Maui’s 9 Best Drinking Tours: Which To Choose?

Maui is famous for its stunning coastlines, warm waters, and incredible marine life — but it’s also a fantastic place to enjoy a drink or two while soaking in the scenery.

Whether you’re looking for a laid-back sunset sail, a lively whale-watching cruise with unlimited drinks, or a visit to a local brewery, Maui offers a variety of drinking tours that combine fun, scenic views, and a taste of island life.

We love the Whale Watching Cruise from Ka’anapali Beach — with a naturalist, open bar, and close-up whale sightings, it’s a perfect blend of activity and relaxation.

Plus, the Original Sunset Cruise with Open Bar from Ka’anapali Beach offers a more classic, sunset-focused experience with the same relaxed vibe. These tours, along with others on our list, give you a great way to enjoy Maui’s waters and flavors.

If you’re wondering whether to spend a day drinking aboard a luxury catamaran or exploring local breweries in a vintage VW bus, our list has options for every style. Each tour offers something different — from whale sightings and snorkeling adventures to romantic sunset sails — so you’re sure to find one that fits your interests and budget.

1. Whale Watching Cruise with Open Bar from Ka’anapali Beach

Set sail into Maui’s winter whale playground on this 2-hour whale-watching cruise departing from Ka’anapali Beach. The tour features a spacious catamaran with plenty of seating, including bean bags on open nets that get you close to the water and the whales.

With the help of a naturalist guide, you’ll learn about humpback whales and their migration habits while enjoying unlimited drinks from an open bar. It’s easy to see why this tour has a perfect 5-star rating based on 720 reviews.

What makes this tour stand out is its combination of accessibility and intimacy — the boat is large enough for comfort but small enough to feel personal.

Guests frequently mention spotting breaching whales just feet from the boat, and the crew’s knowledgeable explanations add an educational touch. The open bar keeps the mood lively, and the two-hour duration hits the sweet spot for a quick but memorable adventure.

Bottom Line: If whale watching in Maui is on your bucket list, this tour offers exceptional value with its all-inclusive drinks, friendly crew, and prime whale sighting opportunities — especially during peak season (December to April).

2. Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

For those who prefer a more refined experience, this luxury sunset cocktail sail offers a 2-hour cruise aboard a state-of-the-art catamaran.

Departing from Ka’anapali Beach, it features an open bar, chef-inspired pupus (appetizers), and breathtaking views of the West Maui Mountains and neighboring islands. The trip is perfect for couples seeking a romantic evening or travelers wanting a chill, scenic escape.

Seasonal whale sightings can sometimes be caught if you’re lucky, but the main focus here is the spectacular sunset. The boat’s luxurious amenities, combined with the relaxed vibe of the open bar, make it stand out as a more upscale option. Guests love the intimate setting and the chance to sip a refreshing drink while watching the sun dip below the horizon.

Bottom Line: This tour appeals to those who want a stylish yet laid-back way to end their day with a drink in hand and Maui’s stunning scenery around them.

3. Maui: Kaanapali Beach 5-hr Snorkel w/ BBQ Lunch & Open Bar

If you’re eager to combine snorkeling, marine life, and drinks, this 5-hour tour is a top choice. The Premier Snorkel Sail departs from Ka’anapali and includes visits to two different snorkel locations based on seasonal conditions, enhancing your chances to see turtles, tropical fish, and perhaps dolphins. The luxury catamaran cruise is comfortable and well-equipped, making it easy to relax between swimming.

Included in the tour is a tropical breakfast, chef-inspired lunch, and an open bar, making it a full-day indulgence. Reviewers highlight the fun of spotting sea turtles and dolphins, and the boat’s experienced crew makes the experience both safe and lively. The 5-hour duration is ideal for travelers wanting a leisurely day of underwater exploration complemented by tasty food and drinks.

Bottom Line: Perfect for snorkel lovers who want a mix of adventure and comfort, this tour offers excellent value for its longer duration and inclusive amenities.

4. Kaanapali: Whale Watching Cruise with Open Bar

Another top whale-watching option, this 2-hour cruise from Kaanapali shares many similarities with its counterpart from Maui, focusing on humpback whale encounters and marine education. The tour takes you into Maui’s prime whale viewing waters, where you’ll get up close and personal with these giant mammals as they breach and play.

What sets this tour apart is the relaxed atmosphere and access to an open bar that makes the experience more festive. The naturalist guides are passionate and eager to share their knowledge about the whales and local marine ecology. With stunning views of Kaanapali Beach and Lahaina, this tour offers both wildlife excitement and scenic beauty in a compact, 2-hour format.

Reviewers emphasize the friendly crew and the thrill of seeing whales breach just nearby, describing it as an “incredible experience.” It’s a great option for travelers who want a shorter tour without sacrificing the chance to see Maui’s magnificent marine life.

Bottom Line: If whale-watching tops your list, this tour combines the thrill of nature with the comfort of an open bar, perfect for a quick but memorable outing.

5. Maui: Kaanapali Beach 4-hour Snorkel w/ BBQ Lunch & Open Bar

Offering a shorter but equally engaging experience, this 4-hour snorkel trip is ideal for travelers who want to explore Maui’s best underwater spots without a full day at sea.

