Islamorada, Florida – The Clever Boater

Location

Region: Florida Keys
Latitude: 24.92429° N
Longitude: -80.62784° W
Waterway Guide: Islamorada, FL

Destination: Islamorada

Islamorada (which translates as Purple Isle) is a popular stop on the way to or from the lower Keys. Islamorada is actually made up of five islands from the north: Plantation Key, Windley Key, Islamorada, Upper Matecumbe Key, and Lower Matecumbe Key. The Overseas Highway (Route 1) connects all five keys with 18 miles of roadway. At its widest point, Islamorada is just 1 mile wide, and much of the area is less than 1/2 mile wide.

There is a lot for boaters to see and do in Islamorada. Good provisioning is available at a Publix supermarket in the middle of the island and a Winn-Dixie just north in Tavernier. There are also many smaller convenience and liquor stores scattered along Route 1.

Where To Eat

Restaurants abound throughout the island, some of the more popular being Marker 88 and The Twisted Shrimps on Plantation Key. Island Grill and Hog Heaven Sports Bar & Grill on Windly Key. Wahoo’s Seafood Bar & Grill, Lorelei Restaurant & Cabana Bar, Islamorada Fish Company, and Lazy Days on Islamorada. These are but a few of the many great places to eat. Ask the locals! We were recommended to try MEAT Eatery & Taproom on Plantation Key, an award-winning burger restaurant featured on Guy Fieri’s Diners, Drive-ins & Dives TV show, and it was excellent!

Shopping Therapy

Shopping abounds with many small boutique-type shops. We enjoyed browsing around Rain Barrel Village on Plantation Key, which is a collection of 6 or 7 vendors (they change periodically). You can’t miss it. There’s a giant spiny lobster in the parking lot! The other highlight is the “World Wide Sportsman” in Islamorada, now owned by Bass Pro Shops. It’s not as big as the mega-Bass Pro Shops, but it does have the sister ship to Ernest Hemingway’s boat “Pilar” on display for you to climb aboard and get a feel for the Old Man of The Sea. (Cuba confiscated the original Pilar, which is displayed near Havana.)

Getting Around

Because Islamorada is spread out on five islands, getting around for boaters can be a bit challenging due to the bridges connecting the islands and the heavy traffic along Route 1. You can get around by bike fairly safely, as there are sidewalks in many areas along Route 1, and in some places, the old Route 1 provides a quieter side route that parallels the main highway. If you are island hopping, a free ride service called “Freebee” will pick you up and drop you off anywhere between Tavernier and Upper Macomb Key. They work on tips and are very friendly and convenient! Uber and Lyft drivers also cover the area during peak times.

There is also the Miami-Dade Bus Service, which covers all of the Upper Keys. Route 301 covers the area between Florida City and Marathon, servicing Islamorada. You can also transfer to the Lower Keys Shuttle bus service in Marathon to travel to Key West. Both are economical and run about every hour or so, but watch schedules. Due to the traffic on Route 1, delays are not uncommon.

Keeping Entertained

Giant Nautical Market – Every February (toward the end of the month), the Upper Keys Rotary hosts a gigantic Nautical Flea Market and outdoor boat show at Founders Park on Plantation Key. Hundreds of vendors are hawking just about anything you can imagine dealing with boating and fishing. There are also several food trucks and drink vendors to keep you fed and hydrated. The Rotary offers special bus services to get you to the market.

Live Music – Most of the bars and restaurants offer live music. Check the local schedules for details.

Theatre of the Sea – A popular marine park for swimming with dolphins, snorkeling, and shows in a lush setting.

Keys History and Discovery Center – This is a modern museum with displays and a great model depicting the early culture and history of the Keys.

History of Diving Museum – A unique museum with relics, exhibits, and equipment showcasing the evolution of diving.

Getting There

There are two main routes to Islamorada by boat. The northern route, the Gulf ICW, runs between the Keys and the Everglades National Park, and the southern route, the outside route, is in the open waters of the Straights of Florida. You need to decide which route you are taking before you leave Biscayne Bay in the north or Marathon in the south, as opportunities to cross between the two routes are very limited due to low bridges or shallow water.

The Northern route is fairly shallow, but it is quite protected. Boats with over a 5-foot draft should consider this route with extreme caution. We draw 4 feet on the Frog and had a few times when our depth sounder was reading less than a foot under the keel. This route gives you access to the marinas and anchorages on the north side of Islamorada, including Plantation Marina, Islamorada Yacht Basin, Coral Bay Marina, and Safe Harbor Islamorada. Several other marinas are on the north side; however, the entrance depths may not be sufficient for drafts over 3 feet. For those preferring to Anchor, there are several good anchorages along Islamorada and Plantation Keys.

The southern route is the outside route in the Straights of Florida. This route is open water, and weather can be a factor. Popular stops on the South side are Three Waters Resort and Marina or, if you can clear a 15-foot bridge, Tavernier Creek Marina. Most taking the outside route skip Islamorada in favor of Key Largo to the North, which has more south-side facilities.

Marinas and Anchorages

Plantation Marina—North Side—This is the most popular marina on the north side and provides excellent access to the Islamorada area from Plantation Key. It has diesel, gas, and pump-out facilities and 85 slips. There is a great anchorage just off its jetty, with access to shore from the marina’s dingy dock.
Three Waters Resort & Marina – South Side – 18 transient slips with a 4.5-5.6 foot approach depth. Diesel, gas, and pump-out services are available.
Islamorada Yacht Basin—North Side—This marina is located in Islamorada proper. It has a few transient slips and a 4.5-foot approach depth. It does not offer fuel, but it does offer pump-out.
Coral Bay Marina—North Side—Coral Bay is a small, very protected marina right in the center of Islamorada. It offers pump-out and repair facilities but no fuel. There is an excellent anchorage just outside the marina entrance.
Safe Harbor Islamorada—North Side—This facility has limited transient slips, but it is worth checking out if you are a Safe Harbor Member. The approach depth is 5 feet, and they offer diesel, gas, and limited repairs.

Where To Find Out More

We suggest checking out the Islamorada Chamber of Commerce website, which offers a good listing of all the activities, restaurants, and shopping available in Islamorada. It can be found at Islamoradachamber.com.

Have you been to Islamorada? What is your favorite spot?
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