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


MAJESTIC MOMENTS - Azimut 88 - 5 Cabins - Nassau - Staniel Cay - Exumas
MAJESTIC MOMENTS
    Azimut 88 - 5 Cabins - Nassau - Staniel Cay - Exumas
  • Azimut 88 Luxury Crewed Motor Yacht
  • Length: 26 m
  • Year: 2019
  • Cabins: 5
  • Berths: 10
  • From $80000 to $90000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 26 m (88' 8")
  • Year: 2019
From $80000 to $90000
per week

BOATBOOKINGS SAYS:
"A 2019 Azimut with everything you need: Jacuzzi, water toys, stabilizer at anchor and underway with a reputable Captain and Chef!"

SERENITY - IAG Yachts 133 - 6 Cabins - Bahamas - Florida - Miami - Nassau
SERENITY
    IAG Yachts 133 - 6 Cabins - Bahamas - Florida - Miami - Nassau
  • IAG Yachts 133 Luxury Crewed Motor Yacht
  • Length: 40.53 m
  • Year: 2016 (2021 Refit)
  • Cabins: 6
  • Berths: 12
  • From $145000 to $175000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 40.53 m (137' 9")
  • Year: 2016 (2021 Refit)
From $145000 to $175000
per week

BOATBOOKINGS SAYS:
"SERENITY is a beautifully elegant crewed motor yacht that is perfect for you and your family and friends to charter in the Bahamas!"

STARSHIP - Van Mill 143 - 5 Cabins - Fort Lauderdale - Florida East Coast - Nassau - Staniel Cay - Exumas - Bahamas
STARSHIP
    Van Mill 143 - 5 Cabins - Fort Lauderdale - Florida East Coast - Nassau - Staniel Cay - Exumas - Bahamas
  • Van Mill 143 Luxury Crewed Motor Yacht
  • Length: 43.59 m
  • Year: 1988
  • Cabins: 5
  • Berths: 12
  • From $120000 to $150000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 43.59 m (148' 3")
  • Year: 1988
From $120000 to $150000
per week

BOATBOOKINGS SAYS:
"Take the helm and embark on an adventure-rich charter in the Bahamas onboard STARSHIP, as you make use of her thrilling toy selection, which includes 5 jet skis."

DR NO - Ferretti 75 - Miami Day Charter Yacht - Miami - South Beach - Florida
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
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 $62500 to $62500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 31.4 m (106' 8")
  • Year: 2009
From $62500 to $62500
per week

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

BELLA TU - Horizon 90 - 5 Cabins - Nassau - Staniel Cay - Exumas
BELLA TU
    Horizon 90 - 5 Cabins - Nassau - Staniel Cay - Exumas
  • Horizon 90 Luxury Motor Yacht
  • Length: 27 m
  • Year: 2019
  • Cabins: 5
  • Berths: 10
  • From $75000 to $85000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 27 m (91' )
  • Year: 2019
From $75000 to $85000
per week

BOATBOOKINGS SAYS:
"BELLA TU is a floating retreat to stimulate the soul and embark on an extraordinary adventure in the utmost luxury."

Lazzara 84 - 5 Cabins - Miami Day Boat Rental - South Beach - Biscayne Bay Miami - Miami - Florida
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."

LISA MI AMORE - Christensen 157 - 6 Cabins - Newport - Bahamas - Marthas Vinyard - Paradise Island - Georgetown - Miami VIEW 1 REVIEW 
LISA MI AMORE
    Christensen 157 - 6 Cabins - Newport - Bahamas - Marthas Vinyard - Paradise Island - Georgetown - Miami
  • Christensen 157 Luxury Crewed Motor Yacht
  • Length: 47.85 m
  • Year: 2005 (2009 Refit)
  • Cabins: 6
  • Berths: 12
  • From $199000 to $219000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 47.85 m (162' 9")
  • Year: 2005 (2009 Refit)
VIEW 1 REVIEW
From $199000 to $219000
per week

BOATBOOKINGS SAYS:
"This luxury yacht is ideal for events and includes a jacuzzi, two jet skis and all the amenities you could want."

LEGEND AND SOUL - Rodriguez Yachts 62 - Miami Day Charter - Miami - Ft Lauderdale
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 $39000 to $39000 per week
Details Enquire
  • Berths: 0
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.9 m (64' 5")
  • Year: 2007
From $39000 to $39000
per week

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

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