Sail Across the Sun 2027: Train's ninth cruise leaves Miami with JET, KT Tunstall and Lisa Loeb aboard

Train plays three sets, one of them built from fan requests, on a four-night Miami-to-Jamaica sailing Feb. 11–15, 2027.

Picture the Norwegian Jewel pulling away from PortMiami in mid-February, a deck full of people who have been waiting all winter to sing along with Train at sea. That's the whole idea, and this is the ninth time the band has built a voyage around it.

Sail Across the Sun returns for its ninth edition Thursday, February 11 through Monday, February 15, 2027, a four-night sailing aboard the Norwegian Jewel from Miami to Ocho Rios, Jamaica, according to the cruise's official site. Cabins book through Sixthman's booking page.

Train plays three separate performances, and one of them is a request set built from fan picks, per The Music Universe. For a band with this many radio singles, letting the boat choose the setlist is a genuine hook. Expect at least one night where the deep cuts come out.

The supporting lineup reads like a well-curated 2000s mixtape with a few surprises. JET and KT Tunstall are the biggest draws after the headliner. Yacht Rock Revue will handle the sunset-party portion of the program, and Lisa Loeb brings the singer-songwriter side. The Original Wailers featuring Al Anderson add some reggae to a voyage that ends in Jamaica, which feels about right. Emerson Hart and The Dan Band round out the upper half.

For a band with this many radio singles, letting the boat choose the setlist is a genuine hook.

Further down, the official lineup lists Pat McGee Band, Adam Ezra Group, Sedona Rose, Raised on TV, Drew Angus, Hummingbird Hotel, Seranation and Shut Up & Dance, and our listing also includes Rock Monahan and Todd Carey. On a ship this size, those are the sets you wander into on the way to dinner and end up staying for. Sixthman's pages haven't been perfectly consistent about the lower tier, so check the lineup page as sailing approaches.

It isn't only music. Comedians Rory Scovel and Marcus Monroe are aboard, tattoo artist Craig Beasley is set up on the ship, and Pat & Amber return for three wine tastings, which the cruise's experience page calls a fan favorite.

For Miami, this is one of the winter's quieter music events: no venue on land, no line at the door, just a departure from the port in mid-February. Most passengers fly in for it. If you live here, the commute is a short drive to the cruise terminal, and you get to skip the airport entirely.

The schedule page will fill in the set times. Until then, there's time to decide which three songs you're requesting.

Sail Across the Sun 2027: Thu, Feb 11 – Mon, Feb 15, from PortMiami to Ocho Rios. Book via Sixthman.

Sources: Sail Across the Sun — Official site (sailacrossthesun.com); Sail Across the Sun — Lineup (sailacrossthesun.com); Sail Across the Sun — Experience (sailacrossthesun.com); Sail Across the Sun — Schedule (sailacrossthesun.com); The Music Universe — Train unveils ninth voyage for 2027 (themusicuniverse.com); Sixthman — Sail Across the Sun 2027 booking (sixthman.net); Wikimedia Commons — Miami Sunset from Cruise Terminal F (commons.wikimedia.org)