Under sail · DINNER AND EVENING SAILING CRUISES

Dinner Sailing Cruises Around the World: 15 to Book

16 sailing trips  ·  seats from $64 each

A table on deck, the harbour lights coming on, a sail that turns for home after dessert. These 15 evening sails are compared on what is served and how long you are out.

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - Boarding at Marriott Frenchman’s Cove
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Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

1.Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

★★★★★★★★★★5.0 · 1,176 reviews · from $119Top of the fleet

Sail Charlotte Amalie harbor aboard The VI Cat, a 54-foot catamaran departing Marriott Frenchman’s Cove. Enjoy sunset views, harbor lights, an open bar, and a dinner of tacos or barbecue, depending on the evening. The relaxed, social cruise lasts about two hours and returns to the same dock.

“The crew Works tirelessly to make sure we had a great time. the drinks kept coming, the food was great and the atmosphere was awesome. I would highly recommend it”

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Kauai: Leila Na Pali Sunset Dinner Sail - The five-hour route, from marina to sunset
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Kauai: Leila Na Pali Sunset Dinner Sail

2.Kauai: Leila Na Pali Sunset Dinner Sail

★★★★★★★★★★4.5 · 524 reviews · 5 hours (approx.) · from $263

Spend about five hours sailing from Port Allen along Kauai’s Na Pali Coast aboard the 50-foot Leila. Expect cliffs, waterfalls, marine life, dinner, mai tais, beer, wine, and a sunset toast. The crew may include captains such as Kevin, Max, or Mike, with routes shaped by ocean conditions.

“The crew was professional and courteous they took amazing care of my bride and ii. Unfortunately Mother Nature beat us up pretty good the sea was heavy! However feeing as poorly as I was the north coast was amazingly beautiful. We highly recommend holo holo they were outstanding.”

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Auckland Harbour Sailboat Cruise Including Three Course Dinner - The view toward Mt. Eden and Auckland’s skyline
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Auckland Harbour Sailboat Cruise Including Three Course Dinner

3.Auckland Harbour Sailboat Cruise Including Three Course Dinner

★★★★★★★★★★4.5 · 476 reviews · from $105

Set sail from Viaduct Harbour aboard a 50-foot yacht for 2.5 hours of Auckland views, sailing, and a three-course dinner. Your crew shares local stories, points out the Sky Tower, Harbour Bridge, Ferry Building, and Mt. Eden, and may let you help with the sails or take the wheel. One arrival drink, jackets, blankets, and onboard toilets are included.

“It was lovely trip to celebrate our Anniversary with our friends . We had absolutely amazing time. All crew was friendly and fun .”

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Marseille: Sunset Sailing Cruise with Dinner and Wine - Sailing toward the Frioul archipelago
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Marseille: Sunset Sailing Cruise with Dinner and Wine

4.Marseille: Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.7 · 453 reviews · 1 day · from $64

Join Goélette Alliance at Marseille’s Old Port for an evening sail aboard the wooden schooner Alliance. You’ll cruise toward the Frioul archipelago, swim in a sheltered cove, eat a fresh vegetarian buffet, sip Provençal rosé, and watch the sun set. The multilingual crew speaks English, French, and Italian, and guide Fabio has earned praise for his friendly explanations.

“The schooner was beautiful and I appreciated that the sailors raised the sails on the way out. It was fun to hear the beautiful live music while eating our tasty dinner. Overall a great evening!”

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Sydney Harbour Tall Ship Twilight Dinner Cruise - Starting at Campbells Cove in The Rocks
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Sydney Harbour Tall Ship Twilight Dinner Cruise

5.Sydney Harbour Tall Ship Twilight Dinner Cruise

★★★★★★★★★★4.5 · 451 reviews · from $63Lowest fare aboard

Meet at Campbells Cove in The Rocks for a twilight cruise aboard a restored tall ship. You’ll pass the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, Luna Park, and more while enjoying dinner and live commentary. Howard and Ruth are among the hosts mentioned for their warm storytelling. A mast climb is available for an extra fee.

