DINING EXPERIENCES

15 Sailing Trips with Dinner, Coast by Coast

48 sailings  ·  from $10 a head

Wind, season and head-count decide more about a day afloat than the brochure does. These 15 sailing trips with dinner are set out with the hours, the price and the swim stops so the choice takes a minute.

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - Arriving at Marriott’s Frenchman’s Cove
Bay, Harbour and Coastal Sailing, Dining Experiences, Dinner and Evening Sailing Cruises, Sailing Tours, St Thomas Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the US Virgin Islands, Tour Reviews, US Virgin Islands Sailing Tours

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 $119Our pick

Sail St. Thomas aboard the 54-foot VI Cat from Marriott Frenchman’s Cove. You’ll enjoy a two-hour evening cruise toward Little Buck Island and Charlotte Amalie, with an open bar, tacos on Tuesdays or barbecue on select nights, sunset views, and harbor lights. Arrive 30 minutes early, and request vegetarian or vegan food 48 hours ahead.

“Beautiful experience! We sat at the front of the boat and drank cocktails through the night. The good was good and we met some great people on the boat.”

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Kauai: Leila Na Pali Sunset Dinner Sail - The ride from Port Allen to the Na Pali Coast
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Kauai: Leila Na Pali Sunset Dinner Sail

2.Leila Na Pali Sunset Dinner Sail

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

Spend about five hours aboard Holo Holo Charters’ 50-foot catamaran Leila, sailing from Port Allen along Kauai’s Na Pali Coast. Expect towering cliffs, waterfalls, marine life, dinner, mai tais, wine, beer, and a sunset Champagne toast. Captain Kevin and other crew members share local stories, but rough seas and spray are part of the deal.

“Informative tour. Beautiful views of the coast. Varied by day, based on weather, but the crew works hard to give you the best experience. Food was excellent & drinks plentiful!”

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Auckland Harbour Sailboat Cruise Including Three Course Dinner - Crossing Waitemata Harbour
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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

Board a 50-foot sailing yacht at Viaduct Harbour for a 2.5-hour evening cruise with a welcome drink, live commentary, and three-course dinner. Sail past the Sky Tower, Harbour Bridge, Ferry Building, and Mt. Eden. You may help raise the sails or try the wheel, with jackets and blankets available.

“Great experience first timer on a sail boat and water, even though the weather was cold and rainy. The two were great, drinks went down well”

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Marseille: Sunset Sailing Cruise with Dinner and Wine - Frioul’s sheltered cove is the heart of the evening
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Marseille: Sunset Sailing Cruise with Dinner and Wine

4.Sunset Sailing Cruise with Dinner and Wine

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

Join the Goélette Alliance at Marseille’s Old Port for an evening sail toward the Frioul archipelago. Swim in a sheltered cove, enjoy a fresh vegetarian buffet with a glass of Provençal rosé, listen to music, and watch the city lights appear on the return. Fabio is one of the guides, and the crew speaks English, French, and Italian.

“A very nice sunset cruise, the buffet dinner was good only they offered pasta and rice with focaccia so Italian food…no fish at all. The atmosphere on the boat was great as well as the crew, they were friendly and professional, they had the sails hoisted by some of the passengers so that they had the impression to be part of the crew. All well organized, I definitely recommend this tour!”

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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 $63

Meet at Campbells Cove in The Rocks for a twilight dinner cruise aboard a restored tall ship, sometimes the 104-year-old Southern Swan. Enjoy dinner, live commentary from hosts such as Howard or Ruth, and views of the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, Luna Park, and more. Mast climbing costs extra.

“Sitting out on the deck of a three mastered tool ship nibbling canapés and sipping bubbles. There is no better way to experience Sydney Harbour and it’s very best.!”

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Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar - Open Bar, Fruit, Cheese, and Meat
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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

Sail from Puerto Aventuras on a two-hour sunset catamaran cruise with hotel pickup, a stocked open bar, tropical fruit, cheese, and meats. The bilingual crew, including staff such as Paola, Mario, and Martin on some sailings, serves drinks and snacks while you watch the sky change over the Caribbean. Minimum age is 10.

“Well well well, this sunset will be the best thing in your vacation. You should make sure that your sailing be guided by Celine . She is all a show and make everything posible so you can enjoy this tour.”

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Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran - Three hours along Aruba’s coast
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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

Meet at Piet’s Pier Bar behind the Hyatt Regency at 5:30 pm for a three-hour Red Sail Sports catamaran cruise. You’ll receive sparkling wine, sail along Aruba’s coast, enjoy a Caribbean-style buffet, and order from an open bar with beer, wine, cocktails, sodas, and juice. Frandy, D’Angelo, and Captain Richard have been praised for their friendly hosting, though the amount of time under sail can vary with weather.

“Worth every dollar spent a wonderful time and crew were very polite funny ,and wonderful to work with”

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Sydney: Tall Ship Harbour Twilight Dinner Cruise - Finding Campbell’s Cove without a scramble
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Sydney: Tall Ship Harbour Twilight Dinner Cruise

8.Tall Ship Harbour Twilight Dinner Cruise

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

Join the Southern Swan or Soren Larsen at Campbell’s Cove for a two-hour twilight sail past the Opera House, Harbour Bridge, Fort Denison, and Luna Park. You can help set the sails, steer the ship, or relax with dinner. The English-speaking crew share harbour and ship stories, with drinks and mast climbing sold separately.

