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Sail the Florida Keys

• Location Guide

Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

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• Matching any competitive offer
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• Advising without bias based on 25+ years of experience
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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

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Legal & safety.

Key West Sailboat Charter Aboard the Tamboo

Our Fleet: the Tamboo

Bareboat or captained charter ~ asa sailing courses*, ocean's edge marina key west, florida 2023 bali 4.2 sailing catamaran 4 cabins - 4 toilets w/sinks - 2 showers 8 passengers max. or 6 passengers maximum if charterer selects and pays for a captain., *charterer selects and pays for an asa qualified captain for asa training..

Specifications

Cabins/berths Toilet w/sink Shower stalls

Beam Draft Water Capacity Fuel Capacity Engine

4 - (8 occupants max.)

23'6"

5' 227 US Gal 169 US Gal

2 x 45HP Yanmar

Interior Features

Air Conditioning

Interior Fans

Generator power

Solar power

Fridge/Freezer

Freshwater Filter

3 burner cooktop

Freshwater electric toilets

Exterior Features

Cockpit Cushions

Bimini Over Helm

Dinghy on Boat Lift

Forward Lounge

Swim ladder

Helm Lounge

Built in BBQ Grill

Fully Equipped Galley

Dishware, Silverware, Cutlery, Cooking Utensils

Serving bowls, platters, pitcher, cookware

Cutting Boards (*please provide your own cutting board, filet knife & cooler for fish*)

Small Appliances such as Coffee Maker,

Blender, Toaster, Microwave

Starter supply of paper towels, dish soap, fresh sponge

Linens & Things ​

Bed Sheets & Blankets (beds will be fully dressed upon arrival)

2 Bath, Wash & Hand Towels per guest

Starter supply of marine grade toilet paper

Navigation Equipment

Apparent wind indicator

Depth sounder

RAYMARINE AXIOM+ GPS/chart plotter

Hand Bearing Compass

Parallel rulers

Stereo/cockpit speakers

VHF mic at helm

Local charts

Cruising Guide to Florida Keys

Bareboat Charters

Bareboat charters. your sailboat. your experience.

Sail Away to Tropical Paradise: Explore the Florida Keys on a Well-Equipped Sailing Vacation

Picture this: a gentle breeze brushes against your face as you navigate the calm, turquoise waters of the Florida Keys. You’re at the helm of a beautiful sailing vessel, equipped with all the amenities you need to make your sailing vacation unforgettable. Whether you choose the Catalina 22′ for a day sail or the Morgan 33′ Out Island for an overnight trip, you can rest assured that your boat is well-equipped for your chosen adventure.

As you board your boat, you feel a sense of excitement and freedom wash over you. You’re in charge of your vacation – you get to plot your course and sail into tropical paradise at your own pace. The warm sun beats down on you, and you can’t help but feel grateful for this opportunity to escape the stresses of everyday life.

If you’re planning a multiple night charter, you can provision at one of the local chain supermarkets and enjoy your fully-equipped galley at your leisure. Or, if you’re just renting for the day, you can grab a packed lunch and set off on your adventure.

The Florida Keys offer a plethora of activities for sailors of all levels. From visiting underwater or land-based state and national parks to local beach bars and restaurants, there’s something for everyone. Take a dip in the crystal-clear waters, explore the mangrove islands, or relax on a secluded beach – the choice is yours.

Whether you choose the Catalina 22′, the Morgan 33′ Out Island, or one of our catamarans, you can rest assured that your boat is well-equipped for your chosen adventure. So go ahead, captain your sailing vacation in the Florida Keys and create memories that will last a lifetime.

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

“Morning Star Charters.”

Let the day Start and stop when and where you desire.

“The Perfect Getaway”

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

Sailing at it’s best

“Morning Star Sailing Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

Enjoy self-prepared meals from your well equipped galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

Bareboat Charter

A bareboat charter means the charterer, as Captain, is solely responsible for the safe operation of the vessel, including all aspects of navigation, anchoring, docking, and controlling the vessel under sail or power. Key West is considered an advanced sailing destination and for the safety of other passengers and the vessel, it is vital the charterer have sufficient experience aboard vessels of a similar size & type as what you are seeking to hire. We also require there be one other person aboard to act as first mate, with enough boating experience to handle the vessel in the event the Captain is injured or goes overboard.

All of our bareboat charters have a 4 day/3 night minimum which is the ideal amount of time to experience one of our Florida Keys sailing itineraries .

