Best Hawaii Sunset Cruises: Romantic Sails on Every Island
There's something magical about watching the Hawaiian sun sink into the Pacific from the deck of a boat. Dolphins often make appearances, whales breach in winter months, and the sky puts on a show that photos can't capture.
Here are the best sunset sails across Hawaii—whether you want an intimate catamaran, a party boat, or a romantic dinner cruise.
Maui Sunset Cruises
Maui's west coast faces directly into the sunset, making it prime territory. December-April, you'll likely see humpback whales as a bonus.
🌅 Premium Sunset Dinner Cruise
Four-course dinner, premium bar, live music. Departs from Ma'alaea Harbor. The most upscale sunset experience on Maui.
Duration: 2.5 hours • Includes: Dinner + open bar
View Maui Tours →⛵ Haleakala Sunset Tour
Not a boat—but worth mentioning. Watch sunset from 10,000 feet at the summit of Haleakala volcano. Otherworldly experience, requires reservations.
View Maui Tours →Oahu Sunset Cruises
Waikiki departures put Diamond Head and the Honolulu skyline behind you as the sun sets. Easy access from most hotels.
🍹 Waikiki Sunset Sail
Budget-friendly catamaran cruise with included drinks. Casual vibe, great for groups. Often spot dolphins and turtles.
Duration: 2 hours • Departs: Waikiki Beach
View Oahu Tours →Kauai Sunset Cruises
Na Pali Coast sunsets are legendary—the cliffs turn gold and pink as the sun drops.
🌺 Na Pali Sunset Sail
Combine Na Pali Coast sightseeing with golden hour. Dinner included. One of Hawaii's most scenic sunset experiences.
Duration: 4.5 hours • Operator: Holo Holo Charters
View Kauai Tours →What to Expect
- Duration: Most cruises are 2-3 hours
- Drinks: Usually included (check what's premium vs. house)
- Food: Ranges from pupus (appetizers) to full dinners
- Seasickness: Catamarans are stable; take Dramamine if sensitive
- What to bring: Light jacket (ocean breeze), camera, cash for tips
Romantic Options
For couples celebrating anniversaries or honeymoons, look for:
- Private or semi-private charters
- Dinner cruises with assigned seating
- Smaller boats (under 30 passengers)
- Cruises with live music