St. Maarten: Caribbean Dinner Cruise & Sunset Sail Catamaran

Summary

Caribbean sunset cruise with Creole dinner and open bar

You’ll board a catamaran in Simpson Bay for an evening of Caribbean sailing with open bar service, a Creole-inspired buffet dinner (think beef bourguignon or mahi mahi), and music drifting into sunset. Shoes come off at boarding—so do most worries. Expect laughter with local crew and a taste of island time you might not shake off easily.

What’s the experience like?

We stepped barefoot onto the catamaran at Simpson Bay marina—there’s something about dropping your shoes in a basket that makes you feel like you’re leaving regular life behind. The air was thick with salt and laughter from the crew, who seemed to know everyone by name after five minutes. I leaned on the rail as we started gliding out, rum punch in hand (the first of… well, more than one), watching the colors over St. Maarten shift from gold to this wild orange that doesn’t really happen anywhere else.

The boat had this easy rhythm—music drifting between soca and old French ballads, plates clinking as snacks came around. Our guide, Li, explained how the coastline changes after storms; she pointed out a little cove where fishermen still bring in their catch at dawn. Dinner was served buffet-style—on Wednesday it was beef bourguignon and chicken with scalloped potatoes (I went back for seconds), but someone said Thursday is all about mahi mahi and rum cupcakes. I tried saying “merci” with my mouth full; Li laughed so hard she almost dropped her tongs.

Dancing happened naturally—nobody forced it, just hips swaying as the sun dipped lower and the deck lights flickered on. There was this moment when everything got quiet except for waves slapping against the hull and someone humming along to the music—I still think about that view sometimes when I’m stuck in traffic back home. The cruise ended too soon for me, honestly, but maybe that’s the point.

Step-by-step itinerary

Day 1 — Evening Caribbean dinner cruise

• Board catamaran at Simpson Bay Resort
• Enjoy open bar and snacks
• Sail along St Maarten coastline
• Watch Caribbean sunset
• Dine on Creole buffet menu
• Dance the evening away

Top questions

What time does the Caribbean dinner cruise start?

Check-in is at 4:45pm for this evening cruise departing from Simpson Bay Resort marina.

Is food included on the St. Maarten dinner cruise?

Yes, a Caribbean buffet style dinner is served on board along with snacks.

Are drinks included during the cruise?

The cruise includes a full open bar throughout the evening.

Where does the catamaran depart from?

The catamaran boards at Simpson Bay Resort marina in Pelican, St. Maarten.

Do I need special clothes or shoes?

No special dress code—T-shirts and shorts are fine; shoes are removed at boarding.

Is this cruise suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels.

What’s on the menu for dinner?

The menu varies: Wednesdays feature beef bourguignon & chicken; other nights offer roasted chicken & mahi mahi plus sides and dessert.

How long does the sunset sail last?

The exact duration isn’t specified but it’s an evening event covering sunset hours along St. Maarten’s coast.

What’s included

Your evening includes boarding a 65-foot sail catamaran at Simpson Bay Resort marina, full open bar service with snacks as you sail St. Maarten’s coastline at sunset, followed by a Creole buffet style dinner served on board—all hosted by a professional local crew before returning to shore later that night.