Updated for 2023
It had been a while since we did a big, official family vacation anywhere besides Ginnie Springs and Orlando, so we were long overdue for a return to the Florida Keys and Key West. The last time we visited was in 2006 on a quick cruise. We docked in Key West for a few short hours, frolicked around Mallory Square and the Southernmost Point buoy and went back to the ship. Before that, we visited as a pre-RaeRae family of four (maybe 1990?), fishing out of Islamorada, parasailing for the first time and using a real hard copy guidebook to get around.
Our Florida Keys Family Vacation
Fast forward way too many years to this trip: Mom just turned 60 and Dad’s not far behind, Rick, Alex and I are in our 30s and Rachel is a spry 25. And don’t forget Sheba! We’re such a mix of ages and interests that traveling together doesn’t always translate into family harmony, know what I mean?
The question on my mind: could we create a weeklong Florida Keys itinerary with the perfect combination of relaxation, adventures and fishing that would appeal to our multigenerational family and the world’s cutest dog?
Planning a 7-Day Itinerary for the Florida Keys
The Florida Keys are consistently included on the top lists of road trips in the U.S. and it doesn’t take long to see why. The moment you’re out of South Florida and past the Florida Everglades, you encounter the Overseas Highway (U.S. 1) and the laid-back Florida Keys vibe is all around. Turquoise water, kitschy souvenir shops hawking shells and motels from a bygone era welcome you to what may as well be a country unto itself. Instantly, conch fritters and key lime pie become dietary staples. It’s like nowhere else in the USA! No sooner did we get to Key Largo than we found ourselves asking why we don’t visit more often.
If you’ve never been to the Florida Keys, this is a great first-timer’s itinerary because you drive the whole length, stay on three different islands and get a taste of it all. Folks who come back to the Keys often end up finding their perfect hotel, favorite restaurant or marina on the first visit, and then return over and over. I think after this trip, we’ve become those people!
RELATED FLORIDA KEYS POSTS
- Dreaming of Islamorada
- What to Do with 48 Hours in Key West
- Wet and Wild at an Underwater Music Festival in the Florida Keys
Note, we drove to the Keys from Jacksonville (7+ hours), so this itinerary reflects the specific needs of nomadic road trippers. If you’re coming from outside reasonable driving distance, it’s easy to fly to the Keys as well. You can start in Miami (MIA) or Key West (EYW), rent a car one way, and fly out of the other airport. It couldn’t be easier, and I may just do that in the future to save a little time.
Pro Tip: When driving to the Florida Keys, I like to start in the middle of the 125-mile chain of islands, then head to Key West for a few days before spending the last night in Key Largo. Doing it this way makes the long drive home a couple hours shorter.
Day 1-3 – Middle/Lower Keys
Fishing with Two Conchs
Half day fishing trips are always going to be for the low-hanging fruit, those easy-to-catch reef fish. Cameron and Jordan put us on the snapper and mackerel, and while we didn’t net anything as big as my last visit to the Keys, we caught more than enough for several dinners! The guys were super professional and friendly, and we’re already talking about linking up with Two Conchs for a full day later this summer to catch mahi and tuna. Learn more here.
Kayak with No Name Adventures
There’s kayaking … and then there’s backcountry kayaking with Big Pine Kayak Adventures. Our awesome guide Chris took us deep into the mangroves where we encountered a variety of birds, crabs and jumping fish. It was a tight squeeze in spots, and we had to pull ourselves along by the branches once or twice, but it was definitely an adventure you can’t get anywhere else.
On the way back to the dock, we spotted manatees under the bridge, and the guys managed to catch a few fish along the way. The best part? Sheba came with us and got to try out her new doggie life jacket.
Look for Key Deer
Wanna see an endangered species up close and personal? The Key deer is the smallest subspecies of the North American white-tailed deer. There are currently less than 1,000 left, mostly concentrated on Big Pine Key and No Name Key. We saw two as we drove to No Name Pub for lunch.
Where to Eat in the Middle/Lower Keys
Located at the new Isla Bella resort complex, Il Postino is a Neopolitan style eatery built around an authentic pizza oven shipped over from Italy. I didn’t know what to expect from an upscale Italian restaurant on the beach but we were pleasantly surprised to find the best pizza, mussels and mozzarella this side of the Atlantic Ocean. Do not sleep on the pizza, y’all! The pasta and pizza are both available in gluten free and were every bit as delicious as the gluten-full. A great option for those with dietary restrictions and/or hoping for a departure from the Keys’ seafood-heavy menus.
Angler & Ale
One of my favorite restaurants in the area! Angler & Ale is on the Hawks Cay property, and is home to panoramic views of the marina and the Hook N Cook experience. We brought our fresh catch from our half day of fishing with Two Conchs and the chef prepared it perfectly, and I’m not kidding. Even Mom, who famously does not like fish, thought it was delish. You get three choices of preparation – blackened, grilled or fried – and we picked all three.
