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Private Key West Day Trip with 4 Scenic Stops

3 Reviews 5.00 out of 5 stars Based on 3 reviews collected by City Sky Diving and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
| Miami, USA
Book online or call us

from $1,100 per group (up to 13)

Lowest Price Guarantee
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Don't miss out!
On average, this is booked 26 (0) days in advance.
13 to 14 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
and 2 more
Italian, Spanish

Overview

This is not a crowded bus tour — it is a private, carefully curated journey through the Florida Keys.

We combine iconic stops, authentic local experiences, and engaging storytelling, allowing you to truly connect with the places you visit rather than simply pass through them. From legendary waterfront cafés and wildlife encounters to breathtaking ocean views and literary history, every stop has been thoughtfully selected.

Travel in comfort aboard our 2025 Mercedes Sprinter, enjoy a relaxed pace, and experience Key West with the flexibility and personalized attention that only a private tour can offer.

This is the Keys — elevated, intimate, and unforgettable

What's Included

  • Snacks
  • Carbonated beverages Soda/Pop
  • Bottled water
    See 2 more

    Meeting and Pickup

    Pickup point

    What To Expect

    Book Online

    Our secure website provides real-time availability, and free, no-hassle cancellations up to 24 hours before your tour begins.
    Read more

    Safe & secure Easy breezy Hassle‑free

    Harriette's Restaurant

    Our first stop is at Harriette's Restaurant, a historic Florida Keys landmark established in 1982 inside a charming former family home.Here, you are not just a customer — you are treated like family.We will spend approximately 30 minutes here, giving you time to enjoy a relaxed coffee break and taste their legendary oversized muffins, famous throughout the Keys and beloved by locals and visitors alike. This stop offers the perfect opportunity to stretch, relax, and begin the journey to Key West with an authentic and flavorful experience.
    Read more

    30 minutes Admission Ticket Free

    Bass Pro Shops

    At this stop, we step into the world of Ernest Hemingway, the legendary author of The Old Man and the Sea.Hemingway lived in Key West in the 1930s, where the ocean became both his inspiration and his playground. In 1934, he purchased his beloved boat, the Pilar, and sailed often between Key West and Cuba in search of adventure.During our visit, you will see a faithful replica of the Pilar and relive the spirit of a time when literature, freedom, and the sea were inseparable.
    Read more

    30 minutes Admission Ticket Free

    Robbie's of Islamorada

    Our next stop is at the iconic Robbie’s of Islamorada, a waterfront landmark in the Florida Keys known for its relaxed atmosphere and unforgettable wildlife encounters.Here, you’ll have the chance to feed the famous tarpon directly from the dock. These impressive fish can grow over 6 feet long and weigh more than 200 pounds, and are known for their strength and spectacular leaps out of the water.Guests may purchase a small bucket of bait and experience the thrill of watching these silver giants rise dramatically from the sea to catch their meal — a true Keys moment you won’t forget
    Read more

    40 minutes Admission Ticket Free

    Seven Mile Bridge

    We will stop to admire the breathtaking Seven Mile Bridge, one of the most iconic bridges in the United States.Stretching across turquoise waters and endless horizon, this engineering masterpiece connects the Middle and Lower Keys and offers one of the most spectacular views of the entire journey.Take a moment to step out, breathe in the ocean air, and capture unforgettable photos surrounded by nothing but sea and sky — a true Florida Keys postcard moment.
    Read more

    30 minutes Admission Ticket Free

    Key West

    Our final stop is vibrant Key West, the southernmost point of the continental United States.Here you will enjoy free time to have lunch, stroll through colorful streets, and discover the island’s most iconic attractions at your own pace. From historic landmarks to lively squares and oceanfront views, Key West offers the perfect mix of charm, culture, and Caribbean spirit.Relax, explore, and experience the island your way before we begin our comfortable return journey.
    Read more

    5 hours Admission Ticket Free

    Show 4 more stops

    Additional Info

    • Confirmation will be received within 48 hours of booking, subject to availability
    • Service animals allowed
    • Public transportation options are available nearby
    • Infants and small children can ride in a pram or stroller
    • Infants are required to sit on an adult’s lap
    • Specialized infant seats are available

    Frequently Asked Questions (7)

    Q: What is the cancellation policy for the Private Key West Day Trip with 4 Scenic Stops?

    A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST). Read more Apr 2025

    Cancellation Policy

    You can cancel up to 24 hours in advance of the tour for a full refund.

    Still have questions?

    We're here to help.
    Activity code: C-5529808P6

    Traveler Photos

    Reviews

    5.00
    3 reviews

    Average 5.00 out of 5 stars based on 3 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor

    5 stars
    3
    4 stars
    0
    3 stars
    0
    2 stars
    0
    1 star
    0
    Don't miss out!
    On average, this is booked 26 (0) days in advance.
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    Frequently Asked Questions (7)

    Activity name

    The answers provided below were previously given in response to questions from City Sky Diving customers.

    Filter by:

    Q: What is the cancellation policy for the Private Key West Day Trip with 4 Scenic Stops?
    A:
    You can cancel up to 24 hours in advance of the tour for a full refund.
    • For a full refund, you must cancel at least 24 hours before the tour start time.
    • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
    • Any changes made less than 24 hours before the tour start time will not be accepted.
    • Cut-off times are based on the tour local time (EST).
    Apr 2025
    Q: What's included in the price?
    A:
    The following is included:
    • Snacks.
    • Carbonated beverages. Soda/Pop.
    • Bottled water.
    • Private transportation.
    • Air-conditioned vehicle.
    Apr 2025
    Q: What is the minimum age for this tour?
    A:

    There is no minimum age for this tour, so bring your wee one along for an adventure..

    Apr 2025
    Q: My date is not available in the calendar, I am just checking to see if it is available?
    A:

    If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

    If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

    Apr 2025
    Q: Is this an accessible tour?
    A:

    Accessibility information for the Private Key West Day Trip with 4 Scenic Stops is as follows:

    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    Apr 2025
    Q: Where is the meeting point for this activity?
    A:

    Detailed check-in instructions – including meeting point address, Google map, and parking information – for Private Key West Day Trip with 4 Scenic Stops will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

     

     

    Mar 2024
    Q: How long does a refund take to reach my card, and can I get it faster?
    A:

    Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

    Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

    If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

    Oct 2026

    What's Included

    Activity name

    • Snacks
    • Carbonated beveragesSoda/Pop
    • Bottled water
    • Private transportation
    • Air-conditioned vehicle

    Additional Info

    Activity name

    • Confirmation will be received within 48 hours of booking, subject to availability
    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    • Infants and small children can ride in a pram or stroller
    • Infants are required to sit on an adult’s lap
    • Specialized infant seats are available

    Report Product Issue

    Activity name