Islamorada is not one island but a string of them, running roughly from mile marker 90 down to mile marker 72 along a single road, the Overseas Highway, with the Atlantic on one side and Florida Bay on the other. Navigate the whole village by mile marker and by which side of US 1 a place sits on, because that is how every local gives directions and how every address here is written.
The top 15, ranked
Ranked by how consistently each pick appears across official Islamorada sources, the local destination marketing organization, and recent independent roundups.
- Top pick
#1Best for The classic Keys stop · #1 of 15Robbie's of Islamorada and the tarpon feeding
Family AttractionLower Matecumbe and the offshore keysOpen daily through the year on a long daytime schedule, with the dock charge and bait sold separately from any boat tripFree with paid optionsA working marina at mile marker 77.5 bayside where dozens of tarpon, some of them well over a hundred pounds, hang under the dock waiting to be hand fed. A small charge covers dock access and a bucket of baitfish, and the same site holds an open air market, boat and kayak rentals, snorkel trips and the ferry to the offshore state park islands.
Local tipHold the fish at the very tip of your fingers and let go early, because the tarpon strike hard and the pelicans standing behind you are quicker still.
- Top pick
#2Best for Snorkeling · #2 of 15Snorkeling Alligator Reef
TourThe reef, the flats and the waterReachable only by boat, with charter and party boat trips running daily through the year and cancelling in strong windTicketedFour miles off Upper Matecumbe, this stretch of the coral barrier reef is a protected preservation area within the Florida Keys National Marine Sanctuary, with mooring buoys instead of anchoring and no fishing or collecting allowed. Depths run from a few feet to about forty, an iron screwpile lighthouse of the 1870s stands over it, and the shallow spur and groove coral is the best snorkeling in the village.
Local tipBook a morning trip rather than an afternoon one, because the wind almost always gets up after lunch and chop ruins the visibility.
- Top pick
#3Best for Fishing · #3 of 15Backcountry and offshore fishing charters
TourThe reef, the flats and the waterCharters run daily through the year on morning, afternoon and full day departures, weather permitting, and book out well ahead in the dry seasonTicketedIslamorada calls itself the sport fishing capital, and the reason is geography: the Gulf Stream runs close in on the Atlantic side while the shallow flats of Florida Bay open west into the Everglades. Marinas here have been sending out both since the 1940s, offering flats skiffs for bonefish, tarpon and permit, offshore boats for sailfish and mahi, and cheap party boats for anyone unsure.
Local tipIf you have never fished here, take a half day party boat first rather than booking a private guide, because backcountry flats fishing is far harder than it looks.
-
#4Best for Families · #4 of 15Theater of the Sea
Family AttractionPlantation Key and Windley KeyOpen daily on a daytime schedule through the year with presentations running to a fixed rota, and interaction programs ticketed separatelyTicketedOpened in 1946 in a flooded quarry left behind by the railroad builders, this is one of the oldest marine parks anywhere and it still runs on a modest, old fashioned scale rather than a corporate one. Dolphin, sea lion and parrot presentations run through the day, there is a lagoon side beach, and a walking tour takes in sea turtles, sharks, rays and crocodilians.
Local tipSwim and interaction programs are booked separately and well in advance, so decide before you arrive rather than hoping for a place on the day.
-
#5Best for Something unusual · #5 of 15Windley Key Fossil Reef Geological State Park
ParkPlantation Key and Windley KeyOpen five days a week from morning to late afternoon with a small per person charge, and ranger guided tours offered through the winter monthsTicketedHenry Flagler's crews quarried this hill to build the Overseas Railroad, and cutting the rock exposed clean vertical sections through an ancient coral reef. Quarry walls eight feet high show whole brain and star corals in cross section, the old cutting machinery is still in place, and just over a mile of trail runs through the pits and the hardwood hammock around them.
Local tipIt closes two days a week and has no shade to speak of on the quarry floor, so come early and bring water rather than turning up at midday.
-
#6Best for Getting off the highway · #6 of 15Lignumvitae Key Botanical State Park
ParkLower Matecumbe and the offshore keysOpen five days a week and reachable only by ferry, private boat or kayak, with a modest landing charge and a separate tour feeTicketedAn island in Florida Bay reachable only by boat, holding one of the last uncut tropical hardwood hammocks in the Upper Keys, the forest that once covered all of these islands. A chemist named William Matheson bought it in 1919 and built a coral rock house with a windmill and cistern, which still stands and can be walked through on the way round the trails.
