(305) 767-3672
Key West Sailing sailboat makes way

Key West Sailing

Book Key West Sailing Charters

   In 1513, Spanish explorer Ponce de Leon sailed the waters around Key West in search of the legendary Fountain of Youth. Nearly 500 years later, Key West sailing charters follow in his wake, offering the same promise of exploration and youthful rejuvenation.  And did we mention some pretty awesome sailing charters?

   Call Key West Charter Boat, fill out a quote form or book a public sail online.  Whichever you choose we’ll find the perfect vessel for you.

   Few experiences stir the soul as standing on the deck of a boat under sail. Whether you’re bareboating a catamaran with friends or throwing a big group party aboard the 105-foot schooner America 2.0, set sail on the tropical breezes of the Keys and you will be transported to a whole different state of mind.  Yes, sailing in The Florida Keys is truly amazing.

public trips

PRIVATE  trips

Fast Quote

Florida Keys Best Sailing

   Key West sailing is some of the best in the world because of where it is in the world: latitude 24° 33’18” N, longitude 81° 46’ 53” W, between the open Atlantic and the Gulf of Mexico. A private sailing charter from here can take you wherever the mood suits. A day sail to uninhabited islands, exploring shallow waters, sailing snorkeling the whole way through. Sound good?

   Choose a sailing excursion to the calmer turquoise waters of the north and you’re likely to get picture-perfect days of relaxed cruising. Just set the auto-pilot, settle back and relax. Head south—where the continental shelf falls off a cliff—and you’re in for some true bluewater sailing. Stiffening winds push you to the horizon as saltwater spray carries the intoxicating smell of freedom in the air.

Key West Sailing Knowledge

   When it comes to planning a sailing trip, there’s no substitute for local knowledge. And nobody knows more about sailing the Florida Keys than Key West Charter Boat. Whether you’re interested in custom sailing trips on a 50-foot luxury catamaran with your family for a week or overnight sailing for two on a 30-foot sloop, call us.

   If you’d like a quick price quote to sunset sail Key West for an evening with your office staff, fill out a quote form. We’ll arrange everything: boat, captain and crew, and the best Key West sailing charter prices.

   Key West Florida is a historic seaport with a variety of daysailers for hire, as well as the bigger Key West yacht rentals. Take a 25-footer out for a full day or half-day trip around the island. Sail past Southernmost Point and see the world-famous buoy marking the point furthest south in the continental United States.

Gallery

More Sailing Info...

Island Sailing Destinations

   Lets Circumnavigate Sunset Key, the island of the rich and famous. Who knows who you could spot sunbathing on their private beach? For a sailing adventure, you’ll long remember, cruise past Chica Boca Key, home to Naval Air Station Key West. With any luck, a squadron of navy fighter jets will take off right in front of you, heading to their carrier in the Atlantic.

   You always have the option of cruising around and dropping anchor whenever the mood suits. Sailing the Florida keys is a family-friendly activity with opportunities to kayak snorkel and explore just about anywhere. Dolphin watching is always a crowd-pleaser. Same for snorkeling North America’s only living coral reef. Designated a national marine sanctuary, the reef is teeming with colorful tropical fish, sea turtles, starfish, conch and hundreds of other aquatic creatures.

   For a more adventurous experience, dive one of the many shipwrecks that dot the coastline around Key West. Several wrecks are in shallow enough water to explore with just snorkeling gear. While those lying in greater depths will require scuba diving experience. Whatever you do while Key West sailing, we recommend ending the day at Mallory Square in downtown Key West for a cold drink and excellent dining.

Dry Tortugas Sailing Charters

   For some excellent mid-distance Key West sailing, head 70 miles west of key west (112 km west of key west) and you’ll reach a remarkable group of islands called the Dry Tortugas. Remote and isolated, the islands are almost entirely undeveloped by man and a haven for wildlife.

