chris F.
1/21/2026
					Our New Happy Place We recently spent a wonderful six days at Hale Napili on Napili Bay in Maui, and from the moment we arrived, we knew we had found our new "happy place." We stayed in a comfortable one-bedroom, upper-floor condo that offered a magnificent sunset view from our beautiful balcony.

The location is a hidden gem. The apartment is perfectly situated within a protected, calm bay, which made our dream of being able to swim at any time of day come true—exactly what we had hoped for on our first trip to Hawaii. The lawn is manicured and lined with palm trees, a serene spot just steps from the sandy beach where we spent hours chilling and watching the whales from our front yard and balcony. A major bonus was seeing sea turtles swimming peacefully around the coral reefs!

The condo itself was very comfortable and well-equipped, with clean, new kitchen amenities. We truly appreciated the complimentary beach gear (towels, chairs, umbrella, floats, and noodles), which added significant value to our stay.

The small, private nature of Hale Napili is a major draw. With fewer than 20 rooms and an elevated lawn area, it feels exclusive, ensuring a lounge chair is always available. The digital key access made everything seamless, and the manager, Jamie, was incredibly kind and accommodating, ensuring all our needs were met—her excellent service instantly made us repeat customers. We quickly realized why every other guest we met had been returning for years: Hale Napili truly is the best-kept secret in all of Maui.

We loved the peaceful atmosphere and the politeness of the other guests. We plan to return to Hale Napili at every opportunity!				
529esrab
1/21/2026
					Great staff/service, complete facilities (except pool), location is a bit far from the airport but we braved the almost 1.5hr back to the airport and honestly, it wasn't that bad - it's quite empty coming from North. Few options for restaurants so it's a good opportunity to cook!



We'll come back here and book a car rental for sure.				
Chris I.
1/03/2026
					One of the best places I ever been . Such a lovely vibe and well maintained appartments.				
Karin J.
12/26/2025
					Amazing family stay at Hale Napili We had an amazing stay at Hale Napili. The location is fantastic, nothing beats the views. The apartment had everything that’s needed for a relaxed stay. The kitchen is fully equiped. We will definitely book Hale Napili again on our next stay at Maui				
W89AJfrankv
12/26/2025
					Our family of 9 rented 3 rooms over Thanksgiving. 3 couples and 3 grandsons ages 16, 14, 9. We all had a fabulous time. This is our third time staying here. Snorkeling was great and we all had a blast swimming, relaxing, eating at our units and using the BBQs. We will return again to relax in Paradise. There are also restaurants and snack stands and a market all within walking distance. Highly recommend staying here.				
Rich
12/08/2025
					We have been going to the Hale Napili for years and it never gets old. The location is divine, the views spectacular, the grounds are lush, beautiful and well kept, and the rooms are comfortable and clean, but the best part is the staff who are so professional but kind and accommdating. Steps from one of the best beaches on the island, .5 a mile from great restaurants and a market. Close but far enough away from it all. We will never stay anywhere else and are already planning our next visit. Mahalo Jamie et al!				
Nicole P.
9/06/2025

Bravo!

Hale Napili rated “excellent” by 99 travelers

Sailing

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West Maui Sailing Tours

Sailing Maui

Teralani Sailing Adventures

What our guests are saying…