Islamorada - Florida Keys Overview

Florida yacht charters

Two hours south of Miami beginning at Mile Marker 73 is a group of 6 islands, Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key including the offshore islands of Indian Key and Lignumvitae Key. Together they make up the destination of Islamorada - a beautiful, eclectic area of the south Floridian coastline. 

Islamorada is nestled between the Everglades National Park and the only coral barrier reef of the Florida Straits. It is is a logical place to visit for one day or stay for weeks and enjoy the local essence of the Florida Keys. There is no shortage of activities to choose from in this lush tropical environment. To begin with, you can Fish in one of the best Sportfishing destinations in the USA that also offer bonefish, tarpon, redfish, and snook fishing in the backcountry.

More on sport fishing in the Florida Keys


If fishing is not for you, spend a day chartering a classic yacht to take you out for an informative eco-tour of the outer islands, swim, snorkel, dive, have a romantic afternoon and dinner on board a classic yacht, enjoy a spa treatment, shop at the local artisan's stores, dine on fresh local seafood at any one of the many Florida style restaurants along the US1 stretch.

Weddings, engagements, Honeymoons, Minimoons are particularly popular on these islands, with the turquoise water and the fresh seafood - this place is the epitome of romance! For more information on chartering a yacht for a honeymoon Please click here.

Suggested 3-day Cruising Itinerary

Islamorada and the key yacht charterDay 1 - Cruise from Islamorada south to Marathon or Hawk’s Cay Resort

Day 2 - Cruise to Bahia Honda or Little Palm Island Resort

Day 3 - Cruise back to the Lorelei in Islamorada Via Hawk’s Channel (Atlantic Ocean) or The Intracoastal Waterway

Suggested 4-day Cruising Itinerary

the keys

Day 1 - Cruise from Islamorada south to Marathon or Hawk’s Cay Resort

Day 2 - Cruise to Key West and dock at the Galleon Marina

Day 3 - Cruise to Little Palm Island Resort or

Day 4 - Cruise back to the Lorelei in Islamorada Via Hawk’s Channel (Atlantic Ocean) or The Intracoastal Waterway

(Itineraries provided by Captain Bill of Windrush - Classic Trumpy)

More on Chartering a Yacht in Florida


CRISTOBAL - Princess 95 - 4 Cabins - Bahamas - Florida - Miami - Nassau - Georgetown VIEW 1 REVIEW 
CRISTOBAL
    Princess 95 - 4 Cabins - Bahamas - Florida - Miami - Nassau - Georgetown
  • Princess 95 Luxury Crewed Motor Yacht
  • Length: 29.64 m
  • Year: 2009 (2014 Refit)
  • Cabins: 4
  • Berths: 8
  • From $46000 to $50000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 29.64 m (100' )
  • Year: 2009 (2014 Refit)
VIEW 1 REVIEW
From $46000 to $50000
per week

BOATBOOKINGS SAYS:
"An element of luxury normally found on much larger yachts with an armada of water toys. We love the massive swimming platform and spacious cabins!"

INTERVENTION
    Azimut 100 - 4 Cabins - Bahamas - Florida - New England - Miami - Fort Lauderdale
  • Azimut 100 Luxury Crewed Motor Yacht
  • Length: 30.48 m
  • Year: 2010 (2016 Refit)
  • Cabins: 4
  • Berths: 8
  • From $48500 to $55000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 30.48 m (103' )
  • Year: 2010 (2016 Refit)
From $48500 to $55000
per week

BOATBOOKINGS SAYS:
"INTERVENTION is a beautiful Azimut 100 that has been newly refitted in 2016 - making her perfect for you to charter around the Bahamas and Florida!"

STARSHIP
    143 Van Mill - 5 Staterooms - Bahamas - Nassau - Exumas
  • 143 Van Mill Luxury Crewed Motor Yacht
  • Length: 43.59 m
  • Year: 1988 (2017 Refit)
  • Cabins: 5
  • Berths: 12
  • From $115000 to $135000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 43.59 m (148' 3")
  • Year: 1988 (2017 Refit)
From $115000 to $135000
per week

BOATBOOKINGS SAYS:
"Make full use of her amazing water toy selection, which includes 5 jet skis. Captain Steve will show you the best that each Bahamian Cay can offer!"

DR NO
    Ferretti 75 - Miami Day Charter Yacht - Miami - South Beach - Florida
  • Ferretti 75 Crewed Motor Yacht
  • Length: 23 m
  • Year: 2011
  • Cabins: 4
  • Berths: 8
  • From $6500 per day
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 23 m (78' 8")
  • Year: 2011
From $6500
per day

BOATBOOKINGS SAYS:
"Big, bold and ready to entertain- ideal for large groups looking to relax!"

