Best Locations to Propose and Plan a Surprise Engagement in Key West
When it comes time to choose the perfect location to ask the love of your life to marry you, there are a lot of options in Key West! If you’re planning to pop the question and want to set up a surprise engagement session, undercover proposal shoot, or similar moment that your significant other is not expecting, then in addition to booking your photography to capture the moment, you’ll need to think about the perfect location.
Knowing which location to choose for your proposal is going to depend on a few things:
Time of Year - Certain locations are only available in certain seasons (for example, an exclusive resort is going to limit off-property guests making dining reservations if they’re at full capacity for those staying with them already), and some though technically “available” aren’t necessarily going to be the best idea (ie, certain beaches from late April to June get inundated with stinky sargassum grass…not the most romantic vibe for the big moment!").
Time of Day - Certain areas make great backdrops at sunset, while others have better lighting earlier in the day. Additionally, if sunset is super important to you and you want those epic “afterglow” photos once the sun has dipped below the horizon, you’re going to want to choose a different location than if you’ll be content with a few quick final sunset pictures before having to depart the venue. And while some venues will only grant access for a proposal after hours, others close early and you need to be there and gone by the time they are! If you’re visiting on a cruise ship for the day, then an After Hours experience at a historic venue is probably not going to be a good fit because you’ll already be back on the ship. In short, timing definitely plays a role in where you propose in Key West!
Privacy - If you’re looking for something totally private with absolutely no chance of anyone else interfering, then you’re of course going to pick a location that is much different than if you want the serendipity and surprise of an entire slew of onlookers. And there are options everywhere in between.
4. Service - I have some clients who simply want a lovely setting but otherwise aren’t looking for any kind of setup, services, or decor. Others want a more full-service experience with valet parking, floral displays, charcuterie, champagne, dinner service, and other perks. Naturally, this will have an effect on which location you choose!
5.Overall Ambience and “Vibe” - This is where personality and personal preference will supersede any logistical or practical conditions. With all other things set aside, the perfect location is the one that speaks to you the most. If you’ve always envisioned a quiet walk down the beach, holding hands as the sun is about to set, finding a spot where you can stop and take in the views of the ocean before popping the question, then of course you’re going to want a beach location of some kind. If you’re a history buff and want to infuse a little bit of Key West nostalgia into the experience, then scheduling it at a local historical venue is going to be more your style. The good news is that Key West has something for everyone!
6. And last but not least, of course, Budget - Some locations are public city or county-owned spaces, and there is no permission required to propose there. Others charge a site fee which can range anywhere from $50 to $5,000 depending on the location and what you want to set up. Some site fees are all-inclusive and come with an array of amenities and services. Some are just a fee to show up, with no private area or special attention provided. Others may have simply a minimum booking requirement (ie, you have to be staying or dining there). And since some locations require extra travel and planning time by your photographer, those will add to the package cost. If your budget is very tight, you’re definitely going to be looking at different spots than if you have more flexibility.
Proposing on a Public Beach in Key West
Getting engaged on one of the beaches in Key West is a great way to incorporate the natural beauty of the islands into your big moment. While Key West is not particularly known for its beaches since we are on such a small island, there are a few locations that I find make great spots for undercover proposal shoots, both for their natural beauty, great lighting, and layouts that allow me to remain in hiding until the moment unfolds. Here are a few favorite beaches where you can pop the question in Key West:
Smathers Beach
When you think of a postcard perfect beach, you probably have the views that Smathers Beach can offer you. This is our most "beachy beach" with sprawling fluffy sand, wooden boardwalks, tall seagrass, and soaring palm trees all along the shoreline. It’s also our largest beach, making it a great choice for a public location because it means we can pretty much always get far enough away from other beachgoers to give you some some semblance of privacy simply by scooting further up or back from the entrance. While positioned on the south end of the island, there are several rock jetties that go out into the water which face West, so those DO give us a relatively direct view of sunset in the background. The main drawback though is that it can be the worst location for the buildup of sargassum grass on the shore, which dries out, gets quite pungent and isn't very pretty in the background. With that said, if the sargassum grass is blowing in on the tide, it’s going to be present on EVERY beach in Key West, even those owned by the resorts, but it seems to build up faster and more prominently on this one in particular. If it’s sargassum season and you want to to use Smathers as your ideal location, I typically recommend a backup spot that we can switch to the day of, since we sometimes don’t know until that day how bad it is going to be. If you’re proposing from about August until about March, then you have less reason to worry about it, but I still like to mention it.
Check out this Sunny Afternoon Proposal, this Afternoon Proposal with additional Family Surprise, and Proposal followed by Sunset Photos.
