7 Day Key West Sailing Itinerary

key west yacht charter- Key West, Florida - you will start your charter from the bustling town and make your way north. 

Overview

Key West, along with the lower Keys offers an exemplary sailing charter! The Keys, famous for their fishing, laid back life, and colorful houses, is the perfect place for you to charter during the winter months. The Keys are on the same latitude as the Bahamas, so you will experience similar weather conditions aka balmy, warm, great winds, and warm seas! The Keys offer private sailing, remote anchorages, uninhabited islands, and some of the best snorkeling and scuba diving in the world!

Day 1: Key West

key west yacht charter itinerary for sailors
- Key West is famous for its pastel-colored houses. 
Embarkation is generally between the hours of 1400 to 1700 where you will be given the yacht briefing, with your own skipper - or a hired skipper. On your first day, we suggest that you get settled in with your yacht, plan your itinerary with your skipper. If there is some time before sunset, you can sail out to one of the close by reefs for some snorkeling! Head out to town and embrace the American, come Bahamian culture, a laid back fish food feast awaits at one of the local restaurants!

Day 2: Key West > (option: Marquesas) or head straight to Newfound Harbour 

exploring key west via the water with our sailing itinerary
- The Keys offer some of the best diving and snorkeling in the whole North American continent. 
On your first day, you have the option to either head west to the uninhabited islands of the Marquesas and explore the locally named 'oasis' or you can head East up the Keys to Newfound Harbour for two days of snorkeling and diving.
 
Should you decide to head towards Newfound Harbour, make sure you stop off on the way and snorkel the well known Reef - there are some buoys you can tie off on. Exploring the Marquesas will leave you with memories of a lifetime. Uninhabited, untouched, natural beauty awaits. Pull up your grill and chuck on some fresh fish - what more could you want for your first day?!

Day 3: Marquesas > Newfound Harbor

explore Looe Key with our sailing itinerary
- Green Turtle in Looe Key reef 
Sail East and head towards the lower keys area. Stopping off in Looe’s Key is an absolute must! Looe's Key is a National Marine Sanctuary with fantastic snorkeling and diving opportunities. There is a famous diving/snorkeling reef from 1 to 80 feet with a great wall - perfect for those scuba enthusiasts!
 
Tie up to one of the mooring balls close by, anchoring is not permitted to protect the coral. After a few hours on the reef head for Newfound Harbor for your overnight stay. You have the choice to either anchor close to the Marina, or book a (rather expensive) berth for the evening. Explore the town and the fantastic restaurants close by!

Day 4: Newfound Harbor > Bahia Honda

Bahia Honda state park - explore with our sailing itinerary
- Areal shot of Bahia Honda
After your evening at Newfound Harbour, continue up towards one of the best spots in the keys the famous Bahia Honda State Park. You can either stay in Rodriguez Key or Tavernier Key. You can also spend the night at Pilot House Marina. 
 
There are some stunning beaches here to explore - so pack your lunch and head for the beach! There are also some lovely walks to be done if you are feeling up for it! It can get humid during the summer, so best to explore in the winter months. Enjoy a lovely long evening, and watch the sunset over the keys. Perfection.

Day 5: Bahia Honda to Big Pine Key

kids playing in Bahia Honda National Park sailing itinerary
- Bahia Honda has some of the best beaches in the whole keys area!
After your morning swim down on the white sand beaches of Bahia Honda, head to yet another nature rester - Big Pine Key for more swimming, exploring kayaking, and hiking. Fishing is huge in Big Pine Key, so make sure you head down to one of the locally ran restaurants to feast on the days catch! Island vibes are true and strong in this part of Florida, so sit back, relax put the phones away and enjoy the laid-back lifestyle.

Day 6: Big Pine key > Key West

Big Pine Cay life style - explore with Boatbookings!
- Oh Island life, don't ya just love it?!
Explore Big Pine Key in the morning before heading back to Key West. Have a leisurely sail towards the harbor stopping off on the way to have lunch either onboard or in a marina. There is usually a mandatory return of the yacht before 1800 on the day before disembarkation for a debrief/checkout out so make sure you allow for plenty of time to get back.
 
It's time to hit the town after your checkout! Key Wests boasts a vibrant island culture, with many restaurants and bars to chat through your weeks sailing! Fresh Fish, rum punches, BBQs line the streets - go on, treat yourself!

Day 7: Disembarkation Key West 

Itinerary exploring key west, Florida.
- Key West Harbour.
Today marks the last day of your itinerary. Disembarkation is usually between 9am - 11am depending on your arrangements, head on into town, or we can arrange for your transfers back to the airport. Don't worry, we are here to provide you with another unforgettable charter in the future!

 
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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 $40000 to $45000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 25.9 m (88' 10")
  • Year: 2010
From $40000 to $45000
per week

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

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!"

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!"

INSATIABLE
    Broward 100 - 3 Cabins - Florida - Bahamas - Nassau - Staniel Cay - Georgetown
  • Broward 100 Luxury Crewed Motor Yacht
  • Length: 29.4 m
  • Year: 1985 (2000 Refit)
  • Cabins: 3
  • Berths: 6
  • From $29500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 29.4 m (100' )
  • Year: 1985 (2000 Refit)
From $29500
per week

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 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.62 m (134' 1")
  • Year: 2008 (2016 Refit)
From $115000
per week

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

HAUMEA_DB
  • 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 1 REVIEW 
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 $52000 to $57500 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 35.36 m (120' 8")
  • Year: 2008
VIEW 1 REVIEW
From $52000 to $57500
per week

BOATBOOKINGS SAYS:
"An elegant, athletic, modern and sexy luxury motor yacht"

BONNIE T
    Rybovich - 3 cabins - Ocean Reef - Florida Keys - Ft Lauderdale
  • Rybovich Fishing Boat
  • Length: 62 m
  • Year: 2004
  • Cabins: 3
  • Berths: 6
  • From $27300 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 62 m (210' 8")
  • Year: 2004
From $27300
per week

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

Jeanneau Sun Odyssey 409
    3 Cabins - 2014 - Miami - Florida Keys
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 12.19 m
  • Year: 2014
  • Cabins: 3
  • Berths: 6
  • From $3100 to $4620 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.19 m (41' 7")
  • Year: 2014
From $3100 to $4620
per week

BOATBOOKINGS SAYS:
"A stylish yacht for sailing the Florida Keys with family!"

Bali 4.1
    4 Cabins - 2019 - Miami - Florida Keys
  • 4 Cabins Bareboat Catamaran
  • Length: 12.35 m
  • Year: 2019
  • Cabins: 3
  • Berths: 7
  • From $3750 to $8250 per week
Details Enquire
  • Berths: 7
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.35 m (42' 11")
  • Year: 2019
From $3750 to $8250
per week

BOATBOOKINGS SAYS:
"Experience the comfort of this 2019 Bali 4.1!"

BRAVO
    Stephens 100 - 3 Cabins - Bahamas - Florida
  • Stephens 100 Luxury Crewed Motor Yacht
  • Length: 30.48 m
  • Year: 1974 - refitted 2008
  • Cabins: 3
  • Berths: 6
  • From $30000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 30.48 m (103' )
  • Year: 1974 - refitted 2008
From $30000
per week

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