CINQUE MARE - Ferretti 88 - Miami Day Charter Yacht - Miami - South Beach - Florida VIEW 1 REVIEW 
CINQUE MARE
    Ferretti 88 - Miami Day Charter Yacht - Miami - South Beach - Florida
  • Ferretti 88 Crewed Motor Yacht
  • Length: 27 m
  • Year: 2006
  • Cabins: 4
  • Berths: 10
  • From $40000 to $40000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 27 m (91' )
  • Year: 2006
VIEW 1 REVIEW
From $40000 to $40000
per week

BOATBOOKINGS SAYS:
"Spacious interior and ample deck space make this the ideal yacht for socialising and entertainment!"

JULIA DOROTHY
    Johnson 103 - Miami Day Charter Yacht - Miami - South Beach - Florida
  • Johnson 103 Luxury Crewed Motor Yacht
  • Length: 31.4 m
  • Year: 2009
  • Cabins: 4
  • Berths: 8
  • From $56000 to $56000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 31.4 m (106' 8")
  • Year: 2009
From $56000 to $56000
per week

BOATBOOKINGS SAYS:
"Luxuruious, stately and incredibly spacious; ideal for a long day of adventure and entertainment!"

Lazzara 84
    5 Cabins - Miami Day Boat Rental - South Beach - Biscayne Bay Miami - Miami - Florida
  • 5 Cabins Crewed Motor Yacht
  • Length: 25.6 m
  • Year: 2008
  • Cabins: 5
  • Berths: 10
  • From $8168 per day
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 25.6 m (87' 4")
  • Year: 2008
From $8168
per day

BOATBOOKINGS SAYS:
"A beautifully upgraded interior and exterior with great outdoor space and a jacuzzi."

LEGEND AND SOUL
    Rodriguez Yachts 62 - Miami Day Charter - Miami - Ft Lauderdale
  • Rodriguez Yachts 62 Crewed Power Catamaran
  • Length: 18.9 m
  • Year: 2007
  • Cabins: 3
  • Berths: 0
  • From $27000 to $29000 per week
Details Enquire
  • Berths: 0
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.9 m (64' 5")
  • Year: 2007
From $27000 to $29000
per week

BOATBOOKINGS SAYS:
"The ultimate crewed powercat for charters in Florida. Cruise from Miami to the famous Florida Keys and beyond!"

MILK MONEY - Westport 130 - 5 Staterooms - Bahamas - Nassau - Paradise Island - Georgetown - Staniel Cay - Exumas VIEW 1 REVIEW 
MILK MONEY
    Westport 130 - 5 Staterooms - Bahamas - Nassau - Paradise Island - Georgetown - Staniel Cay - Exumas
  • Westport 130 Luxury Crewed Motor Yacht
  • Length: 40 m
  • Year: 2009 (Refit 2015)
  • Cabins: 5
  • Berths: 11
  • From $99000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 40 m (136' 4")
  • Year: 2009 (Refit 2015)
VIEW 1 REVIEW
From $99000
per week

BOATBOOKINGS SAYS:
"MILK MONEY is the most technologically advanced 130 Westport ever to be built. Love, care and ultimate dedication went into her construction, which has filtered through into the overall charter experience."

THE CAPITAL
    Ferretti 97 - 4 Cabins - Nassau - Bahamas - Exumas
  • Ferretti 97 Luxury Crewed Motor Yacht
  • Length: 29.57 m
  • Year: 2008 (2018 Refit)
  • Cabins: 4
  • Berths: 8
  • From $56000 to $64000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 29.57 m (100' 5")
  • Year: 2008 (2018 Refit)
From $56000 to $64000
per week

RENAISSANCE
    Hargrave 116 - 5 Cabins - Nassau - Paradise Island - Bahamas - New England
  • Hargrave 116 Luxury Crewed Motor Yacht
  • Length: 35.4 m
  • Year: 2016
  • Cabins: 5
  • Berths: 10
  • From $85000 to $85000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 35.4 m (120' )
  • Year: 2016
From $85000 to $85000
per week

BOATBOOKINGS SAYS:
"This beautiful 2016 Hargrave is perfect for your holiday in New England this summer or in the Bahamas for the winter months!"

AVALON - Delta Marine 46m - 5 Cabins - Nassau - Bahamas - St Barths - Virgin Islands VIEW 4 REVIEWS 
AVALON
    Delta Marine 46m - 5 Cabins - Nassau - Bahamas - St Barths - Virgin Islands
  • Delta Marine 46m Luxury Crewed Motor Yacht
  • Length: 46 m
  • Year: 2009 (2017 Refit)
  • Cabins: 5
  • Berths: 12
  • From $160000 to $170000 per week
VIEW 4 REVIEWS  Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 46 m (156' 4")
  • Year: 2009 (2017 Refit)
VIEW 4 REVIEWS
From $160000 to $170000
per week

BOATBOOKINGS SAYS:
"One of the most striking luxury motor yachts cruising the Bahamas this summer, highly recommended by the Boatbookings team."

