Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Imagine yourself on a beautiful boat gliding across the water, surrounded by the vibrant colors of a Key West sunset. For around $93 per person, this 2-hour sunset dinner cruise offers a blend of scenic views, tropical cuisine, and lively entertainment. Departing from the historic seaport, you’ll board a custom-built yacht and enjoy the warm ocean breeze while sipping drinks and listening to live music. It’s a popular choice, often booked 24 days in advance, and offers a great way to enjoy the island’s natural beauty from the water.

What we love about this experience is how it combines spectacular sunset views with a tropical buffet featuring island-inspired dishes. The relaxed yet festive atmosphere, complete with live steel drum music and complimentary drinks, makes it a memorable evening. On the flip side, one thing to consider is that seating can be limited on the upper deck, especially during the prime sunset hour, and some guests have noted that the timing of the sunset might not always be perfect.

If you’re looking for a romantic outing, a fun group activity, or simply want to see Key West from a different perspective, this cruise could be just right. It suits travelers who enjoy good food, lively music, and don’t mind a bit of crowds or being outdoors during sunset. For those who appreciate a combination of scenic beauty and casual comfort, it’s a solid choice.

Key Points

• Stunning sunset views from the water provide a unique perspective of Key West.
• Tropical buffet includes island-style dishes like pork, fish, plantains, and more.
• Live music adds a lively, festive ambience, with some reviews praising the steel drum performer.
• Drinks are included with unlimited well drinks, beer, and wine, with options to upgrade for premium beverages.
• Seating can be limited on the upper deck, especially during the sunset, so early arrival is advisable.
• The cruise passes notable spots like Mallory Square and the Florida Keys Marine Sanctuary.

Starting Point: The Historic Seaport

The adventure begins at 201 William St., the lively hub of Key West’s waterfront. This location puts you right in the center of activity, with the chance to soak in the maritime atmosphere before boarding your vessel. The boat, a 65-foot custom-built yacht, promises comfort and safety, which many reviewers noted as a reassuring aspect.

Check-in is recommended 30 minutes early, giving you time to settle in, grab a cocktail, and find your spot before departure. The group size is capped at around 100 travelers, maintaining a lively but manageable atmosphere. This is just enough people to create a fun energy without feeling overcrowded.

The Vessel and Boarding Experience

Once aboard, the air-conditioned main cabin offers a cool respite from the sun, with a full bar serving included drinks like margaritas, rum runners, and soft drinks. There’s also a cash bar for those wanting to indulge in premium drinks — a good option if you’re a connoisseur or prefer top-shelf options. Several guests appreciated the full bar and complimented the quality of the drinks, especially the rum punch.

The boat’s interior is designed for comfort, but some reviews mention limited seating on the upper deck. That’s the best vantage point for sunset viewing, so arriving early to snag a spot is wise.

The Meal: Tropical Buffet with Island Flavors

The cruise’s highlight is the buffet dinner, which features island-style dishes such as Caribbean roast pork in mojo, fried fish, grilled chicken, and shrimp salad. Sides include black beans and rice, mashed potatoes, deep-fried plantains, and Cuban bread. The menu is subject to change, but the reviews consistently praise the flavorful, hearty food that complements the tropical setting.

One guest described the food as “ok, typical for this kind of event”, but many appreciated the generous portions and tasty flavors. The buffet is served by friendly crew members, making the dining experience smooth and relaxed. The dinner timing unfortunately overlaps with sunset for some guests, leading to a few missing the full visual experience, which is a common challenge on sunset cruises.

Sunset Viewing: The Main Event

As the sun begins to set, everyone heads to the upper deck to catch the show. The views of the horizon are truly breathtaking, with the sky turning shades of orange, pink, and purple. Several reviews mention that the sunset was “gorgeous” and worth the trip, even if clouds sometimes obscure the view.