Local tipThe ferry runs from Robbie's on a small number of days and departures, so build the day around the boat time rather than the other way round.
-
#7Best for A swim · #7 of 15Anne's Beach
ParkLower Matecumbe and the offshore keysOpen daily from morning until sunset at no charge, with pavilions, restrooms and boardwalk access and no lifeguard on dutyFreeThe Keys have very few real beaches, since a living coral reef offshore stops sand from forming, which makes this narrow oceanside strip at mile marker 73.5 unusually valuable. Three hundred feet of boardwalk runs behind the mangroves to a series of pavilions, the water is warm, calm and shallow a long way out, and leashed dogs are welcome.
Local tipParking is two small strips directly off the highway, so arrive early or late, and take water shoes because the bottom is turtle grass rather than clean sand.
-
8Best for Context · #8 of 15
Florida Keys History and Discovery Center
MuseumUpper Matecumbe and the village centerOpen most days of the week on a daytime schedule with a modest admission charge, and closed one or two days depending on the seasonTicketedThe best single explanation of how these islands came to be settled, covering the wreckers who salvaged cargo off the reef, Flagler's railroad, the 1935 hurricane that destroyed it and the rise of sport fishing. Aquariums, a theater, a research library and a gallery of local artists fill out two floors, and it is the obvious first stop for anyone who wants context.
Local tipDo this on your first afternoon rather than your last, because everything else in the village makes more sense once you have been through it.
-
#9Best for A rainy hour · #9 of 15History of Diving Museum
MuseumUpper Matecumbe and the village centerOpen daily on a daytime schedule through the year with a modest admission charge, and closed on a small number of holidaysTicketedA single minded and genuinely excellent little museum tracing four thousand years of getting people underwater, from breath holding and diving bells to hard hat helmets, rebreathers and undersea habitats. The helmet collection is among the largest anywhere, arranged by country, and there is a strong section on the Keys treasure salvors and the reef research done offshore.
Local tipThis is the best air conditioned hour in the village and a reliable answer to an afternoon squall, which the Keys deliver often in summer.
-
10Best for A family day · #10 of 15
Founders Park
ParkPlantation Key and Windley KeyOpen daily from morning until evening with a per person charge for non residents, and the pool ticketed separately from park entryTicketedForty five acres bayside at mile marker 87 hold the village's own recreation complex, with a groomed shallow water beach on Florida Bay, tiki huts, grills, a playground and volleyball. Behind it sit five lighted tennis courts and an Olympic length outdoor pool, which is claimed to be the only fifty meter pool this far south in the country.
Local tipVisitors staying outside the village pay a gate fee that rises on summer weekends, so it works better as a half day than as a quick stop.
-
11Best for Divers and snorkelers · #11 of 15
San Pedro Underwater Archaeological Preserve State Park
Historic SiteThe reef, the flats and the waterOpen daily from morning until sunset with no charge, reachable only by boat, and buoys must be used in place of anchoringFreeA Dutch built ship sailing with the Spanish treasure flotilla went down here in a hurricane in July 1733, and what is left sits in eighteen feet of clear water south of Indian Key. The cargo was salvaged centuries ago, so the site is a ballast stone mound with replica cannons and an anchor placed among it, ringed by mooring buoys and free to visit.
Local tipThe shallow depth makes this one of the few genuine shipwreck sites a competent snorkeler can work without scuba gear.
-
#12Best for Cycling · #12 of 15Florida Keys Overseas Heritage Trail
ParkPlantation Key and Windley KeyOpen daily at no charge from sunrise to sunset, with some historic bridge sections closed for structural work at any given timeFreeA paved path is being built the length of the Keys along the bed of Flagler's railroad, and the longest finished stretch happens to run through Islamorada, from Key Largo down to about mile marker 72. It uses old railway bridges as viewpoints over open water, and it is separated from the highway, which makes cycling here far less alarming than it sounds.
Local tipRent a bicycle for a morning and ride south from the village center, which puts the ocean on your left and the wind mostly behind you on the way back.
