Key West Itineraries: Day Charters and Multi-Day Routes

Key West’s position at the end of the island chain, with the backcountry to the north, the reef to the south and the Dry Tortugas 70 nautical miles to the west, gives it more variety than almost any other charter port of its size. The itineraries below cover entirely different ground and can be combined for longer voyages.

Day Charter Routes from Key West

Key West to the Marquesas Keys: The Remote Atoll

Depart Key West mid-morning and cruise 20 nautical miles west to the Marquesas Keys – one of only a handful of natural circular atolls in the Western Hemisphere, 6.4 km in diameter and entirely uninhabited. The atoll is protected as part of Key West National Wildlife Refuge, and the snorkelling on the reef edges is exceptional: pristine hard and soft corals, barracuda, nurse sharks and clouds of tropical fish. Your crew sets up a gourmet picnic on a sandbar while you explore. The isolation is complete – no other visitors, no development, just crystal water and birdsong. Return to Key West by late afternoon. Duration: 7–9 hours.

Backcountry Flats and Mangroves: Fishing and Wildlife

Head north into the backcountry – the labyrinth of mangrove islands, tidal flats and shallow channels between Key West and the mainland. This is world-class sight-fishing territory for tarpon, bonefish and permit, and the wildlife is extraordinary: roseate spoonbills, great white herons, frigatebirds, ospreys and dolphins. Your captain navigates the channels while you fish the flats or simply cruise in wonder. Lunch on a deserted mangrove island, set up by your crew. Duration: 6–8 hours.

Key West Reef Snorkel: Sand Key and the Outer Reef

Cruise south from Key West to Sand Key – a shallow reef marked by a lighthouse (built 1853) where brain coral, sea fans and elkhorn formations shelter parrotfish, angelfish, sergeant majors and the occasional nurse shark. The water is just 1.5–6 metres deep, making it perfect for snorkelling straight from the swim platform. Continue to the outer reef for deeper exploration (6–15 metres) where larger fish patrol the walls. Return via the western harbour for a sunset from the flybridge. Duration: 5–7 hours.

3-Day Key West Yacht Charter Itinerary: Dry Tortugas Expedition

Day 1: Key West Exploration

Board your yacht at Key West Bight Marina (Historic Seaport) by mid-morning. Spend the day immersed in Key West’s culture: walk the Victorian Old Town past gingerbread houses and tropical gardens, visit the Hemingway House at 907 Whitehead Street (built 1851, meet the six-toed cats), explore the Harry S. Truman Little White House (where Truman spent 175 days across 11 visits between 1946 and 1952), and browse Duval Street’s galleries and boutiques. Late afternoon, join the Sunset Celebration at Mallory Square – street performers, fire-eaters and food vendors as the sun drops into the Gulf of Mexico. Dinner on the aft deck or ashore at Louie’s Backyard (in its historic pink revival mansion since 1971, with a tiered patio overlooking the water) or Santiago’s Bodega (intimate Spanish tapas on a romantic wraparound patio).

Day 2: Key West to the Dry Tortugas

Depart at first light for the 70-nautical-mile crossing to the Dry Tortugas (roughly 3–4 hours). Watch the open water of the Gulf of Mexico unfold as you cruise west, with no land in sight until Fort Jefferson’s massive walls appear on the horizon. Moor in the sheltered harbour and explore the fort: three tiers of casemates, the officers’ quarters, the magazine rooms, and the cell where Dr. Samuel Mudd was imprisoned. Snorkel the moat wall (teeming with tropical fish just metres from the fortress) and the surrounding reef. In summer, watch loggerhead and green sea turtles come ashore to nest. Your chef prepares dinner on the aft deck as the sun sets behind the fort and the night sky – one of the darkest in the eastern United States – fills with stars. Overnight at the Dry Tortugas anchorage.

Day 3: Dry Tortugas to Key West via the Marquesas

Morning snorkelling at the Dry Tortugas’ outer reef – pristine coral gardens in water so clear the fish seem to float in mid-air. Depart mid-morning and stop at the Marquesas Keys (roughly 50 nautical miles from the Tortugas, 20 nautical miles from Key West) for a late-morning swim and picnic at this uninhabited circular atoll. The snorkelling on the reef edge is exceptional. Cruise the final 20 nautical miles back to Key West, arriving by mid-afternoon with time for a farewell stroll through the old town or a last sundowner at Sloppy Joe’s Bar (opened 5 December 1933, the day Prohibition ended).

4-Day Key West Yacht Charter Itinerary: Lower Keys and Dry Tortugas

Day 1: Key West Culture and the Reef

Board at Key West Bight Marina mid-morning. After settling aboard, cruise south to Sand Key Lighthouse and the shallow reef for a morning of snorkelling over brain coral, elkhorn formations and clouds of tropical fish. Return to Key West for an afternoon ashore: the Hemingway House, Fort Zachary Taylor Historic State Park (built 1845, one of three Florida fortresses to remain under Federal control during the Civil War, now home to Key West’s finest beach), and the sunset at Mallory Square. Dinner at Café Solé (French-inflected Keys seafood) or aboard.

Day 2: Key West to Bahia Honda via Looe Key

Cruise north-east to Looe Key (roughly 25 nautical miles) for world-class reef snorkelling – a spur-and-groove system in 1.5–9 metres of water with goliath grouper, elkhorn coral towers and vivid marine life. After a chef-prepared lunch on the aft deck, continue to Bahia Honda Key (roughly 10 nautical miles). Anchor off the state park’s beach for an afternoon of swimming and paddleboarding, with the photogenic old railroad bridge ruins (Flagler’s Overseas Railroad, 1912) as your backdrop. Sundowners on the flybridge as the Lower Keys sunset sets the sky ablaze.

Day 3: Bahia Honda to the Dry Tortugas

Depart early for the Dry Tortugas (roughly 90 nautical miles from Bahia Honda, 5–6 hours). Arrive by early afternoon and explore Fort Jefferson – the massive hexagonal fortress of 16 million bricks, never completed, never attacked. Tour the casemates, snorkel the moat wall and surrounding reef, and watch for nesting sea turtles (in season). Dinner on the aft deck as the fort’s silhouette darkens against a sky full of stars.

Day 4: Dry Tortugas to Key West

Final morning at the Dry Tortugas: early snorkelling on the outer reef in pristine, uncrowded water. Depart mid-morning for the return to Key West (70 nautical miles, 3–4 hours). Your chef prepares a farewell gourmet brunch on the aft deck – stone crab claws, tropical fruit, key lime pie and Cuban coffee – as the Gulf of Mexico slides beneath you. Arrive at Key West by mid-afternoon for a last wander through the old town.

Guests looking for a longer voyage can combine the 3-day Dry Tortugas route with a 4-day Upper Keys route (Key Largo, Islamorada, Marathon) for a comprehensive 7-day charter spanning the entire Florida Keys from Key Largo to the Dry Tortugas.