“This is a friendly, relaxing and informative experience that takes you into the heart of Sydney and its beautiful harbour. The Captain, host and young crew were a delight, welcoming, and knowledgeable of the history of the harbour and tall ships. The meal was terrific and feel of the boat unforgettable. Accompanied by my adult daughter we had the best time together, catching up, feeling the breeze off the water and in the sails that brought us back to the dock. Thanks!”

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Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar - What happens on the two-hour sail
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Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

6.Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

★★★★★★★★★★4.5 · 424 reviews · 2 hours (approx.) · from $109

From Riviera Maya hotels, you’ll ride to Puerto Aventuras Marina and board a luxury catamaran for about two hours. Expect a stocked open bar, fruit and charcuterie platters, soft music, and sunset views over the Caribbean coast. Crew members such as Paola, Martin, Mario, and Celine have earned special praise for warm service.

“Absolutely wonderful time. It was the last event before heading home. The crew was fantastic and the charcuterie boards a nice touch for serving light appetizers.”

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Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran - An open bar that shapes the evening
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Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

7.Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

★★★★★★★★★★5.0 · 393 reviews · from $137

Board at Piet’s Pier behind the Hyatt Regency at 5:30 pm for a three-hour catamaran sail along Aruba’s coast. You’ll get sparkling wine, an open bar, a Caribbean-style buffet, sunset views, and music that may turn the deck into a dance floor. The boat carries up to 40 people and returns to Palm Beach.

“The crew, food, drinks were amazing. Our views met our expectations. Meeting new friends an absolute bonus! We would recommend this to anyone who is looking for a romantic setting, open to music and lots of laughs!!”

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Sydney: Tall Ship Harbour Twilight Dinner Cruise - Finding Campbell’s Cove at The Rocks
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Sydney: Tall Ship Harbour Twilight Dinner Cruise

8.Sydney: Tall Ship Harbour Twilight Dinner Cruise

★★★★★★★★★★4.4 · 342 reviews · 2 hours · from $77

You spend two hours aboard the Southern Swan or Soren Larsen, leaving from Campbell’s Cove at The Rocks. A guide such as Jim-lad or Howard points out harbour sights while the crew serves dinner and invites you to help with the sails or steer. Expect a relaxed, hands-on cruise with drinks sold separately and a possible mast climb at extra cost.

“Top rated excursion x from start to finish (didn’t want it to end) very welcoming, great crew, great food (gluten free :) ) beautiful sunset x”

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Auckland: Harbour Sailing Cruise with 3-Course Dinner - Sailing Waitematā Harbour under full sail
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Auckland: Harbour Sailing Cruise with 3-Course Dinner

9.Auckland: Harbour Sailing Cruise with 3-Course Dinner

★★★★★★★★★★4.5 · 319 reviews · 2h 30m · from $95

Join Explore Group Auckland for a 2.5-hour evening sail on a 50-foot yacht. You’ll receive a welcome drink, hear stories about Auckland from the crew, and choose a main and dessert from a set menu supplied by The Lula Inn. Crew members may invite you to help sail or try the wheel.

“Fantastic crew aboard, relaxed and engaging skipper and all around excellent experience - an “Aukland “must do”’!”

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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef - From Cabo Marina to Land’s End
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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

10.Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

★★★★★★★★★★4.5 · 290 reviews · 3 hours (approx.) · from $199

Sail from Cabo Marina at 5:00 pm aboard a shared yacht for about three hours. You’ll pass Land’s End, the Arch, and Lovers Beach, then enjoy cocktails, appetizers, and a dinner of shrimp and beef with dessert. The cruise is adults-only, relaxed, and capped at 40 people, not a private charter.

“Wonderful sunset dinner cruise! We enjoyed the more laid back vibe over the “party” ships we saw going out. Bartender still had the drinks flowing with an open bar but there was fewer people and more comfortable places to lounge and take in the views! 5 star service!”

