10 Romantic Experiences in Maui Worth Booking

1.Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

★★★★★★★★★★5.0 · 903 reviews · 2 hours 30 minutes (approx.) · from $166Our pick

Set sail from Ka’anapali Beach on Sea Maui’s 65-foot catamaran for a 2.5-hour sunset cruise with a chef-prepared buffet, full open bar, and seasonal whale watching. Expect indoor and outdoor seating, live music on Wednesdays and Saturdays, and a wet beach boarding if the waves are up.

“Wonderful experience, great staff open bar, nonstop, drinks, Prosecco, and chocolate at the end dinner was amazing and more whales that we could count”

Check availability →Read our full review

2.From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 826 reviews · 2 hours (approx.) · from $139

Sail from Ma’alaea Harbor aboard the Quicksilver for a two-hour sunset dinner cruise. You’ll enjoy prime rib, mahi-mahi, ribs, chicken, or a vegetarian entrée, plus two alcoholic drinks, live island music, table-side service, and views toward Lanai and Lahaina.

“Save your money. The food and boat ride wasn’t worth the $300! The staff was great, but the food wasn’t warm or appealing.”

Check availability →Read our full review

3.Maui Premium Sunset Dinner Cruise & Whale Watch

★★★★★★★★★★4.5 · 504 reviews · 3 hours (approx.) · from $189

Sail from Maalaea Harbor on a sunset whale watch with Pacific Whale Foundation. You’ll enjoy a four-course dinner, alcoholic drinks, live naturalist commentary, and views toward Lana‘i and Moloka‘i. Guides such as Ash and Stevie have been praised for clear, lively talks about whales and ocean care.

“This was an amazing experience. We saw so many whales and the crew was amazing, so educated and helpful!”

Check availability →Read our full review

4.Maui Family and Couple Beach Photo Session

★★★★★★★★★★5.0 · 333 reviews · 1 hour (approx.) · from $99Best value

Meet your photographer at Po‘olenalena Beach for a private, one-hour Maui photo session. Photographers such as Shizen, Sara, Felix, Ian, Brandon, and Nicole guide couples, families, proposals, maternity portraits, and vow renewals through natural and posed shots. You receive 200 to 250 edited images to select from online for purchase.

“Photographer Brandon was awesome so friendly and a great location for our shoot !! Highly recommend .”

Check availability →Read our full review

5.Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

★★★★★★★★★★5.0 · 264 reviews · 1 hour (approx.) · from $420

Fly privately over Maui for about an hour with a pilot-guide such as Steve or Eric, using a headset for clear commentary. See Honolua Bay, Kaanapali, Lahaina, Molokini Crater, Wailea, and Kaho'olawe, then toast the sunset with champagne.

“Great views. Unique approach. Knowledge pilot. This is a once in a lifetime your that is worth the investment”

Check availability →Read our full review

6.From Ma’alaea: Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 218 reviews · 2 hours · from $139

Board the Quicksilver at Maalaea Bay for a two-hour sunset cruise with table-side service, island-style music, two alcoholic drinks, and a three-course dinner. Choose from prime rib, island fish, ribs, chicken, or vegetarian pasta while watching Maui’s coast and neighboring islands from the cabin or upper deck.

“We had obstructed view where we were seated and asked to be moved. Which they did but was told that we would have to share the table, we were a group of 6 and if we had to accommodate others on that table we would have 2 ladies seating with no table. When we asked again, we were finally moved to a suitable area for us. Dinner and dessert were delicious.”

Check availability →Read our full review

7.Private Surf Lesson for Two Near Lahaina

★★★★★★★★★★5.0 · 189 reviews · 1 hour 30 minutes (approx.) · from $145

Meet Rivers to the Sea near Lahaina for a 90-minute lesson built for two people. You’ll practice on land, then work with an instructor such as Sharky, Tanner, Eric, or Kane in the water. Boards, reef shoes, and SPF-50 rash guards are included.

“My two daughters(ages 11,14) took a lesson from instructor Sharky today. It was their first time surfing so we chose to do the small 2 person lesson. The girls got all of his attention unlike some of the bigger group lessons going on around us. The winds have been up so the waves were bigger than expected and my youngest was scared about getting too far out and the size of the waves. Sharky took great care of them and prioritized their safety. They had a great time and both got up on their first attempt. Highly recommend this tour and Sharky.”

Check availability →Read our full review

8.Ka’anapali Luxury Sunset Dinner Sail

★★★★★★★★★★4.8 · 123 reviews · 2h 30m · from $169

Board Teralani’s luxury catamaran from Ka'anapali Beach for a 150-minute sunset dinner sail. Expect a local buffet, open bar, live English-speaking crew, whale and dolphin watching in season, and broad views of the West Maui Mountains. Bring photo ID if you plan to drink.

“This was an awesome experience. Great hosts and delicious food. We were lucky enough to see the whales and they gave us a show. The sunset was beautiful. It was a great memory on our trip. Would highly recommend!!”

Check availability →Read our full review

9.2 Hour Sunset Dinner Sail with Open Bar and Appetizers

★★★★★★★★★★4.7 · 65 reviews · from $149

Board Gemini at Ka’anapali Beach for a two-hour sunset sail with indoor and outdoor seating, island-style barbecue chicken, fried rice, snacks, and an open bar. The crew mixes drinks such as the Gemini Mai Tai, while you watch West Maui’s mountains, Molokai, Lanai, and the setting sun.

“My family and I had a fantastic time on this excursion. It was really easy to meet up at our designated spot in front of the Westin’s Ulu kitchen restaurant. It was not too difficult to get on the boat though it may get a little wet. We had two seniors in our group who had no difficulty getting in the boat plus the crew was super helpful. All throughout the boat ride, the crew kept supplying us with refills of our drinks without us even having to ask. Once again, the service was exceptional. The music playlist was also perfect for cruising the water. The sunset was immaculate throughout…”

Check availability →Read our full review

10.Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

★★★★★★★★★★5.0 · 43 reviews · 2 hours 30 minutes (approx.) · from $289

Spend 2.5 hours aboard Alii Nui’s adults-only catamaran from Maalaea Harbor. Enjoy a five-course dinner, top-shelf open bar, espresso, live sunset views, and roomy deck seating. Captain Bree and Captain Luke have been praised for their warm style, while an onboard photographer offers optional portraits.

“What an amazing luxurious catamaran! Crew was amazing and top notch. From beginning to end, the entire experience was superb! Cannot recommend enough! Adult only was perfect. Drinks were rolling. 5 course meal was well timed. Food was to be expected for a boat trip- but worth it! Nothing beats a sunset view from the water. Best sunset we experienced during our entire trip!”

Check availability →Read our full review