Top 15 Sailing Trips in the World

1.Coral Island Catamaran Cruise with Sunset Dinner

★★★★★★★★★★4.1 · 360 reviews · 6 hours · from $53Our pick

Spend six hours sailing from Chalong Pier to Coral Island for snorkeling, beach time, optional water sports, and a Thai buffet dinner. Guides such as Mimi, Arm, Eddie, TV, and Gigi have earned warm praise for friendly service, while the sunset near Promthep Cape gives this relaxed cruise its finest moment.

“A very good activity in Phuket, no ti be missed. Everything is top notch right from pickup till drop.”

Check availability →Read our full review

2.Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★4.5 · 328 reviews · 5 hours (approx.) · from $114

Cruise Santorini’s caldera on a small catamaran with swimming at Red Beach, White Beach, and the hot springs, then watch Oia’s sunset over a Greek barbecue. Hotel transfers, towels, Wi-Fi, wine, beer, and soft drinks are included. Groups can be as small as 9 or reach 16 people.

“The staff works hard to provide an excellent experience for you. Fantastic food and drink as well! The size of our group was about 16 and it was perfect.”

Check availability →Read our full review

3.Antalya/Kemer: Phaselis Yacht Trip for Families and Couples

★★★★★★★★★★4.5 · 183 reviews · 6 - 8 hours · from $41Best value

Join Captain Muzaffer and the Ginza Travel crew for a 6 to 8 hour yacht trip from Kemer, with optional pickup from Antalya or Belek. Swim at Paradise and Cleopatra bays, eat fresh fish or chicken onboard, and reach Phaselis beach by swimming rather than by guided shore visit.

“we had a lot of fun! we are english speakers, they spoke English fine, the pick up was OK, we didn't know where we were going but they helpfully showed us where on the marina to go. the boat was lovely, so chilled, sun loungers on the top and tables on the bottom. we stopped off at 3 bays, and as another reviewer said, there is no chance to actually explore Phaselis but you'll see it from a distance when they drop you off at the bay. swimming was lovely, good opportunities to take pictures. they just let you get on with it which we appreciated. they play music but…”

Check availability →Read our full review

4.Albufeira: 6-Hour Sunset Dinner Catamaran Cruise with Open Bar

★★★★★★★★★★4.5 · 170 reviews · from $85

Sail from Albufeira along the Algarve coast to Benagil Cave, then land by small boat for a beach BBQ, sunset, drinks, music, and a fire show. The six-and-a-half-hour evening suits couples, friends, and families with older children who want scenery and a lively party atmosphere in one outing.

“I’ve taken dozens of excursions around the world via Viator, and this is 100% the best one I’ve ever been on. This has been the highlight of my Portugal trip thus far. The most beautiful private beach for our catamaran all set up beautifully for dinner, a show and sunset.”

Check availability →Read our full review

5.Hvar: Romantic Sunset Sailing Experience On A Comfort Yacht

★★★★★★★★★★4.9 · 119 reviews · 2 hours · from $76

Set sail from Hvar’s Riva 27 with a skipper such as Viktor, Alex, or Petar, then cruise toward the Pakleni Islands as sunset colors spread across the sea. Bring your own drinks and snacks, choose a shared or private yacht, and enjoy a calm two-hour outing.

“Great afternoon sailing. Beautiful sunset, chill vibes, great crew. Highly recommend”

Check availability →Read our full review

6.3 Hour Sunset Dinner Cruise by Solaris Yacht in Miramar Beach

★★★★★★★★★★4.0 · 97 reviews · 3 hours (approx.) · from $129

Board the 125-foot Solaris at Sandestin’s dock in Miramar Beach for a three-hour dinner cruise. Your captain welcomes you, a server leads you to your table, and live music continues across three decks. Choose your entree in advance, then watch for dolphins, sunset colors, stars, and dancing under the night sky.

“The sunset was beautiful! I enjoyed the shrimp and grits. It was a picturesque experience. Very romantic. We danced and the music selection was very good. The wait staff was attentive.”

Check availability →Read our full review

7.Half-Day Private Romantic Sailing Getaway to Kleftiko

★★★★★★★★★★5.0 · 81 reviews · 5 hours (approx.) Top rated

Spend about five hours sailing south from Agia Kyriaki with a private crew, often including Dimitris, James, Nicko, or Pablo. Swim at striking beaches, explore Kleftiko’s low caves by tender when conditions allow, and enjoy wine, fruit, cheese, music, and plenty of room for your group.

“One of the highlights of our Milos trip. This boat trip to Kleftiko is a must! The cliffs and caves were so beautiful and the water was incredibly blue. We all had an amazing time there and would 100% do this again when we go back. Dimitri and Nicko were awesome host. So friendly and fun. We were going to Santorini a few days later and Nicko gave us a whole list of things to do when we were there too! Both of them were great!”