Am I qualified?

Sail with confidence, am i qualified for bareboat charter.

The Florida Keys is considered an advanced sailing destination, offering great natural beauty in sometimes rare peaceful isolation. There are almost exclusively anchorages in our cruising grounds subject to tidal changes and currents, including open anchorages in the Westerly Island groups.

Our bareboat charter application will help us evaluate your sailing experience to establish your skill level, and that of your first mate, as suitable to these conditions. This application should be filled out in full, providing as much information as possible to validate your skills and experience. Please submit the requested documents together in order to complete the application process. No booking should be considered confirmed until this application has been approved by the reviewing Charter Base Manager. You may be contacted directly to answer any questions they may have.

Bareboat Charter General Qualifications & Requirements

•30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht(s).

•ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran.

•Physically capable of handling the vessel in all situations & conditions (i.e. Managing sails, lines & anchor).

•Must have a qualified First Mate who completes a Crew Resume for approval.

•Must present a valid US driver’s license, or International Passport to verify identity and DOB.

•We reserve the right to approve your application on the condition of having a Check-Out Captain aboard for the first day (or more) at your expense, which would be agreed to in advance as a condition of approval.

•For applicants under the age of 30 or over 74 additional crew requirements may apply.

Don’t be discouraged if your experience isn’t quite strong enough yet. We offer several ways to assist charterers to meet the requirements. As well as being able to offer an ASA instructor accompany you on your bareboat charter so you can achieve your ASA Sailing Certifications , we can also arrange a one or two day refresher for an experienced mariner that might need to get familiar with some of the more advanced systems on newer boats, or just brush up on skills if it’s been awhile. These programs are very flexible and can be personalized to each charter guest.

Download our Captains Application: Captains Application for Sailing Vessels

First Mate’s Application for Sailing Vessels

For Power Vessels

During the charter check-in process, which takes approximately 2½ hours, you will receive a very comprehensive yacht systems orientation, inventory review, safety briefing, and a chart briefing of the cruising area to ensure you are comfortable with your float plan and the vessel. It is required that the Captain & First Mate arrive at the same time and attend the vessel check -in.

Optional Orientation cruise If you are chartering a manufacturer of boat for the first time and would like to do a short orientation sail to familiarize yourself with all the systems and equipment while under way, we highly recommend an orientation sail with a Captain familiar with your sailing vessel. It takes about an hour and they charge $150.00. This is an excellent way to do a shake down sail to make sure you can enjoy your vessel with confidence. This must be booked in advance to ensure there is a Captain available. This is not intended to teach boat handling skills.

[email protected] 305-934-5295

KEEP IN TOUCH

Destination and charter fleet updates, special offers, and more

Bridging the space between reality & paradise.

A luxury sailing catamaran charter with an emphasis on fun and adventure.

Sailing from Ft. Lauderdale, The Keys & The Bahamas.

Come sail with us!

Meet The Crew

Captain -  Scott Clark

He is most at home when on the water.  He enjoys tinkering with everything, but has a flair for all things electrical. He loves sharing stories, creating videos and spending time with his wife and 2 sons.

First Mate - Holly Clark

She is most at home when she is spending time with friends and family. She enjoys cooking, meeting new people, yoga and snuggling with her granddog, Pugsly.

Check Out Our Latest Video!

The Ultimate Guide to an Unforgettable Key West Sailing Vacation

Fort Lauderdale Boat Charter Tours Made Easy, Fun & Affordable

Family Vacations are Incomplete without a Catamaran in the Bahamas

Boat Charter Rules That You Must Be Aware of!

A Day in the Life of a Charter Cat Owner

Mission Accomplished!

Our Mission

Tel. SAIL-TSB-DMB

(724) 587-2362, p.o. box 7696, sebring, fl 33872, ​ [email protected].

Thanks for submitting!

• 305-619-0140

BAREBOAT Charters

Come enjoy our islands in paradise, 3 day / 2 night packages.

Sailing Vacations are so easy with us in the Florida Keys!  The best destinations are in our backyard. 

You can sail, snorkel & explore. Dine aboard under the stars…or ashore at our island’s favorite Tiki Huts.

Sailing in the Florida Keys has never been so easy and affordable.

* Includes FREE Dockage with COOL A/C* * Fuels not Included * *Daily Snorkel Gear Rentals * * Longer stays are available at the same rates per each additional day*

JADE PACKAGE

Catalina 27' - "jade".