Listening to live steel drum music while watching the sunset adds a festive, tropical vibe. It’s an atmosphere that encourages not just awe but also dancing and singing along, making it a lively, joyful experience. The cruise passes by Mallory Square, famous for its sunset celebration, giving you a front-row seat to one of Key West’s iconic sights.

Post-Sunset and Return

After the sun dips below the horizon, the boat heads back to the seaport. The trip concludes after about two hours, leaving you with plenty of time to explore the island’s nightlife or take a leisurely walk along the waterfront. Many guests remarked they felt the value of the experience was high, thanks to the combination of scenery, entertainment, and food.

The Experience: Pros and Cons

What Travelers Love

• The spectacular sunset views from the water, often described as “gorgeous” or “breathtaking”.
• The tropical buffet offers plenty of flavorful options that satisfy a variety of tastes.
• The live music, especially the steel drum performer, creates a festive, island atmosphere.
• The included drinks and friendly crew make for a relaxed, enjoyable evening.

Considerations

• Some reviews mention limited seating on the upper deck, particularly during sunset, so arriving early can be crucial.
• The timing of the meal sometimes overlaps with sunset, causing guests to miss full views.
• A few guests found the dinner average and suggested that improving seating or timing would enhance the experience.
• The price is reasonable given the inclusions, but for some, the value depends on how much you enjoy scenic views and lively ambiance.

Who Will Love This Cruise?

This tour is perfect for romantic couples seeking a scenic, relaxing evening, or for groups of friends wanting to enjoy good food and music in a lively setting. It also appeals to travelers who value authentic tropical experiences, from the music to the cuisine. However, if you prefer a more intimate or less crowded setting, or want to ensure you see the full sunset without interruption, you might want to plan your timing carefully or look for a quieter alternative.

Final Thoughts

The Key West Sunset Dinner Cruise offers a beautiful blend of scenery, cuisine, and entertainment. While some aspects—like seating and timing—could be improved, it remains a popular and enjoyable way to experience the island’s iconic sunset from the water. The value is especially apparent if you enjoy lively atmospheres, flavorful food, and scenic views all in one package.

For anyone looking to combine relaxation with fun, or if you’re celebrating a special evening, this cruise provides a colorful, memorable experience that captures the essence of Key West’s tropical charm. Just plan to get to the upper deck early to secure a good spot, and you’ll likely leave with some stunning photos and warm memories.

FAQs

What is included in the tour price?
The booking price covers the 2-hour cruise, dinner buffet, unlimited well drinks, beer, wine, and soft drinks, and live music. Premium drinks are available for an extra cost with an upgrade.

How long before departure should I check in?
It’s recommended to check in 30 minutes prior to your scheduled departure time to allow for boarding and settling in.

Is there a dress code for the cruise?
While the tour doesn’t specify a strict dress code, casual island attire such as shorts, sundresses, or nice casual wear is suitable. Remember, you’ll be outdoors, so dress comfortably and consider bringing a light jacket if it’s cooler.

Can children join the cruise?
Children are allowed but must be accompanied by an adult. The minimum drinking age is 21 years, so minors can enjoy the cruise but not the drinks.

Will I see the sunset if the weather is cloudy?
The cruise is weather-dependent. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Is seating available on the upper deck?
Seats are limited on the upper deck, especially during sunset. Arriving early can help you secure a good spot, but some reviews suggest more benches would improve comfort.

Is the cruise accessible for people with mobility issues?
While the review from a guest who uses crutches was very positive, the boat does involve some stairs to access the upper deck, so accessibility might be limited for those with significant mobility challenges.

What if I want a premium drink?
Premium drinks are not included and can be purchased at the cash bar if you prefer top-shelf options.

This sunset cruise in Key West offers a lively, scenic, and tasty way to end your day. Whether you’re celebrating, relaxing, or just want to capture that unforgettable sunset view, it’s a tour that likely won’t disappoint — just be sure to plan ahead and arrive early for the best experience.