Florida Keys

Escape into Island Time

Leave Miami behind and cruise south into the laid-back beauty of the Florida Keys. Discover clear tropical water, sandbars, island stops and waterfront destinations aboard your own private yacht, whether you're escaping for the day or setting off on a longer adventure.

01 Clear Water Anchor, swim and snorkel in beautiful tropical surroundings.

02 Island Stops Discover sandbars, waterfront dining and laid-back Keys charm.

03 Your Itinerary Choose a private day escape or continue into a multi-day adventure.

Choose your yacht ↓

45ft Azimut | Caprice

From $1,765.00

45ft Lagoon | Somewhere

From $3,650.00

46ft SeaRay | Grand Admiral

From $2,765.00

52ft Prestige | Molto Piaciuto

From $2,240.00

62ft Pershing | Sea Suite

From $3,530.00

65ft Prestige | Exumas

From $3,060.00

70ft Azimut | Spysea

From $4,825.00

Anchor & Swim

Islamorada Sandbar

Drop anchor in warm, shallow water for swimming, floating, paddleboarding and a relaxed lunch aboard.

Snorkel

Alligator Reef

Swim around the historic lighthouse in clear water filled with tropical fish, subject to calm conditions.

Discover

Robbie’s of Islamorada

Step ashore to feed the famous tarpon, browse the open-air market and enjoy casual local seafood.

Dock & Dine

Marathon

Make the Middle Keys your base for marina dining, reef excursions and an easygoing island evening.

Dive & Snorkel

Sombrero Reef

Explore one of the Middle Keys’ best-known reef sites, marked by its striking offshore lighthouse.

Cruise

Seven Mile Bridge

Cruise beside one of the Keys’ most recognizable landmarks as the Middle Keys open into the Lower Keys.

Swim & Explore

Bahia Honda

Enjoy beautiful water and views of the old railway bridge at one of the Lower Keys’ signature stops.

Stay & Explore

Key West

Dock near the Historic Seaport, explore Old Town and end the day with sunset, dinner and live music.

Optional Adventure

Dry Tortugas

Venture beyond Key West to remote Fort Jefferson for history, snorkeling and extraordinary open-water scenery.

Choose Your Florida Keys Escape

Three routes from Miami, designed for everything from a quick island reset to a complete journey through the Keys.

Two Days / One NightOvernight in Islamorada

Cruise south from Miami to the Upper Keys
Swim at Islamorada Sandbar or snorkel in calm weather
Waterfront sunset dinner and overnight marina stay
Easy morning ashore before returning to Miami

Three Days / Two NightsIslamorada & Marathon

Day 1: Islamorada Sandbar, Robbie’s and island dinner
Day 2: Cruise to Marathon with a reef stop en route
Sombrero Reef, waterfront dining and marina overnight
Day 3: Seven Mile Bridge views and return to Miami

Seven Days / Six NightsThe Complete Keys Journey

Islamorada, Alligator Reef and Marathon
Sombrero Reef, Seven Mile Bridge and Bahia Honda
Explore the Lower Keys before arriving in Key West
Two nights near Old Town and the Historic Seaport
Optional Dry Tortugas day, yacht and weather permitting
Relaxed return north with favorite swim and dining stops

Sample itineraries only. Exact cruising times, reef visits, dockage and the Dry Tortugas option depend on the selected yacht, weather, sea conditions, marina availability and the captain’s approval.

Choose your yacht↑

Choosing from Florida Keys

Use this collection to build a shortlist, then compare the yachts against your dates, guest count and preferred charter length. Check each listing for its description, available options and departure locations. A listed price is a starting point for comparison; request confirmation of the yacht and the complete cost for your plans.

Consider how you want to spend your time aboard: sightseeing, dining, relaxing at anchor or an overnight stay. Discuss the route you have in mind and the facilities your group needs. Availability, crew, permitted guest numbers and itinerary suitability should be confirmed for the particular yacht before you book.