NEVER ENOUGH
    Trinity 157 - 5 Cabins - Bahamas - Nassau - Exumas - Fort Lauderdale
  • Trinity 157 Luxury Crewed Motor Yacht
  • Length: 47.85 m
  • Year: 2006 (2014 Refit)
  • Cabins: 5
  • Berths: 11
  • From $150000 to $150000 per week
Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 47.85 m (162' 9")
  • Year: 2006 (2014 Refit)
From $150000 to $150000
per week

BOATBOOKINGS SAYS:
"This glorious luxury yacht is the perfect charter yacht for guests wanting unadulterated luxury to sail the Caribbean and Bahamas!"

Marquis 43
    Day Charter - 2 State Rooms - Day Charter - Miami
  • Day Charter Crewed Motor Yacht
  • Length: 0 m
  • Year:
  • Cabins: 2
  • Berths: 4
  • From $3000 per day
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Crewed
  • Type: Motor
  • Length: 0 m (0' )
  • Year:
From $3000
per day

BOATBOOKINGS SAYS:
"No better way to enjoy the Miami skyline than with this motor yacht!"

Azimut 42
    3 Staterooms - Day Charter - Miami
  • 3 Staterooms Crewed Motor Yacht
  • Length: 13.29 m
  • Year: 2003
  • Cabins: 2
  • Berths: 4
  • From $3599 per day
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Crewed
  • Type: Motor
  • Length: 13.29 m (45' 9")
  • Year: 2003
From $3599
per day

BOATBOOKINGS SAYS:
"No better way to look out over the incredible skyline of Miami."

RELENTLESS
    Trinity 145 - 5 Cabins - Bahamas - Nassau - Paradise Island - Florida - Fort Lauderdale - Miami
  • Trinity 145 Luxury Crewed Motor Yacht
  • Length: 44.2 m
  • Year: 2001 (2016 Refit)
  • Cabins: 5
  • Berths: 10
  • From $132000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 44.2 m (150' 4")
  • Year: 2001 (2016 Refit)
From $132000
per week

BOATBOOKINGS SAYS:
"Designed for maximum comfort in luxury surroundings."

ANDIAMO
    Symbol 92 - 3 Staterooms - Marathon - Florida - Bahamas - Nassau - Paradise Island
  • Symbol 92 Luxury Crewed Motor Yacht
  • Length: 25.9 m
  • Year: 2010
  • Cabins: 3
  • Berths: 6
  • From $29500 to $29500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 25.9 m (88' 10")
  • Year: 2010
From $29500 to $29500
per week

BOATBOOKINGS SAYS:
"A great motor boat for exploring the waters around the Bahamas and Florida."

INDIGO
    Westport 112 - 4 Staterooms - Nassau - Tortola - Miami - Ft Lauderdale - Newport
  • Westport 112 Luxury Crewed Motor Yacht
  • Length: 34.14 m
  • Year: 2006
  • Cabins: 4
  • Berths: 0
  • From $55000 to $55000 per week
Details Enquire
  • Berths: 0
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 34.14 m (116' 6")
  • Year: 2006
From $55000 to $55000
per week

BOATBOOKINGS SAYS:
"Luxury Westport, refitted in 2020 is an ideal yacht for family and friends in the Bahamas this winter!"

Mangusta 72
    Day Charter - Miami - Bahamas
  • Day Charter Crewed Motor Yacht
  • Length: 72 m
  • Year: 2008
  • Cabins: 3
  • Berths: 6
  • From $3300 to $4500 per day
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 72 m (244' )
  • Year: 2008
From $3300 to $4500
per day

BOATBOOKINGS SAYS:
"The most perfect way to see Miami is from the water on board your very own private yacht!"

Joyce 84 Flybridge
    Day Charter - 2008 - Miami - Ft Lauderdale - Florida
  • Day Charter Crewed Motor Yacht
  • Length: 84 m
  • Year: 2008
  • Cabins: 4
  • Berths: 8
  • From $5500 to $6500 per day
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 84 m (285' )
  • Year: 2008
From $5500 to $6500
per day

BOATBOOKINGS SAYS:
"Sophisticated Joyce 84` available for exploring the Miami coastline."

Astrea 42
    4+2 Cabins (4 double 2 single) - Key West - MIami
  • 4+2 Cabins (4 double 2 single) Bareboat Catamaran
  • Length: 12.58 m
  • Year: 2020
  • Cabins: 6
  • Berths: 12
  • From $4968 to $12414 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.58 m (42' 10")
  • Year: 2020
From $4968 to $12414
per week

BOATBOOKINGS SAYS:
"This new 2020 Astrea 42 is the perfect mid-size cat for sailing with friends and family out of Miami!"

