Home > Kauai > Sunset Sails & Cruises

Kauai Sunset Cruise and Kauai Sunset Sail

Name: Kauai Sunset Sails & Cruises
Brand: Sunset Sails & Cruises
Rating: 4.8 (60 reviews)

The Kauai Sunset Cruise may provide your most romantic evening.

There are 13 tours in this category. Hawaii's Leader in Affordable Activities

Most Popular Tours in this Category

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

Sunset Sails & Cruises Sorted by Specific Tour

Taking a Kauai Sunset Cruise is a peaceful and romantic way to spend an evening.

Of all the island evening activities perhaps the most romantic is the Kauai sunset cruise, sunset sail and cocktail cruises. Kauai is uniquely suited to be a great location to enjoy a romantic sunset sail regardless if you choose to take one that sails along the remarkable Na Pali coastline or choose one that cruises the beautiful South Shore and Poipu coastline. Many cruises are offered at discount pricing.

The Na Pali coastline is certainly a popular destination for a Kauai sunset cruise. This uniquely beautiful and uninhabited setting is one of the most renown coastlines anywhere on the planet. Many of the Hollywood movies you've seen back home have been filmed here and your vantage point from the sea is the only way this coastline can be viewed other than from a Helicopter or Air Tour. The rugged beauty of this area makes it an impossible location for roads of any sort so there are no vehicles producing noise or visual distractions and this makes your sunset cruise all the more special.
The South Shore Poipu Coastline is generally the most calm and tranquil of all Kauai's shoreline throughout most of the year. The small inlets and coves found here provide an interesting perspective when viewed from the sea. A Kauai sunset sail is typically shorter and less expensive than the Na Pali sunset cruises.

A Kauai sunset sail is a good call for any evening of your vacation but perhaps the very best time would be your last evening on the island for a fond farewell.

Norwegian Cruise Line - Pride of America Cruise Ship:

Your Kauai sunset cocktail cruise will not pick you up at the cruise ship pier. Your best bet is to either arrange for a taxi to take you to and from the departure location or to have Tom Barefoot's Tours arrange for a Rent-A-Car shuttle to pick you up at the cruise ship pier. The best timing for most of these Kauai Sunset Tours is going to be on the Thursday of your cruise schedule.

To View Tours Now, jump up page

Checkout Tom's Tips and Insights about Kauai Sunset Sails & Cruises

Tom's Tips - Kauai Sunset Cruise
On most islands in Hawaii there is a clear distinction between what is referred to as a sunset sail and a sunset dinner cruise. Both cruises will usually stay out about 2 hours and the big difference between the two is that the dinner cruises will include dinner and the sunset sails will just offer pupu's or hors d'oeuvres and cocktails. On Kauai, there are some cruises that are sunset cruises and others that are dinner cruises but the distinction between them is not so cut and dry. This is primarily a function of the 'Na Pali Coast'. If you stay south and cruise the Poipu coast the same parameters apply just like on the other islands. You could do a 2 hour sunset cruise or one that includes some more substantial food as well. Because it takes perhaps 4 or even 5 hours to take a cruise from the main port of Port Allen up to Na Pali most people will be wanting to have something to eat as well and hence they provide the full dinner cruise. Other boats will stick to the script of the traditional sunset cruises and provide heavy pupu's as well which for all intents and purposes turns out to be the same thing. Regardless, because the big swells crash along the Na Pali Coastline in the winter months, both types of cruises are 'nixed' during those months and the only game in town will be along the Poipu coastline. Most of these cruises will include some level of food or hors d'oeuvres along with cocktails but we find that these offerings do tend to vary from boat to boat during these winter months.

Do you still have questions about Sunset Sails & Cruises?

Difference Between a Dinner Cruise and a Sunset Sail

Sunset Sails & Cruises Sorted by Company

(8 Reviews, 4.9 Stars)

Blue Dolphin Charters

3 Activity Options

56 foot wide-beam sailing Trimaran, 27' Raft and 63' Catamaran

Blue Dolphin Charters offers spectacular motor sailing cruises to the NaPali Coast of Kauai and to the 'forbidden island' of Niihau. In addition Blue Dolphin also offers whale watches, snorkeling, snuba, dinner cruises, sunset sails and rafting excursions. All emphasis is placed upon customer comfort and its large boats each maintain large walk-in restrooms, fresh water showers and plenty of deck space.
More Info / Buy Now

(8 Reviews, 4.9 Stars)

Kauai Sea Tours

3 Activity Options

24' Rigid Hull Inflatable Rafts, Lucky Lady' 60' Sailing, Power Catamaran

Kauai Sea Tours is a large charter boat company that offers tours off the coast of Kauai and particularly the NaPali Coast with its beautiful 'signature' boat , Lucky Lady. In addition it also provides romantic dinner cruises and whale watches and also has a fleet of specially designed raft boats which are great for exploring caves, snorkeling and racing dolphins.
More Info / Buy Now

(12 Reviews, 4.8 Stars)

