Train, KT Tunstall, Lisa Loeb and More Set Sail for 9th Sail Across The Sun Cruise to Jamaica

The four-night, family-friendly music festival cruise departs Miami in February 2027 aboard Norwegian Jewel.

Published on Feb. 22, 2026

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Train and Sixthman have announced the ninth edition of Sail Across the Sun, a four-night, family-friendly music cruise sailing from Miami to Ocho Ríos, Jamaica on February 11-15, 2027. The lineup includes performances by Train, Jet, Yacht Rock Revue, KT Tunstall, Lisa Loeb, The Original Wailers, and more. Beyond the concerts, the cruise will feature interactive experiences, wine tastings, and other activities.

Why it matters

Sail Across the Sun has become a popular annual music festival at sea, providing fans with a unique opportunity to see their favorite artists in an intimate setting while also enjoying the amenities of a cruise ship. The 2027 edition continues the tradition of bringing together a diverse lineup of musicians for a tropical weekend getaway.

The details

The Sail Across The Sun: 9th Edition cruise will feature three unique live sets from Train, including a fan-selected request performance. Other artists on the lineup include Jet, Yacht Rock Revue, KT Tunstall, Lisa Loeb, The Original Wailers, Emerson Hart, The Dan Band, Pat McGee Band, Rock Monahan, Todd Carey, Adam Ezra Group, Sedona Rose, Raised On TV and Shut Up & Dance. The cruise will also include comedy from Rory Scovel and Marcus Monroe, as well as activities like tattoo sessions, yoga, and the Sail Across the Sun Feud game.

  • The cruise departs Miami on February 11, 2027 and returns on February 15, 2027.
  • Presale signups are open now, with alumni presales set for February 25-27, first round presales March 2-4, and the public on-sale beginning March 10 at 2 pm ET.

The players

Train

An American pop rock band known for hits like "Drops of Jupiter" and "Hey, Soul Sister".

Sixthman

An event production company that specializes in music festivals and cruises.

Norwegian Jewel

A cruise ship operated by Norwegian Cruise Line that will host the Sail Across The Sun cruise.

Ocho Ríos

A port city in Jamaica where the cruise ship will dock, allowing passengers to explore the beaches, mountains, and Dunn's River Falls.

Rory Scovel

An American stand-up comedian who will perform on the cruise.

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What’s next

The public on-sale for the Sail Across The Sun: 9th Edition cruise begins on March 10, 2026 at 2 pm ET.

The takeaway

Sail Across the Sun has become a must-attend annual event for music fans looking to experience their favorite artists in a unique, tropical setting. The 2027 edition promises to continue the tradition of delivering a diverse lineup and a wide range of onboard activities and experiences.