-
#13Best for Wildlife · #13 of 15Florida Keys Wild Bird Center
Family AttractionPlantation Key and Windley KeyThe sanctuary boardwalk is open daily from sunrise to sunset with donations invited, while the separate education center keeps weekday hoursDonation suggestedTen minutes north of the village line at Tavernier, this rescue center treats close to a thousand injured birds a year and keeps around ninety permanent residents that cannot be released. A boardwalk runs out through the mangroves past pelicans, herons, hawks and owls to an open view of Florida Bay, and there is no admission charge.
Local tipGo late in the afternoon when the wild birds come in to roost around the sanctuary, which doubles the number you actually see.
-
#14Best for Quiet water · #14 of 15Long Key State Park
ParkLower Matecumbe and the offshore keysOpen daily from morning until sunset with a per vehicle charge, and camping available by advance reservation onlyTicketedTwenty minutes south of Lower Matecumbe, this park covers a long thin key that was once the site of Flagler's fishing camp, and it is the quietest shoreline within easy reach of the village. Two short trails run through mangrove and hammock, the shallow lagoon behind the beach is made for paddling, and the tent sites face directly onto the Atlantic.
Local tipBring your own kayak or paddleboard if you can, because on site hire here has been intermittent for years.
-
15Best for An evening out · #15 of 15
Morada Way Arts District
Neighborhood LandmarkUpper Matecumbe and the village centerIndividual galleries keep their own daytime hours through the week, with the art walk held on one evening each monthFreeA short side street off the highway at mile marker 81.6 holds the closest thing the village has to a walkable block of galleries and studios, run by a local arts nonprofit. It comes alive for a monthly evening art walk with live music and open studios, and the 1935 hurricane memorial stands a couple of minutes away on the same stretch.
Local tipThe monthly art walk is the only evening in Islamorada that feels like a town rather than a highway, so time a visit around it if the dates work.
Where things cluster
There is one road through the village, so everything sorts by mile marker and by whether it faces the ocean or the bay.
- Plantation Key and Windley KeyThe northern end of the village, where the highway comes down from Key Largo and Tavernier. Founders Park and its Olympic pool sit bayside around mile marker 87, and Windley Key holds both the old quarry that built the railroad and the marine park that filled the flooded pit left behind.
- Upper Matecumbe and the village centerThis is the closest thing Islamorada has to a downtown, a couple of miles of highway holding both museums, the arts district, the hurricane memorial and the big sportfishing marinas. Almost everything worth doing indoors is on this stretch, and it is walkable in places, which is rare in the Keys.
- Lower Matecumbe and the offshore keysThe southern end thins out into narrow road, mangrove and open water. Robbie's marina sits bayside at mile marker 77.5 and is the departure point for the offshore state park islands, while Anne's Beach at mile marker 73.5 is the one genuinely good public swimming beach in the village.
- The reef, the flats and the waterFour to five miles out on the Atlantic side the coral barrier reef runs the length of the Keys, marked by lighthouses and buoyed dive sites. Behind the islands on the bay side, the shallow flats and mangrove creeks of Florida Bay run west into Everglades National Park, and the two together are why this village calls itself a fishing capital.
Make it a day
Reef in the morning, highway in the afternoon
Take a morning snorkel trip out to Alligator Reef while the water is still flat, because the wind builds most afternoons and the trip is the one thing worth arranging in advance. Come back for the tarpon at Robbie's, then work north along the highway through the Discovery Center and the diving museum, and finish with a swim at Anne's Beach.
One day on the water, one day on the road
Spend the first day entirely on the water, either fishing the flats and the reef or taking the ferry from Robbie's out to Lignumvitae Key for the hardwood hammock and the Matheson house. Use the second on land, working the highway from the fossil quarry at Windley Key down through the two museums to Anne's Beach and the heritage trail.
Fish you can feed and water you can stand up in
Start at Robbie's with a bucket of baitfish and the tarpon, which is the single moment most children remember from the Keys. Give the middle of the day to Theater of the Sea or the pool and beach at Founders Park, then finish at Anne's Beach, where the water stays shallow and warm a long way out from the boardwalk.
