Live Music · SAILING

Top 15 Sailing Trips Around the World

18 shows  ·  from $19 a seat

This is the shortlist you would send a friend: 15 sailing trips worth the ticket, each with its price, its traveller verdict and the one thing to know before you book.

Barcelona: Sunset Catamaran Cruise with Live Music - Boarding the catamaran and finding the best seat
Barcelona Concerts, Concerts, Cruises & Boat Tours, Evening Experiences, Sailing, Spain Concerts, Tour Reviews

Barcelona: Sunset Catamaran Cruise with Live Music

1.Barcelona: Sunset Catamaran Cruise with Live Music

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

Sail along Barcelona’s coast on a 78-foot catamaran as the sun sets over the city. You’ll hear live jazz, relax on the nets about 1 meter above the sea, and buy drinks from the onboard bar. The round trip lasts about 1.5 to 2.5 hours and makes no stops.

“Really enjoyed this cruise, great music and service. Beautiful views such a lovely activity to do for a final evening in Barcelona”

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Barcelona: Catamaran Cruise with optional Live Jazz Music - The First View of Barcelona from the Water
Barcelona Concerts, Cruises & Boat Tours, Jazz Concerts, Jazz Concerts in Spain, Sailing, Spain Concerts, Tour Reviews

Barcelona: Catamaran Cruise with optional Live Jazz Music

Barcelona: Sunset Sailing Cruise with Live Music - A Turkish Gulet With Room to Move
Barcelona Concerts, Concerts, Cruises & Boat Tours, Evening Experiences, Sailing, Spain Concerts, Tour Reviews

Barcelona: Sunset Sailing Cruise with Live Music

3.Barcelona: Sunset Sailing Cruise with Live Music

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

Sail Barcelona’s coast for 90 minutes aboard a classic wooden Turkish gulet as the sun drops over the Mediterranean. A musician such as Gustavo or Gus may provide guitar, singing, harmonica, or other relaxed live music. Drinks and snacks are available for purchase, but not included.

“Beautiful experience! Every one was so sweet, live music was great, drinks for purchase, good seating and a long fun ride!”

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Venice: Catamaran Sunset Jazz Cruise with Aperitivo - Finding the red sails near Riva dei Sette Martiri
Cruises & Boat Tours, Evening Experiences, Italy Concerts, Jazz Concerts, Live Music Dinner Cruises, Sailing, Tour Reviews, Venice Concerts

Venice: Catamaran Sunset Jazz Cruise with Aperitivo

4.Venice: Catamaran Sunset Jazz Cruise with Aperitivo

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

Join Andreas and his crew for a relaxed 90-minute sunset cruise from Riva dei Sette Martiri. Sail past San Marco Bay, Giudecca, and toward Lido while a saxophonist plays jazz and bossa nova. You get one drink, Venetian cicchetti, spacious seating, and views that are hard to match from land.

“Really excellent experience vibe was great, views and drinks where nice. Alls I would say is have the option for card payment also for extra drinks. The 1st one is free but we had to Goto a card machine and come back to pay”

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NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols - Inside Manhattan or Manhattan II
Cruises & Boat Tours, Jazz Concerts, Jazz Concerts in New York City, Jazz Concerts in the USA, New York City Concerts, Sailing, Tour Reviews, USA Concerts

NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

5.NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

★★★★★★★★★★4.7 · 568 reviews · 1h 30m · from $134

Spend 90 festive minutes aboard Yacht Manhattan or Manhattan II, sailing from Chelsea Piers past Lower Manhattan, Ellis Island, and the Statue of Liberty. Enjoy assigned seating in a heated salon, holiday cookies, cocoa and treats, live jazz and carols, plus one included champagne, wine, or beer.

“Amazing experience. Band were fantastic, very Christmassy atmosphere. Staff were friendly and attentive. Drinks on the house. NYC skyline was beautiful. Great tour, 10/10”

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Tall Ship Silva Sailing Cruise Ft. a Live Musician - Halifax Harbour Bridge and the Waterfront Boardwalk
Canada Concerts, Concerts, Cruises & Boat Tours, 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

Spend about two hours aboard Tall Ship Silva, leaving from Halifax Waterfront with live acoustic music, harbor views, and a chance to help raise the sails. You will pass the bridges, Cable Wharf, Georges Island, McNab’s Island, and more. Drinks and snacks are sold onboard.