Check availability →Read our full review

8.Waikoloa: Catamaran Sunset Sail with Cocktails

★★★★★★★★★★4.8 · 68 reviews · 1h 30m · from $159

Sail 90 minutes from Anaeho‘omalu Bay aboard Hawaii Nautical’s Spirit of Aloha catamaran. Enjoy cocktails, beer, wine, snacks, and sunset views of Mauna Kea and Hualālai. Captain Mike and his crew have earned praise for friendly service, though beach loading and meeting directions require care.

“The Captain and Crew were all phenomenal. We had a large group with us celebrating a friend's birthday. The crew didn't know we were celebrating but they provided incredible service regardless. Whale watching is never guaranteed but when the captain said we would 100% see whales, that was a strong statement and held true. Amazing cruise with an amazing boat crew.”

Check availability →Read our full review

9.Coral Island & Sunset Dinner by Sailing Catamaran

★★★★★★★★★★3.9 · 68 reviews · 5 hours · from $56

You’ll ride a catamaran from Chalong Pier to Koh Hey, with time for beach walks, swimming, snorkeling, and optional water sports. A Thai, English, or Chinese-speaking guide leads the day, then dinner is served aboard near Promthep Cape as the sun sets.

“Lovely day trip! Great food and lovely boat! only thing is the tour is a lot longer than 5 hours, pick up is at 12 and I got back at 20.45 so just important information for people travelling or if they have evening plans it is a late return! 5 hours tour time is the time on the boat not including travel time.”

Check availability →Read our full review

10.Private Sunset Sailing Charter for Couples from Corralejo

★★★★★★★★★★4.5 · 57 reviews · 4 hours (approx.) · from $181

You’ll sail from Corralejo with local skippers such as Juan, Jorge, Julián, or Martin, stopping near Lobos Island for swimming, snorkelling, paddleboarding, or rest. Dinner, wine, beer, soft drinks, and equipment are included, with about four hours on the water and space for only two people.

“Wunderschöne segeltour mit 2 super netten Skipper!!! Wirklich empfehlenswert und jeden Euro wert! Muss man einfach mal gemacht haben 😊”

Check availability →Read our full review

11.Kaanapali: Sunset Dinner Catamaran Cruise With Drinks

★★★★★★★★★★4.8 · 55 reviews · 2h 30m · from $153

Board Sea Maui’s 65-foot beach-loading catamaran from Ka'anapali Beach for a 2.5-hour sunset cruise. Enjoy an open bar, chef-prepared dinner, a champagne toast, island views, and possible whale or dolphin sightings with crew members such as Carrie, Luke, and Quinn.

“The entire crew was great! They were quick with the drinks and came to us to offer refills, water, and any help with conquering motion sickness.”

Check availability →Read our full review

12.Experience Romantic Sunset Sailing on modern 36ft sail yacht from Zadar

★★★★★★★★★★4.5 · 51 reviews · 2 hours (approx.) · from $90

Set out from Obala kneza Trpimira with a professional skipper such as Luka, Petar, or David. Over two hours, you’ll sail along Zadar’s coast, pass the Sea Organ and Greeting to the Sun, and bring your own chilled drinks and snacks aboard.

“It was a perfect evening. Luka shared history and stories. The sunset was amazing. We enjoyed the treats and wonderful wine.”

Check availability →Read our full review

13.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

14.Experience Romantic Sunset Sailing on a modern 36ft (11m) sail yacht | Hvar

★★★★★★★★★★5.0 · 40 reviews · 2 hours (approx.) · from $77

Meet your skipper at Hvar’s main harbour for a two-hour sunset sail aboard a modern 36ft yacht. You’ll pass the Pakleni Islands, bring your own wine or snacks, and return to the same dock. Skippers such as Petar, Peter, Victor, and Alexander are known for a relaxed, friendly approach.

“This was a fabulous trip. Peter, the skipper, was kind and skilled and very funny to boot. The boat was very nice and the crew timed the sunset perfectly. A super memorable experience on our honeymoon!”

Check availability →Read our full review

15.Panormo: Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 39 reviews · 3 hours 30 minutes (approx.) · from $101

Set sail from Panormo for 3.5 hours aboard a luxury catamaran with English-speaking crew, Prosecco, sushi, local wine and beer, swimming, SUPs, snorkeling, and a sunset sail toward Bali Bay or Skaleta.

“The trip was perfect from start to finish! Brilliant crew, spacious boat, not too many people, good quality food and drink. The sunset and Coast as we sailed were just magical.”

Check availability →Read our full review