Robbie’s of Islamorada
Our day at Robbie’s was one of the most fun surprises and fun days of the whole trip. It was too windy to parasail, so we spent our day drinking rum cocktails from the bar, munching conch fritters and conch-amole (I try every iteration of conch – I am a conch-asseur) and feeding the huge, ravenous tarpon. In addition to food at the Hungry Tarpon and drinks at the Thirsty Tarpon, Robbie’s has fishing charters, eco-tours, jet ski adventures, stand-up paddleboards and kayaks — just about any water-based adventure you could want is here. When you stop at Robbie’s, make sure you plan to spend quality time here.
It’s a great place for families and a Florida Keys bucket list item if ever there was one. Whether you’re doing a ton or not doing much of anything, it’s quintessential Florida Keys and worth every moment you spend making friends at the bar.
No Name Pub
This little hole in the wall, with famous dollar-bill covered walls, opened in 1931. No Name Pub has that old Florida Keys ambiance and is a perfect refueling stop after a long kayaking excursion.
Day 3-6 – Key West
Southernmost Cultural Food & Walking Tour with Key West Food Tours
Yum, yum, yum! I love food tours because not only do you get absolutely stuffed to the gills with local delicacies, you learn so much from local guides. We took this guided three-hour walking tour with Key West Food Tours through historic Old Town with Amy, a Freshwater Conch (someone who’s lived in Key West for at least 7 years). On the menu: Cuban food, conch fritters, fish tacos, key lime pie and a rum runner to wash it all down. Such a great way to get to know Key West – start here on your first visit! Learn more here.
Ultimate Adventure with Fury
This was such a fun, active, wild family day! Fury’s 65′ catamaran was filled with fun, food, drinks and importantly, restrooms! I loved how everything was included: jet skis, parasailing, snorkeling on a lively reef and the wild inflatable water park. My only gripe: I would’ve enjoyed it so much more if I was about 25 years less decrepit than I am. Even still, we old and weary pirates did everything on offer and it really was memorable. My favorite part of the ultimate adventure was seeing my Mom totally kick butt at things she’s never done.
Breakfast and lunch are provided, but don’t expect a gourmet spread. Mostly it’s sandwiches and pastries, but they absolutely do the trick when you’re famished from swimming and jet skiing and frolicking. If you have dietary restrictions, call ahead and confirm what’s available and prepare to bring your own snacks just to make sure you don’t get hungry. Be sure to bring sunscreen, towels and cash for tipping the crew. Learn more here.
Lands End Sunset Sail with Sebago
Sunset is a big deal in the Florida Keys, and nowhere more than Key West. If you have the time to do both, check out Mallory Square for one sundown and hop onboard a catamaran with Sebago for another. Sebago’s sunset sail features all-you-can-drink beer, wine and sangria with light appetizers. Honestly, we didn’t even need a full dinner afterward. It was the perfect pre-cursor to a night out on lively Duval Street. Learn more here.
Key West Room Escape
Casa Antigua is a private residence built in 1919. It was one of Key West’s first hotels; now it’s home to the Key West Room Escape. Themed rooms include Jail Break Havana, Pirate Treasure Hunt and Escape Papa’s Study. I’m not trying to brag (ok, I totally am), but we completed the Disco Inferno in 29 minutes. I love how the room themes reflect Key West’s unique history. A fun thing to do on a rainy day or when you need a break from the heat.
Southernmost Point Buoy
Is it cheesy? Absolutely. Is it the southernmost point in the U.S.? Not even. But we have taken a photo here on every visit to Key West so now it’s become a tradition. There was about a 15 minute line to take photos, and it was nice to see the line of travelers helping to take photos for the next folks in line and so on.
Ernest Hemingway Home and Museum
Key West is one of Hemingway’s most famous haunts. He lived on the island for 10 years and you don’t have to walk far to find a bar, boxing rink or hotel he may have frequented. You won’t find Hemingway himself here nowadays, but his home still houses famous 6-toed cats. The trolley tour passes his house and is a great way to see a lot of the island’s hot spots.
Where to Eat in Key West
Key West Food Tours
Worth repeating! We visited El Siboney for Cuban, Badboy Burrito for fish tacos, Mangoes for conch fritters and Blue Heaven for Key Lime Pie, and each spot was served up with as much Key West character as you could want along with a side of history, culture and about 1.5 miles of leisurely meandering down the island’s colorful streets. A perfect way to encounter Key West especially for the first time visitor. Book here.