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Luxury Sailing Experience Day with Champagne and Lunch or Dinner - Champagne first, then a freshly cooked meal
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Luxury Sailing Experience Day with Champagne and Lunch or Dinner

11.Luxury Sailing Experience Day with Champagne and Lunch or Dinner

★★★★★★★★★★5.0 · 220 reviews · 5 hours 30 minutes (approx.) · from $220

Set out from Lymington Yacht Haven on a spacious Jeanneau yacht with a qualified skipper and crew. Enjoy champagne on arrival, views toward the Isle of Wight and the Needles, and a freshly prepared two course lunch or dinner. You can relax at the helm or have a go at sailing. Trips last about five and a half hours and carry no more than 10 people.

“If you’re in Southampton before or after a cruise, this experience is a great alternative to touring castles, churches or old towns. Incredible value for a 5+ hour adventure activity which includes fabulous lunch or dinner.”

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Hua Hin: Siamtara Sunset Sailing Dinner Cruise with Pickup - Cruising Past Hua Hin, Kao Takiab, and Kao Tao
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Hua Hin: Siamtara Sunset Sailing Dinner Cruise with Pickup

12.Hua Hin: Siamtara Sunset Sailing Dinner Cruise with Pickup

★★★★★★★★★★4.9 · 203 reviews · 4 hours · from $67

Join Captain Eric and his crew aboard the Siamtara, a classic wooden pirate-style sailboat leaving Racer Marina. Cruise past Hua Hin, Kao Takiab, and Kao Tao, swim in warm Gulf waters, try kayaking or paddleboarding, then enjoy a five-dish Thai buffet as the sun sets. Hotel transfers, soft drinks, and equipment are included.

“Excellent activity and something I’ve wanted to do in Hua Hin for a few years. Now being a resident in Hua Hin I wanted to try this activity so that I could write a review for my travel blog called Two Passports Packed, which I will do when I get the chance. Overall an enjoyable afternoon and evening, almost four hours of sailing and socializing and eating and enjoyment. If you are visiting Hua Hin then I have no hesitation in suggesting that you add this activity to your plans.”

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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner - Meeting the crew and leaving Mykonos
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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

13.Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

★★★★★★★★★★4.8 · 122 reviews · 5 hours · from $111

Spend five hours sailing past Mykonos beaches to quiet Rhenia, where you swim and snorkel from the yacht. Captain Stelios, Anastasis, or another assigned crew team serves a Greek buffet, wine, beer, and soft drinks before sunset. Expect changing meeting points, no shore landing, and possible extra charges for transfers.

“We really liked it and the Captain Stelios along with Anastasis were so kind and willing to help , explain and show us the beauty of this island. Totally recomended!!!”

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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - Two hours in a quiet Aegean cove
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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

14.Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

★★★★★★★★★★4.5 · 116 reviews · 5 hours (approx.) · from $114

Join Sunfos Alessia Yachting for a five-hour sailing trip from Agios Ioannis to Rhenia. You’ll pass Mykonos beaches, swim from the yacht, use free snorkeling gear, and eat a Greek buffet with wine, beer, and soft drinks. Crew names vary, with Costas, Joanna, Bobi, Foti, and others praised on past departures.

“It was a great excursion. Everyone enjoyed themselves and would certainly do it again. The staff was great as well.”

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Knysna Sunset Sailing Cruise with Light Dinner and Wine - Leaving Drydock for the Knysna lagoon
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Knysna Sunset Sailing Cruise with Light Dinner and Wine

15.Knysna Sunset Sailing Cruise with Light Dinner and Wine

★★★★★★★★★★4.8 · 96 reviews · 2h 30m · from $124

Join an English or Afrikaans speaking crew aboard the 50-foot Outeniqua, Knysna’s only chartered monohull sailing yacht. With up to 12 people aboard, you’ll sail the lagoon, and possibly pass through the Knysna Heads into the Indian Ocean if conditions allow. Expect two glasses of Cap Classique, a cheese and fruit spread, and a polished sunset sail.

“Apart from the attentiveness and friendliness of the crew, we felt like we were in very safe hands with their experienced skipper. The boat is beautiful and very comfortable and it was an awesome experience sailing out of the Knysna Heads before making our way back into the lagoon.”

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Other ways to get on the water

Sunset Sailing CruisesParty and Music Sailing CruisesSailing Tours with DrinksSailing Tours with Lunch
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