Map
Best time to visit
F
M
A
M
J
J
A
S
O
N
D
The dry season from December into April is the reliable window, with lower humidity, steady breezes, the least rain and the best chance of calm mornings on the reef. It is also the busiest and most expensive stretch, and March and April bring spring break traffic the length of the Overseas Highway. Summer is hot, humid and prone to afternoon storms but delivers the warmest and often clearest water, while the heart of hurricane season from August into October is the period to watch.
Staying over? Compare hotels in Islamorada at Expedia.
Deep Arrival earns a commission when you buy through partner links. It does not change the price you pay.
Islamorada things to do FAQ
Parking, timing, cost, and weather answers for a smoother visit.
How do addresses and directions work in Islamorada?
Everything is given by mile marker and by side of the highway. The green mile marker posts count down from Florida City toward Key West, so Islamorada runs roughly from mile marker 90 at the northern end to mile marker 72 at the southern end. Locals then say bayside or oceanside to tell you which side of US 1 a place sits on. Learn those two conventions and the whole village becomes easy to navigate.
Is Islamorada one island?
No. It is an incorporated village made up of several islands strung along the highway, principally Plantation Key, Windley Key, Upper Matecumbe Key and Lower Matecumbe Key, with smaller keys between and around them. That is why it calls itself the Village of Islands. There is one road through the whole thing, so in practice the distinction matters less than the mile marker.
Are there real beaches in Islamorada?
Fewer than most visitors expect, and this is true of the whole Keys. A living coral reef offshore absorbs the wave energy that would otherwise grind up sand, so natural beaches barely form here. Anne's Beach at mile marker 73.5 is the best free public option, Founders Park has a groomed bayside beach behind a gate fee, and most resort beaches are imported sand. Come for the water rather than the sand.
How far is Islamorada from Miami and Key West?
Roughly seventy five miles from Miami and about eighty miles from Key West, which puts it almost exactly halfway down the chain. Allow around two hours from Miami International Airport in normal conditions and closer to three on a Friday or a holiday weekend, because there is one road and any incident on it stops everything. Key West is a two hour drive south.
Do you need a boat to see the best of Islamorada?
For the reef and the offshore state parks, yes, but you do not need to own one. Charter boats, party boats and snorkel trips run daily from several marinas, Robbie's operates a ferry to Lignumvitae Key, and kayaks can be rented at multiple points along the highway. The islands at Lignumvitae and the wreck at San Pedro are simply unreachable any other way.
What is the hurricane memorial on the highway?
It marks the Labor Day hurricane of 1935, the most intense storm ever recorded to make landfall in the United States, which destroyed the Overseas Railroad and killed more than four hundred people, many of them veterans working on a road crew. The memorial stands near mile marker 82 and holds the ashes of several hundred victims beneath a coral rock monument and a tiled mural.
Keep planning
Use these nearby guides to extend your Islamorada trip with a different pace and a clear next stop.
Hero image: Anne’s Beach, photograph by Bohao Zhao, CC BY 3.0, via Wikimedia Commons. Cropped to 16:9. Image credits. #1 Robbie's of Islamorada and the tarpon feeding: Larry D. Moore, CC BY 4.0, via Wikimedia Commons. #2 Snorkeling Alligator Reef: Jstuby, CC0, via Wikimedia Commons. #3 Backcountry and offshore fishing charters: U.S. National Archives, Public domain, via Wikimedia Commons. #4 Theater of the Sea: Averette, CC BY 3.0, via Wikimedia Commons. #5 Windley Key Fossil Reef Geological State Park: Fredlyfish4, CC BY-SA 3.0, via Wikimedia Commons. #6 Lignumvitae Key Botanical State Park: Jstuby, CC0, via Wikimedia Commons. #7 Anne's Beach: Bohao Zhao, CC BY 3.0, via Wikimedia Commons. #9 History of Diving Museum: Ebyabe, CC BY-SA 3.0, via Wikimedia Commons. #12 Florida Keys Overseas Heritage Trail: U.S. National Archives and Records Administration, Public domain, via Wikimedia Commons. #13 Florida Keys Wild Bird Center: U.S. National Archives, Public domain, via Wikimedia Commons. #14 Long Key State Park: Ebyabe, CC BY-SA 3.0, via Wikimedia Commons.