   Rising out of deep waters in the Gulf of Mexico, the Dry Tortugas are a migration waypoint and breeding ground for hundreds of thousands of birds. Birding enthusiasts will definitely want to bring binoculars for spotting sooty terns, masked booby, and the magnificent frigate bird, to name a few. And anglers will want to bring their rods and reels. The fish population here is also impressive, with over a dozen species to catch, including blackfin tuna, grouper, wahoo, mahi-mahi, and sailfish.

Key West Sailing Charter Variety

   Group charters are a great way to experience Key West sailing. Boat tours cater nearly any occasion, including wedding parties, holiday outings, corporate excursions, even themed events. Privately chartering a sailboat is easy.

   Just tell Key West Charter Boat the size of your party, amenities you’re looking for, the desired length of cruise and any special requests you may have. We’ll put you on the perfect boat for a family reunion sunset cruise or a seagoing party for 50.

   For a swashbuckling sailing adventure, commandeer your own pirate ship. Private charter the 1939 wooden schooner When and If.  The boat belonged to World War II general George S. Patton, so it’s no surprise she’s fast and powerful. Guests are encouraged to join the crew in hoisting sails and trimming them up. You can even take the helm if you like, feeling the same exhilaration as Patton did over 80 years ago.

The Safest Sailing In Key West

   As with anything on the water, safety comes first. Your sailing experience will determine what type and size boat you’re qualified to charter. Big catamarans and mono-hulls require extensive experience in similar type boats. With Key West Sailing there is no shortage in boat variety.

   When you arrive, expect to spend part of the first day going over the entire boat with a certified captain. All operating systems will be reviewed, including lines, setting and retrieving sails, winch and helm operation, navigation and communication equipment, and all safety procedures.

Bareboat Charters & Multiday Trips

   When Key West Sailing you will be asked to demonstrate your docking skills as well as any other handling maneuvers your charter company may require. Trips of a certain duration or distance will require you to file a sail plan and to notify your charter company with any changes to that plan while underway.

   Please allow time at the end of your charter for a complete walk around with captain or charter company member. In order to ensure a great Key West sailing experience, we only book with charter outfits that maintain their boats in constant shipshape condition.

As Remote As You Like

   Sailing the Keys is as close to nature as you can get, with the wind as your power source and aqua green water as far as the eye can see. Perhaps Ponce de Leon was right after all, only instead of a fountain, there was the sea and waves and beaches as white as the wings of a gull.

   Aboard a sailing vessel of any type or size, you feel young and adventurous, as if time is standing still, or maybe even going backwards. Is that really possible? If there’s any place on earth where it could be, it’s Key West.

   Learn more about sailing Key West and the Florida Keys by giving us a call or filling out a quote form.

The wind in our hair, the sound of the boat cutting through the water and a drink in our hand these are moments we won’t soon forget. Five stars.

Shelly Daniels

Key West Sailing

Book Key West Sailing Charters

   In 1513, Spanish explorer Ponce de Leon sailed the waters around Key West in search of the legendary Fountain of Youth. Nearly 500 years later, Key West sailing charters follow in his wake, offering the same promise of exploration and youthful rejuvenation.  And did we mention some pretty awesome sailing charters?

   Call Key West Charter Boat, fill out a quote form or book a public sail online.  Whichever you choose we’ll find the perfect vessel for you.

   Few experiences stir the soul as standing on the deck of a boat under sail. Whether you’re bareboating a catamaran with friends or throwing a big group party aboard the 105-foot schooner America 2.0, set sail on the tropical breezes of the Keys and you will be transported to a whole different state of mind.  Yes, sailing in The Florida Keys is truly amazing.

public trips

PRIVATE  trips

Fast Quote

Florida Keys Best Sailing

   Key West sailing is some of the best in the world because of where it is in the world: latitude 24° 33’18” N, longitude 81° 46’ 53” W, between the open Atlantic and the Gulf of Mexico. A private sailing charter from here can take you wherever the mood suits. A day sail to uninhabited islands, exploring shallow waters, sailing snorkeling the whole way through. Sound good?

