Windstar Caribbean 2028 Cruise with Jerry Diaz

March 20-27, 2028

Island Perfection, Redefined

If you could bottle that easygoing, sun-soaked, flip-flop state of mind Jerry Diaz sings about—you’d end up with an island itinerary a lot like this.

Think less crowds, more hidden gems. We’re talking tiny harbor towns and off-the-radar ports most travelers never see—places where the pace slows down, the water turns that unreal shade of turquoise, and it feels like you’ve stumbled into your own private paradise. Every stop (except Virgin Gorda) comes alive with live music by Jerry Diaz, setting the tone with island rhythms that follow you from shore to ship.

Days drift by effortlessly. Maybe you’re diving straight off the Watersports Platform into glassy, sunlit water… maybe you’re stretched out on deck with a drink in hand, letting the breeze carry you to the next escape. There’s no rush here—just that perfect, barefoot kind of freedom.

Back onboard, the vibe stays just right. Picture a Signature Barbecue by the pool—grill sizzling, ocean stretching out in every direction, and music in the air that makes you want to linger a little longer. It’s the kind of evening that turns into a memory before you even realize it.

And then comes that day—the one you’ll talk about long after the trip is over. A secluded beach. Powder-soft sand. An incredible spread waiting under swaying palms. Cold drinks, warm sun, and the kind of setting that doesn’t feel real until your feet hit the shore. Windstar’s Signature Beach Party is more than a highlight—it’s the moment everything clicks into place.

This isn’t just a cruise. It’s your own island rhythm.

7-Day Itinerary

Roundtrip from San Juan, Puerto Rico

3/20/2028 13:00 EMBARK SAN JUAN
3/20/2028 19:00 DEPARTURE SAN JUAN
3/21/2028 8:00 ARRIVAL CRUZ BAY, ST. JOHN
3/21/2028 18:00 DEPARTURE CRUZ BAY, ST. JOHN
3/22/2028 8:00 ARRIVAL BASSETERRE, ST. KITTS
3/22/2028 17:00 DEPARTURE BASSETERRE, ST. KITTS
3/23/2028 7:00 ARRIVAL GUSTAVIA, ST. BARTHELEMY
3/23/2028 22:00 DEPARTURE GUSTAVIA, ST. BARTHELEMY
3/24/2028 8:00 ARRIVAL PHILIPSBURG, ST. MAARTEN
3/24/2028 22:00 DEPARTURE PHILIPSBURG, ST. MAARTEN
3/25/2028 9:00 ARRIVAL GREAT HARBOUR, JOST VAN DYKE
3/25/2028 22:00 DEPARTURE GREAT HARBOUR, JOST VAN DYKE
3/26/2028 8:00 ARRIVAL VIRGIN GORDA/PRICKLY PEAR, BVI
3/26/2028 17:00 DEPARTURE VIRGIN GORDA/PRICKLY PEAR, BVI
3/27/2028 7:00 ARRIVAL SAN JUAN
3/27/2028 8:00 DISEMBARK SAN JUAN

Early Booking Promotion:

$100 pp onboard credit
Complimentary All Inclusive package

Star Category Suites

Starts at $2912 per person, double occupancy

As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.

Includes categories - SP, SS1, SBS, SBS1
277 square feet
Ocean View or French Juliette Balcony options
Queen bed* (*Limited availability separated as 2 twin beds)
Shower options *based on availability

*There is an additional entertainment fee of $200.00 per person not included in pricing.

Gracious Ocean View Suites

Starts at $3,007 per person, double occupancy

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.

Includes categories - S, S1, S2,S3, BS, BS1
277 square feet
Ocean View or French Juliette Balcony options
Queen bed (or separated as 2 twin beds)
Tub or Shower options *based on availability

*There is an additional entertainment fee of $200.00 per person not included in pricing.

Additional Suite Options Available

Single occupancy is available

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