How to Road Trip Your Honeymoon Through the Florida Keys
Obviously, we’re always proponents of taking a honeymoon (in fact, we love engagement-moons, minimoons, buddy-moons, ALL the moons surrounding marriage), but we haven’t really talked about the road trip kind all that much before. Well, let’s just say that if you’re looking for a tropical adventure honeymoon, that’s as exhilarating and adrenaline-pumping as it is relaxing and romancing, then the Florida Keys might just be perfect for you! Here’s what we suggest: Flying into Miami and making your way down The Keys; when you get to Key West, you can turn in your car and fly right home from the Key West Airport. There are five regions in The Florida Keys to enjoy, explore, and take it easy on, and thankfully, one of our own Wedding Chicks recently went on a five-day/four-night road trip to map it all out for you! So, once you’ve lusted (enough) after these pics, start planning your own trip — these were a bunch of our faves, but OMG is there a ton of great spots to check out.
But why a road trip?
We get it, when you’re thinking about a honeymooning, driving yourselves probably doesn’t come to mind right away. You just spent X amount of months planning a wedding, exerting any energy or effort post-nuptials seems totally unnecessary, right? But here are some things that can illuminate that flawed thinking — because we are 100p behind road tripping after tying the knot.
You can rent that really cool car you’ve always dreamed about.
Sure, you can rent an awesome vintage set of wheels for your wedding getaway car, but how much “play time” do you actually get to have with it? If you’re going on a honeymoon that puts you in the driver’s seat, then you can really go all out with the transpo — for us, that means anything with top-down functionality. How else would you want to take in all the tropical vibes? Miles of palms, stretching sunsets, and limitless turquoise waters that awaken your soul.
You can hotel hop.
Yes, staying in the same hotel for your honeymoon has its perks, especially when you just want to plop down at the pool or the beach and take up residence for the week. But there’s a lot more to be said about doing a sort of resort round robin. You can check out different on-site dining options (and in The Keys, phenomenal epicurean delights — i.e. food and drinks — are among the destination’s primary love languages), swim in several different pools and sunbathe at a bevy of different beach locales, discover everything that some of the best resorts in Florida have to offer (from on/in-the-water excursions and bicycling adventures to on-site spa experiences and unique bar amenities). And, if you do find yourself wanting to hang indoors for that matter-of-honeymoon privacy and intimacy, then you can cozy up and get down in the most luxe and comfiest guest rooms around…
You can throw caution to the wind (quite literally, if you’re cruising with rad rims and no roof!) and make the best photo journal of your just-married joyride.
Any honeymoon will afford you ample opportunities to post pics on your social channels (and make all your friends and fam jealous, no doubt), but, in our opinion, a road trip honeymoon is going to light up your likes and comments. From Key Largo to Islamorada, Marathon to Little Torch Key, and all the way through Key West, be it your fancy breakfasts, your seriously enviable scuba diving sessions, your unique craft cocktails and cute-cafe coffees, or your picturesque schooner sailing tours, your itinerary will be stacked so high, you’ll have content for days.
Make this Florida Keys vacation your best trip ever (and following your best day ever, that should track)
If you’re the couple who lives wildly and spontaneously on the reg, then you’ll have no problem making the most of your multi-day holiday. But if you need a little more motivation or pics to prove that a Florida Keys road trip is the GOAT, then feel freeeee to use Amy’s personal trip log — featuring her fave places to stay, all the culinary/foodie recommendations you could ever need, and her own colorful, unadulterated wanderlust reflections — as your muse…
Day 1
Key Largo Conch House
• This is the perfect spot to stop after you land in Miami - it’s about an hour drive from the airport and way out of the big city
• Island vibes and casual dining at this local favorite
• Plenty of local beers with island flair on the menu
• If you’re in The Keys, you HAVE to try conch in some form, and this is the perfect place to do itThey’re also an award winning seafood restaurant & caterer
Baker’s Cay Resort
• One of the closest resorts to Miami, it feels more like a tropical hideaway, but with a gorgeous modern design
• Views for days
• Grab a bike and go exploring on a packed sandy path