   Choose a sailing excursion to the calmer turquoise waters of the north and you’re likely to get picture-perfect days of relaxed cruising. Just set the auto-pilot, settle back and relax. Head south—where the continental shelf falls off a cliff—and you’re in for some true bluewater sailing. Stiffening winds push you to the horizon as saltwater spray carries the intoxicating smell of freedom in the air.

Key West Sailing Knowledge

   When it comes to planning a sailing trip, there’s no substitute for local knowledge. And nobody knows more about sailing the Florida Keys than Key West Charter Boat. Whether you’re interested in custom sailing trips on a 50-foot luxury catamaran with your family for a week or overnight sailing for two on a 30-foot sloop, call us.

   If you’d like a quick price quote to sunset sail Key West for an evening with your office staff, fill out a quote form. We’ll arrange everything: boat, captain and crew, and the best Key West sailing charter prices.

   Key West Florida is a historic seaport with a variety of daysailers for hire, as well as the bigger Key West yacht rentals. Take a 25-footer out for a full day or half-day trip around the island. Sail past Southernmost Point and see the world-famous buoy marking the point furthest south in the continental United States.

Gallery

More Sailing Info...

Island Sailing Destinations

   Lets Circumnavigate Sunset Key, the island of the rich and famous. Who knows who you could spot sunbathing on their private beach? For a sailing adventure, you’ll long remember, cruise past Chica Boca Key, home to Naval Air Station Key West. With any luck, a squadron of navy fighter jets will take off right in front of you, heading to their carrier in the Atlantic.

   You always have the option of cruising around and dropping anchor whenever the mood suits. Sailing the Florida keys is a family-friendly activity with opportunities to kayak snorkel and explore just about anywhere. Dolphin watching is always a crowd-pleaser. Same for snorkeling North America’s only living coral reef. Designated a national marine sanctuary, the reef is teeming with colorful tropical fish, sea turtles, starfish, conch and hundreds of other aquatic creatures.

   For a more adventurous experience, dive one of the many shipwrecks that dot the coastline around Key West. Several wrecks are in shallow enough water to explore with just snorkeling gear. While those lying in greater depths will require scuba diving experience. Whatever you do while Key West sailing, we recommend ending the day at Mallory Square in downtown Key West for a cold drink and excellent dining.

Dry Tortugas Sailing Charters

   For some excellent mid-distance Key West sailing, head 70 miles west of key west (112 km west of key west) and you’ll reach a remarkable group of islands called the Dry Tortugas. Remote and isolated, the islands are almost entirely undeveloped by man and a haven for wildlife.

   Rising out of deep waters in the Gulf of Mexico, the Dry Tortugas are a migration waypoint and breeding ground for hundreds of thousands of birds. Birding enthusiasts will definitely want to bring binoculars for spotting sooty terns, masked booby, and the magnificent frigate bird, to name a few. And anglers will want to bring their rods and reels. The fish population here is also impressive, with over a dozen species to catch, including blackfin tuna, grouper, wahoo, mahi-mahi, and sailfish.

Key West Sailing Charter Variety

   Group charters are a great way to experience Key West sailing. Boat tours cater nearly any occasion, including wedding parties, holiday outings, corporate excursions, even themed events. Privately chartering a sailboat is easy.

   Just tell Key West Charter Boat the size of your party, amenities you’re looking for, the desired length of cruise and any special requests you may have. We’ll put you on the perfect boat for a family reunion sunset cruise or a seagoing party for 50.

   For a swashbuckling sailing adventure, commandeer your own pirate ship. Private charter the 1939 wooden schooner When and If.  The boat belonged to World War II general George S. Patton, so it’s no surprise she’s fast and powerful. Guests are encouraged to join the crew in hoisting sails and trimming them up. You can even take the helm if you like, feeling the same exhilaration as Patton did over 80 years ago.

