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


SWEET ESCAPE - Christensen 130 - 6 Cabins - Nassau - Staniel Cay - Exumas - Bahamas
SWEET ESCAPE
    Christensen 130 - 6 Cabins - Nassau - Staniel Cay - Exumas - Bahamas
  • Christensen 130 Luxury Crewed Motor Yacht
  • Length: 39.62 m
  • Year: 1993
  • Cabins: 6
  • Berths: 12
  • From $115000 to $135000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 39.62 m (134' 1")
  • Year: 1993
From $115000 to $135000
per week

BOATBOOKINGS SAYS:
"SWEET ESCAPE is a fantastic vessel to explore the Bahamas this summer with a fantastic range of water toys!"

PIPE DREAM - Westport 130 - 5 Cabins - Nassau - Paradise Island - Exumas - Bahamas - Fort Lauderdale - Florida East Coast
PIPE DREAM
    Westport 130 - 5 Cabins - Nassau - Paradise Island - Exumas - Bahamas - Fort Lauderdale - Florida East Coast
  • Westport 130 Luxury Crewed Motor Yacht
  • Length: 39.62 m
  • Year: 2014
  • Cabins: 5
  • Berths: 10
  • From $140000 to $140000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.62 m (134' 1")
  • Year: 2014
From $140000 to $140000
per week

BOATBOOKINGS SAYS:
"Live out your dream Bahamas luxury cruise on PIPE DREAM!"

EVA - Mangusta 92 - 4 cabins - Miami - Nassau VIEW 1 REVIEW 
EVA
    Mangusta 92 - 4 cabins - Miami - Nassau
  • Mangusta 92 Crewed Motor Yacht
  • Length: 28.04 m
  • Year: 2007
  • Cabins: 4
  • Berths: 8
  • From $48000 to $48000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 28.04 m (95' 8")
  • Year: 2007
VIEW 1 REVIEW
From $48000 to $48000
per week

BOATBOOKINGS SAYS:
"Magnificent Mangusta available to explore the most incredible waters of the Bahamas."

JUST ENOUGH - Custom 140 - 5 Cabins - Fort Lauderdale - Florida East Coast VIEW 4 REVIEWS 
JUST ENOUGH
    Custom 140 - 5 Cabins - Fort Lauderdale - Florida East Coast
  • Custom 140 Luxury Crewed Motor Yacht
  • Length: 43 m
  • Year: 2012
  • Cabins: 5
  • Berths: 11
  • From $139000 to $149000 per week
VIEW 4 REVIEWS  Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 43 m (146' 4")
  • Year: 2012
VIEW 4 REVIEWS
From $139000 to $149000
per week

BOATBOOKINGS SAYS:
"You will not get enough of the thrill, excitement, and fun aboard JUST ENOUGH on your Miami cruise!"

M3 - Intermarine Savannah 147 - 5 Cabins - Palm Beach - Florida - New England - Nassau - Exumas - Bahamas
M3
    Intermarine Savannah 147 - 5 Cabins - Palm Beach - Florida - New England - Nassau - Exumas - Bahamas
  • Intermarine Savannah 147 Luxury Crewed Motor Yacht
  • Length: 44.81 m
  • Year: 2002
  • Cabins: 5
  • Berths: 10
  • From $130000 to $149500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 44.81 m (152' 5")
  • Year: 2002
From $130000 to $149500
per week

BOATBOOKINGS SAYS:
"Magnificent, majestic, and marvelous! Climb aboard M3 and experience an unforgettable Bahamas cruise!"

SCOTT FREE - President 114 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas VIEW 6 REVIEWS 
SCOTT FREE
    President 114 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas
  • President 114 Luxury Crewed Motor Yacht
  • Length: 34.75 m
  • Year: 2008
  • Cabins: 4
  • Berths: 8
  • From $52000 to $54000 per week
VIEW 6 REVIEWS  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 34.75 m (118' 7")
  • Year: 2008
VIEW 6 REVIEWS
From $52000 to $54000
per week

BOATBOOKINGS SAYS:
"Experience the essence of freedom as you journey throughout the Bahamas on SCOTT FREE."