Higgs Beach
Higgs is the smallest public beach in Key West, but its size is actually also one of its greatest assets. Everything it has to offer is very close together, making showing up for a proposal incredibly easy and straightforward (there’s literally NO way you can go the wrong way), and also making it possible to get a wide variety of photos in lots of different settings in a short amount of time (perfect for surprise engagements, when you’ll no doubt be eager to go celebrate and call your family). On the flip side, the small size means close proximity to the parking, which means a shorter/less anticipation-building approach as you get to “the spot”, so it can feel a tad less "exclusive" than the other beaches. It has a historic fortress (West Martello Tower) and coral sea wall, sections of greenery and palm trees, and the added bonus of not one, but two piers that can be great spots to capture photos as well.
There are also two sections of beach...the east side is smaller with its densely packed sand being more conducive to strolling to look at the water, so you rarely get out there to find many lounging beachgoers on that side, often given it a feel that you’ve got the whole area to yourself. The more tightly packed sand is also easier to walk in if one is wearing high heels, so there’s that consideration as well. The west side of Higgs Beach, however, is your typical fluffy beach sand where you can walk in the water. The one drawback is it’s going to be busier on that side, with people lounging watching sunset, playing volleyball, listening to live music in the adjacent pavilion, or jogging by for their evening workout.
Check out this Beach Proposal and For/Pier Photos, this Short Undercover Proposal with Friend Group, and this Proposal in the Key West Garden Club followed by Beach Portraits which, for an extra fee, they will allow you to come in and take photos amongst the flowers and butterfly garden, and you can even propose under their white gazebo or at the top of the hill overlooking the water if you choose.
Fort Zachary Taylor
Fort Zachary Taylor State Park is the largest and most natural location we have on the island of Key West. With its quiet walking trails, sprawling open field, plentiful natural foliage, and natural beach lined with Australian Pines, Royal Palms, and Sea Grape bushes, there is no shortage of places to capture photos of your undercover proposal. Since it faces west, it also has the most direct view of sunset on the island aside from Mallory Square, but keep in mind this also makes it a popular spot for others at that time of day as well, so jockeying for position can be a bit tough sometimes. The beach has a more natural appearance with areas of coral rock and shells as well as areas of soft sand. While it tends to be relatively quiet in the afternoon, you can sometimes run into groups still hanging out, but with so many areas to shoot in, it's easy to change to another spot on short notice. There's also has a historic civil war-era fortress that can make a great overlook to pop the question from the top of the ramparts, but that part of the park does close at 5, so sessions in the fort have to be scheduled earlier than those scheduled by the water. Like any location it has all of these “pros” but to me, one main “con” is that they close RIGHT at sunset, which can be such a bummer when there’s an epic sunset with beautiful colors forming (often the most vibrant skies happen 5 to 15 minutes AFTER the sun has dipped below the horizon) and we have no choice but to leave. Other than that, it’s a lovely place to ask your significant other to marry you! Check out this Top of Fort Proposal, this one Overlooking the Harbor, and this one On the Beach.
Sammy Creek Landing
If you’re staying in the Lower Keys such as Big Pine, Cudjoe Key, Sugarloaf, Summerland, Bay Point, or Big Coppitt, and don’t want to go all the way into Key West for your undercover proposal session, OR if you’re looking for a location that not that many people utilize (so you’ll have photos that nearly no one else gets, AND you can pretty much almost guarantee you’ll have the whole place to yourself), then Sammy Creek might be your top pick! Located about 30 minutes from Key West and way down into the quiet stretches of Sugarloaf Boulevard (the same road that is home to the famous “jumping bridge”)….technically referred to as “Old State Rd 4A” at that point….it is a cute little park tucked away next to a canal on one side and the Atlantic Ocean on the other. There’s a crisp white pea rock area overlooking the water, a small kayak launch with big coral rocks making up the sea wall, there’s a bridge which can be used for a cool vantage point, and several nice palm trees and greenery for a tropical feel. While it’s small size might not make for a big epic expansive wide angle vista, the drive out to the location is through very quiet mangrove lined roads, completely off the beaten path, adding a sense of adventure to your arrival.
Proposing at a Local Resort in Key West
If you’re staying at one of Key West’s beautiful resorts during your stay, you may be tempted to consider it for your Surprise Engagement session while on the island. After all, you’re already there, so getting to the location will not be an issue, and if you decide to combine some other activity like dinner, then your significant-other will definitely not suspect anything. While these are indeed great reasons to choose a resort as your proposal location, there are a few things to keep in mind.
First is availability. Because resorts often also double as event venues for weddings, parties, and corporate meetups, your first hurdle might be making sure they have the capacity to accommodate your request to use the grounds for a proposal.