Lagoon 40
    3 Cabins - 2020 - Miami - Florida Keys
  • 3 Cabins Bareboat Catamaran
  • Length: 11.89 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $3500 to $7700 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.89 m (40' 1")
  • Year: 2020
From $3500 to $7700
per week

BOATBOOKINGS SAYS:
"Hop onboard this new 2020 Lagoon 40 and explore the Keys in style!"

CLAIRE - Trinity Yachts 150 - 5 Cabins - Fort Lauderdale - Miami - Nassau - Paradise Island - Staniel Cay VIEW 1 REVIEW 
CLAIRE
    Trinity Yachts 150 - 5 Cabins - Fort Lauderdale - Miami - Nassau - Paradise Island - Staniel Cay
  • Trinity Yachts 150 Luxury Crewed Motor Yacht
  • Length: 45.71 m
  • Year: 2003 (2017 Refit)
  • Cabins: 5
  • Berths: 11
  • From $139500 to $150000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 45.71 m (155' 11")
  • Year: 2003 (2017 Refit)
VIEW 1 REVIEW
From $139500 to $150000
per week

BOATBOOKINGS SAYS:
"Beautfiully re-fitted with an expansive collection of toys. Perfect for the adventurer and active guest!"

Bali 4.5
    4 + 2 cabins (4 double 2 single) - 2018 - Miami
  • 4 + 2 cabins (4 double 2 single) Bareboat Catamaran
  • Length: 13.6 m
  • Year: 2018
  • Cabins: 6
  • Berths: 10
  • From $6126 to $14622 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.6 m (46' 4")
  • Year: 2018
From $6126 to $14622
per week

BOATBOOKINGS SAYS:
"Sail Biscayne Bay and the Florida Keys in comfort on this 2018 Bali 4.5!"

ANTARES
    Westport 130 - 5 Cabins - Nassau - Bahamas - Marsh Harbour - Florida
  • Westport 130 Luxury Crewed Motor Yacht
  • Length: 39.62 m
  • Year: 2008 (2016 Refit)
  • Cabins: 5
  • Berths: 10
  • From $115000 to $115000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.62 m (134' 1")
  • Year: 2008 (2016 Refit)
From $115000 to $115000
per week

BOATBOOKINGS SAYS:
"ANTARES is the perfect charter yacht for exploring the Bahamas in the comfort of unrivalled luxury!"

HAUMEA
    Fontaine Pajot MY37 - 3 Cabins - Florida and the Bahamas
  • Fontaine Pajot MY37 Bareboat Power Catamaran
  • Length: 11 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From $3456 to $7974 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Motor
  • Length: 11 m (37' 8")
  • Year:
From $3456 to $7974
per week

BOATBOOKINGS SAYS:
"A comfortable and stylish power catamaran MY 37!"

VIVERE - Azimut 116 - 5 Cabins - Newport - Fort Lauderdale - Bahamas VIEW 2 REVIEWS 
VIVERE
    Azimut 116 - 5 Cabins - Newport - Fort Lauderdale - Bahamas
  • Azimut 116 Luxury Crewed Motor Yacht
  • Length: 35.36 m
  • Year: 2008
  • Cabins: 5
  • Berths: 10
  • From $53000 to $59000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 35.36 m (120' 8")
  • Year: 2008
VIEW 2 REVIEWS
From $53000 to $59000
per week

BOATBOOKINGS SAYS:
"An elegant, athletic, modern and sexy luxury motor yacht to cruise the Florida Keys and the Bahamas this winter."

BONNIE T
    Rybovich - 3 cabins - Ocean Reef - Florida Keys - Ft Lauderdale
  • Rybovich Fishing Boat
  • Length: 18.9 m
  • Year: 2004
  • Cabins: 3
  • Berths: 6
  • From $27300 to $27300 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 18.9 m (64' 5")
  • Year: 2004
From $27300 to $27300
per week

BOATBOOKINGS SAYS:
"Youll have a bonnie time on expertly lead BONNIE T!"

Bali 4.1
    3 Cabins (3 double) - Miami - Florida
  • 3 Cabins (3 double) Bareboat Catamaran
  • Length: 12.2 m
  • Year: 2017
  • Cabins: 3
  • Berths: 8
  • From $5060 to $6632 per week
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.2 m (41' 8")
  • Year: 2017
From $5060 to $6632
per week

BOATBOOKINGS SAYS:
"The revolutionary Bali 4.1 catamaran, ideal for exploring the south coast of the USA."

Lipari 41
    4 Cabins - Miami
  • 4 Cabins Bareboat Catamaran
  • Length: 11.89 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • From $5600 to $6650 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.89 m (40' 1")
  • Year: 2013
From $5600 to $6650
per week

BOATBOOKINGS SAYS:
"Brand new Lipari 41 available in Miami!"

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