A Destination & Culture Like Nowhere Else

The truly unique culture of this legendary island is best experienced on the open water. Let Waypoints arrange the ultimate Key West vacation.


Key West is like no other destination in the world, combining history, natural beauty, and culture for a one-of-a-kind paradise. Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffet, are just some of the famous locals.

Sightseeing, diving, fishing, water sports, golf, and shopping are just some of the adventures you can have shore side. Your cruising adventure will feature pristine waters, remote islands, white sand beaches, and epic sunsets as only Key West can deliver.


Real Escape Jeanneau 449

Boat in water

Real Escape Jeanneau 449

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Southern Crosser Fountaine Pajot Lucia 40 (3/2)

Fountaine Pajot Lucia 40

Southern Crosser Fountaine Pajot Lucia 40 (3/2)

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Travel Itinerary

Day 1: Stock Island Marina Village to Little Palm Island (24 NM)

Set sail from Stock Island Marina Village for Little Palm Island, a private island resort, and enjoy dining on world-class cuisine at the resort’s restaurant.

Reservations for dockage and dinner are highly recommended (dock master: 305.872.2524 or dockmaster@littlepalmisland.com; dining: 305.872.2551). Once ashore, look for the famed miniature key deer and tropical birds.

Day 2: Looe Key/Marathon (25 NM)

Looe Key is 5 miles south of Little Palm Island. It’s one of the most colorful, alive of all the reefs in the Florida Keys. Enjoy snorkeling and swimming then set sail for Boot Key Harbor in Marathon where there are a number of choices for marinas or anchorages. There are plenty of restaurants and bars to choose from in Marathon, one of the larger cities in the Keys.

Day 3: Sombrero Key/Long Key Bight (23 NM)

Relax and enjoy breakfast onboard with a slow and easy start this morning, or you may consider a trip out to Sombrero Key for snorkeling. After leaving Boot Key Harbor follow Hawk Channel and set a course for Long Key Bight to anchor overnight.

Day 4: Indian Key (8 NM)

Today, take a short sail to Indian Key for some exploration. Indian Key was the Dade County seat from 1836 to 1840. Approximately 1 mile south of Indian Key, you’ll find mooring buoys marking the remains of the Spanish sailing galleon, “San Pedro,” in about 18 feet of water.

Day 5: Duck Key (20 NM)

Want to spend some time enjoying luxury in the Keys? Set sail for the first-class Hawk’s Cay Resort on Duck Key (60 acres of beautiful resort property). At low tide, depth in the channel is 5 feet so plan your entrance at high tide (for reservations: 888.395.5539). Cool off in one of their 5 swimming pools, dine at your choice of restaurants, relax and enjoy spa treatments and more at this amazing resort.

Day 6: Bahia Honda Key (23 NM)

Depart Duck Key heading west back towards Key West via Bahia Honda State Park. Dinghy to shore where you’ll find a gift shop, an old historic railway bridge and a lovely swimming beach on the bay side.

Day 7: Key West (30 NM)

Head back to Stock Island Marina Village today. Spend tonight at the docks in this first-class marina. Enjoy a dinner at Matt’s Stock Island Bar & Grill or take the free shuttle into Historic Key West.

Day 8: Disembark

Consider a delicious Cuban breakfast sandwich and a Cafe con Leche at DeLuna’s Cafe onsite. Disembark by noon.