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304 North Cardinal St.
Dorchester Center, MA 02124
Explore Key West’s waters with kayaking, paddle boarding, and sailboats on a private, all-in-one adventure that combines fun, relaxation, and stunning views.
Dock Side Adventure Kayak, Paddle Boarding, Sunfish Sailboats: An In-Depth Look at a Water Lover’s Delight
Travelers looking to combine a mix of active water sports with laid-back island vibes will find the Dock Side Adventure in Key West a compelling choice. This experience, offered by Serenity Sailboat Charters, promises a full day of aquatic fun with access to kayaks, paddle boards, sailboats, and even snorkeling gear, all aboard a spacious double-deck slide boat. At $143 for roughly eight hours, it’s an all-in-one package designed for those who want variety and flexibility without multiple bookings.
One aspect we really appreciate is the full access to different water toys—from stand-up paddleboards to Sunfish sailboats—allowing guests to customize their day and enjoy multiple forms of water recreation. Plus, the floating mat and the shaded lounge area make it easy to relax between active sessions. However, potential participants should note that the lunch isn’t included, so bringing your own or planning a meal is advisable. This tour suits those who want a flexible, playful day on the water—perfect for families, groups of friends, or curious solo travelers seeking a taste of everything.
Sailing fans have several other Key West options to choose from
The tour kicks off at 6810 Front St, Naval Air Station Key West, giving you easy access from many accommodations nearby or via local transit. With a schedule running daily from 9:00 AM to 8:00 PM, you have plenty of flexibility for early mornings or late afternoons—ideal for avoiding the midday heat or catching sunset views.
The duration of around 8 hours means you’re not rushed. You can spend your time leisurely paddling, sailing, or simply lounging on the floating mat. This is especially appealing if you’re someone who prefers unhurried days on the water rather than quick, packed excursions.
Guests are given full access to four stand-up paddle boards and four kayaks, perfect for pairs or small groups. The two Sunfish sailboats (14 ft) open up options for those wanting to try sailing, even if they’re beginners. The 11 ft Boston Whaler is available for snorkeling or spearfishing at nearby spots—these are within a 10-minute boat ride, offering convenient access to interesting reefs or marine life.
The inclusion of snorkeling equipment encourages exploration beneath the surface, adding an extra layer of adventure. Some reviews mention the boats are well-maintained, making for a safe and enjoyable experience, even for first-timers. The boat itself, a 30 ft double deck slide boat, is a highlight, equipped with a Bluetooth speaker system, ice chest, and outdoor grill—meaning you can relax, groove to your favorite tunes, and enjoy a picnic or barbecue lunch if you bring your own.
The shade provided on the deck helps beat the sun’s strongest rays, and the large floating mat offers a perfect spot for sunbathing or socializing. The boat’s outdoor grill and ice chest suggest that you can prepare snacks or even a barbecue meal, which enhances the experience with a casual, fun dining option.
While lunch isn’t included, the availability of a grill means you can have a customized meal on board—something many guests appreciate. The Bluetooth speaker system is a nice touch for creating a lively atmosphere or relaxing tunes during downtime.
The boat allows easy access to snorkeling spots, making it versatile for those who want to explore underwater life. The boat ride to excellent snorkeling or spearfishing spots—just a quick 10-minute trip—is a major plus, especially for guests who want to combine water sports with marine exploration.
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This experience is private, meaning your group won’t be sharing the boat with strangers. This can provide a more relaxed, personalized environment, especially if you’re celebrating a special occasion or just prefer a more intimate outing. The private nature of the tour allows for tailored timing and activities, making it ideal for families or groups with specific interests.
At $143 for an entire day of activities, the price offers good value—especially considering the variety of watercraft and the length of the experience. Renting multiple water toys individually could be more costly elsewhere, and the convenience of having everything in one package is a significant perk.
This adventure appeals to water enthusiasts of all levels—beginners or seasoned paddlers and sailors—who want variety and flexibility. It’s perfect for families, groups of friends, or solo travelers who appreciate the chance to explore at their own pace. If your ideal day includes splashing around, sailing, and relaxing in the sun, this tour aligns well with your plans.
It’s less suited for those who prefer guided tours with fixed itineraries or who want included meals. Also, if you’re prone to seasickness or dislike active water sports, you might want to consider your comfort level before booking.
The Dock Side Adventure provides a well-rounded, flexible day of water-based fun in Key West. The combination of kayaking, paddle boarding, sailboats, snorkeling gear, and a spacious deck boat creates an environment that’s both lively and laid-back. The opportunity to customize your day while enjoying excellent amenities on a private boat makes it stand out among typical water excursions.
Pricing, for what you get, is reasonable, especially considering the length and variety of activities. The experience really shines for those who want a personalized, multi-activity day and enjoy the natural beauty of the Florida Keys from the water.
This tour is best suited for adventure seekers who don’t mind a bit of physical activity and want to explore the ocean’s surface and below, all while having the option to relax and soak in the scenery.
Is this a group tour or private experience?
This is a private tour, meaning only your group will participate, offering a more personalized and relaxed environment.
What is included in the tour?
You get full access to four kayaks, four stand-up paddle boards, two Sunfish sailboats, snorkeling equipment, and use of the 30 ft double deck slide boat with amenities like Bluetooth speakers, ice chests, and grills.
Are meals included?
No, lunch is not included. You might want to bring your own or plan to purchase food separately, especially if you want to enjoy the boat’s grill.
What’s the starting point and schedule?
The tour begins at 6810 Front St, Naval Air Station Key West, and runs daily from 9:00 AM to 8:00 PM, giving you plenty of flexibility in planning your day.
How long is the experience?
Approximately 8 hours of water fun and relaxation, giving you ample time to explore and unwind.
Can I bring service animals?
Yes, service animals are allowed on this tour.
What physical condition should I have?
Participants should have a moderate level of physical fitness, given the active water sports involved.
Is snorkeling included?
Yes, snorkeling equipment is provided for exploring underwater spots accessible within a short boat ride from the main vessel.
In all, if you’re seeking a day full of water activities with the option to chill and enjoy the scenery, this private, multi-activity adventure in Key West offers an excellent blend of excitement and relaxation at a fair price.