The Safest Sailing In Key West

   As with anything on the water, safety comes first. Your sailing experience will determine what type and size boat you’re qualified to charter. Big catamarans and mono-hulls require extensive experience in similar type boats. With Key West Sailing there is no shortage in boat variety.

   When you arrive, expect to spend part of the first day going over the entire boat with a certified captain. All operating systems will be reviewed, including lines, setting and retrieving sails, winch and helm operation, navigation and communication equipment, and all safety procedures.

Bareboat Charters & Multiday Trips

   When Key West Sailing you will be asked to demonstrate your docking skills as well as any other handling maneuvers your charter company may require. Trips of a certain duration or distance will require you to file a sail plan and to notify your charter company with any changes to that plan while underway.

   Please allow time at the end of your charter for a complete walk around with captain or charter company member. In order to ensure a great Key West sailing experience, we only book with charter outfits that maintain their boats in constant shipshape condition.

As Remote As You Like

   Sailing the Keys is as close to nature as you can get, with the wind as your power source and aqua green water as far as the eye can see. Perhaps Ponce de Leon was right after all, only instead of a fountain, there was the sea and waves and beaches as white as the wings of a gull.

   Aboard a sailing vessel of any type or size, you feel young and adventurous, as if time is standing still, or maybe even going backwards. Is that really possible? If there’s any place on earth where it could be, it’s Key West.

   Learn more about sailing Key West and the Florida Keys by giving us a call or filling out a quote form.

The wind in our hair, the sound of the boat cutting through the water and a drink in our hand these are moments we won’t soon forget. Five stars.

Shelly Daniels

Key West Sailing

Book Key West Sailing Charters

   In 1513, Spanish explorer Ponce de Leon sailed the waters around Key West in search of the legendary Fountain of Youth. Nearly 500 years later, Key West sailing charters follow in his wake, offering the same promise of exploration and youthful rejuvenation.  And did we mention some pretty awesome sailing charters?

   Call Key West Charter Boat, fill out a quote form or book a public sail online.  Whichever you choose we’ll find the perfect vessel for you.

   Few experiences stir the soul as standing on the deck of a boat under sail. Whether you’re bareboating a catamaran with friends or throwing a big group party aboard the 105-foot schooner America 2.0, set sail on the tropical breezes of the Keys and you will be transported to a whole different state of mind.  Yes, sailing in The Florida Keys is truly amazing.

 

Public trips

Private trips

call us

(305) 767-3672

 

Have questions?  Want immediate answers?  Our expert staff is standing by 24hrs a day 7 days a week to answer all your Key West charter questions.  Call now!

The Florida Keys Best Sailing

   Key West sailing is some of the best in the world because of where it is in the world: latitude 24° 33’18” N, longitude 81° 46’ 53” W, between the open Atlantic and the Gulf of Mexico. A private sailing charter from here can take you wherever the mood suits. A day sail to uninhabited islands, exploring shallow waters, sailing snorkeling the whole way through. Sound good?

   Choose a sailing excursion to the calmer turquoise waters of the north and you’re likely to get picture-perfect days of relaxed cruising. Just set the auto-pilot, settle back and relax. Head south—where the continental shelf falls off a cliff—and you’re in for some true bluewater sailing. Stiffening winds push you to the horizon as saltwater spray carries the intoxicating smell of freedom in the air.

Key West Sailing Knowledge

   When it comes to planning a sailing trip, there’s no substitute for local knowledge. And nobody knows more about sailing the Florida Keys than Key West Charter Boat. Whether you’re interested in custom sailing trips on a 50-foot luxury catamaran with your family for a week or overnight sailing for two on a 30-foot sloop, call us.

   If you’d like a quick price quote to sunset sail Key West for an evening with your office staff, fill out a quote form. We’ll arrange everything: boat, captain and crew, and the best Key West sailing charter prices.

