If you’re looking for a way to see Miami from a fresh perspective, a private sailing trip around Biscayne Bay might just be your best bet. This experience offers the chance to skip the crowded, cookie-cutter tours and instead tailor your cruise to your preferences. Whether you’re celebrating a special occasion, seeking a peaceful day on the water, or simply want to enjoy stunning views, it’s worth considering.
What we love about this experience? First, the personalized approach means you get a cruise that’s truly tailored to your interests and timing. Second, the variety of optional activities and stops—snorkeling, paddleboarding, or just relaxing—gives you flexibility. But a possible consideration? This tour requires you to book in advance (usually around 43 days ahead), and the price might seem steep for some. Overall, it’s best suited for travelers who appreciate privacy, customization, and a bit of luxury in their water adventures.
Key Points

- Highly rated with a perfect 5.0/5 based on 73 reviews, and a 99% recommendation rate.
- Flexible durations from 4 to 12 hours, so you can choose how long to enjoy the bay.
- Personalized routes and activities—snorkeling, paddleboarding, or even an overnight trip.
- Includes luxury yacht for up to six guests, equipped with amenities like restrooms, outdoor shower, ice, and water.
- An authentic Miami experience with stops at iconic sites like Stiltsville, Key Biscayne, and Biscayne National Park.
- Excludes the US Coast Guard-certified captain fee ($50), which is an important consideration for budgeting.
Discover Miami from the Water: A Closer Look
This private sailing experience on a stylish 40-foot Beneteau yacht promises a more intimate way to explore Miami’s famous Biscayne Bay. Unlike larger, group-oriented cruises, this is all about customizing your cruise to what you want. Whether you’re after scenic sightseeing, water activities, or simply relaxing under the sun, the tour can be molded around your preferences.
The boat itself offers a comfortable, sleek, and modern setting. With space for up to six guests, it’s perfect for small groups—families, friends, or couples who want a special day on the water. The onboard amenities—restrooms, an outdoor shower, fridge, and ice—add a level of comfort that makes the experience more convenient.
What makes this tour stand out is the flexibility. You can choose from a variety of routes and durations. A shorter 4-hour trip might focus on key sights like Key Biscayne and Stiltsville, with options to swim or paddleboard. Longer trips can incorporate snorkeling at Biscayne National Park or even an overnight cruise for an extra special memory. This approach is great for travelers who want more than just a set itinerary.
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The Itinerary Breakdown
Let’s walk through what you might experience. Each stop offers something unique, and the best part is that you can decide how long to linger or whether to skip certain sites.
Stop 1: Key Biscayne – This upscale island features landmarks like President Nixon’s vacation home, the Bill Baggs Lighthouse, and No Name Harbor. It’s a peaceful spot for anchoring and swimming, perfect for kicking off your trip with some relaxation and water fun. The review from a recent guest describes it as a “beautiful” stop, emphasizing the chance for a refreshing swim.
Stop 2: Stiltsville – This collection of historic stilt houses is one of Miami’s most quirky sights. Built during the Prohibition and post-WWII eras, Stiltsville offers a glimpse into Miami’s past. Watching the sunset from here is a highlight, according to visitors, and you can take photos of these unique homes from the water.
Stop 3: Miami Skyline & Virginia Key Beach – As you cruise under the Rickenbacker Bridge, you’ll get stunning vistas of Miami’s modern skyline and waterfront. Virginia Key Beach Park is an excellent spot to anchor, relax, or paddleboard. Some trips include a barbecue of skirt steaks (a fan favorite among reviews), which adds a fun and tasty element to the day.
Stop 4: Biscayne National Park – For those interested in snorkeling, this is a real treat. The tour can include a reef experience near Miami, provided weather and time permit (best with 5+ hours of daylight and an early departure). This is a rare chance to explore underwater life close to the city.
Stop 5: Elliott Key – The largest key in Biscayne National Park, Elliott Key, is a quieter alternative to crowded beaches. It’s perfect for swimming, sunbathing, and paddleboarding. The nearby sandbar is a popular spot, and a trip here is often praised in reviews for its peaceful vibe.
The Practicalities
The tour includes water, ice, safety gear, and onboard facilities—all essentials for a comfortable day. Not included? The $50 fee for a US Coast Guard-certified captain—a requirement for the trip. While some might see this as an extra, it’s an important safety measure, especially when exploring beyond Miami’s shores.
Pricing is set at $425 per person, which on the surface might seem high, but when you consider the exclusivity, customization, and amenities, it offers solid value. For instance, the reviews suggest guests found the experience top-tier, with mentions of excellent service and memorable moments.
What the Reviews Say
Guests consistently praise the tour’s flexibility and the quality of the experience. One reviewer described it as “perfect for a sunset or proposal,” highlighting Rodrigo’s professionalism and attention to detail. Others loved the dolphin sightings, the stunning sunset views, and the food—particularly the skirt steaks, which seemed to surprise many with their flavor. The boat and crew receive high marks for their friendliness and ability to cater to different preferences, especially with kids.
Who Should Consider This Tour?
If you enjoy intimate, customizable trips and want a mix of sightseeing, water activities, and relaxation, this experience is ideal. It’s especially fitting for couples celebrating a special moment, small groups wanting privacy, or travelers who appreciate a touch of luxury. Keep in mind, it’s best if you’re comfortable with a moderate price point and booking ahead.
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Practical Tips and Final Thoughts

