Route Overview & Navigation
The standard routing from Miami to Key West follows the Atlantic (oceanside) of the Keys, with the option to transit through channels to the Gulf (bayside) at several points. The passage can be completed in a single overnight run of approximately 14 to 16 hours at 10 knots, but the recommended charter itinerary is five to seven days, allowing time for exploration at each stop.
Departure from Miami
Most charters depart from Island Gardens Deep Harbour, Miami Beach Marina, or Rickenbacker Marina. The initial leg passes through Biscayne Bay and Government Cut, then south along the oceanside of Key Biscayne and into Biscayne National Park.
The Hawk Channel
This is the primary navigation route along the Atlantic side of the Keys, running between the reef line and the islands. It is well-marked and maintained at depths of 8 to 12 feet in most sections. Vessels with drafts exceeding 7 feet should exercise caution and follow charted channels.
Gulf Side (Florida Bay)
The bayside offers calmer waters and spectacular shallow-water scenery, but navigation is more challenging. Depths are frequently 4 to 6 feet, with unmarked shoals. This route is best suited for tenders and smaller vessels.
Tidal Considerations
Tidal range in the Keys is modest (1 to 2 feet), but currents through the channels connecting the Atlantic and Gulf sides can be significant — particularly at Bahia Honda Channel and Moser Channel. Plan transits for slack tide when possible.
Weather Windows
The ideal charter season is November through May, when northeast trade winds provide consistent 10 to 15 knot breezes and the risk of tropical weather is minimal. Summer months (June through October) bring calmer seas but afternoon thunderstorms and hurricane risk.
Day 1-2: Biscayne National Park & Key Largo
Biscayne National Park
The first stop south of Miami, Biscayne National Park encompasses 173,000 acres of marine environment, including the northernmost section of the Florida Reef Tract — the third-largest barrier reef system in the world. Elliott Key and Adams Key offer anchorages in 6 to 10 feet of water with excellent snorkeling directly from the yacht.
Key Largo
The largest of the Florida Keys at 33 miles long. Key Largo is the gateway to John Pennekamp Coral Reef State Park, the first undersea park in the United States. The Christ of the Abyss statue, a 9-foot bronze sculpture submerged in 25 feet of water, is one of the most iconic dive sites in the Western Hemisphere.
Marinas
Ocean Reef Club (private, membership or reciprocal required) offers the most exclusive marina facilities in the Upper Keys, with berths for vessels up to 120 feet. Marina Del Mar and Anchorage Resort & Yacht Club provide alternatives for visiting yachts.
Dining Ashore
The Fish House (Key Largo, seafood institution), Sundowners (waterfront, sunset views over Florida Bay), and Mrs. Mac's Kitchen (local institution since 1976, known for chili and key lime pie).
Anchorages
Rodriguez Key (north of Key Largo) offers a protected anchorage in 7 to 9 feet with a sand bottom. Pumpkin Key, a private island at the southern end of Card Sound, provides a scenic backdrop.
Day 3: Islamorada — The Sport Fishing Capital
Islamorada, a village encompassing six islands in the Upper Keys, has been the sport fishing capital of the world since the 1950s. The waters here offer access to the Gulf Stream (approximately 15 miles offshore), the backcountry flats of Florida Bay, and the reef line — three distinct fishing ecosystems within a short tender ride.
Fishing
Offshore, the Gulf Stream produces blue marlin, sailfish, wahoo, and mahi-mahi. The reef line yields yellowtail snapper, grouper, and hogfish. The backcountry flats are legendary for bonefish, permit, and tarpon — the "Grand Slam" of fly fishing. Islamorada's fishing guides are among the most experienced in the world; book well in advance during peak season.
Marinas
Bud N' Mary's Marina is the historic center of Islamorada's fishing culture, with charter boats departing daily. Whale Harbor Marina and Postcard Inn Marina offer transient berths. For superyachts, anchorage off Islamorada with tender access is the standard approach.