   Key West Florida is a historic seaport with a variety of daysailers for hire, as well as the bigger Key West yacht rentals. Take a 25-footer out for a full day or half-day trip around the island. Sail past Southernmost Point and see the world-famous buoy marking the point furthest south in the continental United States.

The wind in our hair, the sound of the boat cutting through the water and a drink in our hand these are moments we won’t soon forget. Five stars.

Shelly Daniels

Island Sailing Destinations

   Lets Circumnavigate Sunset Key, the island of the rich and famous. Who knows who you could spot sunbathing on their private beach? For a sailing adventure, you’ll long remember, cruise past Chica Boca Key, home to Naval Air Station Key West. With any luck, a squadron of navy fighter jets will take off right in front of you, heading to their carrier in the Atlantic.

   You always have the option of cruising around and dropping anchor whenever the mood suits. Sailing the Florida keys is a family-friendly activity with opportunities to kayak snorkel and explore just about anywhere. Dolphin watching is always a crowd-pleaser. Same for snorkeling North America’s only living coral reef. Designated a national marine sanctuary, the reef is teeming with colorful tropical fish, sea turtles, starfish, conch and hundreds of other aquatic creatures.

   For a more adventurous experience, dive one of the many shipwrecks that dot the coastline around Key West. Several wrecks are in shallow enough water to explore with just snorkeling gear. While those lying in greater depths will require scuba diving experience. Whatever you do while Key West sailing, we recommend ending the day at Mallory Square in downtown Key West for a cold drink and excellent dining.

Dry Tortugas Sailing Charters

   For some excellent mid-distance Key West sailing, head 70 miles west of key west (112 km west of key west) and you’ll reach a remarkable group of islands called the Dry Tortugas. Remote and isolated, the islands are almost entirely undeveloped by man and a haven for wildlife.

   Rising out of deep waters in the Gulf of Mexico, the Dry Tortugas are a migration waypoint and breeding ground for hundreds of thousands of birds. Birding enthusiasts will definitely want to bring binoculars for spotting sooty terns, masked booby, and the magnificent frigate bird, to name a few. And anglers will want to bring their rods and reels. The fish population here is also impressive, with over a dozen species to catch, including blackfin tuna, grouper, wahoo, mahi-mahi, and sailfish.

We booked a private sailing charter down to the Dry Tortugas.  The experience was nothing short of amazing.

Taylor Foley

Key West Sailing Charter Variety 

   Group charters are a great way to experience Key West sailing. Boat tours cater nearly any occasion, including wedding parties, holiday outings, corporate excursions, even themed events. Privately chartering a sailboat is easy.

   Just tell Key West Charter Boat the size of your party, amenities you’re looking for, the desired length of cruise and any special requests you may have. We’ll put you on the perfect boat for a family reunion sunset cruise or a seagoing party for 50.

   For a swashbuckling sailing adventure, commandeer your own pirate ship. Private charter the 1939 wooden schooner When and If.  The boat belonged to World War II general George S. Patton, so it’s no surprise she’s fast and powerful. Guests are encouraged to join the crew in hoisting sails and trimming them up. You can even take the helm if you like, feeling the same exhilaration as Patton did over 80 years ago.

The Safest Sailing In Key West

   As with anything on the water, safety comes first. Your sailing experience will determine what type and size boat you’re qualified to charter. Big catamarans and mono-hulls require extensive experience in similar type boats. With Key West Sailing there is no shortage in boat variety.

   When you arrive, expect to spend part of the first day going over the entire boat with a certified captain. All operating systems will be reviewed, including lines, setting and retrieving sails, winch and helm operation, navigation and communication equipment, and all safety procedures.

Bareboat Charters & Multiday Trips

   When Key West Sailing you will be asked to demonstrate your docking skills as well as any other handling maneuvers your charter company may require. Trips of a certain duration or distance will require you to file a sail plan and to notify your charter company with any changes to that plan while underway.

