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    1. Local experiences
    2. /Things to do in Key West…
    3. /Aerial Activities
    4. /Scenic Flights
    5. /Key West Beach Proposal Flight
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    Key West Beach Proposal Flight

    Turn a Key West flight into a beachside proposal

    4.9 stars• 273 reviews
    From$682incl. taxes and fees

    Duration

    30 mins

    Ideal For

    Up to 4 people

    Includes

    Private flight, beach banner

    Highlights

    Plan your proposal from the air on a private flight over Key West. Fly past local landmarks and over clear waters before circling a beach banner with your message.

    • Fly past Key West landmarks and out over clear waters
    • Circle a beach banner reading "WILL YOU MARRY ME"
    • Choose whether to propose above the banner or after landing
    • Share the moment aboard a private charter flight

    Know before you go

    • Arrive at least 20 minutes early for check-in and a pre-flight briefing
    • Bring government-issued photo ID for every traveler age 18 or older
    • Weight limit: 275 lbs per seat and 600 lbs total for flights of 30 minutes or less
    • Expect flight plans to change, be canceled, or be upgraded for operational needs, air traffic control, weather, or pilot discretion

    Cancellation Policy

    Cancel at least 48 hours before your scheduled flight for a refund minus booking charges. Cancellations within 48 hours, late arrivals, and no-shows are non-refundable. A $50 non-refundable rebooking fee applies outside 48 hours. Receive a full refund if weather disrupts the flight and rescheduling is unavailable.

    FAQs

    Wear shoes that secure around your ankle or heel. Do not wear loose clothing, jewelry, or hats, and tie up long hair securely. You may want a jacket.

    Bring only a cell phone or GoPro; a harness is provided. Other camera types are not permitted.

    Keep all items and body parts inside the aircraft at all times. You are responsible for any loss or damage caused to the aircraft, equipment, or environment.

    Meeting details

    3471 S Roosevelt Blvd, Key West, FL 33040

    Experience provided by Fly-KeyWest
    Experience provided by Fly-KeyWest

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #DXNPUX

    Private Flight

    $682.86

    Up to 4 guests maximum

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    273 reviews•Google Maps
    257
    8
    0
    0
    4

    Damian (also spelled Damien in some reviews) is clearly the heart of this operation, and he comes up again and again as the reason people love their experience. Guests describe him as friendly, knowledgeable, and genuinely attentive, pointing out wildlife like sharks, turtles, stingrays, and dolphins mid-flight. One aerial photographer even praised his ability to nail specific angles and flight patterns for professional reef photography, which speaks to a level of skill that goes well beyond the typical tour pilot. The rides themselves get consistent praise for being smooth and scenic, with the Florida Keys providing a backdrop that reviewers say simply cannot be appreciated from the ground. One guest has now flown four times over six years, which says a lot. A practical tip from the reviews: ask about removing the doors for completely unobstructed views if that appeals to you. There is one isolated complaint about difficulty reaching someone by phone for a booking inquiry, so if you have trouble getting through, it may be worth trying a different contact method rather than giving up entirely. That aside, the overwhelming pattern here is of a well-run, memorable experience led by a pilot who genuinely cares about showing guests the best of the Keys.

    What people are saying

    Review 1 of 5
    5/5

    Amazing addition to the trip. Highly recommend as kids loved the helo, the views are amazing, and you really get a feel for the ecosystem with all the islands, and inlets. Do it early as it helps you understand the island and all the others activities being offered. Fly Key West Helos team was great, and even refunded us for unused flights.

    Photo of Jeremey Thomas

    Jeremey Thomas

    July 2, 2026

    Review 1 of 1
    5/5

    Amazing addition to the trip. Highly recommend as kids loved the helo, the views are amazing, and you really get a feel for the ecosystem with all the islands, and inlets. Do it early as it helps you understand the island and all the others activities being offered. Fly Key West Helos team was great, and even refunded us for unused flights.

    Photo of Jeremey Thomas

    Jeremey Thomas

    July 2, 2026

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