Dining
Morada Bay Beach Cafe (waterfront dining on a private beach, monthly Full Moon parties), Pierre's (upscale French-Floridian in a historic house), Islamorada Fish Company (casual waterfront, excellent for lunch), and Midway Cafe (breakfast institution).
Theater of the Sea (1946)
One of the oldest marine mammal parks in the world, offering swim-with-dolphins experiences in a natural lagoon setting.
Robbie's Marina
A Key's institution where visitors can hand-feed enormous tarpon from the dock. The adjacent market sells local art and crafts.
Day 4: Marathon & The Seven Mile Bridge
Marathon, in the Middle Keys, serves as the geographic and logistical center of the island chain. The Seven Mile Bridge — both the modern span and the historic Old Seven Mile Bridge alongside it — is the most recognizable landmark in the Keys.
The Seven Mile Bridge
Originally built by Henry Flagler as part of the Overseas Railroad (completed 1912), the current bridge opened in 1982. The old bridge, now partially converted to a pedestrian and cycling path, extends 2.2 miles into the ocean and offers one of the most dramatic walks in Florida. The bridge connects Marathon to Bahia Honda Key.
Marinas
Boot Key Harbor is the primary anchorage and marina complex in Marathon, with facilities for vessels of all sizes. Faro Blanco Resort & Yacht Club offers transient berths with resort amenities. Hawks Cay Resort on Duck Key (north of Marathon) has a full-service marina accommodating vessels up to 110 feet.
The Turtle Hospital (2396 Overseas Highway)
A working veterinary hospital for sea turtles, offering guided educational tours. It has rehabilitated and released over 1,500 turtles since 1986.
Crane Point Hammock
A 63-acre nature preserve containing one of the last remaining stands of thatch palm hammock in North America, along with pre-Columbian and Bahamian artifacts.
Dining
Keys Fisheries (dockside, famous for their lobster reuben), Castaway Waterfront Restaurant (sunset views), and Burdines Waterfront (casual, on the harbor).
Day 5: Bahia Honda & The Lower Keys
Bahia Honda State Park
Consistently rated among the best beaches in the United States, Bahia Honda's Sandspur Beach and Calusa Beach offer Caribbean-quality sand and water in a natural setting. The park's location between the Atlantic and Gulf creates unusually clear water for the Keys. Anchorage is available in the Bahia Honda Channel (watch currents) or off the oceanside beach in 8 to 12 feet.
Big Pine Key & The National Key Deer Refuge
Big Pine Key is home to the endangered Key deer, a miniature subspecies of the white-tailed deer standing only 24 to 32 inches at the shoulder. The National Key Deer Refuge encompasses 9,200 acres across several islands. The Blue Hole, a former quarry now filled with fresh water, is the largest body of fresh water in the Keys and home to alligators and turtles.
Looe Key National Marine Sanctuary
Located approximately 5 nautical miles south of Big Pine Key, Looe Key is one of the premier snorkeling and diving sites in the Keys. The spur-and-groove coral formations are among the most pristine in the Florida Reef Tract, with visibility frequently exceeding 60 feet.
The Lower Keys Character
South of Marathon, the Keys become noticeably quieter and less developed. The pace slows, the vegetation becomes more tropical, and the water clarity improves. This is the section of the Keys that most closely resembles the Caribbean.
Provisioning Note
Marathon is the last major provisioning stop before Key West. Ensure the yacht is fully stocked before departing the Middle Keys, as options in the Lower Keys are limited.
Day 6-7: Key West — The End of the Road
Key West, at Mile Marker 0, is the southernmost city in the continental United States — closer to Havana (90 miles) than to Miami (160 miles). The city's character is a unique blend of Caribbean, Cuban, and American influences, with a history shaped by wrecking, cigar manufacturing, Ernest Hemingway, and the U.S. Navy.
Marinas
Key West Bight Marina is the primary facility in the historic harbor, with berths for vessels up to 200 feet. Galleon Resort & Marina and A&B Marina offer alternatives in the harbor area. For superyachts exceeding 200 feet, anchorage in the outer harbor with tender access to the Bight is standard. Customs clearance is available at the Key West harbor for vessels arriving from or departing to international waters.
