What is the difference between the Sunset Sail and the Sunset Dinner Cruise?

The main difference is the food. The sunset dinner cruise includes a full dinner, while the sunset sail features a great spread of appetizers and lighter bites. Both cruises include live music, an open bar, and classic Key West sunset views.

What should I wear on a Key West sunset cruise? Is there a dress code?

There is no dress code. Key West is laid-back, so wear what feels comfortable. Some guests dress up, while others keep it casual in sandals. If you are unsure, go with comfortable resort wear and bring a light layer for after sunset.

What should I bring with me?

Bring a light jacket or sweater (it can feel cooler on the water), sunglasses, your phone or camera for photos, and a valid ID if you plan to enjoy the open bar. If you are prone to motion sickness, bring your preferred remedy.

Where do we check in, and how early should we arrive?

Plan to arrive 30-45 minutes before departure to allow time for parking, check-in, and boarding. Sunset hours are a busy time in Key West, so arriving early helps your cruise start stress-free.

Is parking available, and what is the best way to handle it?

Parking can be limited near the waterfront during peak hours, so build in extra time. Public lots and garages plus a short walk are often the easiest option. Rideshare is also a great choice if you want to skip the parking search.

What happens if the weather is bad?

Safety comes first. If conditions are not safe (storms, high winds, rough seas), the cruise may be delayed, rescheduled, or canceled. Light rain does not always stop a trip, and some of the best sunsets happen after passing showers.

Will I get seasick on the cruise?

Most guests do fine, but if you are prone to motion sickness, take precautions ahead of time. Eat something light beforehand, stay hydrated, consider motion sickness bands or medication, and once onboard, get fresh air and look toward the horizon.

Is this cruise family-friendly? Can kids come?

Yes, sunset cruises are a fun family activity. Kids love being out on the water and watching the sky change colors. Adults can enjoy the open bar, and non-alcoholic options are typically available.

Is the cruise accessible for guests with mobility concerns?

Many guests with mobility concerns can still enjoy the cruise, but accessibility can vary by vessel and boarding conditions. Contact the team in advance so they can recommend the best option and plan for smoother boarding.

What time does the cruise leave, and will we definitely see the sunset?

Departure times typically adjust seasonally to match the sunset. The crew plans the route and timing to maximize sunset views, but nature controls cloud cover. Even on partly cloudy evenings, the sunset colors can be incredible.

Sunset Cruises in Key West

The Best Sunset Cruises In Key West

Sunset Cruises with Barefoot Billy’s

Key West sunsets are legendary and Barefoot Billy’s makes it easy to experience them from the water on one of our Key West’s signature sunset cruises. These relaxing sunset boat cruises in the Florida Keys offer stunning views as the sky fills with vibrant colors and the sun sinks below the horizon. Cruise along the coast, enjoy the ocean breeze and take in iconic sights during one of the most unforgettable experiences in Key West. Our sunset cruises all include open bar, delicious food and live music.

Open Bar & Live Music

~~$99.95~~ $79.95

2 hours
All ages

Key West's Dinner Cruise

Join us on Key West’s legendary sunset dinner cruise. This is a Key West staple and a must-do dinner reservation. Experience a true taste of Key West with great food, live music and unlimited open bar.

Kids 5 & under eat free!

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Open Bar & Live Music

~~$89.95~~ $69.95

2 hours
All ages

Sunset Sail Cocktail Cruise

Join us Key West’s best sunset sail aboard this luxury sailing catamaran. Enjoy unlimited drinks, great appetizers and the world renown Key West sunset as our local musician fills the background with tropical island music.

Kids 5 & under eat free!

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About Our Sunset Cruises In Key West

Option 1: Key West Sunset Dinner Cruise

dinner cruises in key west florida barefoot billys (1)

Experience the ultimate waterfront dining experience in Key West. The official dinner cruise of Key West is a staple and a must-do dining experience. Enjoy a tropical buffet dinner featuring island-inspired favorites like Caribbean jerk chicken, fresh local fish, tender pulled pork, fresh salads, fresh veggies and desserts. Relax with live music, unlimited drinks and breathtaking sunset views as you cruise the waters of Key West.

Perfect for a romantic evening, family-friendly fun or group celebrations. This Key West dinner cruise delivers unforgettable sunset dining on the water. Reservations required!

Option 2: Sunset Sip & Sail Cruise

Looking for a more laid-back way to enjoy the sunset? Our Sip & Sail Sunset Cocktail Cruise is a Key West favorite. This catamaran cruise is perfect for guests who want great views without a full dinner. This trip features a great selection of appetizers such as Jamaican jerk chicken sliders, BBQ meatballs, veggies trays, cheese platters, pita and humas and much more. Sail into the evening aboard our spacious luxury catamaran and enjoy unlimited draft beer, wine, mixed drinks, including margaritas, rum runners, champagne and more.

This sunset cruise also features live music. Enjoy unrestricted panoramic views of the sun setting over the Gulf. This sunset sail in Key West is perfect for relaxing, celebrating special occasions or soaking up classic island vibes.

Premium Drink Package Upgrade

Each of our sunset cruises includes unlimited mixed drinks with house liquors. Upgrade for just $19.95 to enjoy unlimited mixed drinks made with top-shelf liquors including Tito’s, Captain Morgan, Tanqueray, Jack Daniel’s, Jim Beam, or similar premium brands.

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dinner cruises in key west florida barefoot billys (1)

Sunset Cruise Reviews

GREAT CREW AND VIEW

This was a great experience. The boat was clean and accommodating. The view of the sunset was spectacular. The drinks were delicious and plentiful. I would highly recommend this trip!

– Peter | Tripadvisor

GREAT TIME

Great time, well with it. Crew were knowledgeable and helpful. My daughters (both in their 20’s) thoroughly enjoyed. The sail gives great views of the island from the ocean. Highly recommend this tour!

– Charlie G. | Tripadvisor

WONDERFUL EXPERIENCE

It was so much fun!! Highly recommend doing this with your friends and family. We had a blast. Honestly well worth it. Jake even took photos for us and sent them to each group!

– Clarissa F. | Tripadvisor