She is great weekend/day charter boat.  She includes a n ice-box; Roller furler; Bimini; Sleeping for 4; Swim platform; Lazy jacks; PFDs.

SALINA PACKAGE

Catalina 30' - "Salina"

Main & Roller Furled Jib; Tiller, Inboard Diesel; Galley w / Ice Box;  Head ; VHF; GPS; PFD’s; Compass; Bimini; Swim Ladder; USCG Equipment; Chart & Anchor – 4′ 6″ Fixed Keel.

Limit 4 aboard

SERENDIPITY PACKAGE

Irwin 34 - "serendipity".

Main & Roller; Furled Jib; Air Conditioning; Wheel Steering; Inboard Diesel; Water; Galley w / Ice Box;Head; VHF; GPS; Swim Ladder; Compass; Bimini; USCG Equipment; Chart & Anchor – 4′; Fixed Keel

SAYONARA PACKAGE

Beneteau 51 Oceanis - "Sayonara"

This vessel spares little when it comes to accommodations: 4 stateroom cabins with separate head/showers. She boasts 2 onboard A/C units; generator, ice maker, entertainment center, hot/cold water, wine cooler, swim platform, full galley, etc. 

Call for Pricing

Information.

• In the event of any weather cancellation determined by the customer or Florida Keys Sailing a “rain check” may be given. Sorry No Refunds.
• No SCUBA tanks.
• No smoking or vaping while on board.
• Bareboat Charters begin 9AM on Day 1 and end 5PM on Day 3. 3 Days and 2 Nights w / dockage at Keys Fishery & Marina is included.
• If staying aboard the night before. Check in time is:  4PM to 5PM. Sorry… no later arrivals.
• We require Tow Boat US Insurance or Seatow insurance memberships. No charter may begin prior to having that membership ID. 
• Navigation Limits are 50 NM from our sailing location. This includes sailing to Key West, FL.
• All boats need to be taken from and returned to: Keys Fishery & Marina 35th St. Gulfside Marathon, FL.
• Federal and State Laws require a proper checkout of all vessels, including the completion of Bareboat Agreement.

• SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
• By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
• By E-Mail: [email protected]
• By Telephone: 305-619-0140
• Marathon Chamber of Commerce
• Get Knotted - Animated Knots
• Sombrero Lighthouse Data and Marine Forecast

Copyright© 2020 Florida Keys Sailing™, LLC

305-393-1394

[email protected]

Welcome to KeyZ Charters

Unique florida keys boat charters & boat tours.

KeyZ Charters in Islamorada is the perfect family adventure for exploring the Florida Keys , Everglades National Park , and South Florida. From Islamorada snorkeling and sunset cruises to bird-watching charters, eco-tours, and Florida Keys boat tours, our charters are exhilarating.

Based in South Florida, our boat charters and private boat tours can take you up close to popular Florida landmarks such as Indian Key, Lignumvitae Key , Alligator Reef lighthouse, and Everglades National Park. Whether you like snorkeling, watching the sunset on a boat, bird watching, or relaxing on a sandbar, KeyZ Charters offers private boat tours and private charters that can be customized for any type of adventure.

Florida Keys Sightseeing Charters

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From The Mainland to the Mangroves Catalog Story

Our services, private boat tours & charters in islamorada & florida keys.

Discover the natural wonders of the Florida Keys with KeyZ Charters' unforgettable eco-tours in Islamorada . Our knowledgeable guides will take you on an adventure through the crystal-clear waters, lush mangroves, and diverse wildlife habitats. Whether you're interested in birdwatching , spotting dolphins, or simply immersing yourself in the beauty of the Florida Keys, our eco-tours offer a unique and relaxing way to explore this stunning area. 

KeyZ Charters snorkeling tours in Islamorada take you to some of the best snorkeling locations in the Florida Keys . Our tours are designed for all ages, and our professionally trained guides will give you access to the best sites in the area, including coral reefs and diverse marine life. You may even have the chance to spot manatees or dolphins during your Islamorada snorkeling tour . 

• Sunset Cruises

A KeyZ Charters sunset cruise is the perfect way to unwind and take in the breathtaking beauty of the Florida Keys . As you sail along the calm waters, you'll enjoy the soothing sound of waves lapping against the boat and the refreshing ocean breeze. Our Islamorada sunset cruises showcase the stunning colors of the sky as the sun dips below the horizon, creating an unforgettable and romantic experience. 

