Live Music · SAILING

Top 10 Sailing Trips Around the World

10 shows  ·  from $20 a seat

This is the shortlist you would send a friend: 10 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

2.Barcelona: Catamaran Cruise with optional Live Jazz Music

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

Sail for 90 minutes from Moll de Drassanes along Barcelona’s coast on a spacious catamaran. Buy a drink at the onboard bar, stretch out on the front netting, and add live jazz for a relaxed soundtrack. This is a scenic ride, not a guided sightseeing tour.

“the jazz music set the right mood for the whole journey”

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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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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

10.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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