Sunset Sailing Cruises Around the World: 15 to Book

Catamaran Sailing Trips, Catamaran Sailing Trips in Spain, Malaga Sailing Tours, Sailing Tours, Spain Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Spain, Tour Reviews

Malaga: Catamaran Sailing Trip with Sunset Option

1.Malaga: Catamaran Sailing Trip with Sunset Option

★★★★★★★★★★4.4 · 8,613 reviews · 1 - 1.5 hours · from $16Top of the fleet

Sail from Malaga for 1 to 1.5 hours along the coast as the sun drops behind the mountains. You can sit on the front nets, listen to chillout music, and add a glass of Spanish cava or a romantic light show. English and Spanish crew members are on board. Live music runs on selected Wednesdays, Fridays, and Sundays until mid-September.

“It's always an excellent option, during the day as during sunset!”

Check sailing dates →Read the whole sail review

Catamaran Sailing Trips, Catamaran Sailing Trips in Spain, Party and Music Sailing Cruises, Sailing Tours, Spain Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Spain, Tour Reviews, Valencia Sailing Tours

Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

2.Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

★★★★★★★★★★4.1 · 4,270 reviews · 1 hour - 90 minutes · from $17

Sail from Valencia’s marina along the Mediterranean coast on a spacious catamaran. Choose a daytime or sunset departure, then settle into cushioned seating or pay extra for the front nets. Sunset trips include a glass of cava, while selected Wednesday sailings feature a live DJ.

“We really enjoyed enjoyed the Catamaran trip, the scenery was beautiful the boat nets were comfy, staff friendly and helpful, a very relaxing experience. it was chilly in November so definadvuse wrapping up warm. The sunset was stunning, but the red purple sky afterwards was incredible... definitely a highlight of our trip! Would love to go back in the summer for a daytime trip.”

Check sailing dates →Read the whole sail review

Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

3.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

Check sailing dates →Read the whole sail review

Lisbon Sailing Tours, Portugal Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Lisbon, Sailing Tours with Drinks in Portugal, Sunset Sailing Cruises, Sunset Sailing Cruises in Lisbon, Sunset Sailing Cruises in Portugal, Tour Reviews, Tours

Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

4.Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

★★★★★★★★★★4.9 · 3,114 reviews · 2 hours · from $41

Spend two hours aboard a small sailboat with a skipper and guide, passing Belém Tower, the Discoveries Monument, MAAT, Alfama, and Christ the King. Choose daytime, sunset, or night sailing. The crew speaks English, Spanish, and Portuguese, serves one drink, and keeps the group to 10 people.

“Benny & Miguel were wonderful hosts. Benny was very informative and gave excellent information. They were very respectful and we received complimentary drinks. They asked to take photos which was very nice and respectful .”

Check sailing dates →Read the whole sail review

2-Hour Experiences, Lisbon Sailing Tours, Portugal Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Lisbon, Sailing Tours with Drinks in Portugal, Sunset Sailing Cruises, Sunset Sailing Cruises in Lisbon, Sunset Sailing Cruises in Portugal, Tour Reviews, Tours

2 Hour Lisbon Sunset and Wine Sailing Tour

5.2 Hour Lisbon Sunset and Wine Sailing Tour

★★★★★★★★★★5.0 · 2,680 reviews · 2 hours (approx.) · from $66Best loved

Join a shared sailing cruise of up to 12 people from Lisbon’s Alcântara marina. Your skipper handles the sailing while you enjoy Portuguese wine, views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and a sunset over the Tagus. Guides such as Joe, Henry, JP, and Bruno are praised for friendly conversation and local insight.

“It was a great experience. They upgraded us to a luxury boat free of cost. Excellent customer service. Loved the cruise.”

Check sailing dates →Read the whole sail review

Cabo San Lucas Sailing Tours, Mexico Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Mexico, Sunset Sailing Cruises, Sunset Sailing Cruises in Mexico, Tour Reviews

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

6.Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

★★★★★★★★★★5.0 · 2,267 reviews · 2 hours 30 minutes (approx.) · from $109

Sail Cabo San Lucas Bay for 2.5 hours aboard a 50-foot vessel with a maximum of 16 people. You’ll pass Lover’s Beach and El Arco, enjoy unlimited drinks and light appetizers, and watch sunset from the water. Crews have included Tito, Chino, Chava, Aldo, and Ronnie, though assignments vary.

“The sailing was awesome! Gorgeous views. Really good appetizers. Staff was fun and entertaining. Got some great pics.”

Check sailing dates →Read the whole sail review

Oahu Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Oahu, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

7.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89

Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.

“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”

Check sailing dates →Read the whole sail review

Madeira Sailing Tours, Portugal Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Portugal, Tour Reviews, Tours

Funchal: Sunset Sailing Tour

8.Funchal: Sunset Sailing Tour

★★★★★★★★★★4.7 · 2,144 reviews · 3 hours · from $58

Sail from Funchal with up to 20 people on a relaxed evening trip led in English or Portuguese. Look for dolphins and whales, stop to swim or snorkel beneath Cabo Girão, and watch the sunset from the sea. Drinks are included, but food, transport, and shoes on board are not.

“Victor and Bruno were great. Victor really cared for our daughter who was a bit scared initially as the sea was not flat. Very attentive to everyone onboard and the scenery was amazing!”

