Top Beaches and Visitable Smaller Islands in the Upper and Middle Florida Keys

Anne’s Beach (MM 73.5, on Lower Matecumbe Key, at the southwest end of Islamorada) is more picnic spot than full-fledged beach, but die-hard tanners congregate on this lovely, tiny strip of coarse sand that was damaged beyond recognition by storms in 1998 and then again in 2019 by Hurricane Irma. The place has since been spruced up a bit and features a 1,300 foot boardwalk that winds through mangroves, six pavilions with picnic tables, and clean(ish) restrooms. Windsurfers like this spot, as do people with dogs, who sometimes don’t like to clean up after them.

A better choice for real beaching is Sombrero Beach, in Marathon, at the end of Sombrero Beach Road (near MM 50). This wide swath of uncluttered beachfront actually benefited from Hurricane George in 1998, with generous deposits of extra sand and a face-lift courtesy of the Monroe County Tourist Development Council. More than 90 feet of sand is dotted with palms, Australian pines, and royal poincianas, as well as with grills, clean restrooms, and Tiki huts for relaxing in the shade. It's also a popular nesting spot for turtles that lay their eggs at night.

If you're interested in seeing the Keys in their natural, pre-modern development state, you must venture off the highway and take to the water. Two backcountry islands that offer a glimpse of the "real" Keys are Indian Key and Lignumvitae Key. Visitors come here to relax and enjoy the islands' colorful birds and lush hammocks (elevated pieces of land above a marsh).

Named for the lignum vitae ("wood of life") trees found there, Lignumvitae Key supports a virgin tropical forest, the kind that once thrived on most of the Upper Keys. Over the years, human settlers imported "exotic" plants and animals to the Keys, irrevocably changing the botanical makeup of many backcountry islands and threatening much of the indigenous wildlife. Over the past 25 years, however, the Florida Department of Natural Resources has successfully removed most of the exotic vegetation from this key, leaving the 280-acre site much as it existed in the 18th century. The island also holds the Matheson House, a historic structure built in 1919 that has survived numerous hurricanes. You can go inside, but it's interesting only if you appreciate the coral rock of which the house is made. It's now a museum dedicated to the history, nature, and topography of the area. More interesting are the Botanical Gardens, which surround the house and are a state preserve. Lignumvitae Key has a visitor center at MM 88.5 (tel. 305/664-2540).

Indian Key, a much smaller island on the Atlantic side of Islamorada, was occupied by Native Americans for thousands of years before European settlers arrived. The 10-acre historic site was also the original seat of Dade County before the Civil War. Interestingly, from an archaeological standpoint, you can see the ruins of the previous settlement and tour the lush grounds on well-marked trails (off Indian Key Fill, Overseas Hwy., MM 79). Since 2021, that park has only been accessible by kayak launch, as the boat ramp was closed due to storm damage and though it's now years later, it has yet to reopen.

If you want to see both islands, plan to spend at least half a day. You can rent your own skiff, powerboat, paddleboard, or kayak from Robbie’s of Islamorada, U.S. 1 at MM 77.5 (on the bay side), on Islamorada. Robbie’s also does fishing trips, jet ski, and eco-tours through passages among the sea-grass beds that rim the many protected shallow bays. You’ll get to cruise among the hundreds of small, uninhabited mangrove and hardwood hammock islands, which host an amazing variety of wildlife and create the island network of the Florida Bay.

Watersports in the Florida Keys

There are literally hundreds of outfitters in the Keys who will arrange all kinds of water activities, from cave dives to parasailing. Below are the operators we think are most reliable and expert.

Florida Keys Boating

 

In addition to the rental shops in the state parks, and such peer-to-peer online resources as GetMyBoat.com and BoatSetter.com, you’ll find dozens of outfitters along U.S. 1 offering a range of runabouts and skiffs for boaters of any experience level. Captain Pip’s, U.S. 1 at MM 47.5, Marathon (captainpips.com; tel. 800/707-1692 or 305/743-4403), is a top operator. They charge $269 to $429 per day. Overnight accommodations ($129–$269) are available at their marina and include a 10 percent discount on boat rentals. Rooms are Key West comfortable and charming, revamped with new linens, hardwood floors, pine paneling, and in some, full kitchens.

