WORLDWIDE · SAILING

Best Live Music Sailing Trips Worldwide — Our Top 11

11 shows  ·  from $20 a seat

This is the shortlist you would send a friend: 11 live music sailing trips worth the money, each with its price, its traveller verdict and the one thing to know before you commit.

Barcelona: Sunset Catamaran Cruise with Live Music - Barcelona’s skyline from the sea
Barcelona Live Music, Evening Experiences, Live Music, Live Music Cruises, Sailing, Spain Live Music, Tour Reviews

Barcelona: Sunset Catamaran Cruise with Live Music

1.Sunset Catamaran Cruise with Live Music

★★★★★★★★★★4.7 · 3,024 reviews · 1.5 - 2.5 hours · from $33Our pick

Watch Barcelona’s sunset from a spacious catamaran with live jazz, coastal views, a relaxing net area, and reasonably priced drinks onboard.

“This was a great activity, the entire crew was very friendly and the music was an amazing addition. It was a very enjoyable time and the view we got was memorable and beautiful.”

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Barcelona: Catamaran Cruise with optional Live Jazz Music - Barcelona from the sea, not from a tour guide
Barcelona Live Music, Jazz Shows, Live Music, Live Music Cruises, Sailing, Spain Live Music, Tour Reviews

Barcelona: Catamaran Cruise with optional Live Jazz Music

2.Catamaran Cruise with optional Live Jazz Music

★★★★★★★★★★4.7 · 1,797 reviews · 1.5 hours · from $20Best value

Review of Barcelona’s 90-minute Catamaran Orsom cruise, with coastal views, onboard drinks, optional live jazz, pricing, tips, and practical details.

“All my guests really enjoyed the cruise. The vibe was really chill, the jazz music was super relaxing, the boat was comfortable. We could ask for nothing more!”

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Barcelona: Sunset Sailing Cruise with Live Music - Boarding the wooden gulet
Barcelona Live Music, Evening Experiences, Live Music, Live Music Cruises, Sailing, Spain Live Music, Tour Reviews

Barcelona: Sunset Sailing Cruise with Live Music

3.Sunset Sailing Cruise with Live Music

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

Review of Barcelona’s 1.5-hour sunset gulet cruise with live music, skyline views, onboard bar, pricing, tips, and practical advice.

“The live music is actually a ‘one man’ performance. Just very average and very short. The view is nice but the boat seems a bit small. It’s crowded.”

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Venice: Catamaran Sunset Jazz Cruise with Aperitivo - Finding the catamaran near Via Garibaldi
Evening Experiences, Italy Live Music, Jazz Shows, Live Music, Live Music Cruises, Sailing, Tour Reviews, Venice Live Music

Venice: Catamaran Sunset Jazz Cruise with Aperitivo

4.Catamaran Sunset Jazz Cruise with Aperitivo

★★★★★★★★★★4.7 · 1,206 reviews · 1.5 hours · from $94

Review of Venice’s 90-minute sunset catamaran cruise with live jazz, cicchetti, spritz, prosecco, lagoon views, and practical tips.

“Brilliant experience on the last day of our holiday . Was with a mix of ages from 30 plus to 60 plus and everyone enjoyed it”

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NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols - Boarding at Chelsea Piers, Pier 62
Jazz Shows, Live Music, Live Music Cruises, New York City Live Music, Sailing, Tour Reviews, USA Live Music

NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

Tall Ship Silva Sailing Cruise Ft. a Live Musician - Georges Island and the open harbour view
Canada Live Music, Halifax Live Music, Live Music Cruises, Sailing, Tour Reviews

Tall Ship Silva Sailing Cruise Ft. a Live Musician

6.Tall Ship Silva Sailing Cruise Ft. a Live Musician

★★★★★★★★★★4.0 · 289 reviews · 2 hours (approx.) · from $40

Review of Halifax’s 2-hour Tall Ship Silva cruise, with live music, harbour views, sail hoisting, onboard drinks, tips, and practical details.