Historic District
Duval Street is the main commercial thoroughfare, running from the Gulf to the Atlantic. The Ernest Hemingway Home and Museum (907 Whitehead Street) preserves the author's residence from 1931 to 1939, complete with the famous six-toed cats. The Harry S. Truman Little White House served as the president's winter retreat. Fort Zachary Taylor State Park offers the best beach in Key West and a well-preserved Civil War-era fort.
Dining
Cafe Sole (French-Caribbean, intimate), Santiago's Bodega (tapas, local favorite), Latitudes on Sunset Key (accessible only by boat, waterfront fine dining), Better Than Sex (dessert-only restaurant), and Louie's Backyard (oceanfront, established 1983).
Sunset Celebration at Mallory Square
A nightly ritual featuring street performers, artists, and food vendors, timed to the sunset over the Gulf of Mexico. While touristy, it remains a genuine Key West tradition.
Departure Options
From Key West, charters can return to Miami via the same route, continue west to the Marquesas Keys and Dry Tortugas (see our dedicated guide), or cross the Florida Straits to Cuba (90 nautical miles, requires specific documentation) or the Bahamas.
Fishing & Water Sports Along the Route
The Florida Keys offer some of the most diverse fishing and water sports opportunities in the world. Each section of the archipelago presents distinct conditions and target species.
Key Largo & Upper Keys Fishing
The reef tract off Key Largo provides excellent bottom fishing for yellowtail snapper, mutton snapper, and grouper. The deeper waters beyond the reef produce mahi-mahi, wahoo, and sailfish. John Pennekamp Coral Reef State Park offers world-class snorkeling and diving on the only living coral barrier reef in the continental United States. The Christ of the Abyss statue, a 9-foot bronze sculpture submerged in 25 feet of water at Key Largo Dry Rocks, is one of the most photographed underwater sites in the Keys.
Islamorada Sportfishing
Known as the Sport Fishing Capital of the World, Islamorada offers access to the Gulf Stream within 5 miles of shore. The Hump, an underwater seamount approximately 12 miles offshore, is a legendary deep-drop fishing spot producing swordfish, tilefish, and queen snapper. The flats on the bayside hold bonefish, permit, and tarpon — the Grand Slam of flats fishing. Hiring a local guide through Bud N' Mary's Marina or World Wide Sportsman is recommended for first-time visitors.
Marathon & Middle Keys
The waters around Marathon offer excellent bridge fishing (the old Seven Mile Bridge pilings hold large tarpon and snapper), reef fishing on Sombrero Reef, and backcountry fishing in the shallow waters of Florida Bay. The wreck of the Thunderbolt, an intentionally sunk 188-foot vessel in 115 feet of water, is a premier dive site.
Lower Keys & Key West
The Lower Keys backcountry offers some of the most productive flats fishing in the chain, with less pressure than Islamorada. Key West's charter fleet operates from the Historic Seaport, offering half-day and full-day trips targeting everything from tarpon on the flats to blue marlin in the Gulf Stream. The Marquesas Keys, 30 miles west, are legendary for permit fishing.
Water Sports
Beyond fishing, the Keys offer kiteboarding (particularly at Long Key and Bahia Honda), paddleboarding through mangrove tunnels, kayaking in the backcountry, and parasailing off Key West. Most charter yachts carry snorkeling equipment, paddleboards, and kayaks as standard water toys.
Provisioning, Fuel & Practical Planning
A successful Keys charter requires careful provisioning and fuel planning, as services become increasingly limited south of Marathon.
Provisioning Stops
Key Largo has Publix and Winn-Dixie supermarkets with full selections. Islamorada has a Publix and several specialty food shops. Marathon has the last major Publix before Key West, along with a Winn-Dixie and several marine supply stores. Key West has multiple grocery options including Fausto's Food Palace (a local institution since 1926) and a Publix. For luxury provisioning, arrange through a Miami-based provisioning company before departure — they can deliver to your departure marina with 48-hour notice.
