sailboat charter naples florida

Sailboats Unlimited

Bareboat and Crewed Sailing Charters

Bareboat and Crewed Sailing Charters in Naples, Florida since 1985!

Crewed Sailing Charters

Choose from a 2 hour “taste of sailing”, a half-day “jaunt along the beach” sailing the wind, a full day “adventure to Marco Island” sightseeing or romantic sunset or moonlight cruise.

Bareboat Charters

Let us help you plan a complete Florida sailing vacation from a simple overnight to a couple of weeks

Types of Charters

Choose your desired charter.

When choosing a sailing charter, you want to choose with confidence. Established in Naples in 1985, providing romantic getaways, sunset/sunrise trips, once in a lifetime sailing experiences for families on vacation, and corporate team building adventures.

About sailboats unlimited, naples most trusted sailboat chartering company since 1985.

The best experience you will have while visiting beautiful Naples, Florida

Located in sunny Naples, Fl, we have specialized in crewed sailing charters, bareboat sailing charters, yacht deliveries, and yacht maintenance since 1985.

When visiting Naples, FL or any of the surrounding areas, you have the opportunity to take our sailboats out onto the beautiful gulf. Let us charter you and your guest, or reserve the entire yacht for your guest. Sunset and moonlight cruises, half day and full day cruises. We have something for every scenario.

Our bareboat yacht charters are on boats ranging from 34′ to 42′. Half day to weekly bareboat charters are available. Preliminary checkout available by phone or fax. Prices vary depending on vessel. 34′ ocean racers and up to 42′ luxury cruising yachts. Large parties can be accommodated, with up to 16 on the Danmark, a 40′ Sloop U.S. Coast Guard inspected vessel.

Enjoy the unique Florida experience sightseeing and watching the dolphins at play. Kick back and be pampered or you take the helm. Free sailing instruction during the charter.

• Book a Cruise
• Cruise Schedule
• “Cool Beans” Catamaran
• “Lil’ Beans” Pontoon
• Photos & Video
• Five-Star Reviews
• Directions & Parking

Take a Virtual Journey with Cool Beans

Choose a day-sail, champagne sunset or a private catamaran cruise below to enjoy a sailing adventure aboard our 42 foot sailing catamaran, Cool Beans .

If you’re looking for something different we can explore Keewaydin Island or one of the many other hidden treasures aboard Lil’ Beans , our luxury pontoon.

Day-Sail Cruise

Price includes a delightful escape to the beautiful waters of the Gulf of Mexico. Relax and enjoy your sailing experience on our beautiful catamaran while watching the abundant sea life and native birds of Southwest Florida.

During our day sails, we do stop for approximately 35 minutes at one of the many beautiful beaches of Southwest Florida – Keeywaydin Island, a barrier island in South Naples to swim, explore , and collect shells.

(Please note stopping at the beach is based on weather conditions. If it is too rough/choppy in the Gulf, the Captain may choose not to include a stop at the beach. Also know that to get to shore, you must swim in. We drop anchor in approx. 6 feet of water, approx. 30 yards off shore. Life jackets and floaties provided if needed. You are also welcome to stay on the boat to soak in the sun and scenery during the stop if you do not want to swim.)

• Complementary – soda, water, beer and chardonnay included
• You can also bring aboard additional food/snacks and beverages (no red wine please) on-board. Due to insurance liability, hard liquor is not allowed on our vessels.
• Smoking and Vaping are prohibited.

Gratuity Extra

Please note: 18% Gratuity will be added for parties of 7 or more.

• * Children must be at least two-years old.
• ** 24 hour prior notice cancellation policy for parties of 6 or under
• *** 48 hour prior notice cancellation policy for parties of 7 or more

Champagne Sunset Cruise

See Southwest Florida the way it was meant to be seen . . . by water! Escape from the crowds and set sail to take in our beautiful sunset. Sit back and enjoy a warm breeze in your face, a glass of champagne in your hand and the view of one of the most beautiful sunsets you will ever experience. Sail back to port and marvel at the view of the Gulf of Mexico and Naples/Marco Island beaches with the sunset lighting your way.

• Complementary – soda, water, beer and chardonnay included
• Complementary glass of champagne at sunset

Private Day-Sail or Sunset Cruise

 Would you like to have the boat to yourselves? Booking a “Private Cruise” is the perfect way to celebrate any occasion while enjoying your privacy. Choose from one of our Day Sails or our Champagne Sunset Cruises and leave the rest to us. Price includes items described above for your specific choice of cruise.

