Sunset Sailing Cruises with Makena Coast Charters in Wailuku
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required for this seated cruise.
Overview
Set sail aboard Makena Coast Charters’ Winona for an unforgettable Hawaiian sunset cruise featuring whale watching, open bar hospitality, and stunning coastal views off Wailuku, Maui.
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
Check-in: 30 minutes before your activity start time
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Adventure Photos
About This Adventure
Embark on a memorable Sunset Sailing Cruise aboard the charming Hawaiian catamaran "Winona," where you'll enjoy Aloha hospitality, delicious appetizers, and an open bar. Experience the thrill of whale watching and hear inspiring stories from the crew as you sail through the beautiful Pacific waters, supporting Maui's recovery.
About
Treat yourself and your loved ones to experience a beautiful Sunset Sailing Cruise and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamaran. “Winona” is the only Hawaiian-built, well-kept & spacious catamaran where you’ll experience true Aloha hospitality. Our floating Tiki Bar serves Hawaiian pu pu's, offering an open bar (Locally brewed beer, seltzers, Hawaiian cocktails), refreshment drinks, and much more.
Our boat is a barefoot vessel. We kindly ask that you wear footwear that’s easy to slip off—or simply go barefoot—while on board.
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our captain and crew on a heartfelt journey across the beautiful Pacific waters. They've faced immense challenges and are eager to share their stories of hope and perseverance with you. Lovely atmosphere and awesome photo opportunities! - The chance to see spinner dolphins, whales, and other sea life while we're out!
By booking this tour, you're not only treating yourself to an unforgettable adventure but also supporting our dedicated local team as we navigate through these tough times. Your presence helps us keep Winona sailing and aids in the recovery of those who call Maui home. Come be a part of our story and create lasting memories while making a meaningful difference in supporting our local small business and end a day in Maui on a high note.
Your Itinerary:
Check-In
- September 1st through February 28th check-in time: 4:00 p.m., departure time: 4:30 pm, return time: 6:30 pm
- March 1st through August 31st check-in time: 4:30 pm, departure time: 5:00 pm, return 7:00 pm
- Maalaea Harbor, address: 233 Maalaea Rd. Wailuku, HI 96796 vessel name "Winona" Sail Catamaran - Makena Coast Charters.
- All guests sign in and complete the liability waiver.
- Our boat is a barefoot vessel. We kindly ask that you wear footwear that’s easy to slip off—or simply go barefoot—while on board.
What’s included:
- Appetizers
- Open bar (beers/seltzers/cocktails)
- Soft Drinks, juice, water
- Island-Style Music
- Experienced Captain and Crew
- Whale watching (December – April)
- Sailing experience to and from locations
- Two restrooms on board
What's excluded
- Hotel Pick-Up and Drop-Off
- Parking Validation (see below)
What to bring with you:
- A light jacket or shawl
- For infants 0-6 months old parents must bring a coast guard approved life vest
- Cash gratuities for crew
Parking
- Ma’alaea Harbor is $1 per hour; we recommend paying for 3 hours total. This parking lot uses a QR code payment system. Arrive early to pay via the QR code (you will need to know your license plate number). Please be aware of where you are parking and follow the parking instructions found on the parking signs. We are not responsible for cars that get towed.
Adventure Tips
Arrive Early for Best Seating
Boarding early ensures you get a prime spot on deck for unobstructed views during the sunset and whale sightings.
Bring a Light Jacket
Evenings on the water can get breezy, so pack a windbreaker or light jacket to stay comfortable as the sun sets.
Motion Sickness Precautions
If you are prone to seasickness, consider taking preventative measures before boarding, as ocean swell can vary.
Respect Wildlife Viewing Distance
Maintain respectful distance to humpbacks and dolphins; the crew ensures adherence to marine protection guidelines.
Local Insights
Wildlife
- Humpback whales migrating off Maui’s coast
- Spinner dolphins frequently spotted nearshore
History
Maui’s waters have long been revered in Hawaiian culture as a place of both sustenance and spirituality, with whale migration intertwined with local traditions.
Conservation
Makena Coast Charters actively promotes responsible wildlife viewing practices to protect marine life and supports Mauis ongoing coral reef and habitat restoration efforts.
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Adventure Hotspots in Kahului
Frequently Asked Questions
Recommended Gear
Windbreaker or Light Jacket
Protects against cool ocean breezes as the sun sets.
fall|winter|spring specific
Sunglasses
Reduces glare off the water during afternoon sailing.
summer|null specific
Motion Sickness Medication
Helpful for those susceptible to seasickness on open water.
Camera or Smartphone
Capture vivid sunsets, whales, and island coastline.