• Hang out in a hammock, or relax in an Adirondack chair with your toes in the sand
• Be sure to grab a swing at the ocean facing tequila bar, Dry Rocks, and watch the sunset with a drink and their award-winning Key Lime Pie (their version is no joke)
Gus’ Grille at Reefhouse Resort & Marina
• Perched on the second floor, Gus’ Grille offers incredibly-creative Continental-style cuisine in a location that shines at hosting the most gorgeous Florida Keys sunsets
• Known for their fresh local seafood, be sure to try the crab cakes and the Mac Attack
• Friendly staff, great service, and cool, casual vibes
Day Two
Cheeca Lodge & Spa
• Cheeca Lodge & Spa is a mini paradise
• Lush and tropical plants all around
• The spa is a must visit, it’s a relaxing oasis
• Soothing and deeply-hypnotic fountains kickstart your relaxation
• We were lucky to book a couple’s massage with some indulgent enhancements, including a CBD oil and all-over extra-hydrating elixir — both were amazing
Atlantic’s Edge at Cheeca Lodge & Spa
• Lunch is always better when you’re sitting on the sand
• Order a piña colada and take in more stunning blue water views
• Billed for having the most delectable island-inspired cuisine, Atlantic’s Edge would be our lunch place for life just for serving its iconic lobster and brie grilled cheese
Gardenia’s Bistro
• Located inside Island Home Garden Center, we spotted Gardenia’s Bistro while toing and froing around the island
• This cute coffee shop/sustainable cafe and bistro has plenty of shaded seating and yummy eats
• The in-hut-happy atmosphere makes you want to stay longer, though, so you may need to order a 2nd cup
• Sit and relax or wander around the gardens and the nursery, pick up some fresh fares from locals
• Would be a perfect spot for a bridal shower (but, since this is your honeymoon, maybe just a fun afternoon with your new hubs or wifey)
Robbie’s of Islamorada
• Shop for antiques, grab some food from local vendors and take advantage of some cute photo opps (mentioned that earlier, right?) at Robbie’s
• We posted up at The Hungry Tarpon Restaurant and Bar on its large ocean-facing patio for dinner. It’s an ultra-casual ultimate dive bar atmosphere where you can order a fish sandwich and listen to some rhythmic island tunes
Day Three
Isla Bella Beach Resort
• The most luxurious and elevated experience on the island, the tropical setting is almost unreal
• Built in 2019, ALL guest rooms are open and ocean-facing
• It’s a super decadent scene, but it still has a super-chill vibe, we keep likening it to White Lotus
• Oh! And don’t be shocked if you rub elbows with a celeb… this place is remote, yet on the radar of so many famous people
Mahina at the Isla Bella Beach Resort
• Mahina, which means Moon in Hawaiian, symbolizes the full-circle transformation of the menu. The modern design restaurant approach was influenced by the hotel’s easy access to fresh local ingredients, as well as the ambience of the property’s oceanfront dining surrounded by coconut palms and panoramic sunset views.
• The food is incredible, the most upscale we’ve had on the island so far
• Outstanding service
• Views from every table
• And a plethora of healthy options (because honeymoons don’t always call for gluttonous desserts and deep-fried room service)
The Old Seven Mile Bridge
• Reopened in January of this year (2022), this famed bridge is a tourist’s dream (and one for the active couple who still want to keep busy on their largely relaxing trip)
• Rent a bike and ride the bridge
• Unbelievable views
• It was such a fun experience to ride over the water, and tbh, can you even say that you went to The Keys if you didn’t ride over this landmark?
Little Palm Island Resort & Spa
This exclusive, adults-only private island resort epitomizes honeymoon escape to us
You can only enter the island via The Truman (their private ferry) or by a seaplane
• Amazing decor is everywhere, and while the stay is pricey, it’s your honeymoon - so if ever there was a time to splurge, you’re looking at it!
• 30 thatched-roof guest bungalow suites (these are 2-person suites, so only 60 guests can stay at one time, max)
• If you check out their IG tagged photos - you’ll see lots of beautiful people and all their ‘influential’ blue check marks
Arrival in Key West Just some things to KIM (keep in mind)
• Almost everything in walkable in Key West
• Parking is a bear so hop on a bike or just walk to all the must-see destinations
• Key West only has one natural walk-in beach, all of the others are man made
• The attire is extremely casual, so you can leave your heels and makeup kit at home (you’ll sweat it off anyway)
• Pack lightweight, breathable clothes, a hat and sunscreen
• The Key West atmosphere is very laidback, island style and island time — so, really don’t feel like you need to impress anyone other than each other!!