A&B Lobster House
Want a nice night out at a classic lobster house? Overlooking the famous Key West Bight, A&B Lobster House has panoramic views of the marina and is a gorgeous place for a nice sunset dinner. If you love fresh seafood cooked to perfection, this is your place. We tried every iteration of lobster, from risotto to bisque, along with Key West pink shrimp, oysters Rockefeller and the freshest pompano. All mouthwatering.
Go early (or stay late!) to grab a drink at Berlin’s speakeasy, paneled with dark wood and reminiscent of Hemingway’s time on island. Learn more here.
Matt’s on Stock Island
The Brooklyn of Key West, Stock Island is quickly becoming a destination in its own right. We are definitely staying at the stylish Perry Hotel on our next visit to the Keys. At Matt’s Stock Island Kitchen & Bar, they serve up American Coastal Comfort Food. Lots of seafood but plenty of great options for beef-a-tarians in your family.
We might have ordered more than we bargained for, because our enthusiastic server Rustan convinced us that everything on the menu was No. 1. He was not wrong! We loved the Admiral Tower, a fisherman’s tackle box filled with oysters, shrimp, lobster, tuna, yellowtail snapper ceviche and stone crab claws on ice. Matt’s is a must in the Keys.
Latitudes on Sunset Key
Rae was the only member of our group who’d been to Latitudes before, and she still has a picture of “the best steak in the world” that she ate there many years ago. We didn’t get any steak on this visit – it was breakfast time – but we did love the location and the lobster benedict. If you sit outside on the patio, the sea breeze is the perfect accompaniment to breakfast.
Day 6-7 – Upper Keys
Yes, we were on the way home, but we had to make time for one more gorgeous sunset! One more key lime pie! One more order of conch fritters! We actually tried to skip dessert at Sundowners but our awesome server wouldn’t let us. What’s one more mile high wedge of meringue after a week of taste-testing the best pie in the world?
We watched our last Florida Keys sunset over Florida Bay and the patio of Sundowners. Definitely one of the hallmark dining spots in the Upper Keys.
John Pennekamp State Park
John Pennekamp Coral Reef State Park is 70 square miles of mangrove swamps, coral reefs and wildlife, and it’s one of the coolest places to snorkel in the Keys as home to the “Christ of the Deep” statue. You can book glass bottom boat tours and snorkeling excursions for the whole family.
Where to Stay on a Florida Keys Family Vacation
The key to the Keys this trip was having somewhere big enough to house all of us. Six grown-ups and one pup need quite a bit of space, as you might imagine! Fortunately, we had some great options on both Duck Key and Key West. The Florida Keys are such a good destination for bigger family groups, not just because of the selection of varied activities that match just about anybody’s desires, but the accommodations are ideal. We had no trouble finding pet friendly 3-bedroom+ villas in the Florida Keys with room to breathe, full kitchens, washing machines and separate bathrooms. I strongly believe that having our own spaces helped us to have a conflict-free trip.
Hawks Cay Resort is one of my favorite spots to stay in the Keys! The recently completed a $50 million renovation of the 60-acre property, with 250 2/3 bedroom villas and 177 guest rooms. Our villa even had its own plunge pool – a must after fishing all day. Kayaks and stand-up paddleboards are free to use in the saltwater lagoon, and there’s an adults-only pool area, too. You can book fishing, diving and water sports, so it’s absolutely a place to call home for a week if you so desire. Learn more here.
Also check out: Cheeca Lodge
The Laureate has been newly reimagined since Hurricane Irma and now features all suites and crisp, clean, ocean-themed decor. We had three ample bedrooms, two balconies (one overlooking water), three bathrooms and a full kitchen. It was an ideal situation for our big family who absolutely could cram into one room but really would prefer our own space at the end of a sun-filled, adventurous day.
The pool area is small but well appointed with amenities like games, towels and a fridge full of complimentary coconut water. Score! The Laureate is extremely pet friendly, providing beds and water bowls for the four-legged family members.
Covered parking is included, and real talk, the staff at the Laureate were the friendliest we encountered anywhere. A relatively easy drive in to Duval Street. Learn more about the Laureate here.
Verdict? This 7-day itinerary for the Florida Keys family vacation rocked our collective little world. Some of us were stretched outside our comfort zones – it was Mom’s first time kayaking, jet-skiing and feeding hungry tarpon, and while we’re all completely exhausted, it was our best vacation in years.
Why don’t we pop down more often? I think now that we’ve had this little reminder of how good life is in the Florida Keys, we will.
The Florida Keys and Key West hosted our trip, but as always, opinions are all our own, and you only get our honest take, no matter who’s footing the bill. Thanks to everyone in the Keys who made our visit so special. We can’t wait to come back! Please note, this post may contain affiliate links. If you make a purchase using these links, we may earn a commission at no extra cost to you. We thank you for supporting the partners that keep Angie Away and The Jet Sisters a free travel resource!
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