Islamorada Key with Islander Resort
A Girls Weekend at Islander Resort in Islamorada, Florida
If you’ve ever wanted a Florida getaway that feels more like an all-inclusive tropical escape than a typical beach trip, let me introduce you to Islander Resort. It’s located right in the heart of Islamorada, and it combines everything that makes the Keys special with the comfort of a full-service oceanfront resort — sunrise over the Atlantic, frozen drinks by the pool, late nights around the firepit. This time it was me and three friends, down for our annual girls weekend.
Friday: Road Trip to the Keys, Key Lime Pie & First Impressions
We met Friday morning at WolfMoon in Bonita Springs for coffee and matcha before heading south. The drive is honestly part of the whole thing — somewhere after the Everglades, everything just starts to feel different. Bluer water, slower pace, you can feel yourself downshifting before you’ve even arrived. From the Fort Myers area it’s about three and a half to four hours depending on traffic, which is the right amount of road trip for a long weekend. Any farther into the Keys and I’d want to stay longer to justify the drive, but Islamorada hits that sweet spot — far enough to feel like an escape, close enough that it doesn’t eat your whole week. And I’ll say this now: the Keys aren’t where I’d send someone chasing big sandy beaches or that turquoise, crystal-clear water. That’s never really been the draw for me. People come here for the atmosphere. It’s slower. It doesn’t feel like mainland Florida at all.
Our first stop was Blond Giraffe Key Lime Pie Factory in Tavernier — worth the detour just for the pie, but my favorite part was actually their lock wall, where visitors leave personalized locks behind. We added one for our trip, so now there’s a tiny piece of us hanging somewhere in the Keys permanently.
Before checking in, we made one non-negotiable stop at Islamorada Brewery & Distillery. I’ve been coming here for years and it’s become a ritual at this point — hole- in-the-wall energy, tons of character, something for literally everyone. Local beer, frozen drinks, cocktails, spirits, even their famous Capri Sun-style pouches. I’ve brought a lot of different people through those doors over the years and never once seen someone leave without finding their drink.
After that, we headed to Islander Resort to check in. Walking the property for the first time, I genuinely forgot I was still in Florida. Palm trees, ocean views, that tropical landscaping — it felt more like Mexico or the Caribbean than somewhere you can reach by car in a few hours. The resort’s been part of Islamorada for more than 75 years, and it balances that legacy feel with updated rooms and amenities really well.
We stayed in one of the twelve Poolside Cabana Rooms, and it beat my expectations by a lot. High ceilings that made the room feel enormous even with four girls and all our luggage, two queen beds, private pool loungers and cabana chairs right outside the door, and just steps from the ocean.
One thing worth knowing if you’ve never stayed in the Keys: the waterfront experience is different from what most of us on the Gulf Coast are used to. At Islander, it’s beautiful, but the shoreline is rocky rather than soft sand — you get staircase access into the ocean, docks, plenty of spots to lounge and take it in, but not a walk-straight-into- shallow-water beach. If you’re expecting Clearwater or Siesta Key, you’ll be surprised.
Again, though — never really been the reason I come here. I can find soft-sand beaches almost anywhere in Florida. What I come to the Keys for is the pace. Time genuinely moves differently down there. The schedule stops mattering as much and the trip becomes about the people you’re with instead of how much you can pack in. The waterfront at Islander fit that completely — private without being exclusive, plenty of families around but never crowded. There’s also enough going on that you could stay on property the entire weekend and never feel like you missed anything: yoga on the lawn, Seabreeze Social with complimentary sangria, moonrise bonfires, glow mini golf, pickleball, paddleboarding, kayaking, beach volleyball, and snorkeling and sunset cruises departing right from Sunrise Pier.
Dinner at Drift on the Beach & Sunset at Lorelei Restaurant & Cabana Bar
That first night we ate at Drift on the Beach, Islander’s oceanfront restaurant — open-air, ocean views, the kind of setting that makes even a regular dinner feel like vacation. The ceviche served inside a coconut was the standout, unlike any ceviche I’ve had before.
After dinner, on a local’s suggestion, we headed to Lorelei Restaurant & Cabana Bar for sunset. If you’re in Islamorada, this one earns its spot on the itinerary — grab a drink, find a seat near the water, and just watch the day end. The Key Lime Colada is genuinely life-changing.
Saturday: Sunrise, Matcha & Snorkeling
We were up at 6 AM to catch sunrise over the Atlantic, and it was worth the alarm — completely clear sky, sun coming up between the palm trees just steps from our room. One of those moments that makes you stop and actually notice where you are.
