Exploring the Private Sunset Cruise around Key West

If you’re considering a memorable way to end your day in Key West, this private sunset cruise might just be what you’re looking for. With top ratings and hundreds of happy travelers, it’s clear that many find this experience both relaxing and picturesque. It’s a great option if you want to avoid crowded spots and instead enjoy the sunset from your own vessel, guided by an expert captain.
What really draws people in are the personalized nature of the tour—it’s just your group—and the stunning views of the islands and waterfront mansions. Plus, the chance to spot dolphins and marine life adds a fun, spontaneous element. That said, keeping in mind the cost of $350 for up to six people is worth considering, especially if you’re traveling solo or as a couple, since it’s priced per group.
One thing to note: this is a 2-hour experience, so if you’re looking for a longer adventure or dinner cruise, you might want to explore other options. But for those wanting a peaceful, scenic, private moment at sunset, this cruise hits the right notes. It’s best suited for couples, small groups, or anyone craving a calm, scenic finale to their day in the Keys.
Key Points

- Private experience: Your group, your schedule, no crowds.
- Expert captain: Knows the best spots for sunset viewing and wildlife spotting.
- Scenic stops: Sunset Key, Mallory Square, and quiet waters.
- Comfort and convenience: Cooler with chilled water provided.
- Ideal for romance: Perfect setting for a special evening.
- Book in advance: On average, booked 34 days ahead, so plan early.
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Why This Sunset Cruise Stands Out

We love that you’re not just hopping onto any boat—you’re getting a private, tailored experience with a captain who knows the area well. This isn’t a generic tour; it’s designed to give you peaceful, beautiful moments away from the hustle of crowded beachfronts. The boat itself looks clean and well-kept, making it a comfortable setting for a couple, a small family, or friends wanting quality time.
The views of Sunset Key and waterfront mansions from the water are often described as breathtaking. Many reviews highlight how the tour takes you past iconic sights like the southernmost point buoy and offers a different perspective of the island’s beauty. Plus, cruising around Sunset Key gives you a chance to see the stunning beaches and lush surroundings from a peaceful vantage point.
Guides like Captain Don, the star of many reviews, add a layer of authenticity and warmth that travelers really appreciate. They aren’t just pointing out sights—they’re sharing stories, fun facts, and making sure everyone feels safe and comfortable. The reviews consistently mention how knowledgeable and friendly Don is, making the experience even more enjoyable.
Detailed Itinerary Breakdown
Starting Point and Duration
The adventure begins at 5950 Peninsular Ave, Key West, with the tour lasting approximately 2 hours. This short but sweet window is perfect for fitting into an evening plan, especially if you’re after a relaxed, not rushed experience.
First Stop: Southernmost Point Buoy
The cruise starts by cruising past the famous southernmost point buoy, a must-see landmark. But instead of fighting crowds at the pier, you’ll get to see this iconic spot from the water, making for a more tranquil photo op.
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- Classic Key West Schooner Sunset Sail with Full Open Bar
- Sunset Sail on Historic Schooner in Key West
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Second Stop: Sunset Key
Next, your captain will steer around Sunset Key, an exclusive island with beautiful beaches and impressive waterfront homes. This part of the cruise is all about soaking in the scenery—crisp views of the mansions, turquoise waters, and quiet beaches that are often hidden from land-based tours. It’s a peaceful stretch where you can relax and take in the stunning surroundings.
Final Stop: Mallory Square View
As the sun dips closer to the horizon, the boat cruises past Mallory Square, where crowds gather to watch the sunset along with street performers, musicians, and vendors. From the water, you get a different perspective on the lively scene, with fewer crowds and a peaceful backdrop.
Wildlife and Marine Life
Many reviews highlight dolphin sightings during the cruise, adding a wild element to the experience. Guides are known for their knowledge, and you might find yourself marveling at tarpon, barracuda, or other marine creatures along the way. The live commentary enriches the journey, providing context and stories about the local waters and wildlife.
What to Expect on the Tour