PURPUS - Bali 4.1 - 3 cabins - Florida - Keys VIEW 2 REVIEWS 
PURPUS
    Bali 4.1 - 3 cabins - Florida - Keys
  • Bali 4.1 Crewed Catamaran
  • Length: 12 m
  • Year: 2020
  • Cabins: 3
  • Berths: 0
  • From $17066 to $18550 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 0
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 12 m (40' )
  • Year: 2020
VIEW 2 REVIEWS
From $17066 to $18550
per week

BOATBOOKINGS SAYS:
"Brand new to the fleet for winter 2022 and into 2023! Great space for 6 guests to explore the Keys!"

SMART - Vanquish 40 - 1 Cabin - Miami - Florida East Coast - Southeast USA
SMART
    Vanquish 40 - 1 Cabin - Miami - Florida East Coast - Southeast USA
  • Vanquish 40 Luxury Crewed Motor Yacht
  • Length: 12.19 m
  • Year: 2021
  • Cabins: 1
  • Berths: 2
  • From $30000 to $30000 per week
Details Enquire
  • Berths: 2
  • Cabins: 1
  • Crew: Crewed
  • Type: Motor
  • Length: 12.19 m (41' 7")
  • Year: 2021
From $30000 to $30000
per week

BOATBOOKINGS SAYS:
"SMART is the wise choice to explore Florida's East Coast!"

CECE - Vanquish 45 ft - 1 Cabin - Miami - Florida - Southeast USA
CECE
    Vanquish 45 ft - 1 Cabin - Miami - Florida - Southeast USA
  • Vanquish 45 ft Luxury Crewed Motor Yacht
  • Length: 13.71 m
  • Year: 2022
  • Cabins: 1
  • Berths: 2
  • From $22800 to $32000 per week
Details Enquire
  • Berths: 2
  • Cabins: 1
  • Crew: Crewed
  • Type: Motor
  • Length: 13.71 m (46' 3")
  • Year: 2022
From $22800 to $32000
per week

BOATBOOKINGS SAYS:
"Live out your ideal romantic cruise on CECE!"

THE SPACE BETWEEN - Leopard 46 - 3 Cabins - Fort Lauderdale - The Florida Keys - Miami - The Bahamas
THE SPACE BETWEEN
    Leopard 46 - 3 Cabins - Fort Lauderdale - The Florida Keys - Miami - The Bahamas
  • Leopard 46 Luxury Crewed Catamaran
  • Length: 14 m
  • Year: 2011
  • Cabins: 3
  • Berths: 6
  • From $18600 to $21000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2011
From $18600 to $21000
per week

BOATBOOKINGS SAYS:
"Perfectly suited for a family or group of couples to explore The Florida Keys."

Déjà Vu - Fontaine Pajot 50(2020)- 4 Cabins - Key West - Florida
Déjà Vu
    Fontaine Pajot 50 (2020) - 4 Cabins - Key West - Florida
  • Fontaine Pajot 50 (2020) Luxury Crewed Catamaran
  • Length: 15 m
  • Year: 2020
  • Cabins: 4
  • Berths: 0
  • From $26250 to $26250 per week
Details Enquire
  • Berths: 0
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15 m (51' )
  • Year: 2020
From $26250 to $26250
per week

BOATBOOKINGS SAYS:
"Fishing, Sushi and the most welcoming Crew make this a stand-out charter on The Keys!"

ELLA ROSE - Princess UK 62 - 3 Cabins - Miami - Florida East Coast - Nassau - Bahamas
ELLA ROSE
    Princess UK 62 - 3 Cabins - Miami - Florida East Coast - Nassau - Bahamas
  • Princess UK 62 Luxury Crewed Motor Yacht
  • Length: 18.9 m
  • Year: 2015
  • Cabins: 3
  • Berths: 6
  • From $36000 to $43200 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 18.9 m (64' 5")
  • Year: 2015
From $36000 to $43200
per week

BOATBOOKINGS SAYS:
"Embark on a refreshing cruise and bloom like a flower on ELLA ROSE!"

