Private Key West Tour in a Small Group From Miami

If you’re considering a day trip from Miami to the iconic island of Key West, you’re probably weighing your options for tours that balance comfort, sightseeing, and value. This private Key West experience, limited to just five travelers, promises a personalized touch with plenty of iconic sights and opportunities to soak up the sunshine. While it’s not the cheapest way to go—it costs $1,155 per group—it offers the kind of intimate, flexible experience that can truly enhance your visit.

Two things we especially like about this tour are the scenic drive across the Seven Mile Bridge—which is often heralded as one of the most impressive engineering feats in the Keys—and the chance to explore Key West at your own pace during your free time. Plus, the small group size means fewer crowds and more personalized attention. On the flip side, a potential downside is the long travel time, which leaves a decent chunk of the day on the road. This tour is best suited for those who want a relaxed, guided experience with minimal hassle—ideal for travelers who appreciate comfort and convenience but don’t mind a full day away from Miami.

Key Points

• Intimate group setting with a maximum of five travelers, ensuring personalized service
• Scenic drive across the famous Seven Mile Bridge and through the Everglades
• Flexible free time in Key West to explore at your own pace
• Includes hotel pickup and drop-off, making logistics simple
• Entry to attractions like the Southernmost Point included, but some museums have extra fees
• Snorkeling option available with an open bar, perfect for adventure lovers

A Closer Look at the Itinerary

This tour is built around a comprehensive day of sightseeing, with each stop carefully curated to give you a taste of what makes Key West special. It begins with a pickup from your Miami hotel and a comfortable ride in an air-conditioned vehicle. When you’re on the road, you can just sit back and enjoy the scenery, knowing someone else is navigating the often tricky Overseas Highway.

The Overseas Highway and Seven Mile Bridge

We loved the way this part kicks off—nothing beats the views during the drive over the Seven Mile Bridge, which stretches across the Gulf and the Atlantic. It’s an incredible feat of engineering, and if you’re into scenic drives, this alone can be worth the trip. Plus, since it’s a private tour, you’re not tied to a bus full of strangers. Instead, you get a relaxed atmosphere, with the freedom to appreciate the view or ask questions.

Driving through the Everglades

On your way down, you’ll pass through the Everglades, which adds a touch of nature’s wildness to the journey. While it’s a quick drive-through rather than an in-depth tour of the Everglades, it’s a nice way to add some natural splendor to your day.

Exploring Duval Street

Once you arrive in Key West, the tour hits Duval Street, the island’s lively heart. It’s compact but packed with charm—restaurants, shops, and pub historic spots. We hear from travelers that “it’s where the heartbeat of the city comes to life,” which is pretty accurate. You get about an hour here to wander, grab a drink, or just soak up the vibrant atmosphere.

Rain Barrel Village and Hemingway’s House

Next, you’ll visit the Rain Barrel Village, an open-air complex lined with local art and crafts—great for picking up unique souvenirs or just strolling through a lush, tropical setting. Then, there’s a stop at the Ernest Hemingway Home and Museum. Although the admission fee isn’t included, many find it worthwhile to peek into Hemingway’s former residence and see the famous polydactyl cats. It’s one of the most popular tourist spots in Key West, and a must for literary fans or history buffs.

Relaxing at Smathers Beach

Later, you’ll spend around two hours at Smathers Beach, the largest public beach in Key West. It’s perfect for relaxing, sunbathing, or trying out some water sports—jet skis, paddleboards, or volleyball if you’re feeling active. Travelers love this stop for its crystal-clear waters and palm-lined shores, though it can get quite busy during spring break months like March and April.

The Southernmost Point and Museum Visit

One of the most iconic stops is the Southernmost Point buoy—a must-see photo op, marking the southern tip of the continental US. It’s quick, but it’s one of those sights that makes you feel like you’ve truly been somewhere special. You also have the option to visit the Key West Museum of Art & History at the Custom House, which is free to admire from the outside, though entry has a fee.

Return to Miami

After a full day of exploring, you’ll be driven back to Miami, with plenty of time to reflect on your trip and share photos. The drop-off is included in the price, making this a seamless experience.

What We Think About the Costs and Value

While $1,155 for a private group might seem steep at first glance, it’s important to weigh what’s included. This price covers transportation, hotel pickup and drop-off, bottled water, and the flexibility of a small, private experience. You’re avoiding the crowds and rigid schedules of larger tours, which can make a real difference.

However, extras like museum entries ($15 or so) and optional activities like snorkeling aren’t included, so budget accordingly if those interest you. If you’re someone who values comfort, personalized attention, and the ability to explore at your own pace, many travelers feel this price offers good value. But if you’re on a tight budget, more affordable group tours could be worth considering.

Practical Tips and Considerations

• Timing matters: Most travelers find the tour is booked about 32 days in advance, so plan ahead if possible.
• Long day, but relaxing: With around 12 hours total, including travel, be prepared for a full day on the road.
• Weather-dependent: If weather turns poor, the tour might be canceled or rescheduled, so keep an eye on the forecast.
• For snorkeling: It’s optional, but if you do choose to add it, be aware it’s with an open bar, which can be fun but also requires responsible drinking.
• Group size: Having just five travelers means more flexibility and less waiting, making it ideal for those who prefer a quieter, more tailored experience.

Who Should Consider This Tour?

This experience suits travelers who want a luxurious, stress-free way to see the best of Key West without the hassle of organizing transportation or managing large groups. It’s great for couples, small groups of friends, or small families who prioritize comfort and personalized service. If you’re someone who loves scenic drives, iconic sights, and leisurely exploration, this tour checks a lot of boxes.

It’s less ideal if you’re on a tight budget, or if you prefer to spend more time at specific attractions and less on the road. The full-day commitment can be tiring, especially if you’re not used to long travel days, so consider your stamina and interests before booking.

Final Thoughts

This private Key West tour offers a well-rounded blend of scenic driving, sightseeing, and free time. The small group setting creates a more personal experience that many travelers appreciate, especially if they’re looking to avoid the chaos of larger tours. While the price might not be for everyone, the convenience and comfort could make it worth it, particularly for those who want a relaxed, curated day discovering one of Florida’s most iconic islands.

If you’re after a flexible, intimate way to see Key West without the stress of planning every detail yourself, this tour could be a smart choice. Just remember it’s a full day, so pack your patience and sun protection—those views and experiences make it worthwhile.

FAQ

Is hotel pickup included?
Yes, the tour offers hotel pickup and drop-off, making your day more seamless and convenient.

How long is the total tour?
The entire experience lasts approximately 12 hours, including travel time and sightseeing.

What’s the group size?
This is a private tour for up to 5 travelers, so you won’t be sharing the vehicle with strangers.

Are meals included?
No, lunch isn’t included, so plan to bring snacks or dine during your free time in Key West.

Can I participate if I don’t want to snorkel?
Absolutely. Snorkeling is optional; your main focus can be on sightseeing and relaxing.

What is the cost?
It’s $1,155 per group, which covers transportation, bottled water, and the personalized experience.

Is this tour suitable for families?
While not specifically marketed as family-friendly, it can work for small families, especially those comfortable with a full day of travel.

What attractions are included?
Stops include Duval Street, Rain Barrel Village, Hemingway House (admission not included), Smathers Beach, the Southernmost Point, and optional museum visits.

What should I bring?
Bring sunscreen, comfortable shoes, a hat, sunglasses, and any personal items for a day at the beach and sightseeing.

If you’re craving a relaxed, intimate trip down to Key West with flexible exploring opportunities, this tour might just be the perfect fit. It balances scenic drives with enough free time to enjoy the island’s highlights, making for a memorable day out.