St Thomas Legends Luxury Dinner Sail from the Ritz Carlton

Imagine watching the sun set over the Caribbean Sea while you sip a glass of champagne and enjoy a carefully curated three-course meal. For a taste of luxury and local flavor, the Legends Dinner Sail aboard the Lady Lynsey II is a compelling choice. Starting from the elegant Ritz-Carlton in St. Thomas, this 2.5-hour cruise costs around $119 per person, offering a blend of fine dining and scenic sailing.

What we love? First, the dedicated service ensures you’re not just another passenger, but treated to attentive care—whether you’re relaxing inside the cabin or soaking up the ocean breeze from the spacious deck. Second, the menu is locally inspired, showcasing seasonal island ingredients in a thoughtfully crafted three-course dinner. We also appreciate the premium open bar, with options ranging from craft beers to Champagne, making this sail feel like a true celebration.

A potential drawback? The experience hinges on good weather; if the skies turn gloomy, the cruise might be canceled or rescheduled, which could be inconvenient if you’re on a tight schedule. Also, parking at the Ritz-Carlton is $25, so plan accordingly.

This tour is best suited for those seeking an elegant, relaxed evening with a flavor of the Caribbean. Whether you’re celebrating a special occasion or simply want a memorable way to end a day on the island, this experience delivers on both scenery and cuisine.

Key Points

• Luxury experience with dedicated service and premium drinks
• Locally inspired three-course dinner with fresh, seasonal island ingredients
• Breathtaking views of the Caribbean sunset from a spacious deck
• All-inclusive bar featuring craft beers, wines, champagne, and top-tier liquors
• Comfortable setting with options for private indoor seating or open-air deck
• Weather-dependent — good weather is essential for the best experience

A Closer Look at the Legends Luxury Dinner Sail

When you step aboard the Lady Lynsey II at The Ritz-Carlton, you’re entering a scene of understated elegance. The marina buzzes with anticipation, and you’ll instantly sense that this isn’t just a run-of-the-mill boat tour. Instead, it’s a carefully curated experience that balances comfort, flavor, and scenic beauty. The boat itself is spacious, with ample room to enjoy the ocean breeze or settle into the cozy interior if you prefer a cooler setting.

The departure at 5:30 pm coincides perfectly with sunset, allowing you to witness the sky transforming into a palette of oranges, pinks, and purples. As the boat gently slips away from the dock, the crew begins serving the locally inspired three-course dinner, which is a highlight of the experience. The menu is curated specifically for this sailing, emphasizing seasonal island ingredients, which means each dish reflects the freshest local produce and flavors.

The Dining Experience

The menu is designed to be a culinary snapshot of St. Thomas. We loved the way the dishes are presented—well-balanced, flavorful, and thoughtfully paired with the drinks available on the open bar. You might find yourself savoring a Caribbean-inspired appetizer, followed by a main course featuring local seafood or island vegetables. The desserts are likely to be just as enticing, rounding out the meal with a sweet note.

The premium open bar is noteworthy, offering a selection of specialty cocktails, top-tier liquors, and local craft beers from St. John Brewers. The inclusion of craft beers and hard seltzers adds a modern touch, appealing to those who appreciate quality drinks without the fuss. The wine list includes premium reds and whites, and of course, champagne is available for toasting the sunset.

Scenic Views and Atmosphere

What sets this cruise apart is its scenic setting. You’re not just eating; you’re experiencing a panoramic view of the Caribbean Sea, with the setting sun casting a golden glow over the water. The deck is ideal for those who love to feel the wind, take photographs, or just relax and take in the scenery. For couples or small groups, the private seating options mean you can enjoy intimacy amidst the natural beauty.

Practicalities and Considerations

The tour lasts approximately two and a half hours, making it a manageable addition to your evening plans. Most travelers find the timing perfect—early enough to avoid the chill of night but late enough to catch that magical sunset. The boat caps at 45 passengers, so it feels intimate without being crowded.

On the downside, if weather conditions turn poor, the cruise might be canceled, and you’ll need to keep an eye on the forecast. Parking at the Ritz-Carlton costs $25, so budget that into your plans. Also, gratuity isn’t included, so consider tipping your crew for excellent service—generally 15-20% is customary.

Who Will Enjoy This?

This experience suits adventurous food lovers, couples celebrating special moments, or anyone who wants a relaxed yet refined way to see the sunset. It’s ideal if you appreciate local cuisine, quality drinks, and scenic sailing, and don’t mind a slightly higher price point for a more intimate, premium experience.

The Value of the Legends Dinner Sail

When you weigh the $119 cost, think about what’s included: a three-course meal, a premium open bar, and an unforgettable sunset backdrop. The quality of the food, the freshness of the ingredients, and the attentive service elevate this above typical dinner cruises. It’s not just a boat ride; it’s a curated experience that highlights the best of what St. Thomas has to offer—great flavors, beautiful scenery, and a touch of luxury.

The experience provides excellent value for travelers wanting an elegant evening without the fuss of a full-day excursion. Plus, with free cancellation up to 24 hours in advance, it’s a low-risk way to add a memorable highlight to your trip.

Final thoughts

If you’re after a refined, scenic, and authentic Caribbean dining experience, the Legends Luxury Dinner Sail is a strong choice. It’s especially suited for those who want a relaxed, intimate setting with good food and drinks. The combination of local flavors, stunning vistas, and attentive service makes it a memorable way to end a day in St. Thomas.

However, it’s worth noting that the experience is weather-dependent, and parking costs can add up. But if the skies are clear, and you’re ready for a taste of Caribbean elegance, this sail offers a delightful escape from the hustle.

FAQ

How long is the dinner sail?
The cruise lasts about 2 hours and 30 minutes, including sailing, dining, and enjoying the sunset.

What’s included in the price?
You get a three-course dinner inspired by local cuisine, plus an open bar featuring specialty cocktails, premium wines, champagne, and top-shelf liquors.

Is parking available nearby?
Yes, onsite parking is available at the Ritz-Carlton for $25.

Can I participate if I have dietary restrictions?
Yes, alternative food items can be arranged with 72 hours’ notice, though additional costs may apply.

What should I wear?
Smart casual is appropriate. Bring layers if you tend to get chilly in the evening, especially if sitting outside on the deck.

Is the experience suitable for children?
Most travelers can participate, but the cruise is designed more for adults seeking a relaxed, intimate experience.

What happens in case of bad weather?
If weather cancels the cruise, you’ll be offered a different date or a full refund.

How do I book?
You can reserve online, and confirmation is provided immediately after booking.

In summary, the St Thomas Legends Luxury Dinner Sail offers a refined, scenic way to enjoy the Caribbean sunset. It’s a great fit for those looking to combine local flavors with a touch of elegance, all within a relaxed, intimate setting. Whether celebrating a special occasion or simply indulging in a memorable evening, this cruise promises a genuine taste of island luxury.