Islamorada - Florida Keys Overview

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
Day 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

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
- Westport 130 Luxury Crewed Motor Yacht
- Length: 39.62 m
- Year: 2014
- Cabins: 5
- Berths: 10
- From $140000 to $140000 per week
BOATBOOKINGS SAYS:
"Live out your dream Bahamas luxury cruise on PIPE DREAM!"
- IAG Yachts 133 Luxury Crewed Motor Yacht
- Length: 40.53 m
- Year: 2016 (2021 Refit)
- Cabins: 6
- Berths: 12
- From $165000 to $196000 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!"
- Horizon 90 Luxury Motor Yacht
- Length: 27 m
- Year: 2019
- Cabins: 5
- Berths: 10
- 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."
- Trinity Yachts 164 Luxury Crewed Motor Yacht
- Length: 49.99 m
- Year: 2010 (2022 Refit)
- Cabins: 5
- Berths: 10
- From $199000 to $230000 per week
BOATBOOKINGS SAYS:
"The most luxurious tri-deck yacht for adventure exploration!"
- Lazzara 116 Luxury Crewed Motor Yacht
- Length: 35 m
- Year: 2009 (2022 Refit)
- Cabins: 5
- Berths: 10
- From $75000 to $79500 per week
BOATBOOKINGS SAYS:
"You will surely want to stay onboard forever after your Bahamian cruising adventure with family on NAMASTAY!"
- Westport 130 Luxury Crewed Motor Yacht
- Length: 39 m
- Year: 2007 (2014 Refit)
- Cabins: 5
- Berths: 10
- From $125000 to $143750 per week
BOATBOOKINGS SAYS:
"Step onboard PLAN A for epic charters with friends and family around New England in the summer and the idyllic Bahamian islands in the winter."
- Hargrave 101 Luxury Crewed Motor Yacht
- Length: 30 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $50000 to $55000 per week
BOATBOOKINGS SAYS:
"CARBON COPY is a perfect yacht for stylish cruising with your family and friends in Florida, the Bahamas and New England."
- Van Mill 143 Luxury Crewed Motor Yacht
- Length: 43 m
- Year: 1988 (2017 Refit)
- Cabins: 5
- Berths: 12
- From $120000 to $135000 per week
BOATBOOKINGS SAYS:
"Set your sights on STARSHIP and slip into bliss, where every Bahamas moment is too good to miss!"
- Leopard 46 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2011 (2017 Refit)
- Cabins: 3
- Berths: 6
- From $18600 to $21000 per week
BOATBOOKINGS SAYS:
"From shore to sheen and sea to serene, every moment feels just right aboard THE SPACE BETWEEN!"
- Horizon 25m Luxury Crewed Motor Yacht
- Length: 25 m
- Year: 2006 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $40000 to $55000 per week
BOATBOOKINGS SAYS:
"Trade ordinary for extraordinary turquoise scenes aboard LEXINGTON across the Bahamas’ pristine dreams."
- Ferretti 850 Luxury Crewed Motor Yacht
- Length: 25 m
- Year: 2022
- Cabins: 4
- Berths: 9
- From $60000 to $68000 per week
BOATBOOKINGS SAYS:
"Catch the moment, catch the breeze, and catch the Bahamas aboard THE BRASS RING!"
- Cheoy Lee Bravo 84 Crewed Motor Yacht
- Length: 26 m
- Year: 2012 (2018 Refit)
- Cabins: 3
- Berths: 6
- From $29500 per week
BOATBOOKINGS SAYS:
"Explore Florida like a queen as you revel in the homey comfort of JUS CHILL`N!"
- President 87 Crewed Motor Yacht
- Length: 26 m
- Year: 2007
- Cabins: 4
- Berths: 8
- From $40000 to $45000 per week
BOATBOOKINGS SAYS:
"Real and unforgettable experiences await in the Bahamas aboard the luxurious AURELIA!"
- Sunseeker 90 Ocean Luxury Crewed Motor Yacht
- Length: 27 m
- Year: 2026
- Cabins: 4
- Berths: 8
- From $90000 to $100000 per week
BOATBOOKINGS SAYS:
"In seas of blue where dolphins roam, 1 LORENA feels like home!"