LIQUID ASSET - Azimut 66 - 3 Cabins - Boston - Northeast USA - South Florida - Bahamas
LIQUID ASSET
    Azimut 66 - 3 Cabins - Boston - Northeast USA - South Florida - Bahamas
  • Azimut 66 Luxury Crewed Motor Yacht
  • Length: 20.33 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $32000 to $36000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 20.33 m (69' 4")
  • Year: 2020
From $32000 to $36000
per week

BOATBOOKINGS SAYS:
"Have a great Bahamas cruise worth spending on LIQUID ASSET!"

GEM - Sunseeker 68 - 3 Cabins - Miami - Florida - Southeast USA - Bahamas
GEM
    Sunseeker 68 - 3 Cabins - Miami - Florida - Southeast USA - Bahamas
  • Sunseeker 68 Luxury Crewed Motor Yacht
  • Length: 20.73 m
  • Year: 2014
  • Cabins: 3
  • Berths: 6
  • From $36000 to $39000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 20.73 m (70' 9")
  • Year: 2014
From $36000 to $39000
per week

BOATBOOKINGS SAYS:
"Memories are priceless treasures, so create more on GEM!"

LITQUIDITY - Azimut 68 - 4 Cabins - Bal Harbour - Miami - Florida East Coast - USA
LITQUIDITY
    Azimut 68 - 4 Cabins - Bal Harbour - Miami - Florida East Coast - USA
  • Azimut 68 Luxury Crewed Motor Yacht
  • Length: 20.73 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $40000 to $40000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 20.73 m (70' 9")
  • Year: 2018
From $40000 to $40000
per week

BOATBOOKINGS SAYS:
"Cruising has never been so lit on the luxury yacht LITQUIDITY!"

LAGO PARADISE - Sunseeker Manhattan 70 - 4 Cabins - Miami - Florida East Coast - Southeast USA - Bahamas
LAGO PARADISE
    Sunseeker Manhattan 70 - 4 Cabins - Miami - Florida East Coast - Southeast USA - Bahamas
  • Sunseeker Manhattan 70 Luxury Crewed Motor Yacht
  • Length: 21.24 m
  • Year: 2022
  • Cabins: 4
  • Berths: 8
  • From $45000 to $55000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 21.24 m (72' )
  • Year: 2022
From $45000 to $55000
per week

BOATBOOKINGS SAYS:
"Let the captain take the helm and have an unforgettable cruise in the Bahamas on LAGO PARADISE!"

VOLO - Monte Carlo 70 - 4 Cabins - Miami - Florida East Coast - Southeast USA - Bahamas
VOLO
    Monte Carlo 70 - 4 Cabins - Miami - Florida East Coast - Southeast USA - Bahamas
  • Monte Carlo 70 Luxury Crewed Motor Yacht
  • Length: 21.34 m
  • Year: 2012
  • Cabins: 4
  • Berths: 8
  • From $39000 to $42000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 21.34 m (72' 10")
  • Year: 2012
From $39000 to $42000
per week

BOATBOOKINGS SAYS:
"Fulfill your ideal Bahamas cruise on VOLO!"

LION - Sunseeker 72 - 4 Cabins - Miami - Florida East Coast - USA
LION
    Sunseeker 72 - 4 Cabins - Miami - Florida East Coast - USA
  • Sunseeker 72 Luxury Crewed Motor Yacht
  • Length: 22 m
  • Year: 2006
  • Cabins: 4
  • Berths: 8
  • From $36000 to $36000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 22 m (74' 4")
  • Year: 2006
From $36000 to $36000
per week

BOATBOOKINGS SAYS:
"Reward yourself from your daily grrr-ind on LION!"

BORN TO RUN - Sunseeker 73 - 3 Cabins - Miami - Florida Keys - West Palm Beach
BORN TO RUN
    Sunseeker 73 - 3 Cabins - Miami - Florida Keys - West Palm Beach
  • Sunseeker 73 Luxury Crewed Motor Yacht
  • Length: 22 m
  • Year: 2013
  • Cabins: 3
  • Berths: 6
  • From $30000 to $32000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 22 m (74' 4")
  • Year: 2013
From $30000 to $32000
per week

BOATBOOKINGS SAYS:
"BORNTO RUN is an excellent choice for exploring the Eastern Seaboard on the getaway of a lifetime!"