Check sailing dates →Read the whole sail review

Barcelona Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Barcelona, Sailing Tours with Drinks in Spain, Spain Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Barcelona, Sunset Sailing Cruises in Spain, Tour Reviews

Barcelona: Midday or Sunset Sailing with Open Bar and Snacks

9.Barcelona: Midday or Sunset Sailing with Open Bar and Snacks

★★★★★★★★★★4.9 · 2,044 reviews · 2 hours · from $33

Set out from Marina Port Vell on a two-hour sailing trip with a skipper and crew. Choose midday light or sunset color, share a boat with up to 10 people or book privately, and enjoy cava, wine, beer, soft drinks, snacks, music, and a swim stop when conditions allow. Crew members such as Faith, Vicky, Rodrigo, and Eduardo are known for warm service and clear safety briefings.

“This was so brilliant, Faith & Rodrigo were highlights, looking after my friends and I so well. We swam in the ocean & the drinks were always topped up, I highly recommend this trip!!”

Check sailing dates →Read the whole sail review

Aruba Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sunset Sailing Cruises, Tour Reviews

Aruba Sunset Sail with Appetizers and Open Bar

10.Aruba Sunset Sail with Appetizers and Open Bar

★★★★★★★★★★4.5 · 2,024 reviews · from $92

Spend about two hours aboard Red Sail Sports’ catamaran, sailing along Aruba’s coast near Palm Beach as the sun sets. Junior handles drinks, while crew members such as Brandon, Lizzie, Captain D, Joshua, and William have helped create the lively mix of music, stories, and dancing. Expect appetizers, an open bar, and a return to Piet’s Pier Bar.

“Joshua and his crew were great and accomo on the boat. It started on time and even tho visibility was low during the beginning of Hurricane Melissa, just being in the ocean was a relaxing time.”

Check sailing dates →Read the whole sail review

Porto Sailing Tours, Portugal Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Porto, Sailing Tours with Drinks in Portugal, Sunset Sailing Cruises, Sunset Sailing Cruises in Porto, Sunset Sailing Cruises in Portugal, Tour Reviews

Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

11.Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

★★★★★★★★★★5.0 · 1,978 reviews · 2 hours · from $41

Join a small-group or private two-hour cruise from Douro Marina with a welcoming crew such as Miguel, Henrique, Eric, or Francesco. You’ll pass Porto’s bridges, Ribeira, Gaia, and Foz do Douro, hear local stories, enjoy a welcome drink and port wine, and possibly reach the Atlantic. Bring a jacket for the cooler water.

“The captain and crew were wonderful and informative, always communicated on with qhere to meet, etc. The sunset view was the absolute cherry on top of a cruise filled with a few laughs and historical info on Porto. Highly recommend!!”

Check sailing dates →Read the whole sail review

Barcelona Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Spain Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Barcelona, Sunset Sailing Cruises in Spain, Tour Reviews

Barcelona: Sunset Sailing Cruise with Live Music

12.Barcelona: Sunset Sailing Cruise with Live Music

★★★★★★★★★★4.2 · 1,787 reviews · 1.5 hours · from $27

Spend 90 minutes aboard a classic wooden Turkish gulet, sailing along Barcelona’s coast as the sun goes down. You’ll hear live music, perhaps guitar, vocals, saxophone, or piano depending on the sailing, and can buy drinks and snacks from the onboard bar. Bring a jacket, comfortable shoes, and a camera.

“Plenty of free flowing soft drinks and wines all day. Great crew and amazing sunset. Perfect day trip!”

Check sailing dates →Read the whole sail review

Aruba Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sunset Sailing Cruises, Tour Reviews

Aruba Happy Hour Sunset Sail with Savory Bites and Cocktails

13.Aruba Happy Hour Sunset Sail with Savory Bites and Cocktails

★★★★★★★★★★4.5 · 1,488 reviews · from $84

Spend about two hours sailing from Palm Beach aboard a 40-foot trimaran with up to 34 people. The crew serves unlimited cocktails, Aruba Ariba drinks, nonalcoholic beverages, and small bites at your seat. Richard, Shaka, Vino, Jose, and Captain Martin have all been part of the welcoming crew, though staffing may vary.

“The sunset cruise was very relaxing and entertaining! Our captain and his assistants were all great. The food and drinks were good. Very intimate small group and we all had such a great time. Thank you Octopus tours.”

Check sailing dates →Read the whole sail review

Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

14.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Join Danger Charters at 255 Front Street for a two-hour sunset sail with up to eight wines, five beers, soft drinks, and wine-paired hors d’oeuvres. Crews including Mary, James, Connor, and Molly are known for warm service, stories, blankets on cool evenings, and a relaxed small-boat setting.

“Great crew, excellent wine, delicious hors d’oeuvres, beautiful sunset ~ perfect evening! Plus, the limited number of guests was definitely preferred.”

Check sailing dates →Read the whole sail review

Lisbon Sailing Tours, Portugal Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Lisbon, Sunset Sailing Cruises in Portugal, Tour Reviews

Lisbon: Daylight or Sunset on a Vintage Sailboat

15.Lisbon: Daylight or Sunset on a Vintage Sailboat

★★★★★★★★★★4.9 · 1,265 reviews · 2 hours · from $64

Spend two hours on a vintage sailboat with guides such as Eduardo, Carlotta, or Angelo. From Santo Amaro Dock, you’ll pass Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, Christ the King, Praça do Comércio, and São Jorge Castle while enjoying Portuguese snacks, white or rosé wine, water, or fruit juice.

“This was our first time on a sailboat, and it was an unforgettable experience. Eduardo and Carlotta were incredibly warm and welcoming, the views were absolutely stunning, and the snacks and beverages were delicious - we highly recommend trying the green wine! The music and overall atmosphere made for a perfectly relaxing time on the water. We truly couldn’t recommend this experience more. It was a beautiful highlight of our trip to Lisboa.”

Check sailing dates →Read the whole sail review