   Please allow time at the end of your charter for a complete walk around with captain or charter company member. In order to ensure a great Key West sailing experience, we only book with charter outfits that maintain their boats in constant shipshape condition.

As Remote As You Like

   Sailing the Keys is as close to nature as you can get, with the wind as your power source and aqua green water as far as the eye can see. Perhaps Ponce de Leon was right after all, only instead of a fountain, there was the sea and waves and beaches as white as the wings of a gull.

   Aboard a sailing vessel of any type or size, you feel young and adventurous, as if time is standing still, or maybe even going backwards. Is that really possible? If there’s any place on earth where it could be, it’s Key West.

   Learn more about sailing Key West and the Florida Keys by giving us a call or filling out a quote form.

Private trips

Gallery

Book Now

&

$ave 

Best Charters Best Prices

Deep Sea Fishing
Let The Battle Begin…
Inshore Fishing
The Game Is Stealth…

Custom Fishing

Custom Fishing Trips…

Overnight Trips
How Long Will You Stay?
Large Charters
Big Group? No problem…
Sailing Charters
Ride The Wind…
Snorkeling
Explore Our Tropical Beauty…
Scuba
An Underwater Discovery…
Boat Rentals
Be Your Own Captain…
Cuba Charters
The Forbidden Fruit…
Dry Tortugas
A National Treasure…
Sunset Cruises
Liquid Beauty…
Jet Ski Rental
High Speed Entertainment…
Spearfishing
Hand To Tail Combat…
Glass Bottom Boat
Under The Sea And Still Dry…
Custom Charters
Built Just For You…

Lobstering

A Deliciously Fun Time…

Luxury Yachts

The Best Or Nothing…

Book Now

&

$ave 

Best Charters Best Prices

Deep Sea Fishing
Let The Battle Begin…
Inshore Fishing
The Game Is Stealth…

Custom Fishing

Custom Fishing Trips…

Custom Charters
Built Just For You…
Overnight Trips
How Long Will You Stay?
Large Charters
Big Group? No problem…
Sailing Charters
Ride The Wind…

Luxury Yachts

The Best Or Nothing…

Lobstering

A Deliciously Fun Time…

Snorkeling
Explore Our Tropical Beauty…
Scuba
An Underwater Discovery…
Boat Rentals
Be Your Own Captain…
Cuba Charters
The Forbidden Fruit…
Dry Tortugas
A National Treasure…
Sunset Cruises
Liquid Beauty…
Jet Ski Rental
High Speed Entertainment…
Spearfishing
Hand To Tail Combat…
Glass Bottom Boat
Under The Sea And Still Dry…

Book Now

&

$ave 

Best Charters Best Prices

Deep Sea Fishing
Let The Battle Begin…
Inshore Fishing
The Game Is Stealth…

Custom Fishing

Custom Fishing Trips…

Custom Charters
Built Just For You…
Overnight Trips
How Long Will You Stay?
Large Charters
Big Group? No problem…
Sailing Charters
Ride The Wind…

Luxury Yachts

The Best Or Nothing…

Snorkeling
Explore Our Tropical Beauty…
Scuba
An Underwater Discovery…
Boat Rentals
Be Your Own Captain…
Cuba Charters
The Forbidden Fruit…
Dry Tortugas
A National Treasure…
Sunset Cruises
Liquid Beauty…
Jet Ski Rental
High Speed Entertainment…
Spearfishing
Hand To Tail Combat…
Glass Bottom Boat
Under The Sea And Still Dry…

NAVIGATOR

Home » Key West Sailing

Call Us

(305) 767-3672

GEO

Key West Charter Boat,

3200 Harriet Ave,

Key West, FL 33040

United States Of America

U

OBSERVE

NAVIGATOR

GEO

Key West Charter Boat,

3200 Harriet Ave,

Key West, FL 33040

United States Of America

U

OBSERVE