• Historic Island Tours

KeyZ Charters' historic island tours of Indian Key and Lignumvitae Key , offer a unique way to experience the rich history and natural beauty of Islamorada & the Florida Keys. Explore Indian Key, the first county seat of Monroe County, and discover the fascinating past of this once-thriving community. Your tour also includes a visit to Lignumvitae Key, home to Florida's oldest botanical gardens, showcasing a diverse array of native plants & wildlife. 

• Custom Combination Tours

Create your perfect Florida Keys adventure with KeyZ Charters' custom combination boat tours . Our flexible options allow you to mix and match activities to suit your interests and preferences. Combine Islamorada sightseeing, snorkeling , visits to historic islands , and even catching a stunning sunset on a private boat charter . Our experienced team will work with you to create an unforgettable, tailored experience in the beautiful Florida Keys. 

Islamorada Half Day Excursions

Make the most of your time in the Florida Keys with KeyZ Charters' 4-hour half-day excursions . Our customizable tours allow you to experience the best of Islamorada by combining activities like snorkeling , eco-touring , and relaxing at a sandbar . Whether you're looking for adventure or relaxation, our half-day excursions offer the perfect blend of activities to suit your preferences. 

Islamorada Sandbar Tours

Unwind and enjoy the beauty of the Florida Keys with KeyZ Charters' Islamorada sandbar tours . Our unique experiences take you to pristine sandbars just off the coast of Islamorada, Key Largo, Marathon, and throughout the Florida Keys. Swim in the crystal-clear waters, snorkel among the vibrant marine life, or simply relax and soak up the sun on these stunning sandy oases. Our sandbar tours provide the perfect escape during your Florida Keys vacation. 

Photos from our Florida Keys Boat Tours

Quick Links

• Ecotour Report
• Accessibility Statement
• Cookie Policy
• Islamorada Eco-Tours
• Islamorada Snorkeling

Get in Touch

KeyZ Charters 77522 Overseas Highway Islamorada, FL 33036

Stay Connected

Discover the beauty of the Florida Keys with KeyZ Charters, offering unique boat tours and private charters in Islamorada . Our experienced captains provide unforgettable adventures, from eco-tours and snorkeling to historic island visits and stunning sunset cruises . Explore popular landmarks like Indian Key , Alligator Lighthouse and more aboard our comfortable deck boats. Whether you're interested in Islamorada eco-tours , snorkeling excursions , historic island tours , or Everglades adventures , KeyZ Charters has the perfect trip for you. KeyZ Charters is your gateway to exploring the natural wonders of South Florida. Perfect for families and groups seeking a personalized Florida Keys experience . 

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• Florida Keys
• Inspiration

Florida Keys has 8 Photos

Related Locations

• Florida Yacht Charter

Featured Yachts in Florida Keys

AQUASITION | From US$ 150,000/wk

Latest florida keys yachting news.

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

• Florida Keys Charter Itinerary
• Browse Florida Keys Charter Yachts
• Luxury Motor Yachts for Charter in Florida Keys
• Luxury Sailing Yachts for Charter in Florida Keys
• Luxury Catamarans for Charter in Florida Keys
• Florida Keys Yacht News

Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

New England

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

KENSHO | From EUR€ 850,000/wk

WAYFINDER | From EUR€ 375,000/wk

STARSHIP 185' | From US$ 275,000/wk

MARIA | From US$ 230,000/wk

LADY ELAINE | From US$ 225,000/wk

GIGI | From US$ 225,000/wk

TCB | From US$ 215,000/wk

MYSORAH | From US$ 200,000/wk

ASPEN ALTERNATIVE | From US$ 199,000/wk

FAM | From US$ 195,000/wk

GLORY | From US$ 179,000/wk

ZOOM ZOOM ZOOM | From US$ 175,000/wk

AVALON | From US$ 155,000/wk

FOCUS | From US$ 150,000/wk

RELENTLESS | From US$ 150,000/wk

PERSISTENCE | From US$ 140,000/wk

ANTELOPE IV | From US$ 140,000/wk

CLAIRE | From US$ 139,500/wk

Florida Yacht News

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Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Bloody Pirate

• Information

The Bloody Pirate is a beautiful schooner sailboat in the luxurious Florida Keys. She is named after the famous Code Rum cocktail drink. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight. With her classic lines and open interior you'll feel right at home. Her professional crew will enable you enjoy a relaxing cruise or you may try a real hands-on sailing experience. She is the perfect vessel to take you to the abundance of tropical reefs in the Florida Keys to snorkel and explore. She is particularly suited to large group charters.