- Symbol 92 Luxury Crewed Motor Yacht
- Length: 28 m
- Year: 2010 (2023 Refit)
- Cabins: 3
- Berths: 6
- From $34500 to $34500 per week
BOATBOOKINGS SAYS:
"Go for glow in the Bahamas aboard ANDIAMO, where sunlit days and starry nights steal the show!"
- Riva Argo 90 Crewed Motor Yacht
- Length: 28 m
- Year: 2019
- Cabins: 4
- Berths: 6
- From $95000 to $120000 per week
BOATBOOKINGS SAYS:
"The infinite starry sky hits differently as you watch it on BEYOND BEYOND in your Bahamas cruise!"
- Ferretti 960 Crewed Motor Yacht
- Length: 29 m
- Year: 2014 (2023 Refit)
- Cabins: 5
- Berths: 10
- From $60000 to $69000 per week
BOATBOOKINGS SAYS:
"Your Bahamas cruising vacation is more than cocktails and wines; on SOL SHINE, it's about timeless moments wrapped in sea breeze and sunshine!"
- Lazzara 112 Luxury Crewed Motor Yacht
- Length: 34 m
- Year: 2004 (2023 Refit)
- Cabins: 5
- Berths: 10
- From $77000 per week
BOATBOOKINGS SAYS:
"LADY KRISTINA is designed for discovering the Bahamas at an easy pace, with generous spaces, steady comfort, and a crew focused on your enjoyment."
- Hargrave 116 Luxury Crewed Motor Yacht
- Length: 35 m
- Year: 2016
- Cabins: 5
- Berths: 10
- From $90000 to $90000 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!"
- Broward 124 Luxury Crewed Motor Yacht
- Length: 37 m
- Year: 2007 (2019 Refit)
- Cabins: 5
- Berths: 10
- From $85000 per week
BOATBOOKINGS SAYS:
"Discover the magic of the Bahamas with CAMILLE, a premier luxury yacht offering endless comfort and adventure at sea!"
- Custom 140 Luxury Crewed Motor Yacht
- Length: 43 m
- Year: 2012
- Cabins: 5
- Berths: 11
- From $119000 to $139000 per week
BOATBOOKINGS SAYS:
"You will not get enough of the thrill, excitement, and fun aboard JUST ENOUGH on your Miami cruise!"
- 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
BOATBOOKINGS SAYS:
"This new 2020 Astrea 42 is the perfect mid-size cat for sailing with friends and family out of Miami!"
- 4 Cabins Bareboat Catamaran
- Length: 12.19 m
- Year: 2008
- Cabins: 4
- Berths: 10
- From $5050 to $5850 per week
- Fontaine Pajot MY37 Bareboat Power Catamaran
- Length: 11 m
- Year:
- Cabins: 3
- Berths: 6
- From $3456 to $7974 per week
BOATBOOKINGS SAYS:
"A comfortable and stylish power catamaran MY 37!"
- Azimut 116 Luxury Crewed Motor Yacht
- Length: 35.36 m
- Year: 2008
- Cabins: 5
- Berths: 10
- From $60000 to $65000 per week
BOATBOOKINGS SAYS:
"An elegant, athletic, modern and sexy luxury motor yacht to cruise the Florida Keys and the Bahamas this winter."
- 4 Cabins Bareboat Catamaran
- Length: 12.5 m
- Year: 2012
- Cabins: 4
- Berths: 10
- From $5450 to $6350 per week
BOATBOOKINGS SAYS:
"Sleek lines and a modern interior, a brilliant choice for charter."
- 3 Cabins Bareboat Catamaran
- Length: 10.36 m
- Year: 2012
- Cabins: 3
- Berths: 6
- From $4450 per week
- 4 Cabins Bareboat Catamaran
- Length: 12.35 m
- Year: 2019
- Cabins: 3
- Berths: 7
- From $3750 to $8250 per week
BOATBOOKINGS SAYS:
"Experience the comfort of this 2019 Bali 4.1!"
- 4 Cabins Bareboat Catamaran
- Length: 12.61 m
- Year:
- Cabins: 4
- Berths: 8
- From $5750 per week
- Azimut 62 Crewed Motor Yacht
- Length: 18.9 m
- Year: 2010
- Cabins: 3
- Berths: 6
- From $39000 to $39000 per week
BOATBOOKINGS SAYS:
"The crew on WARREN KELLY will keep you entertained and laughing while you cruising the Florida Keys in this Azimut 62S."



