Second is budget. Depending on what else the property has booked, depending on their internal policies with regard to usage of the grounds, and depending on what you want to do while on site, there may be a venue rental or site fee that you’ll need to pay over and above your room rate and/or dinner plans. Unfortunately every resort is different, and the fees I’ve seen have ranged anywhere from $100 to $5000, so there is really no way to quote that without talking to your specific resort. Also, becuase resort locations do require more legwork, logistics, permissions and planning time on my part as well, it falls under our hourly admin/planning time on top of your photography package, so just some things to budget for.
And last is Suitability. Even if a resort location is available and within budget, it may not necessarily be the most suitable for an undercover proposal. Since these are shot from a clandestine vantage point (usually), we have to think about hiding spots, line of sight to wherever you’ll be dropping to one knee, and lighting that will hit the area around the time you’ll be proposing. Where a natural environment like a beach is a little more forgiving because it’s so open, a resort can sometimes present challenges like too narrow of a distance between where your photographer can hide and where you can propose, or have things that stifle the options for what shots we can get like fences, outbuildings, signage, or they’ll have things like swim buoys or jetskis floating in the water in the background.
Once you’ve figured out the availability, rates, and suitability of your particular resort, then it can indeed make a meaningful (and logistically carefree) spot to plan the perfect proposal.
Here are a few local resorts that I’ve had experience photographing proposals in, and my thoughts on each one’s particular pros and cons:
The Reach Resort (with dinner at Four Marlins)
One resort that is amazing for proposals is The Reach! Between the picturesque gazebo that stretches out over the water, their beautiful private beach, premier oceanfront dining with Four Marlins, and an experienced team who are pros at making undercover proposals go off without a hitch, it’s often a favorite among couples who want a great experience, a beautiful setting, and a convenient location. Their “Tide to Table” package allows you to have dinner out on the beach, giving a romantic end to a perfect evening. The property is also beautifully laid out with lots of picturesque spots for photos, including the beach, the gazebo, an upstairs overlook, and a lush green lawn area. As with any resort location, prior permission from their event staff is required, and depending on your date, time, and vision and needs for your proposal, additional site fees may apply.
The Reach also has a sister property, Casa Marina Resort, known for their "Toes in the Sand" package where you can have dinner at your own private table out on the sand, either before or after your proposal, and that’s a beautiful spot as well. Right now that property is undergoing an 80+ million dollar renovation with priority access being (rightly) limited to their wedding couples, so rather than showcase that location only to have you very possibly not be able to plan it there, I’m waiting until that is done and then will update this post at that point! :)
Hyatt Centric Key West (with dinner at Four Flamingoes)
The most recent addition to this list as of August 2023 is the Hyatt Centric Resort on Front Street. While definitely a favorite venue for weddings, it was not until my client reached out that he wanted to do dinner at their newly remodeled Four Flamingoes restaurant that I even had this location on my radar for a proposal. I’m so glad I did, because it was perfect! They set up a lovely table on their private beach overlooking the water, in a quiet area nestled off to the side so they would have some privacy, and because they were arriving for dinner but needed extra time to valet the car and possibly hang out on the dock for a few minutes until their table was ready, it gave the perfect alibi for why they needed to get there early. From an undercover standpoint, there are so many nooks and crannies around the restaurant that I was able to easily duck behind fences and hedges as they made their entrance, then the restaurant staff were kind enough to let me use their employee “out” door at the back to get a good vantage point as they were seated at their table. I had a perfect view of them but could remain undetected until the big moment. Now, if you’re looking for a huge sprawling sand beach, this won’t be your venue. While their beach is private, it is very small. Definitely great for a cozy romantic dinner date, but just keep that in mind if beach photos are your thing! They do, however, have a nice dock that is great for photos, and several pretty spots around the hotel. As you can see from the photos, their proximity to the harbour made for a lovely sunset at the end!
Little Palm Island (with dinner at their exclusive Dining Room)
This is a super exclusive resort accessible only by boat in Little Torch Key. During certain times of year, you can book dinner reservations at their on site waterfront restaurant, and schedule your proposal out on the beach at the same time. They have very attentive and wonderful staff on site who can bring just about any vision to life, and the quiet surroundings and variety of scenes and settings around the property are wonderful to take a variety of photos after you’ve popped the question. Just keep in mind that this location is about a 40 minute drive out of Key West, so you’ll need to account for needing extra buffer time to get there and back. In addition, the extra roughly hour to 90 minutes of necessary early arrival to catch and ride the ferry, plus possible waiting time after sunset to take it back to shore, will require a custom package upgrade with photography, but if you’re looking for a super private and upscale experience, this is your best pick! Keep in mind as with any resort location, prior permission and minimum booking/reservation requirements may be required.