PROVISIONING SERVICE

Calypso sailing offers a provisioning service to help get your charter off to a great start. With a little prior organization you can arrive to a vessel that is fully provisioned to your own tastes. We can provide food shopping lists, food and cocktail menus to  ensure that all your necessary and favorite items are all onboard and ready for your charter. We are happy to arrange any of your vacation essentials for you so you don't have to waste valuable vacation time shopping. 

Feel free to contact us about shipping some items to us ahead of time also we will make sure they are waiting onboard for you.

Please call for all departure times or for further information.

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• ORC Member Packages
• Charter Packages
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• Cancellation Policy

Private Yacht Charter – Dinner Cruises to Multi-Day Boat Trips

The Motor Yacht Somerset is a fully restored 58′ 1971 Trumpy Cruiser, available now for your next yacht charter. Somerset was restored to concours level in 2013, and is ready to charter in Florida, The Florida keys, and the Bahamas, as well as for member use at the Ocean Reef Club. Ideal for sunset cocktail cruises, dinner parties, and island-hopping vacations, Somerset is the perfect vessel to host your family and friends in classic style and comfort.

The Motor Yacht Somerset

The Motor Yacht Somerset has been completely rebuilt from the ground up. The refit has included a new bottom, keel frames and floors, rebuilt engines, new generators and systems, an entirely new interior and new paint. Somerset is basically a brand new Trumpy Yacht after this restoration. The interior pays homage to the quality and style synonymous with the Trumpy Name.

• Accommodation
• Description
• Specifications

The aft master cabin features a queen size center-line berth, the guest stateroom offers a full queen and the forward crew quarters sleep two additional in over-under bunks. Two spacious, tiled aft heads (the master cabin head is ensuite), both with separate stall showers. Forward of the master and guest cabins is the completely new galley.

The galley is equipped with a stainless sink, Miele 4-burner cooktop/oven and Vitrofrigo refrigeration system with Isotherm freezer. Built-in washer/dryer. New furnishings have been custom designed and made for the boat. The vessel is heated with a reverse cycle heating system and is air conditioned. Somerset’s interior is finished with the original butternut paneling in the main salon as well as teak in the wheelhouse, aft deck and galley. Her sole is cork.

Private Boat Trip on Somerset

From day trips, half-day trips, and sunset cruises, to overnight trips through the Bahamas or along the Florida Keys, you can book a private yacht charter with our captain and chef and receive everything you need for a relaxing and luxurious time on the water. Browse our yacht charter packages and book today, or contact us for custom charter options.

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View packages/sample itineraries.

• Our Charters

Welcome to Tropical Charters Florida Keys

Welcome aboard Tropical Charters! Choose your own adventure with us exploring the Lower Florida Keys. Our vision is to create amazing voyages and long-lasting memories for you and your crew. With so many affordable options and float plans to choose from with us, your day aboard with us is sure to be second to none, and perfectly Tropical! Know what you want to do and where you want to go? Let us know! Not sure? Let us consult with you for your perfect day. Contact us with any questions!

HALF DAY CHARTERS

Full day charters, sunset charters.

MULTI DAY CHARTERS

Testimonials.

Five stars doesn’t seem enough. I have booked twice and each time I had a perfect experience. Austin pays attention to every detail and goes out his way to ensure you will have not only a great time but a memorable time. Book with Tropical Charters you will not be disappointed.

This was our first time in the Florida keys and we had limited time there so we wanted to make the most of it. This was, by far, our favorite experience while there. So much that we booked him twice. He took us fishing and to a beautiful white sand beach key. Tropical Charters proved to be knowledgeable and professional while still providing a super laid back vibe. We know where we’re booking next time we’re in the Keys. Thanks, Austin, for showing us newbies a piece of paradise.

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Bareboat Charter Florida

• Fishing Charters Florida

Pleasure Charters Florida

boat rental florida keys

Pristine boating experience.

Unwind in the sea and set yourself free

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About Rental Boat

Seafaring paradise boat rentals in florida keys.