Fuel Availability
Diesel and gasoline are available at major marinas throughout the Keys, but prices increase as you move south. Key Largo and Islamorada offer competitive fuel prices. Marathon is the last reliable fuel stop before Key West for vessels with limited range. Key West fuel is the most expensive in the chain. Plan fuel stops based on your vessel's range and consumption — running out of fuel in the Lower Keys is a serious inconvenience, as towing services are limited and expensive.
Tidal Considerations
The Keys have a mixed tidal pattern with relatively small tidal ranges (1-2 feet). However, tidal currents through bridges and channels can be significant — up to 3 knots through some passes. Plan bridge transits and channel passages with the tide when possible. The Intracoastal Waterway through the Keys (Hawk Channel on the ocean side) carries 5-6 feet minimum depth, but local knowledge is essential for navigating the bayside.
Weather Planning
The Keys are exposed to both Atlantic and Gulf weather systems. Winter cold fronts bring northwest winds of 15-25 knots for 2-3 days, followed by settled conditions. Summer brings afternoon thunderstorms, typically between 2-6 PM, that are intense but brief. Hurricane season (June-November) requires monitoring NOAA forecasts. The Keys have mandatory evacuation orders for hurricanes — vessels must depart well in advance of any approaching storm.
Communications & Connectivity
Cell coverage is reliable throughout the Upper and Middle Keys but becomes spotty in the Lower Keys and is nonexistent west of Key West. Satellite communication is recommended for extended charters. VHF Channel 16 is monitored by the Coast Guard throughout the Keys. The Coast Guard maintains stations at Islamorada, Marathon, and Key West.
Medical Facilities
Mariners Hospital in Tavernier (Upper Keys) and Fishermen's Hospital in Marathon (Middle Keys) provide emergency medical services. Lower Keys Medical Center in Key West is the southernmost hospital. For serious emergencies, air evacuation to Miami's trauma centers is available via Coast Guard helicopter or private air ambulance. Ensure the yacht carries a comprehensive first-aid kit and that at least one crew member has first-aid training.
Frequently Asked Questions
How long should a Keys charter be? A minimum of 5 days is recommended to cover Miami to Key West at a comfortable pace with time for exploration. Seven days allows for more leisurely stops and side trips. For a comprehensive experience including the Marquesas or Dry Tortugas, plan 10-14 days.
What size yacht is best for the Keys? Vessels of 50-100 feet are ideal for Keys cruising. They can access most marinas and anchorages while providing comfortable accommodations. Vessels over 150 feet may have difficulty at some marinas and anchorages in the Middle and Lower Keys. Center consoles and sport fishing boats (30-50 feet) are excellent for day trips and fishing charters.
Is the Overseas Highway (US-1) visible from the water? Yes, the highway and its bridges are visible from the ocean side throughout most of the Keys. The Seven Mile Bridge is particularly dramatic from the water. Some guests combine a yacht charter with a rental car, leaving the yacht at a marina and driving sections of the highway for a different perspective.
Can we cross to Cuba from Key West? Cuba is 90 nautical miles from Key West. U.S. regulations regarding travel to Cuba change frequently — as of 2025, specific licenses are required for most categories of travel. Consult with a maritime attorney before planning a Cuba crossing. Customs clearance is available at Key West for international departures.
What about lobster season? Florida's recreational lobster mini-season occurs on the last consecutive Wednesday and Thursday of July. Regular lobster season runs August 6 through March 31. A Florida saltwater fishing license and lobster permit are required. Bag limits apply. The mini-season is extremely popular and the Keys become very crowded — book well in advance or avoid the Keys during this period.
Are pets allowed on charter yachts? Policies vary by vessel. Many charter yachts accommodate well-behaved dogs. Discuss pet policies during the booking process. Note that pets are restricted in some national parks and wildlife refuges along the route.