- Book well in advance—most guests reserve about a month and a half ahead to secure their preferred date.
- Factor in the $50 captain fee when budgeting.
- Prepare for variable weather—the tour is canceled if the weather is poor, but you’ll be offered a different date or full refund.
- Bring your own snacks or drinks if you want additional treats, as only water and basic amenities are included.
- Consider your activity level—paddleboarding and snorkeling are optional and might require some physical effort, but instructors are available if you want lessons.
- Think about timing—departures before 10 AM are best for including Biscayne National Park snorkeling, especially in good weather.
The Sum Up

This private sailing experience on Biscayne Bay offers a unique, tailored way to explore Miami’s beautiful waters. The combination of a stylish yacht, customizable itinerary, and friendly crew makes it a memorable choice for those seeking a more personal and flexible adventure. It’s perfect for travelers who value quality over quantity, and who want to craft their perfect day on the water.
While the price might be a consideration for some, the exclusivity, comfort, and variety of stops justify the cost for many. If you’re after stunning views, a bit of adventure, and the chance to experience Miami from a different angle, this tour is well worth considering.
Whether celebrating a special occasion or simply wanting to treat yourself to a unique day, this trip has the potential to be a highlight of your Miami visit. Just remember to plan ahead and communicate your preferences to maximize your experience.
Private Sailing on the Miami Bay – Biscayne Bay
“I was proposing to my girlfriend, and Rodrigo was absolutely awesome and made sure everything was perfect. He helped me pick the perfect time, took…”
FAQs

How long does the tour last?
The duration ranges from about 4 to 12 hours, depending on your chosen itinerary and stops. You can customize how long you want to stay at each location.
What is included in the price?
The price covers the yacht, water, ice, safety equipment, restrooms, and an outdoor shower. The US Coast Guard-certified captain fee ($50) is extra.
Can I choose my route and activities?
Yes, this is a fully customizable experience. You can opt for snorkeling, paddleboarding, an overnight stay, or specific sightseeing stops.
What are the main stops I’ll see?
Key Biscayne with its landmarks, Stiltsville, Miami’s skyline, Virginia Key Beach Park, Biscayne National Park, and Elliott Key are the highlights.
Is this experience suitable for children?
While the tour isn’t explicitly marketed for families, the reviews mention that the captains are great with kids. It’s best if children are comfortable on boats and able to enjoy water activities.
What if the weather turns bad?
The tour is canceled if weather conditions are poor, but you’ll be offered a different date or a full refund.
If you’re after a flexible, luxurious way to enjoy Miami’s waters and scenery, this private sailing trip could be just what you need. It balances adventure, relaxation, and personalized service in a way that’s hard to beat.
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