Robbie’s Rent-a-Boat, U.S. 1 at MM 77.5, Islamorada (tel. 305/664-9814), is another reliable source. It rents 16- to 24-foot boats for $195 to $325 for a half-day and $275 to $385 for a full day.

If you want to see the Keys by water without captaining your own rig consider Dolphin Bay Watersports, 13201 Overseas Highway, (behind the Holiday Inn Express) Marathon (tel. 305/902-8655;), whose 1-hour jet-ski tours will take you on a guided tour of the area and its marine life. Tours are $109 per jet ski and carry up to three to four passengers including children.

Florida Keys Canoeing & Kayaking

 

I can think of no better way to explore the uninhabited backcountry on the Gulf side of the Keys than by kayak or canoe, as you can reach places that big boats just can't get to because of their large draft. Manatees will sometimes cuddle up to the boats, thinking them to be another friendly species.

Many area hotels rent kayaks and canoes to guests, as does Florida Bay Outfitters, U.S. 1 at MM 104, Key Largo (tel. 305/451-3018), which rents its vessels for use in and around John Pennekamp Coral Reef State Park for $40 to $55 for a half-day, $55 to $70 for a full day. Florida Keys Kayak and Sail, U.S. 1 at MM 75.5, Islamorada (tel. 305/664-4878), the Kayak Shack at Robbie’s Pier, offers kayak, paddle board and jet ski backcountry tours, botanical-preserve tours of Lignumvitae Key, historic-site tours of Indian Key, and sunset tours through the mangrove tunnels and saltwater flats. Tour prices and times vary, so consult their website.

Big Pine Kayak Adventures, operating out of the Old Wooden Bridge Fishing Camp, 1791 Bogie Dr., MM 30, Big Pine Key (tel. 305/872-2241), rents kayaks for self-guided tours, and will even ferry you and your kayak on a shallow water power boat into the back country. Or, take a guided tour for $150/person for four hours.

Nature lovers can slip through the silent backcountry waters off Key West and the Lower Keys in a kayak, discovering the flora and fauna that make up the unique Keys ecosystem, on Blue Planet Kayak Tours’ (tel. 305/809-8110) 2.5 to 3 hour, $60 starlight tour. All excursions are led by an environmental scientist. No previous kayaking experience necessary.

Florida Keys Diving & Snorkeling

 

Just 6 miles off Key Largo is a U.S. Navy Landing Ship Dock, the latest artificial wreck site to hit the Keys -- or, rather, to be submerged 130 feet below the Keys.

The Florida Keys Dive Center, 840001 Overseas Highway, Islamorada (tel. 305/852-4599), takes snorkelers and divers to the reefs of John Pennekamp Coral Reef State Park and environs every day. PADI (Professional Association of Diving Instructors) training courses are available for the uninitiated. Cost is $60 per person to snorkel including gear, and $105 per person to dive (plus an extra $25 if you need to rent all the gear).  

Key Largo Scuba Diving, 102900 Overseas Hwy., Key Largo (tel. 305/391-4040), offers over 100 reef and wreck dives and snorkeling excursions to places such as the famous Christ of the Abyss statue, the USS Spiegel Grove, and more. Snorkeling trips start at $70 and dive trips start at $100.

Florida Keys Fishing

 

Robbie’s Partyboats & Charters, U.S. 1 at MM 77.5, Islamorada (tel. 305/664-8070 or 664-8498), located at Robbie’s Marina on Lower Matecumbe Key, offers day and night deep-sea and reef-fishing trips aboard a 65-foot party boat. Big-game fishing charters are also available, and “splits” are arranged for solo fishers. Party-boat fishing costs about $100 for a half-day morning tour or five-hour night trip A four-hour afternoon trip is $75 per person. Charters run about $365 for three-quarters of a day, $450 for a full day.


Bud n’ Mary’s Fishing Marina, U.S. 1 at MM 79.8, Islamorada (tel. 800/742-7945 or 305/664-2461), one of the largest marinas between Miami and Key West, is packed with sailors offering backcountry fishing charters. This is the place to go if you want to stalk tarpon, bonefish, and snapper. If the seas are not too rough, deep-sea and coral fishing trips can also be arranged. Sportfishing charters range from $1,000 to $1,200 for a half-day, to $1,600 to $2,500 for a full day; back country fishing trips are much cheaper, starting at $600 for a half-day to $950 for a full day based on two people, though some can take more.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.