The boat is equipped with a cooler filled with chilled bottles of water, which is a nice touch, especially after a day in the sun. The vibe is casual and relaxed—think of it as a floating lounge with plenty of space to sit back, sip your drink, and enjoy the sunset.
The captain is described as accommodating and personable—many reviews mention how friendly and knowledgeable Captain Don is. He’s great at sharing interesting facts about the area, making the cruise both scenic and educational. This personal touch really elevates the experience, especially for first-time visitors.
The Experience’s Value
At $350, the price might seem steep if you’re traveling alone, but it turns into a solid value for a private experience for up to six people. You get exclusivity, a tailored route, and the chance to enjoy the Keys from a unique perspective.
Numerous reviews praise the value for money, emphasizing how this cruise feels special and intimate compared to crowded sunset spots on land. Many guests mention that the experience exceeded their expectations, calling it a highlight of their trip.
Who Should Consider This Tour?
This cruise is ideal for romantic couples looking for a peaceful, scenic sunset experience. It also works well for small groups or families who want a private outing. If you’re someone who appreciates a calm atmosphere, personalized attention, and stunning views, this is a safe bet.
If you’re traveling with children, consider their comfort with boat rides and the 2-hour duration. The relaxed nature and the safety focus mentioned in reviews suggest it’s suitable for most travelers.
Final Thoughts
In a nutshell, this Private Sunset Cruise around Key West offers a genuinely personalized, scenic, and relaxing way to end your day. The combination of knowledgeable guides, beautiful views, and the chance to see marine wildlife makes it stand out among other sunset options. It’s especially suited for those who value quiet, intimate experiences over crowded sunset spots.
While the price may seem high for some, the exclusivity and quality of the tour—plus the beautiful scenery—make it worth considering if you want a memorable, peaceful evening on the water. Whether celebrating a special occasion or simply wanting a break from land-based sightseeing, this cruise is a lovely way to experience the Keys.
Private Sunset Cruise around Key West
“Donny is amazing! Highly recommend! He was very knowledgeable and great with the kids. We ended up booking another excursion with him the following…”
FAQ

Is this tour suitable for children?
Many reviews mention that guides like Captain Don are great with kids, and the tour is generally calm and scenic. It could be suitable if your children are comfortable on boats and enjoy water views.
How long is the cruise?
The tour lasts approximately 2 hours, giving you ample time to relax, enjoy the scenery, and watch the sunset without feeling rushed.
What is included in the price?
The cost covers the private boat, the services of the captain, and a cooler with chilled bottled water. It’s a private tour, so only your group participates.
Do I need to book in advance?
Yes, on average, this experience is booked 34 days ahead. Making reservations early helps secure your preferred date, especially in peak season.
What landmarks will we see?
Key sights include the southernmost point buoy, Sunset Key, and Mallory Square. The tour also offers opportunities to spot dolphins and marine life.
Is there any flexibility in the itinerary?
The guide is known for accommodating the best sunset spots and adjusting timing slightly to make the most of the sunset.
What is the meeting point?
The cruise starts at 5950 Peninsular Ave, Key West and ends back at the same location.
Are there any cancellation policies?
Yes, cancellations are free if made at least 24 hours in advance. Cancellations within 24 hours are non-refundable.
Is this experience weather-dependent?
Yes, if canceled due to poor weather, you’ll be offered a different date or a full refund. Constantly check the forecast as water conditions matter.
Can service animals participate?
Yes, service animals are allowed on the tour.
If you’re looking for a peaceful, scenic, and private way to enjoy the sunset in Key West, this cruise offers a lovely blend of beauty, comfort, and expert guidance. It’s a small splurge that tends to leave a big impression.
More Private Tours in Key West
- PRIVATE Welcome to Key West Walking Tour
- Private Full-Day Tour of Florida Keys from Key Largo to Key West
- Key West Private Luxury Charter Rental: Boat Rental with Captain
- Bimini Charters – Private 3hr Catamaran Charters, Sail & Snorkel
- Private Charter 6 Passenger Sandbar, Snorkel, Dolphins
- Private Tour of Florida Keys from Marathon to Key West
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More Key West experiences we've covered
- PRIVATE Welcome to Key West Walking Tour
- Key West Glass-Bottom Boat Tour with Sunset Option
- Custom Charters with a Local Captain
- Mel Fisher Maritime Museum Admission Ticket
- Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
- Key West Sunset Sail with Live Music, Drinks and Appetizers
- Private Full-Day Tour of Florida Keys from Key Largo to Key West
- Dolphin & Snorkel
- Private Sunset Cruise around Key West
- Dolphin Watching and Snorkeling Adventure in Key West
- Marathon Coffins Patch Reef Snorkel & Sandbar Tour
- Fort East Martello Ghost Tour & VIP Robert the Doll Experience