“Randomly picked the cruise on the Silva as something to do while away celebrating our anniversary and had the absolute best experience! The crew were friendly and the live entertainment was fantastic. Such an enjoyable way to see Halifax! Have already recommended The Silva to friends and family and will be back for another sail next year!”

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NYC: Evening Jazz Cruise on the Yacht Manhattan - Meeting at Chelsea Piers and getting settled
Evening Experiences, Jazz Shows, Live Music, Live Music Cruises, New York City Live Music, Sailing, Tour Reviews, USA Live Music

NYC: Evening Jazz Cruise on the Yacht Manhattan

Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone - Starting near Via Giuseppe Garibaldi
Evening Experiences, Italy Live Music, Jazz Shows, Live Music, Live Music Cruises, Sailing, Tour Reviews, Venice Live Music

Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone

8.Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone

★★★★★★★★★★5.0 · 240 reviews · 1 hour 30 minutes (approx.) · from $96Top rated

See Venice at sunset on a 90-minute catamaran cruise with prosecco or spritz, cicchetti, live saxophone, and lagoon views.

“Must do when in Venice! Vessel is large and stable. Crew friendly Mixed music of live sax and relaxing smooth recorded music. We had aperol and cicchetti was adequate and tasty! Cruising slowly past many Venice sights the vessel manuevered so as to take photos easily. Overall a highlight of our trip to Venice, it is an serene relxing experience and unforgetable!”

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Jazz and Chill Out Sailing in Barcelona - Finding Catamaran Orsom at Port Vell
Barcelona Live Music, Jazz Shows, Live Music, Sailing, Spain Live Music, Tour Reviews

Jazz and Chill Out Sailing in Barcelona

9.Jazz and Chill Out Sailing in Barcelona

★★★★★★★★★★4.5 · 221 reviews · 1 hour 30 minutes (approx.) · from $26

Relax on Barcelona’s Catamaran Orsom with live jazz, sea views, drinks, and a 90-minute cruise from Port Vell.

“The whole experience was very pleasant and enjoyable. My friends and I had an amazing time relaxing on the catamaran with live music playing every now and then.”

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Sunset Sailing in Barcelona & Live Music by Aperol - Sailing past Port Vell and Barceloneta
Barcelona Live Music, Evening Experiences, Live Music, Sailing, Spain Live Music, Tour Reviews

Sunset Sailing in Barcelona & Live Music by Aperol

10.Sunset Sailing in Barcelona & Live Music by Aperol

★★★★★★★★★★4.0 · 157 reviews · 1 hour 30 minutes (approx.) · from $27

Review of Barcelona’s 90-minute sunset sailing with live music, skyline views, onboard drinks, practical tips, drawbacks, and booking advice.

“TERRIBLE EXPERIENCE. THEY CANCELLED, AND HAVE NOT REFUNDED ANY $. DO NOT BOOK WITH THIS COMPANY!!! So, the cruise was cancelled by the cruise company due to rough wave conditions (received no notice of the cancellation until we arrived at the dock). This was in August, 2024. It is now November and the company has not provided the promised refund.”

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Halifax: Tall Ship Harbor Sailing Cruise with Live Music - Raising the largest sails in Halifax Harbour
Canada Live Music, Halifax Live Music, Live Music, Live Music Cruises, Sailing, Tour Reviews

Halifax: Tall Ship Harbor Sailing Cruise with Live Music

11.Tall Ship Harbor Sailing Cruise with Live Music

★★★★★★★★★★4.5 · 75 reviews · 2 hours · from $42

Sail Halifax Harbour aboard the Tall Ship Silva with live music, landmark views, sail raising, and a relaxed two-hour cruise.

“What a beautiful time on the water. Garry, was an amazing entertainer. We really enjoyed our time on the water. Everyone was so friendly. I was pleasantly surprised of the bathrooms. They were clean and well maintained. I would recommend as a great way to see Halifax.”

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