11 Live Music Sailings, Anywhere They Sail

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

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

Sail from Key West for about two hours aboard a spacious catamaran with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

Check availability →Read our full review

2.Sunset Sailing Cruise with Live Music

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

Spend 90 minutes cruising Barcelona’s coast aboard a classic Turkish gulet as the sun drops over the Mediterranean. You’ll have room to move between the upper and lower decks, listen to live guitar, singing, saxophone, piano, or other scheduled music, and buy drinks or snacks from the onboard bar. English and Spanish assistance is available.

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

Check availability →Read our full review

3.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Fury’s 65-foot catamaran, with live local musicians, unlimited margaritas, champagne, beer, wine, soda, and seasonal appetizers. You can dance, sit on the sundeck, or watch the sunset from shaded decks. The cruise returns to Greene Street in time for dinner.

“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”

Check availability →Read our full review

4.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Board the Sandie Cat at 201 William Street for a two-hour Key West sunset sail with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The three-deck catamaran offers broad sunset views, though the food is snack-sized and the mood can range from calm to lively. Captain Anna has earned praise for her friendly, confident handling of the boat.

“Great drinks and fun crew! We had a great time on the boat and enjoyed the music and the other guests.”

Check availability →Read our full review

5.Live Music Sunset Sail

★★★★★★★★★★5.0 · 285 reviews · from $70Top rated

Set out from Frederiksted Pier for a roughly two-hour catamaran sail along St Croix’s west coast. Local live music, unlimited Cruzan rum punch, fruit punch, and water keep things easygoing as you pass Frederiksted and Sandy Point National Wildlife Refuge. Shoes come off onboard, and the boat carries up to 48 people.

“Taylor and B are awesome! Great crew, super friendly she will even clean your shoes lol 😂 the drinks were also great.”

Check availability →Read our full review

6.Aruba Sunset Sail with Caribbean Dinner and Live Music

★★★★★★★★★★4.5 · 224 reviews · from $109

Sail Aruba’s coast from Piet’s Pier toward Eagle Beach and the lighthouse, with steel-drum music, an open bar, and a Caribbean buffet served aboard a catamaran. You’ll watch the sunset from the deck, then raise the sails again for more music and sea views. Check in 30 minutes early; hotel transfers are not included.

“Excellent! Funny crew, good music, good cocktails and fine food. On a buffet was salad with rancho dressing, coconut rice, baked potatoes with veggies, grouper with creole seasoning, chicken in mushroom sauce and some sort of lasagna. Everything was very tasty. The only thing I was missing was a mojito or margarita because all cocktails were sweet.”

Check availability →Read our full review

7.Sunset Sailing in Barcelona & Live Music by Aperol

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

Sail for about 90 minutes from Moll de les Drassanes aboard a wooden Turkish gulet or replacement vessel. You’ll watch the sun drop behind Barcelona, see Port Vell and Barceloneta from the water, and hear live music that may range from acoustic guitar to saxophone. Drinks and small snacks cost extra, and the boat returns to the starting point.

“Great music! It made the night! We took my daughter age 18 and she enjoyed the sunset. Music was enjoyable acoustic covers. The crew was kind.”

Check availability →Read our full review

8.2-Hour Sunset Sail with Live Music

★★★★★★★★★★4.7 · 130 reviews · 2 hours · from $79

Spend two hours aboard Sebago Watersports’ spacious Marquesa catamaran, sailing past Key West’s Historic Seaport, Mallory Square, and Fort Zachary Taylor. Your captain positions the boat for sunset while live music, unlimited drinks, and passed appetizers keep the evening moving. Premium drinks cost extra, and you should arrive 30 minutes early.

“Really good service and boat trip! Tips were pushed a bit too much, the service was good enough that I think everyone would’ve tipped anyway”

Check availability →Read our full review

9.Nights of Lights Sail w Live Music& Sunset Opt

★★★★★★★★★★4.8 · 97 reviews · 90 minutes - 2 hours · from $69

Cruise from Vilano Beach into St. Augustine for 90 minutes to two hours of Nights of Lights views, live music, and complimentary drinks. Choose sunset or evening departure, then watch the Bridge of Lions and Castillo de San Marcos glow from the water. Bring warm clothes, arrive 30 minutes early, and expect light snacks rather than a full meal.

“beautiful opportunity to see nights of lights without fighting street traffic. fun life band. unlimited beer wine and margaritas. hospitable and attentive crew. one of the better sunset cruises we've done here.”

Check availability →Read our full review

10.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 Halifax Harbour cruise. You’ll pass Georges Island, Historic Properties, the waterfront, and the Northwest Arm, with live music from performers such as Gary or Tommy. If weather allows, the crew may invite you to help raise the ship’s huge sails.

“It was a really nice boat trip with great music played by Tommy.”

Check availability →Read our full review

11.Romantic Sailboat Sunset: Live Music, Premium Bar & Dinner -Cabos

★★★★★★★★★★4.5 · 3 reviews · 3 hours (approx.) · from $272

Set sail from Cabo Marina Tu Enamorado at 5 p.m. for a three-hour sunset cruise toward El Arco. You’ll receive a signature cocktail, antipasto, the Baja Duo dinner, dessert, live music, and a premium open bar. Hotel pickup is optional, and the boat returns to the marina.

“Beautiful tour! Our group of 3 couples had an amazing experience. Absolutely recommended. The staff was friendly and very attentive, the views were spectacular, and the food was delicious! Perfect romantic sunset cruise to end our trip off.”

Check availability →Read our full review