• ** 48 hour prior notice cancellation policy

Lil’ Beans Pontoon Island Beach and Sunset Adventures

Enjoy a Private 2 ½ hour Luxury Pontoon Tour for Up to 6 Guests for our Day Excursions or a 2 hour Sunset Excursion. Our Pontoons are perfect for Island hopping, up close Eco/Nature and Shelling on Keeywaydin Island. A “Must Do” while visiting SW Florida! (Sunset Charter arrives back to dock approximately 15 minutes after Sunset)

Keewaydin Island– A Deserted Barrier Island

Keewaydin Island is an 8 mile long unabridged barrier island just to the north of Marco. A fantastic sandy beach stretching the length of the island, with great shelling and opportunities to see plenty of wildlife. It serves as a sanctuary for wildlife and a popular recreational destination, especially at weekends. Keewaydin provides a great opportunity to experience Florida’s natural coast and is a vital nesting ground for Least Terns and Loggerhead Sea Turtles.

Hide-A-Way Beach/Sand Dollar Island – An Unspoiled Gulf Beach

Located just north of Tigertail Beach you’ll find Sand Dollar Island which abounds with wonderful seashells and is absolutely breathtaking and totally natural. Many of Florida’s beach-nesting shorebirds that face conservation challenges can be regularly spotted on Sand Dollar, including the Snowy Plover, Least Tern, Black Skimmer, American Oyster Catcher, and Wilson’s Plover.

• GOOD FOR CHARTERS COMPLETED BY SEPTEMBER 30 th , 2024
• * Price includes soda and water
• ** Children must be at least two-years old
• *** 48 hour prior notice cancellation policy

Groups & Special Occasions

Small intimate sunset weddings.

Make memories to cherish for a lifetime when you exchange wedding vows during your Cool Beans private sunset sail. Whether you have something particular in mind or need ideas, we can provide some wonderful options to assure that your wedding is everything you expect and more.

Romantic Sailing Excursions

Create the perfect moment to ask your significant other for their hand in marriage with a private cruise along the beautiful waters of Southwest Florida. Ask us how we can help to make your interlude aboard the Cool Beans a magical event to treasure for a lifetime.

Private Anniversary Cruise Celebrations

Reaffirm your love for one another alone or among special friends and loved ones aboard the Cool Beans. Your private sailing excursion is sure to be fun, romantic and memorable.

The Ultimate Birthday Private Cruise

Making a magical birthday celebration aboard the Cool Beans is one of our specialties. Whether your event is for a family daytime cruise, adventure among friends or a private sunset intimate sail, we are here to make your birthday cruise an event to remember.

Bachelorette Party

What a great way to celebrate the Bride to Be with her “Last Sail Before the Veil!” Specializing in small groups up to 20, booking a Bachelorette Party with Cool Beans Cruises will truly create a lasting memory..

Share the gift of a Cool Beans Cruise!

...now serving Fort Myers Beach!

Take Your Next Adventure With Mainsail Naples!

About Mainsail Naples

Come explore Florida's beautiful Paradise Coast aboard an exhilerating Corsair 37 trimaran racing sailboat! Take in the beautiful sights of Fort Myers Beach, watch dolphins put on a show, or simply cruise offshore and experience the freedom of feeling the wind in your sails. As a Florida native with over 30 years boating experience, Captain Art Rodriguez finds his greatest joy in sailing and will happily help you create the adventure you seek. Contact us for more information. Se habla español.

Frequently Asked Questions

What should i bring on my sailing excursion.

Wear a bathing suit, clothes, and shoes that you don't mind getting wet in. Bring a hat, a long sleeve and lightweight coverup, sunscreen, water shoes, a dry change of clothes, a towel, a waterproof camera, and any food and drinks you may want. Bring your own cooler or utilize ours. Feel free to bring your own beer and white wine, keeping in mind we do not allow red wine, liquor, or glass containers aboard. We will provide waters and sodas.  If you are prone to seasickness or are unsure, check with your doctor and consider bringing an over-the-counter seasick medicine.

What can I expect from my day aboard?

Captain Art will pick you up at the dock at Snug Harbor if available. Should the dock be too full, he will pick you up on a dinghy for a short ride to the sailboat.  The sailboat is motored  out through Matanzas Pass.  Once out in the Gulf of Mexico, the sails can be raised and your sailing adventure begins! You will likely see dolphins and a variety of fish. If you're really lucky, you might see a sea turtle or manatee. Perhaps you'd like to just relax and sunbathe or maybe you'd like to learn a little about sailing. Partaking in a sailing day is a very physical thing especially when considering the sea conditions and weather factors, so participants should be physically capable and strong swimmers. Swimming is at one's own risk.

What if there's inclement weather?

The Captain will determine if weather conditions will deem the trip unsafe and/or unenjoyable. If such determination is made, the Captain will cancel and make every effort to reschedule with you. Not having enough wind to raise sail will not warrant cancelling a scheduled trip.

Is there a bathroom on board?

Yes! The "head" (that's boat lingo for "bathroom") is located at the forward part of the main cabin.

How many people can I bring? Is it kid-friendly?

The boat can comfortably fit six passengers, not including the Captain. We welcome children ages 12 and older, and minors must be accompanied by a parent or guardian.

Can I bring alcohol aboard?

Yes, you may bring beer and white wine. Due to our liability insurance, liquor is not permitted aboard. As beverages often spill while under sail, we do not permit red wine. For everyone's safely, we ask that you do not bring glass containers on the boat. We will provide water and sodas.