The luxury catamaran takes you along the west coast for snorkeling at prime locations, where you’ll encounter sea turtles, coral reefs, and tropical fish. The tour includes a barbecue lunch and open bar, ensuring you stay refreshed after your aquatic adventures.

Guests report feeling the warm sun on their face while cruising in comfort, with many sightings of dolphins and turtles. The tour strikes a good balance between active snorkeling and relaxing on deck, making it suitable for families or those with limited time. The value lies in the combination of quality snorkeling sites, food, and drinks, all packed into a four-hour window.

Bottom Line: A solid choice for snorkelers wanting to maximize underwater time with a relaxed pace and inclusive refreshments.

6. Maui: 2 Hour Sunset Dinner Sail with Open Bar and Appetizers

This 2-hour sunset dinner sail is perfect for those seeking a peaceful, scenic experience. Departing from Maui’s coast, the catamaran offers ample cushion seating in sun or shade options, making it comfortable for everyone. The tour includes a complimentary bar with vodka, rum, beer, wine, and champagne, plus delicious appetizers to enjoy while watching the sun set over the ocean.

What makes this tour stand out is the focus on the spectacular Maui sunset, with views of the nearby islands and the West Maui Mountains. The wind in your hair and the calm waters create a perfect setting for relaxing and unwinding. Many reviews mention the friendly crew and the quality of the drinks and appetizers.

Bottom Line: Ideal for couples or anyone wanting a romantic, low-key evening with drinks, good food, and breathtaking scenery.

7. Original Sunset Cruise with Open Bar from Ka’anapali Beach

This classic 2-hour sunset cruise is one of the most highly-rated tours, with over 1,193 reviews praising its reliability and ambiance. The “front-row seat” to Maui’s sunset includes cocktails, snacks, and views of Lanai, Molokai, and Kahoolawe. The unlimited drinks from a premium bar make it a lively yet laid-back experience.

The itinerary emphasizes wildlife watching, with chances to see dolphins and whales during winter. Guests love the friendly crew and the quality of the snacks and drinks. It’s a great option if you want a well-rounded, popular sunset cruise with a reputation for satisfying travelers.

Bottom Line: This tour offers excellent value and a dependable experience, especially for those who want to soak in Maui’s iconic sunset with drinks in hand.

8. Brewery and Beach Cruise in a Vintage VW Bus

Looking for something different? This 3-hour vintage VW bus tour takes you to South Maui’s scenic spots, including a visit to Maui Brewing Co for a beer flight and a secret beach. The tour offers a relaxed, nostalgic vibe, with commentary about the island’s local brewing scene and natural beauty.

While the rating is lower (3/5) based on only two reviews, the tour’s appeal lies in its quaint vintage vehicle and the chance to sample Maui’s craft beers while enjoying the island landscape. You’ll also visit a secluded beach where you can unwind and take photos.

The lunch options at the brewery are varied, and the laid-back atmosphere makes it a good choice for those who prefer a more intimate, quirky experience.

Bottom Line: Perfect for those interested in local brews and unique transportation, but check recent reviews for confirmation of quality.

9. 2 Hours Holo Holo Sunset Cocktail Sail with Open Bar

This 2-hour sunset cruise offers a more intimate experience with delightful cocktails and chef-inspired appetizers. Departing from Maui, it provides breathtaking views of the coastline and nearby islands, ideal for couples wanting a romantic evening. The premium open bar includes signature cocktails, wine, and beer, making it a relaxing way to end your day.

The reviews are limited but positive, emphasizing the beautiful scenery and the calm, leisurely pace. It’s less crowded than some larger cruises, making it suitable for those seeking a quieter, more personal experience.

Bottom Line: A good pick for couples or small groups looking to enjoy Maui’s sunset with drinks and light bites in a relaxed setting.

How to Choose the Best Drinking Tour in Maui

When selecting a drinking tour in Maui, consider your interests: Do you want whale watching or a romantic sunset? Are you interested in snorkeling combined with drinks (like this snorkel tour), or do you prefer craft beer (brewery tours)? Budget is also a factor — tours range from around $103 to $183, often including food and drinks. Think about timing: whale season peaks December through April, and sunset cruises are ideal for evening relaxation.

Booking early, especially during peak seasons, ensures you secure a spot. If you’re traveling with kids or prefer a shorter experience, look for tours with a quick but rich experience, like the 2-hour whale watch or the sunset sail.

Final Thoughts

Maui offers a wide variety of drinking tours that combine scenic beauty with refreshing drinks and local experiences. Whether you’re after the excitement of whale watching, a romantic sunset sail, or a craft beer adventure, there’s an option for you.

For families or those pressed for time, shorter tours like the 2-hour whale cruise provide a quick but memorable outing. For a more luxurious vibe, the sunset cocktail sail is hard to beat.

Remember to book early, especially during the busy winter whale season or peak summer months. No matter which tour you choose, you’re sure to enjoy Maui’s stunning scenery, lively atmosphere, and friendly crew. Cheers to a memorable trip!