Explore the best boat rental experiences in the Florida Keys! With our diverse fleet, including bareboat charters Florida, pleasure charter, and fishing charters, discover the ultimate adventure on Florida's stunning waters. Whether you seek the freedom of a bareboat charter Florida to explore at your own pace, the luxurious indulgence of a private pleasure charter Florida, or an exciting fishing expedition, we've got you covered. Our Florida Keys boat rentals promise unforgettable journeys amidst captivating landscapes and vibrant marine life. Cruise through azure waters, visit iconic destinations like Key West, and create lasting memories with family and friends. Choose your ideal vessel and set sail for an unparalleled maritime experience in this tropical paradise. Book your Boat rental near in Florida Keys today and immerse yourself in the beauty and excitement of these breathtaking islands. Unlock adventure and relaxation on the waterways while making unforgettable memories.

Our Services

Browse our extensive selection of boat rental florida keys.

Take a bareboat charter in the beautiful Florida Keys boat rentals and set out on an incredible sea adventure where the wide open waters serve as your playground. You will have an unparalleled sense of freedom with this exclusive bareboat charter in Florida experience, as you will have complete control over how you want to navigate the stunning waters. Savor the pristine splendor of the Keys while exploring at your own speed and taking in the breathtaking scenery that appears around every corner. Among the stunning scenery of Florida's well-known islands, a smooth and customized travel experience is guaranteed by our Boat Rentals Florida Keys services. Take in the excitement of discovery and make lifelong memories against the backdrop of these breathtaking waters. Plan your vacation with ends our Bareboat Charter in Florida .

Fishing Charter Florida

Searching for a fishing trip in Florida that will never be forgotten? Find excellent charters for fishing boats for rent! Florida provides a variety of possibilities, whether you're looking to hire a fishing boat locally or are organizing a thrilling deep-sea fishing excursion. Discover immaculate waters and effortlessly bring in your daily haul. Alternatively, you can rent fishing boats and enjoy the independence of exploring the stunning coastline at your own speed. Deep-sea fishing charters in Florida offer top-notch equipment and knowledgeable captains for an unparalleled fishing experience for individuals seeking a guided fishing adventure. Don't pass up the opportunity to throw a line into Florida's pristine seas and make lifelong memories while traveling on one of these amazing fishing charters. Find Fishing Charter in Florida at budget-friendly rates.

Pleasure Charters provides pleasure boat rentals in the Florida! You may begin your exploration of the breathtaking Florida Keys with the ultimate maritime experience offered by our pleasure boat rentals keys. Nothing compares to the elegance and exclusivity of pleasure charters, whether you're holding a birthday party, arranging a business function, or organizing a weekend retreat with friends and family on the serene waters of Florida Key. Discover the allure of Pleasure Island Charters, where grandeur and the wide sea meet. Choose us for top-notch pleasure boat rentals, and create memories that will last a lifetime in Florida's paradise basking in the sun. Now, embark on a thrilling and leisurely excursion with Pleasure Charters! Discover subtropical paradise and unparalleled serenity with our top-notch Pleasure charters in Florida .

01 Bareboating Charters

02 fishing charters, 03 pleasure charters.

Explore Paradise with Florida Keys Boat Rentals

With our first-rate boat rentals, experience the Florida Keys' breathtaking splendor like never before. Take in the azure seas of the Atlantic Ocean and the Gulf of Mexico while exploring these tropical islets at your own speed. All tastes are catered to by our fleet, which includes Blue Skies Charter and a range of bareboat charter choices in Florida. We provide the greatest boat rental experience in the Florida Keys.

Discover well-known locations like as Islamorada, Marathon, and Key West by using our bareboat charter, fishing charter and pleasure charter Florida keys services. Every destination offers a distinctive fusion of breathtaking scenery and lively local culture, guaranteeing an enjoyable and unforgettable vacation. Our top emphasis is safety, and we provide comprehensive instructions on local laws, meteorological patterns, and fundamental boating safety precautions.

Take a boat ride that is sustainable and learn about the influence that boating has on the environment. Our boat rentals provide a memorable time in the Florida Keys, whether your preference is for romantic sunset cruises, fishing charters, or private pleasure tours.

Our Expertise

Embark on an unforgettable voyage with our luxury boat charters.

At Blue Skies Charters, we have a passion for the open sea, redefining sailing experiences and offering first-rate, unparalleled services to our customers. Our fleet of luxurious high-performance vessels sets us apart from other run-of-the-mill boat charter companies, ensuring that each voyage lets you discover the beauty of pristine waters, idyllic coves, and beaches and experience the ultimate sailing thrill. From sunset cruises to private island vacations, we enable you to navigate your nautical dreams and transform them into realities.--> Florida Keys with Blue Skies Charters.-->