“fab trip, great hosts , good food and great that guests could contribute to trip”

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Auckland: Harbour Sailing Cruise with 3-Course Dinner - Meeting at Viaduct Harbour
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Auckland: Harbour Sailing Cruise with 3-Course Dinner

9.Harbour Sailing Cruise with 3-Course Dinner

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

Sail Auckland’s Waitemata Harbour aboard a 50-foot yacht for 2.5 hours, with a welcome drink, live commentary, and a three-course meal from The Lula Inn. You can help sail or try the wheel, then watch the Harbour Bridge, skyline, sunset, and city lights appear. Jackets and blankets are provided.

“I found the dinner cruise on line so didn’t know what boat we were travelling on and was absolutely wrapped when we got into the sailing boat, Peter , Vicky and Lydia were fantastic and the service for food and drinks was great thankyou”

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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef - Drinks, appetizers, and dinner on the water
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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

Set sail from Cabo San Lucas at 5:00 pm for a three-hour sunset cruise past Land’s End, the Arch, and Lovers Beach. You’ll enjoy a welcome cocktail, premium open bar, appetizers, dinner with shrimp and beef, and dessert. The boat holds up to 40 people, and the minimum age is 18.

“The staff is amazing. The ambience is excellent. The boat is beautiful. The food is cold. You had no choice in what to eat and they threw it at you no appetizer no dessert all the alcohol you want again the service was excellent.”

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Sydney Harbour: Tall Ship Vivid Dinner Cruise - Meeting the ship at Campbell’s Cove
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Sydney Harbour: Tall Ship Vivid Dinner Cruise

11.Tall Ship Vivid Dinner Cruise

★★★★★★★★★★4.4 · 272 reviews · 1h 30m · from $65

Cruise Sydney Harbour aboard the Soren Larsen or Southern Swan during Vivid Sydney. You’ll see the Opera House, Harbour Bridge, Circular Quay, and other illuminated waterfront sites from the water, with dinner, wine, or fruit juice included. Guides such as Howard add ship history, while the open deck gives you room to move and take photographs.

“Great night maybe a little more clearer commentary as space is limited. Thanks”

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Aruba Sunset Sail with Caribbean Dinner and Live Music - Steel drums, crew humor, and the social mood
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Aruba Sunset Sail with Caribbean Dinner and Live Music

12.Aruba Sunset Sail with Caribbean Dinner and Live Music

★★★★★★★★★★4.5 · 224 reviews · from $109

Sail Aruba’s coast from Piet’s Pier toward Eagle Beach and the lighthouse, with steel-drum music, an open bar, and a Caribbean buffet served aboard a catamaran. You’ll watch the sunset from the deck, then raise the sails again for more music and sea views. Check in 30 minutes early; hotel transfers are not included.

“Excellent! Funny crew, good music, good cocktails and fine food. On a buffet was salad with rancho dressing, coconut rice, baked potatoes with veggies, grouper with creole seasoning, chicken in mushroom sauce and some sort of lasagna. Everything was very tasty. The only thing I was missing was a mojito or margarita because all cocktails were sweet.”

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Luxury Sailing Experience Day with Champagne and Lunch or Dinner - Champagne, lunch, and the rhythm of the day
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Luxury Sailing Experience Day with Champagne and Lunch or Dinner

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

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

Spend about five and a half hours aboard a modern Jeanneau yacht from Lymington Yacht Haven. Your skipper and crew handle the sailing, or you can try the helm. Expect champagne on arrival, a freshly cooked two-course meal, views toward the Isle of Wight and the Needles, and room for 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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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Starting at Fira’s old port
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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

14.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $96

Spend about six hours sailing Santorini’s caldera with a shared group of up to 130 people. Hike the volcano, swim to Palea Kameni’s warm springs, eat a Greek buffet with wine, and watch sunset near Oia. Guides including Tito, Toto, and Cesar have led departures, while pickup is available for an added cost.

“This tour was great. Everything from the pickup to the stops was excellent. The guide was really amazing too. You should totally do it.”

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Kauai: Napali Coast Sunset Sailboat Tour with Dinner - Meeting in Eleele and getting ready to board
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Kauai: Napali Coast Sunset Sailboat Tour with Dinner

15.Napali Coast Sunset Sailboat Tour with Dinner

★★★★★★★★★★4.6 · 207 reviews · 4h 30m · from $247

Join Holo Holo Charters in Eleele for a 4.5-hour sunset cruise along Kauai’s Nāpali Coast. You’ll see sea cliffs, valleys, waterfalls, and beaches from a 50-foot catamaran, with Hawaiian-style dinner, drinks, island stories, and a champagne toast. Captain Dave, Max, Kevin, Gabe, and Jackie have all led past departures, though crew assignments can change.

“This is an excellent tour on a catamaran for 4.5 hours. You can beat the views on this trip. Drinks were great and the food was pretty good for being on a boat. Wear clothes that can get a little wet, the ride there is bumpy.”

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