Cruising guide to Key West and the Florida Keys

09th Feb 2021
old lighthouse on island

The Florida Keys offers so many beautiful islands to explore by yacht charter that it’s hard to choose where to stop for your itinerary. You’ll have a hard time fitting everything in as there are so many fun things to do in Key West and the surrounding area. We’ve shared our recommendations of where to go for a dream vacation below in our cruising guide to Key West. New! We now offer day charters from Key West on weekdays. Find out more.

Our base is in Stock Island Yacht Club & Marina, Key West, the most southern point in the USA, and it’s the perfect location to start your adventure. This island is known for its fun atmosphere and has plenty to keep you entertained as the sun sets and night falls. Key West is excellently placed for you to discover the best of the Florida Keys…

Dry Tortugas National Park

For adventure, head to the seven islands that make up Dry Tortugas National Park. You can snorkel the coral reefs in turquoise water, explore 19th century Fort Jefferson, see old lighthouses and relax on sandy beaches.

Top 10 itinerary stops for sailing Key West

1 Elliott Key

Part of Biscayne Bay National Park, this attractive and wild island in the north is only accessible by boat. Take a picnic with plenty of water and explore Elliott Key’s interesting walks such as the Elliott Key trail, which takes in the mangrove coast, Spite Highway and Point Adelle, plus much more. It’s one of our top things to do in our cruising guide to Key West.

  • Must-see: The one-mile hiking loop around the island
  • Anchorage: 30+ berths available at Elliott Key Harbor
  • Distance: Elliott Key is 30nm from Key Largo and 18nm to Elbow Reef

2 Elbow Reef

Elbow Reef is an awesome place for diving fans thanks to the area’s clear water, interesting wrecks and drift diving off Nelson’s Ledge. With shallow areas, it’s also great for beginners. Just off Key Largo, the reef has Elkhorn Gorgonian coral and you might see rays and turtles if you’re lucky.

  • Must see: Tonawanda and City of Washington wrecks
  • Anchorage: Mooring balls are available but get there early
  • Distance: Elbow Reef is 13nm from Key Largo

3 Key Largo

If being underwater with flippers and a tank is your thing, then this is the place just for you! Key Largo features one of America’s first underwater national parks and is popular with divers from around the world thanks to its plentiful reefs. If you want to stay on top of the water, try the kayak tours through the mangroves. It’s definitely one of our favorites in our cruising guide to Key West.

4 Indian Key

Tour the historical ruins that were burned to the ground following a surprise attack in 1840 during the Second Seminole War. There aren’t any facilities on this island so bring provisions with you. Watch the local marine life, such as trunkfish, stingrays and sharks, or visit the shipwreck of the Spanish flotilla’s San Pedro which was lost in 1733. Use the mooring buoys at high tide and kayak to the island to help protect the seagrass beds and their valuable biodiversity.

5 Long Key

Get closer to nature on this island, which is a haven for birdlife, including least terns and piping plovers. Get your walking shoes on and head ashore for the tidal barren, or salt pan, where you are likely to see the birds. Keep an eye out for the holes made by fiddler crabs. If you get hungry, head to Lime Tree Bay resort’s Florida Boy Bar and Grill.

  • Must-see: Golden Orb nature trail in Long Key State Park
  • Anchorage: Sheltered anchorage within Long Key Bay
  • Distance: Long Key is 25nm from Marathon

6 Marathon Key

Known as the heart of the keys and also for its care of green and loggerhead turtles. Visit the Turtle Hospital, which has been open since 1986 and taken care of 1,500 injured sea turtles. Marathon is also a premium Florida Keys destination with plenty of shops to browse and waterfront dining options.

  • Must-see: The Turtle Hospital
  • Anchorage: Marathon marina has 226 moorings and a dinghy dock
  • Distance: Marathon is 10nm from Bahia Honda Key

7 Sombrero Reef

To see plenty of marine life, head to Sombrero Reef with its inquisitive, colorful reef fish and branching and boulder corals. You may spot moray eels, nurse sharks, stingrays, snapper, parrotfish, French angels, purple sea fans and so much more! The reef is next to the iconic Sombrero Key Light, first lit in 1858.

8 Bahia Honda Reef

Bahia Honda State Park is a great spot for nature lovers ashore or underwater with snorkeling, swimming, fishing, kayaking, hiking trails and cycle routes. If you want to sunbathe you will find some white sand beaches and if you snorkel off the reef, look out for the spiny lobster and queen conch.

  • Must-see: Bahia Honda State Park
  • Anchorage: West-side between the two bridges
  • Distance: Bahia Honday Reef is 34nm from Key West

Stock Island Yacht Club

9 Key West

There are two photos you need to take when visiting Key West. The first is to see the monument to the most southern point of the continental US and the second is of the blazing sky at sunset. The sunset celebration is one of the most fun activities in our cruising guide to Key West and this view captured the hearts of Mark Twain and Tennessee Williams, as well as many more.

  • Must-see: Sunset at Mallory Square
  • Anchorage: Stock Island Yacht Club & Marina
  • Distance: Key West is 6.5nm from Wisteria Island

10 Islamorada

For the sports fishing fans, this pretty island has waters teeming with marlin and tarpon. If you get time, head to the shallows of the Islamorada Sand Bar, which is located on either side of the boating channel in Whale Harbor just offshore Islamorada. The Alligator Reef is also nearby with its shipwreck, the USS Alligator, which is surrounded by 500 species of marine life.

Find out more about our Key West fleet or read more on our blog.