NOT YET - Riva 76 - 3 Cabins - Miami - Florida East Coast - USA
NOT YET
    Riva 76 - 3 Cabins - Miami - Florida East Coast - USA
  • Riva 76 Luxury Crewed Motor Yacht
  • Length: 23.16 m
  • Year: 2021
  • Cabins: 3
  • Berths: 6
  • From $69000 to $99000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 23.16 m (78' )
  • Year: 2021
From $69000 to $99000
per week

BOATBOOKINGS SAYS:
"If not today, when? So pack your bags and explore Florida's East Coast on NOT YET!"

MILAMO - Sunseeker 76 Yacht - 4 Cabins - Aventura - Miami - Florida East Coast - Southeast USA
MILAMO
    Sunseeker 76 Yacht - 4 Cabins - Aventura - Miami - Florida East Coast - Southeast USA
  • Sunseeker 76 Yacht Luxury Crewed Motor Yacht
  • Length: 23.16 m
  • Year: 2022
  • Cabins: 4
  • Berths: 8
  • From $62000 to $68000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 23.16 m (78' )
  • Year: 2022
From $62000 to $68000
per week

BOATBOOKINGS SAYS:
"MILAMO showcases her natural bravado, a real head-turner!"

CORAGGIO - LAZZARA 80 - 3 Cabins - Fort Lauderdale - Miami - Bahamas
CORAGGIO
    LAZZARA 80 - 3 Cabins - Fort Lauderdale - Miami - Bahamas
  • LAZZARA 80 Crewed Motor Yacht
  • Length: 24 m
  • Year: 2004
  • Cabins: 3
  • Berths: 0
  • From $30000 to $35000 per week
Details Enquire
  • Berths: 0
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 24 m (81' )
  • Year: 2004
From $30000 to $35000
per week

AZURE - Azimut 80 - 4 Cabins - Bahamas
AZURE
    Azimut 80 - 4 Cabins - Bahamas
  • Azimut 80 Crewed Motor Yacht
  • Length: 24 m
  • Year: 2004
  • Cabins: 4
  • Berths: 8
  • From $33000 to $38000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 24 m (81' )
  • Year: 2004
From $33000 to $38000
per week

BOATBOOKINGS SAYS:
"Great selection of water toys on board!"

PRAYING FOR OVERTIME - Princess UK 85 - Miami - Florida East Coast - Southeast USA - Bahamas
PRAYING FOR OVERTIME
    Princess UK 85 - Miami - Florida East Coast - Southeast USA - Bahamas
  • Princess UK 85 Luxury Crewed Motor Yacht
  • Length: 25.93 m
  • Year: 2012
  • Cabins: 4
  • Berths: 8
  • From $43200 to $45000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 25.93 m (88' 1")
  • Year: 2012
From $43200 to $45000
per week

BOATBOOKINGS SAYS:
"You will definitely wish for an extended stay on PRAYING FOR OVERTIME as you cruise the enchanting Bahamas."

THE PEDDLER - Dreamline 26 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas
THE PEDDLER
    Dreamline 26 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas
  • Dreamline 26 Luxury Crewed Motor Yacht
  • Length: 26.21 m
  • Year: 2019
  • Cabins: 4
  • Berths: 8
  • From $65000 to $69000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 26.21 m (89' 5")
  • Year: 2019
From $65000 to $69000
per week

BOATBOOKINGS SAYS:
"THE PEDDLER offers you an unforgettable cruising experience across the Bahamas."

SLIPAWAY - Hargrave 92 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas
SLIPAWAY
    Hargrave 92 - 4 Cabins - Fort Lauderdale - Florida East Coast - Bahamas
  • Hargrave 92 Luxury Crewed Motor Yacht
  • Length: 28.04 m
  • Year: 2001
  • Cabins: 4
  • Berths: 10
  • From $49000 to $49000 per week
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 28.04 m (95' 8")
  • Year: 2001
From $49000 to $49000
per week

BOATBOOKINGS SAYS:
"You will never sleep on the fun aboard SLIPWAY as you explore the beauty of the Bahamas."

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