Spend a day in Miami’s Sailing Capital,
Coconut Grove

By Lori Kahn | May 22, 2018

A truly special way to see Miami, from Miami Beach to Key Biscayne and even all the way down to the Florida Keys, is from the water. With its prime location on Biscayne Bay, Coconut Grove has long been the sailing capital of Miami and what better way to explore the waters of Biscayne Bay than via a sailboat straight from the Grove?

A look back to a sailor’s paradise

Coconut Grove is known as a truly lush, subtropical Miami gem full of bohemian independence and style. What people may not know is that it also has a rich sailing history as well. The neighborhood’s location right on Biscayne Bay made it a favorite stop for mariners attracted to its fresh water springs and easy access from the mouth of the Miami River. After the Cape Florida Lighthouse opened in 1825, light keepers and their assistants became frequent visitors to Coconut Grove as well as the salvagers of disabled ships, coming in to ply their trade.

In the late 1870s, an accomplished sailboat designer by the name of Ralph Monroe came from Long Island to Miami on a sailing vacation and fell in love with the Grove’s beautiful climate and eclectic group of adventurers who had already come to call this little area home. From titled counts, writers, naturalists, Bahamians in search of opportunity, and even the son of famed writer Harriett Beecher Stowe, Coconut Grove was born.

In 1887, a group of locals started the Biscayne Bay Yacht Club, electing Ralph Munroe as Commodore. The Grove’s sailing club status was thus born. Today you can visit Ralph Monroe’s historic 1891 home, “The Barnacle,” now a state park. A sailor’s dream at the time, Monroe’s home included a fully equipped boathouse workshop, on-site blacksmith shop, nearby sawmill and also offered state-of-the-art facilities unlike any other in the region. Egret, a replica of one of Munroe’s 28-foot ships, is now moored offshore for history and maritime buffs to admire.

The Grove, present-day

Today the Grove is still home to the Biscayne Bay Yacht Club as well as the Coconut Grove Sailing Club, Coral Reef Yacht Club, the U.S. Olympic Sailing Center and Shake-a-Leg Miami, a unique boating center serving the disabled and disadvantaged communities as well as the general public. Coconut Grove has also continued its legacy as a renowned sailing community with many world-class regattas taking place during the season, including the Columbus Day Regatta, the Orange Bowl Regatta, US World Cup Regatta, Miami Sailing Week, and many more.

This really is a great place to rent a boat to take out for the day, join in on one of those famed regattas, or even bring your own sailboat to explore the surrounding waters. Where else can you find a local yacht club, sailing club and marina all within walking distance of one another? There are also local outfitters that rent paddleboards, which is a great way to explore the mangroves.

Stay a few days at the famous Mayfair in Coconut Grove and you will get to not only enjoy the local sailing, but also amenities like their rooftop pool and lounge, spa treatments for the wind weary, and delicious dining, as well as the surrounding Mayfair and Cocowalk shopping experiences.

The perfect sailing voyage

Visit Dinner Key Marina, Florida’s largest wet slip marina, where you'll find more than 500 slips as well as sailing charter companies. There are also local captains who offer everything from day cruises and family catamaran trips to sunset sails. For the beginning sailor, schedule a weekend getaway to obtain your Basic Keelboat Certification, a program that will prepare you to take out a sailboat on your own anywhere in the world.

Dinner Key is conveniently located within walking distance to Monty’s Raw Bar and the Grove Bay Grill, both offering casual waterfront dining with great views and fresh seafood. There are sailing charters and academies located among the docks at Dinner Key specializing in everything from romantic day cruises, lessons, catamaran trips or family onboard adventures.

You’ll find Coconut Grove Kayak & SUP where you can rent stand-up paddleboards and kayaks. To cruise further offshore, rent a boat from American Watersports located on South Bayshore Drive by Monty’s.

Nearby by at Shake-A-Leg Miami, there’s more than the usual charters and sailing lessons. This adaptive water sports facility helps anyone who wants to enjoy the bay whether therapeutic or recreational. Some of the very worthy initiatives of Shake-A-Leg include working with veterans, children and adults with disabilities, as well as offering summer camps, after school programming, mentoring and more. Rent a powerboat, canoe, kayak or sailboat. If you’re in town for a full moon you won’t want to miss the full moon sail.

Be Offshore is a casual cruising company that will provide you with a boat, captain and a 19-mile route around Miami’s best sights. Be Offshore offers private or shared trips but if you opt for a private tour, you’ll have the freedom to customize your trip. Better yet, join a group tour and you’ll see everything from the famed mansions of Star Island to the private homes of Fisher Island.

With the wind at your back, a day of sailing is an idyllic way to spend a day or longer in Coconut Grove.

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