“We all enjoyed this very much. Would definitely go again and recommend to anyone visiting Halifax. But the fact I have to put a longer comment is annoying”

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NYC: Evening Jazz Cruise on the Yacht Manhattan - Starting at Chelsea Piers and settling aboard
Cruises & Boat Tours, Evening Experiences, Jazz Concerts, Jazz Concerts in New York City, Jazz Concerts in the USA, Live Music Dinner Cruises, Live Music Dinner Cruises in New York City, Live Music Dinner Cruises in the USA, New York City Concerts, Sailing, Tour Reviews, USA Concerts

NYC: Evening Jazz Cruise on the Yacht Manhattan

7.NYC: Evening Jazz Cruise on the Yacht Manhattan

★★★★★★★★★★4.8 · 285 reviews · 1h 30m · from $134

Spend 90 minutes aboard the 1920s-style Yacht Manhattan, listening to the Boat Band as you pass the Statue of Liberty, Ellis Island, and Lower Manhattan. Your booking includes one drink and an assigned table in the climate-controlled grand salon, with open decks available for fresh air and photos.

“For anyone that enjoys Jazz, I highly recommend this cruise right here. It’s an hour 1/2 around the NYC skyline. One complimentary drink and you may order small chessboard or beer nuts. It doesn’t do full entrees, but the prices are reasonable. I’ll be doing it again for sure and the band is called The Boat Band, was excellent.”

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Sunset Jazz Catamaran Cruise with Aperitivo and Live Saxophone - Along Giudecca and the Zattere waterfront
Cruises & Boat Tours, Evening Experiences, Italy Concerts, Jazz Concerts, Sailing, Tour Reviews, Venice Concerts

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

Set out from Via Giuseppe Garibaldi for a 90-minute sunset sail past San Marco, Giudecca, San Giorgio Maggiore, Lido, and the Biennale Gardens. You get a prosecco or spritz, light cicchetti, recorded jazz and live saxophone, with blankets available when the evening turns cool.

“Just a very average tour. Wouldn’t take again, especially for the cost. The jazz musician only played about 20 minutes and then they had loud music. Not relaxing. Also the captain of the boat smoked continuously which then made the boat smell like smoke. The two ladies that worked on the boat were very pleasant”

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Jazz and Chill Out Sailing in Barcelona - Live jazz, cool music, and the social mood onboard
Barcelona Concerts, Cruises & Boat Tours, Jazz Concerts, Jazz Concerts in Spain, Sailing, Spain Concerts, 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

Set out from Portal de la Pau aboard the Catamaran Orsom for 90 minutes of live jazz, cool music, sea air, and Barcelona skyline views. Afternoon and early evening departures include bar service, onboard toilets, and a smooth route near the port and main beach.

“Vessel set sail on time, overall experience was a 10/10 for a nice, relaxing boat ride with live music most of the time. For just a short duration sail, the captain sticks to the main beach area by the port and does a couple of down and backs. Exactly what we wanted for an affordable price.”

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Sunset Sailing in Barcelona & Live Music by Aperol - A simple route past Port Vell and Barceloneta
Barcelona Concerts, Concerts, Cruises & Boat Tours, Evening Experiences, Sailing, Spain Concerts, 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

Sail Barcelona’s coast for about 90 minutes aboard a wooden Turkish gulet or replacement vessel, with live music, sunset views, and a paid bar. You’ll leave from Moll de les Drassanes, pass Port Vell and Barceloneta, and return to the same dock. Commentary is not included.

“It was a nice boat ride but not a tour. There was no narration about what we were seeing. The Jazz music was one saxophone player, and not really Jazz.”

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Halifax: Tall Ship Harbor Sailing Cruise with Live Music - Raising the Largest Sails in Halifax Harbour
Canada Concerts, Concerts, Cruises & Boat Tours, Sailing, Tour Reviews

Halifax: Tall Ship Harbor Sailing Cruise with Live Music

11.Halifax: Tall Ship Harbor Sailing Cruise with Live Music

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

Board the three-masted Tall Ship Silva at Cable Wharf for a two-hour cruise around Halifax Harbour. Enjoy live music, commentary, waterfront views, and the chance to help raise the sails when conditions allow. Performers such as Gary and Tommy have added a lively, personal touch to the ride.

“Gary, the performer and guide, was very knowledgeable, witty and an incredible performer! It was a great way for my best friend and I to recover from the night before at the Lower Deck.”