Holo-Holo Charters

4 Activity Options

61' and 48' Sailing Catamarans, 38' Raft

Holo Holo Charters offers a variety of boat tours on Kauai on large, powerful and stable catamarans. Tours include beautiful snorkel and dolphin watch excursions to the NaPali Coastline, raft tours of NaPali during the summer months, dinner sunset cruises, whale watching and tours to the forbidden island of Niihau.
More Info / Buy Now

(32 Reviews, 4.8 Stars)

Captain Andy's Expedition

3 Activity Options

55' Sailing Catamaran, 55' Gold Coast Yachts, 30' and 38' RAIV

Captain Andy's Sailing Adventures for years has offered tours to see the spectacular NaPali Coastline of Kauai. Sailing large and luxurious Gold Coast Yacht Sailing Catamarans, Captain Andy's will take you snorkeling and dolphin watching as well as provide romantic dinner and sunset cruises. In addition you can enjoy rafting adventures to the NaPali Coast.
More Info / Buy Now

Recent Reviews

"Leila" Sunset Dinner Sail - Summer - Holo-Holo Charters

Absolutely awesome! Breathtaking views and fantastic crew. Evan Murlin

Akialoa Poipu Sunset Sail - 2 Hour - Captain Andy's Sailing Adventures

We had a lovely trip with on the Akialoa Sunset Sail. Smooth sailing and they even ordered up dolphins to swim in front of the boat. Lynn Gabenski

"Leila" Sunset Dinner Sail - Summer - Holo-Holo Charters

Our Sunset Dinner Sail with Holo Holo was amazing! We are sailors/boaters back on the mainland so.. Britne Field

Akialoa Poipu Sunset Sail - 2 Hour - Captain Andy's Sailing Adventures

Had a great time. My husband got a little naucious after going below and using restroom, other than thst everything was great!! Shay Monson

Na Pali Sunset Dinner Cruise 4 Hour - Blue Dolphin Charters

Our party of four (2 couples) did the NaPali Sunset Dinner Cruise on Thursday May 10, and had an.. Nancy Werner

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Most excellent way to celebrate our anniversary! Captain Claire and crew were superb. Chef Kevin.. Laurie Welch

Lucky Lady-Whale Watch Cocktail Cruise - Kauai Sea Tours

Fantastic experience on the Lucky Lady. Captain Kaua'i does an amazing job. The scenery was.. Bryce Austin

2 Hour South Shore Sunset - Blue Dolphin Charters

Tom helped arrange the blue dolphin sunset your last minute. Captain Chad was very entertaining as.. Anna Cho

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

We had a wonderful experience sailing with Captain Andy. We appreciated the input about what we.. Jean Richardson

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Tom's Barefoot Tours were great to work with and made our booking experience very easy/stress.. Mitch Adams

2 Hour South Shore Sunset - Blue Dolphin Charters

A great meal, excellent, friendly service, lovely sunset.
Karhleen Colling

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

This was a highlight of our trip. The crew was excellent. I would recommend this tour. N Bippert

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Outstanding! Our captain Tony and the crew were fantastic, The chef made a meal you would expect in.. Michael Mann

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Stunning, amazing views of the Napali coast line. Catamaran was very comfortable, staff was very.. Jim Bamberg

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

First--I usually don't write reviews but felt compelled because this trip was so amazing. Food.. Monica Bottoms

"Leila" Sunset Dinner Sail - Summer - Holo-Holo Charters

Such an incredible time ! This sunset cruise was beyond amazing and my husband and I had a blast... Melissa Mckinney

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

Wonderful cruise with a great crew. I would do it again. Adam Stenson

Akialoa NaPali Sunset Dinner Sail - Captain Andy's Sailing Adventures

This tour was perfect for us on our second evening on Kaua'i. Captain Cory along with his crew.. Joel Hough

Akialoa NaPali Sunset Dinner Sail - Captain Andy's Sailing Adventures

We cruised with Captain Sterling on 6/2/17. Other than being sea sick, the cruise was fantastic... Julia Smith

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

One of the best excursions we went on. Loved every minute of it. The staff was over the top.. Celia McKay

Lucky Lady-Na Pali Snorkel Cruise with Sunset Dinner - Kauai Sea Tours

I thought this tour was great! Captain Kauai and his crew really went over the top to make sure.. Kelly Schulte

Lucky Lady-Na Pali Sightsee Sunset Dinner Cruise- Kauai Sea Tours

It was rock 'n' roll on the high seas on Mother's Day - very exciting and the views.. Barbara Murphy

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Excellent ride, view, dinner, and drinks. We had an amazing boat ride, saw a beautiful sunset, and.. Joanne Ross

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

We had a truly marvelous time aboard the Star NaPali Dinner Sunset Sail. The boat was clean and had.. Chris Dixon

Akialoa Poipu Sunset Sail - 2 Hour - Captain Andy's Sailing Adventures

Fun way to end the day and get a great view of the sunset. Its very relaxing! This was our second.. Colleen Weyrens

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Great trip, fantastic crew. The food was excellent. Saw some whales and really enjoyed the trip around the coast. NATHAN WELLS

