St. John: Sunset Sail with Open Bar & Hors D'oeuvres

Summary

Sail Pillsbury Sound at sunset with drinks food and island views

You’ll board a 55-foot catamaran in St. John for an easygoing sunset sail across Pillsbury Sound—with champagne from the open bar in hand and trays of hors d’oeuvres making their rounds. Watch the sky change colors over Cruz Bay as your local crew shares stories and steers you gently back in time for dinner plans—or maybe just more island wandering.

What’s the experience like?

We stepped barefoot onto the Daydreamer catamaran just as the sky over Cruz Bay started turning that weird gold-pink color—like someone dimmed the lights but forgot to turn them off all the way. The crew greeted us with easy smiles and a glass of something cold (champagne, I think, but honestly I was distracted by how salty the air tasted). There were maybe twenty of us, but it didn’t feel crowded—everyone sort of melted into their own corners, leaning on railings or flopping onto cushions. Our captain, Mark, pointed out Turtle Bay as we glided past, telling us about how locals head there for quiet swims when tourists get noisy.

I didn’t expect the wind to be so soft out on Pillsbury Sound. It felt like a warm hand brushing my hair back—nothing dramatic, just gentle. Someone behind me laughed at a joke I missed; I caught myself smiling anyway. The open bar was actually open (not just rum punch), so we tried some local beer after our second round of bubbly. The crew brought around trays of snacks—tiny skewers with pineapple and something smoky that I still can’t name. My partner tried to ask what it was in his best attempt at island patois; one of the deckhands grinned and said, “Just eat it—you’re here now.” Fair enough.

The sun dropped lower and everything went kind of quiet for a minute—no one talking, just water slapping against the hull and this slow orange glow sliding across St. John’s hills. I thought about how far away home felt right then (in a good way). We drifted back toward Cruz Bay in time for dinner reservations, but honestly? Part of me wanted to stay out there until it got dark enough not to see anything at all. That feeling stuck with me longer than I expected.

Step-by-step itinerary

Day 1 — Sunset sail with open bar and views

• Board 55′ catamaran Daydreamer
• Sail in Pillsbury Sound waters
• Enjoy open bar and hors d'oeuvres
• View north shore beaches of St. John
• Watch Caribbean sunset under full sail
• Return to Cruz Bay for dinner

Top questions

Is pickup included for this St. John sunset sail?

No hotel pickup is mentioned; boarding is from Cruz Bay near Westin.

What drinks are served on the sunset sail?

The tour includes champagne plus a full open bar with various drink options.

Are food allergies accommodated on this cruise?

Yes, alternative food items can be arranged with 72 hours’ advance notice; extra costs may apply.

Is this sunset sail suitable for children or infants?

Yes, infants and small children can ride in a pram or stroller during the cruise.

How long does the St. John sunset sail last?

The exact duration isn’t listed but you return to Cruz Bay before dinner time.

Does this tour include any stops or swimming?

No swimming stops are mentioned; it’s a relaxing sailing experience only.

What’s included

Your evening includes sailing aboard a 55-foot catamaran from Cruz Bay with all fees covered, unlimited drinks from an open bar (including champagne), assorted hors d’oeuvres served by the crew throughout the cruise, and guidance from local staff before returning ashore near Westin in time for dinner plans.