Maui Cruises & Sailing Tours - Page 2

33 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Maui. Our unbiased ratings help you find the perfect experiences for your trip.

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4.54

Maui Sunset Cruise with 4-Course Dinner

From $178

1 provider live

Savor a 4-course meal with local flavors

Sunset cruise

4.53

Maalaea Powerboat Sunset Cruise

From $279

1 provider live

Experience Maui's golden hour

Air-conditioned cabin retreat

4.51

Maui Haleakala Sunset and Stargazing Audio Tour

From $20

1 provider live

Witness breathtaking sunsets

Take the tour when you want

4.49

Maui Sunset Tour with Dinner

From $314

1 provider live

Witness a breathtaking sunset atop Haleakala

Private transportation

4.46

Lahaina Golden Hour Sail and Whale Watch

$100-$107

2 providers combined

Immerse in romantic Maui views at golden hour

Beer, white wine, sparkling wine, and cocktails

4.42

Maui Whale Watching Sail

From $148

1 provider live

Experience the thrill of whale watching

Buffet lunch

4.41

Maui Catamaran Sunset Dinner Sail (Adults-Only)

From $289

1 provider live

Sail into the Maui sunset

Top-shelf open bar featuring signature wines & premium spirits

4.37

Maui Whale Watching Sail & Lunch

From $137

1 provider live

Experience breathtaking whale watching

Underwater hydrophones to hear whale songs

4.36

Maui Canoe Sailing Experience

From $179

1 provider live

Sail the stunning Wailea coast

Bottled water

4.17

Maui Catamaran Sunset Sail

From $159

2 providers combined

Sail into golden hour on a luxury catamaran

Sunset sail on a 65’ luxury catamaran

4.1

Maui Sailing on a Floating Tiki Bar 2 hr

From $119

1 provider live

Sail on a charming Hawaiian catamaran

Two restrooms on board

3.87

Maui Sunset Sail from Ma'alaea Harbor

From $138

1 provider live

Sail into a breathtaking sunset

Appetizers