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Sunset Catamaran Cruise with Live Music in Barcelona - Leaving Moll de les Drassanes and Port Vell
Barcelona Concerts, Concerts, Cruises & Boat Tours, Evening Experiences, Sailing, Spain Concerts, Tour Reviews

Sunset Catamaran Cruise with Live Music in Barcelona

12.Sunset Catamaran Cruise with Live Music in Barcelona

★★★★★★★★★★4.0 · 60 reviews · 1 hour (approx.) · from $18Best value

Sail Barcelona’s coast from Moll de les Drassanes on a solar-powered catamaran, passing Port Vell and the Olympic Port. You can buy drinks and snacks onboard, enjoy live music from June to September, and support Mediterranean plastic cleanup and coral planting.

“The description of this cruise was written similar as 2 other cruises on Viator. Those cruises had live music and a cocktail bar, so it leaves you to think this experience is very similar. But nothing could be further from the truth unfortunately. It was just an ordinary ferry boat and you get 1 free drink which was just a soda or a beer in a can. It wasn’t the special experience that I expected or that they make it sounds as. The “chill music” they’re speaking of is just some quiet music on the speakers in the background. I booked this because my aunt was into town and I…”

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New York City: Holiday Jazz Classic Motor Yacht Cruise - What the 90 minutes actually includes
City Tours, Cruises & Boat Tours, Jazz Concerts, Jazz Concerts in New York City, Jazz Concerts in the USA, New York City Concerts, Sailing, Tour Reviews, USA Concerts

New York City: Holiday Jazz Classic Motor Yacht Cruise

13.New York City: Holiday Jazz Classic Motor Yacht Cruise

★★★★★★★★★★4.5 · 35 reviews · 1h 30m · from $134

Spend 90 minutes aboard Classic Harbor Line’s Manhattan or Manhattan II, a 1920s-style motor yacht with a heated glass salon, holiday jazz trio, cookies, and one included drink. You’ll pass Battery Park, the Financial District, Governors Island, Ellis Island, and the Statue of Liberty after dark.

“Excelente actividad, el equipo muy amable. Las cosas y la música increíble. 100% recomendable.”

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La Serenissima: Lagoon Cruise on Catamaran with Classical Music - Setting out from Via Giuseppe Garibaldi
Classical Concerts, Classical Concerts in Italy, Classical Concerts in Venice, Cruises & Boat Tours, Italy Concerts, Sailing, Tour Reviews, Venice Concerts

La Serenissima: Lagoon Cruise on Catamaran with Classical Music

14.La Serenissima: Lagoon Cruise on Catamaran with Classical Music

★★★★★★★★★★5.0 · 30 reviews · 1 hour 30 minutes (approx.) · from $72

You’ll spend 90 minutes aboard a roomy catamaran, gliding past Venice’s waterfront neighborhoods, San Servolo, other lagoon islands, an iconic church, and the Biennale Gardens. Classical music plays on board, and your ticket includes one drink, from prosecco and spritz to beer or soft drinks.

“Loved this cruise! They switched between classic and classic rock music lol but it was amazing. Loved seeing Venice this way. Much easier than walking and easier for my mom with mobility issues to get into than a gondola. Loved the drinks and snacks. If in Venice again I would do this tour again even though I’ve already done it. Very relaxing after a long day.”

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New York City Dinner Cruise on Luxury Yacht with Live Music - Under the Brooklyn Bridge and Manhattan Bridge
City Tours, Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Live Music Dinner Cruises, Live Music Dinner Cruises in New York City, Live Music Dinner Cruises in the USA, New York City Concerts, Sailing, Tour Reviews, USA Concerts, VIP

New York City Dinner Cruise on Luxury Yacht with Live Music

15.New York City Dinner Cruise on Luxury Yacht with Live Music

★★★★★★★★★★4.0 · 11 reviews · 3 hours (approx.) · from $175

Board at Pier 36 for a three-hour evening cruise with a private table, five-course plated dinner, live music, full bar, and views of the Brooklyn Bridge, Statue of Liberty, One World Trade Center, and Manhattan skyline.

“The food was tasty and the crew worked hard and were very attentive. It was fun. The only suggestion my husband and I both had is we wish there had been a loud speaker announcing what we were seeing on the skyline. This is our first time in New York and we had no idea what we were looking at.”

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