Breakfast was at Cafe Moka, and it turned into one of my favorite stops of the whole trip. It’s less a coffee shop and more a scattering of tiny hidden rooms — books, propagated plants, pottery, home decor, coffee — like wandering through someone’s really eclectic backyard. Their house-made syrups live up to the hype; I got a banana coconut matcha I’m still thinking about — fresh, creamy, tropical, not overly sweet. I also tried the avocado toast, which was fine, but the drinks and the atmosphere were clearly the stars.
Later we went out for a snorkeling excursion with Island Adventures. The staff was great and the company made it fun regardless, but the visibility wasn’t great that day because of recent wind, so we didn’t see as much as we’d hoped. Next time I’d probably book a half-day boat charter instead. One tip: if they offer you a pool noodle, take the pool noodle.
Booking through them also got us private access afterward to the pool and bar at The Ashley House, so we posted up there for a while before heading back to the resort.
Dinner at Island Grill, Cards at Lorelei's & S'mores by the Water
That night we got dressed up, took an embarrassing number of photos around the property, and went to Island Grill for dinner. Everywhere in the Keys has that come-as- you-are energy, and it makes the whole weekend feel easy. After dinner we grabbed a deck of cards and went back to Lorelei’s for drinks and a few rounds before heading back to the resort.
We ended the night at Firelight Cove making s’mores by the water — the resort had pre-packed kits ready for guests, and there’s something genuinely fun about roasting marshmallows under palm trees after a full day in the sun.
Sunday: Yoga, Veuve Brunch & One Last Slow Morning in the Keys
Sunday turned out to be one of my favorite days, mostly because we finally stopped trying to fit things in. It was cloudier than the day before, but honestly it suited the mood. We wandered the property, took photos, got coffee, and made it to the resort’s complimentary yoga class on the lawn at 9:30. The oceanfront yoga was a genuinely great addition — one of my favorite things the resort offered. After that we went to Drift on the Beach for their Veuve Clicquot brunch, which was the perfect last meal: champagne, brunch cocktails, ocean views, nowhere to be.
We checked out sometime between 1 and 2 PM, and before the drive home we squeezed in some souvenir stops at Rain Barrel Village, Shell World, and Sandal Factory. Souvenir shopping in the Keys is genuinely elite — oversized sweatshirts, shell decor, beachy home finds that actually feel specific to the Keys instead of generic tourist-shop stuff.
Girls Trip Details & Matching Swag Bags
One of my favorite parts of the weekend wasn’t even in Islamorada — it was all the planning that happened before we left. Half the fun of a girls trip is the prep, and putting together everyone’s welcome packets was one of my favorite parts of the process.
Each packet included: Instagram handles, content shot lists, weekend schedules, themed drinks, photo inspiration.
And of course, matching swag bags, because no girls trip is complete without them.
Inside each one: a plush oversized towel, Case-Mate waterproof phone cases, matching belt bags, snacks from UNREAL, matching bracelets, sunscreen shimmer, and Magic Mind energy shots.
I’ll link everything here for anyone planning their own trip: Amazon Store Front :)
My Final Thoughts
Huge thank you to Islander Resort for hosting us and letting us experience a side of the Keys that’s pretty different from how I usually travel. If I’m planning a trip for myself, I’m usually booking a flight to a big city — walkable neighborhoods, coffee shops, rooftop bars, trying to cram in as much as possible. Slowing down is not my specialty. But this trip was a good reminder that the opposite is worth doing sometimes — a weekend with your friends where there’s nowhere to rush off to and nothing to do except enjoy where you are.
There’s something about Islamorada that feels different from the rest of Florida, and Islander captures it. Honestly, it’s almost too good to share — the kind of place that makes you want to keep it to yourself just so it stays exactly like this.
Almost. :’)
But if you’re planning a girls trip, celebrating something, or just want a different kind of Florida getaway, this is one I’d have to recommend.
Screenshot-Worthy Weekend Itinerary
Friday
7:00 AM – Coffee at WolfMoon
8:00 AM – Drive to Islamorada
12:00 PM – Key Lime Pie Factory stop
1:00 PM – Islamorada Brewery
2:00 PM – Check into Islander Resort
6:00 PM – Dinner at Drift
7:30 PM – Sunset at Lorelei’s
Saturday
6:00 AM – Sunrise at the resort
8:00 AM – Breakfast at Cafe Moka
10:00 AM – Snorkeling excursion
2:00 PM – Pool + drinks
6:00 PM – Dinner at Island Grill
8:00 PM – Cards at Lorelei’s
9:30 PM – S’mores at Firelight Cove
Sunday
8:30 AM – Slow morning + coffee
9:30 AM – Yoga on the lawn
11:00 AM – Veuve Clicquot brunch at Drift
1:00 PM – Pack up + final resort photos
2:15 PM – Souvenir shopping stops
4:00 PM – Head home