With Florida’s southernmost dining scene at your doorstep, Key West serves up experiences worth savoring. Skip the chain restaurants like Hard Rock Cafe – the real gems are on the water. Sunset dinner cruises stand out as the best way to combine local flavors with unforgettable views. Our favorite outings pair Caribbean-inspired cuisine with intimate yacht settings, offering better food and smaller crowds than the big party boats.
Particularly impressive are the boutique sailing tours that include fresh seafood spreads and premium drinks while dolphins play in the wake. The most memorable meals here aren’t about white tablecloths – they’re about fresh catch and golden sunsets.
Take a look at our tested picks for Key West’s top dining adventures:
Key Points
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The Hard Rock Cafe on Duval Street offers a music-themed dining experience with a fixed-price menu featuring classic American fare and a family-friendly Lil Rocker menu.
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Sunset dinner cruises in Key West provide panoramic views of the Gulf of Mexico, a tropical food buffet, an open bar, and live music for an immersive experience.
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Key West Sunset Cruise offers a 65-foot yacht, a tropical-themed buffet dinner, unlimited well-mixed drinks, and stunning views of the Keys’ natural beauty.
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The Sunset Buffet Dinner Cruise features a maximum capacity of 56 guests, an open bar, and live music, though reviews are mixed.
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The Dolphin Watching & Snorkeling Adventure combines a dolphin watching and snorkeling excursion with a sunset dinner cruise, offering a comprehensive and scenic experience.
Hard Rock Cafe Key West Dining Experience
Although located on the bustling Duval Street, the Hard Rock Cafe Key West offers diners a music-themed dining experience complete with rock ‘n’ roll memorabilia.
The restaurant features a fixed-price 2- or 3-course menu with classic American fare like burgers, ribs, salmon, and steak, plus vegetarian options.
Diners can enjoy a coffee, tea, or soft drink, with alcoholic beverages available for purchase.
The Hard Rock Cafe also caters to families with a Lil Rocker menu for children.
Wheelchair accessibility, stroller access, and service animals are allowed.
While the dining experience has received generally positive reviews, some customers have reported issues with prepaid meals and food quality.
Read our full review: Hard Rock Cafe Key West Dining Experience Review
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Key West: Sunset Dinner Cruise With Open Bar & Live Music
Typically, visitors to Key West can experience a sunset dinner cruise with an open bar and live music. This 2-hour excursion allows guests to marvel at panoramic views of the sunset over the Gulf of Mexico.
The cruise features a tropical food buffet with options like roast pulled pork, fried fish, and Cuban bread. An open bar serves up margaritas, rum runners, and more. Live music plays on the upper deck after dinner.
Priced from $89.95 per person, this cruise is likely to sell out, so booking in advance is recommended. Reviews highlight the memorable experience, quality food, and friendly crew.
Read our full review: Key West: Sunset Dinner Cruise With Open Bar & Live Music Review
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Key West Sunset Cruise: Dinner and Drinks Included
For those seeking a memorable evening in Key West, the Key West Sunset Cruise: Dinner and Drinks Included offers a captivating experience.
Departing from the historic seaport, guests will embark on a 65-foot custom-built yacht, where they’ll enjoy a tropical-themed buffet dinner, unlimited well-mixed drinks, and live music.
The menu features Caribbean-inspired dishes like pulled pork, grilled chicken, and fried fish.
As the sun dips below the horizon, passengers can relax and soak in the stunning views of Key West, Mallory Square, and the Florida Keys National Marine Sanctuary.
With positive reviews highlighting the friendly crew and beautiful setting, this sunset cruise is a must-do for those seeking a unique and memorable dining experience in Key West.
Read our full review: Key West Sunset Cruise: Dinner and Drinks Included Review
Book now: Check availability
Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music
The Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music offers travelers a chance to experience the beauty of the Florida Keys while indulging in a delectable Caribbean-inspired feast.
With a maximum capacity of 56 guests, this cruise features an open bar and live music, allowing passengers to unwind and savor the stunning sunset.
The cruise departs from the Historic Seaport Pier, conveniently located next to Waterfront Brewing Company and Schooners Wharf.
Although not wheelchair accessible, the cruise is suitable for most travelers.
While the overall rating is 2.5/5 based on two reviews, one guest, Christine_T, enjoyed the sunset, DJ, food, and drinks.
Read our full review: Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music Review
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Dolphin Watching & Snorkeling in Key West With Sunset Dinner Cruise and Open Bar
This adventurous excursion in Key West allows travelers to witness the incredible marine life of the Florida Keys.
Over the course of 5 hours, participants can go dolphin watching, snorkel, and enjoy a sunset dinner cruise with an open bar and live music.
The tour includes a variety of Caribbean-inspired dishes like pulled pork, grilled chicken, and fried fish.
While reviews are mixed, with some noting issues with scheduling and service, most praise the knowledgeable crew, enjoyable activities, and beautiful sunset.
Travelers are advised to pack light, bring essentials, and be prepared for potential wait times during check-in and dining.
Read our full review: Dolphin Watching & Snorkeling in Key West With Sunset Dinner Cruise and Open Bar Review
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Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Travelers visiting Key West can embark on a captivating sunset sail that offers a full bar, live music, and a delectable dinner.
The 2-hour cruise includes an open bar, a tropical food buffet, and live entertainment. Guests can also opt for a 3-hour morning snorkeling trip, which provides fresh juices, muffins, fruit, and cereals.
Both experiences depart from the meeting point at 201 William St, Key West, with arrivals 40 minutes prior to departure. Confirmation is received at booking, and the tours accommodate up to 80 travelers.
Priced from €153.99 per person, the experiences offer free cancellation up to 24 hours in advance and a reserve now, pay later option.
Read our full review: Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling Review
Book now: Check availability
Recap
Key West offers a variety of exceptional dining experiences, from sunset cruises with live music to snorkeling adventures with a dinner buffet. Whether you’re looking for a romantic evening or a fun-filled outing, there’s something to suit every taste and budget. These top-rated options provide the perfect way to savor the flavors and scenery of this charming Florida destination.