Southernmost Beach Resort
• Although it’s a giant property, it feels small and intimate because it’s spread out over several separate blocks in the southernmost, Old Town Key West setting
• The tropical landscaping and use of such a pretty, vibrant color palette make this resort a total paradise
• Pick from one of the three pools, order yourself a SoMo signature sip, and relax
• You can also hole up in an ocean-front hammock to soak up the sun and listen to the waves
• Hop on a bike provided by the resort, ride all over Key West and hit all the hot spots
• The resort is located just a couple blocks from Duval street where there’s tons of attractions (from a trolley tour to the best damn Key Lime Pie shoppe - yes, with an E at the end! - around)
Four Marlins at The Reach Resort
• Four Marlins is right across the street from Southernmost Beach Resort
• Take in panoramic ocean views, vacation-loved libations, and elevated dining
• Personal vote for the Fish & Chips: You’ve never seen or tasted anything like it, but you can’t go wrong with anything on their menu
• We also had the crab-topped fried green tomatoes, the short ribs app, and the coffee-rubbed filet, all of which were undeniably delish (as was the service)
Day Four
Breakfast at Blue Heaven
• Super casual vibe for breakfast, but they are open all day serving up Keys and Caribbean-style seafood specialties
• Be sure to try “Rick’s Really Good Pancakes” and a Bloody Mary if that’s what you need (and who doesn’t?)
• There’s usually a wait so be prepared for that — though we didn’t see it, it’s said they have the best waiting area around with ping pong, pool tables, and a shady place to hang out and wait for your table
Tour & Tasting at Hemingway Rum Company
• Highly recommend the tour & tasting
• Located in a historical brick building, which was once a tobacco warehouse - it’s super cool (temp wise) inside and has recently been remodeled to include a production facility, experience center, tasting room, and trading post
• If you’re a Hemingway fan — you’ll learn a lot and you can pose for a selfie with him
• They have daily tours and cocktail classes, and when you walk in this building, you feel like you’re transported out of Key West
• This would be an amazing guest or wedding party experience for those who fly in a few days prior — that is, if you decide to plan a road trip after having your wedding in Key West
Pepe's Cafe Key West
• Pepe’s is the oldest eating house in the Keys; it opened in 1909 when Teddy Roosevelt was president
• Harry Truman was a regular
• The food is amazing and the service was excellent, we actually got this recommendation from a local and it did not disappoint
• If you can’t make a decision as to what to get, go for the special — their dailies are great, and anything they suggest is bound to be super yummy
Conch Tour Train
• Hop on the train to explore the city, learn more about its history, and hear some tour guide humor (their private, hour-long tours are actually offered in Mandarin, German, French, Spanish, Italian, Portuguese, and English, so everyone can enjoy!)
• If you do this, you can take note of all of the places you want to visit and then hit the sidewalks
Schooner Sunset Sail With Sebago Key West
• This was, hands down, the most relaxing couple of hours we had on our entire trip
• We highly recommend booking this experience
• Our captain Rachel and her crew, David and Mario, made the sail so special and fun
• You don’t need a jacket, but you might want to reapply sunscreen before you head out (the sun reflecting off the water is intense!)
• The sail includes spiked and non-alcoholic drinks and a very yummy snack
• The sunset speaks for itself, and if you’ve never experienced one, on the water, this is 100 percent the place to do it
Firefly Café Key West
• Arguably the most elevated, upscale dining in Key West
• Firefly’s cuisine makes you feel like you’re sitting down in New York or San Francisco, but surprises you with southern delicacies that are familiar, yet totally unexpected — buttermilk biscuits, shrimp and grits, mac and cheese. It’s all stellar
• They specialize in spritz cocktails (which is my personal favorite drink EVER), so that was an extra special treat
• The restaurant is in what seems to have been a two-story house transformed into a super hip restaurant with indoor and outdoor seating on the 2nd story patio
• This is the kind of place where you can talk and laugh with your table neighbors, making for an even more memorable experience
Day Five
The Key West Butterfly & Nature Conservatory
• The Key West Butterfly & Nature Conservatory caters to all — young and old
• When you walk into the conservatory, you immediately see that everyone, and I do mean everyone, is in absolute awe of the beautiful butterflies, birds, plants, and two stars of the show Scarlet & Rhett — the resident flamingos (they were our fave!!)
• It feels really magical, artistic, and romantic, and it’s completely worth the trip
Whatever kind of honeymoon you’re after is easily achievable in the Keys, but having the opportunity to see it ALL is what we’re loving about the road trip scenario. Start mapping yours out right now!