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

My wife and I had a great time on this cruise. The captain and crew were super accommodating and.. Steve Guns

Lucky Lady-Whale Watch Cocktail Cruise - Kauai Sea Tours

We went on a whale watching tour with Caltain Geoff this past Wednesday. What a great tour!! We saw.. Anna Chamberlain

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

A fantastic experience. The boat is lovely, the staff were excellent hosts, the food was delicious and the views were stunning. It really was perfect. Sally Webster

Akialoa NaPali Sunset Dinner Sail - Captain Andy's Sailing Adventures

We visited Kauai in the beginning of December and wanted to experience the Napoli Coast with style!.. Jennifer Tomer

Akialoa NaPali Sunset Dinner Sail - Captain Andy's Sailing Adventures

Our tour was great and the crew was even better! Nothing but good things to say! Amy Hulbert

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Been on many dinner cruises....this was the best....food better than any of the 4stars here on the island

J Bruce Reading

Lucky Lady-Na Pali Sightsee Sunset Dinner Cruise- Kauai Sea Tours

My husband and I had an amazing experience during our honeymoon. Our captain Kauai and his crew.. Sonya M

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Most excellent! Would definitely recommend to anyone! Miki Schnackel

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

We had a fabulous time on the Southern Star. Views were spectacular, lots of commentary about what.. Dusti Tornay

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

We had a wonderful time on our Sunset Cruise. Our captain and his first mates were exceptional. .. Carolyn O'Neill

"Leila" Sunset Dinner Sail - Summer - Holo-Holo Charters

Fantastic tour guides. Benjamin Bojda

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

Awesome crew, good food, amazing sunset views, recommended! The boat goes against the wind for 50%.. Arthur Geranium

Na Pali Sunset Dinner Cruise 4 Hour - Blue Dolphin Charters

A fabulous experience, saw spinner dolphins that played with the boat for a very long time, saw sea.. Maureen Schou

Akialoa Poipu Sunset Sail - 2 Hour - Captain Andy's Sailing Adventures

This was a wonderful experience. Lots of actual sailing, very friendly mates, good food and plentiful drinks. Our whole family loved it. A must-do! Louis Gombos

Star NaPali Dinner Sunset Sail - Captain Andy's Sailing Adventures

Spectacular. The boat, crew, menu was awesome. Didn't realise tho that bar doesn't open.. Sean Sierakowski

Lucky Lady-Na Pali Sightsee Sunset Dinner Cruise- Kauai Sea Tours

We went out on a beautiful Saturday afternoon.. Our captain was Kauai. Our deckhands were.. Sonja Philip

Na Pali Sunset Dinner Cruise 4 Hour - Blue Dolphin Charters

Best tour experience on Kauai..we've gone on either snorkeling or dinner sails with Blue.. Robert Bentley

"Holo-Holo" NaPali Sunset Sightsee w/Dinner- Holo-Holo Charters

We had an awesome time. Were able to see the Humbacks, turtles & dolphins & a beautiful sunset. Thanks for the memories. Becki Normandeau

Video Transcript

Just one point of understanding with regard to the island of Kauai and Sunset Sails.

We have Dinner Cruises and we have Sunset Sails. They're very, very similar in terms of what they do. One has dinner as well as cocktails, and they're both out at sunset time. The Sunset Sails generally are going to have cocktails and hor d'oeuvres. In Hawaii they call them pupus. They're usually out a little bit shorter. The Dinner Cruises, as discussed in a previous section can be as long as five hours. Sunset Sails are more in the two-hour area and go out from the main ports of Poipu and Port Allen, Nawiliwili, but they're just out for the short period of time, and not as big a deal as the Dinner Cruises. They're a lot of fun. They're less expensive, and people really enjoy them. It's one of the best things to go out and see the green flash on the ocean on a Sunset Sail.

If you have any questions about Tours or Activities in Hawaii, just give us a call, or check out tombarefoot.com. We're here to help.

State Wide Sunset Sails & Cruises

Taking a Hawaii sunset cruise may prove to be the most romantic and relaxing moments of your vacation. Sunset cruises probably won't rank high on your list of adventure items on your trip but may instead be the simple ending to a perfect day.

More Info / Buy Now

Sunset Sails & Cruises on Oahu

A variation of the dinner sunset cruise is what is fondly referred to in Hawaii as the "booze cruise". This usually includes just "pupus" (appetizers) and an open bar plus entertainment.

More Info / Buy Now

Sunset Sails & Cruises on Maui

Many vessels on Maui can take you on a sunset cruise, most leaving from Lahaina harbor. Catamarans, sloops, schooners, and even power vessels - no matter what boat on Maui you take, one thing is certain, it will be the beginning of an evening you will remember for a long time to come.

More Info / Buy Now

Sunset Sails & Cruises on "The Big Island" of Hawaii

Sunset Sails off the coast of the Big Island of Hawaii provide the ultimate in relaxation. The beauty of the ocean and the colors of the sunset provide a remarkable experience to conclude your Hawaiian day.

More Info / Buy Now