Sunset Key (with dinner at Latitudes)
Similar to Little Palm, Sunset Key is another exclusive private island accessible only by ferry, however instead of driving up the Keys, this is in Key West itself, about a 7 minute boat ride from the docks at Opal Key Resort. While the beach is available only for use by guests of the Sunset Key Cottages (or owners/guests of the privately owned homes on the island), if you happen to be staying out there, you can enjoy a lush and luxurious experience for your proposal (availability permitting with no other events happening the same day). If you’re not staying on the property, you can technically also book the site fee just as you would for any other event, so depending on how lavishly you want to throw your proposal, that is certainly an idea! With its breathtaking views of sunset off the dock, the delicious dining at Latitudes restaurant, and the quiet tropical setting make it a very special place to pop the question.
Marriott Beachside (with dinner at Tavern ‘N’ Town)
I put this one last because while I had a great time shooting at Marriott Beachside, and it’s one of my personal favorite places to go to dinner at Tavern N Town (making it a great and easy recommendation for dinner afterward), the only really scenic spot to propose is on or near the lookout pier, which from an undercover logistical standpoint, can be a challenge given that my only option to capture the photos is to be way down at the other end, in which case you could have the pillars in the shot, or if I go onto the pier itself once you get to the end, we run the risk of your significant-other noticing me and catching wind of what’s about to happen. Further, while it has never been an issue with regard to other people being on the pier, since it is available to all guests, the possibility of getting out there and not having the space to yourself is definitely something to consider. I would say that if you’re a Marriott Guest, having dinner on site, and want just an easy and simple logistic for a sweet proposal before you head inside to celebrate, then it’s a great option, but if you’re looking for a location with a ton of variety and want to take lots of photos in a range of settings afterward, it might not be the best spot. Keep in mind, as with all resort properties, you’ll need prior permission from their staff.
Other Unique Locations to Propose in Key West
If you aren't necessarily looking to propose on the beach, here are a few unique alternative locations...some require general admission be paid if the shoot will happen during business hours, and some will require you to book the space for an hour after closing. Additionally, a Sunset Sail proposal would require additional coverage, or non-shooting time in your photography package to cover the length of the sail (generally 2 to 3 hours).
Proposing on the “When and If” Schooner
If you want a private experience out on the water, there’s nothing quite as special as taking a sunset tour around the harbour on a historic schooner or sailboat. This particular shoot pictured is from the “When and If”, which does an absolutely fantastic job taking care of their guests. The captain and the owner of the boat are super knowledgeable about the boat’s past, and it’s pretty cool to listen to them tell stories about her history. For this and other sailboat type trips, I typically board and pretend to be a member of the crew, or feign some assignment like I’m there to take photos for their website (to explain why a member of the crew would have a huge camera with them, lol). Then at the perfect moment, you can use any part of the deck to pop the question, and afterwards enjoy a little champagne toast, spend some time snuggling with the sunset in the background, and even - if you wish - drive the boat as well.
If you’re not looking for something super private and want to make the sunset cruise seem more like just part of a regular day of activities, you can instead book a Sebago Sunset Sail as a regular guest. I try to blend in and pretend I’m there to take photos of the water, then adjust my position as you get to the front desk for the big moment.
Proposing at the Hemingway House Museum
Known for it’s famous former resident, Ernest Hemingway, this venue is a great choice for couples who want a bit of Key West history infused into their photos. Because it is a public attraction, it’s very easy to schedule without tipping off your other-half that you might be “up to something”….just another fun excursion in Key West, honey! You enter through the brick perimeter gate as if you’re just coming for a visit, proceed around the grounds and then at the right moment, pop the question with the famous house in the background. Alternatively, you can also propose in the lush greenery in a more shaded spot (and then go have photos with the house int he background instead later) if you choose. There is so much greenery, tropical flowers, lush green grass, the open wraparound two level veranda, and of course, the famous six-toed cats. You can book through general admission with the other visitors (just keep in mind they will likely be visible in the photos in the background), or you can speak with their events team and book the venue after hours.
Key West Lighthouse
Proposing at the Key West Lighthouse is a truly magical experience, in my opinion. Of all the venues that I photograph undercover proposals, the Lighthouse is about the only place that includes a private experience where you have the entire grounds to yourself, and they also make it special by setting up flowers, a charcuterie, and champagne with chocolate covered strawberries for you to enjoy after the big moment. After meandering around the location, you propose under the lighthouse with the tower behind you, and then enjoy some of the picturesque scenes around the Keeper’s Quarters before we make the long climb up the spiral staircase to the top for sunset photos overlooking all of Key West. Like any attraction-based venue, it is based on availability and extra costs are involved, with various Lighthouse Packages available.
With so many amazing places around the island to plan a surprise engagement, were you able to pick a favorite!?
I hope this guide was helpful in giving you some insight as to what each place looks like and how it shows up in camera when you book me as your proposal photographer in Key West.