Do you take credit cards?

You can use your credit card by using the book now tab and we accept cash and payment through Venmo, Paypal, Cash App, and Zelle.

Talk to me about safety...

Our vessel and business meet all local and federal safety requirements. Each passenger is provided a life jacket and the vessel is equipped with a first-aid kit and all Coast Guard required boating safety equipment. The boat is up-to-date with all regularly scheduled maintenance. Each time the boat is used, all surfaces are fully sanitized in accordance with CDC guidelines in an effort to protect against the spread of Covid-19 and all other communicable germs. The cockpit and inside cabin of the boat have non-slip flooring, though all areas of the boat get wet and can get slippery, especially when under sail. We strongly suggest non-slip, close-toed water shoes or sailing shoes and exercising awareness and caution at all times. Situations and weather can change unexpectedly, so in order to keep you safe, the Captain needs your constant cooperation.

Day sails are a 3-hour minimum for $550. Each additional hour after is $125  with trip length tailored to your wishes. These rates are per private charter for up to 6 guests. Prices are subject to change and do not include gratuity.

*Note: We do not accept credit cards. Cash, Venmo, Paypal, Cash App, or Zelle only please.

At Mainsail Naples, Captain Art is ready to help you plan your upcoming day sail so all that’s left for you is to enjoy it! Call, text, or send us an email and we’ll get back to you as soon as possible.

[email protected]

239-777-5826

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Basic Information

Naples Yacht Rental

Anchor rides | naples boat rental, naples yacht rental, and private yacht charters, why is naples, florida a fantastic location to rent a boat or charter a yacht.

Naples is the ideal location to charter a yacht or boat due to the year-round mild weather, the turquoise ocean, and miles of white powder Florida shoreline.

Fortunately, using anchorrides.com has made going on the water easier and more pleasant than ever before!

You can easily browse a sizable selection of boats and yachts for rent in Naples, Florida, thanks to Anchor Rides! You can narrow your boat or yacht rental search by price, the number of passengers and other factors as well as by date.

The majority of Naples Yacht Rentals are available for full or half-day rentals, and some can even be rented for overnight or several days. You can choose the ideal duration for your journey.

You can choose from a wide range of boat rentals thanks to our enormous collection of boats and yachts. Despite the fact that we do provide captainless Naples boat rentals for a more affordable boating experience, the majority of our yacht rentals include a licensed captain and crew (included in the price).

Renting a boat or yacht is less stressful when there is a licensed captain on board, allowing you to spend more time having fun. The local Captains can advise you on where to go and what to do for a flawlessly planned day because they are local experts on the Naples, Florida area.

You're covered by the Anchor Rides crew!

For those of you who want even more out of your Naples yacht charter experience, we also provide a fantastic selection of upgrades and extracurricular activities! Jet ski rentals, water activities, open bar and food service, and organizing special events are some of our most popular requests.

We can make everything you can imagine happen. To begin organizing your ideal Naples Yacht Rental experience right away, get in touch with a member of the Anchor Rides team.

How to Take Advantage of Naples Yacht Charters, Boat Rentals, and Anchor Rides

The process of renting a yacht from Anchor Rides is meant to be simple and stress-free. You can spend more time on the water and less time worrying about the specifics of your vacation thanks to our straightforward booking process. Here are a few quick steps to help you secure your Naples Yacht Charter. 

Search regionally:

Use our built-in Google Maps search engine to look up places close to where you are or where you want to go. We'll generate a list of available rental boats and yachts in your area when you enter your city or zip code.

Choose a date for departure.

Make sure to search by date so that we only show you yachts that will be available on your desired day. 

Select a Boat:

We have a selection of more than 600 boats. When the "Featured" icon appears in the thumbnail, it denotes a well-liked and regarded rental choice.

Requesting and verifying availability:

Once you have narrowed your search to a few affordable possibilities, send an online availability request. The boat owner will decide whether to accept or reject your charter based on their most recent schedule and availability.

Request a rental:

Once you've chosen a boat, simply use our simple web platform to pay a modest deposit to reserve your reservation. Your rental or lease will include a return of the security deposit.

Choose your crew and captain:

Each boat has its own roster of available captains. You can pick the Captain you wish to be in charge of the boat.

Get started:

Anchor Rides does all the labor-intensive tasks so you can relax and take it all in. To start your day of boating pleasure in Naples, simply meet your captain at a prearranged spot. Remember to bring your swimsuit!

What Perks and Advantages Come With Renting a Yacht or Chartering a Yacht From Anchor Rides?

No hidden fees or transparent pricing:.

There are so many businesses that charge you extra money at the port. In order to alleviate your concerns about unanticipated costs, Anchor provides all-inclusive pricing on our website.

Professional and courteous crew:

Our Naples Captains have not only completed rigorous training programs and obtained US Coast Guard certifications, but they have also been personally chosen by the owner and you based on their friendliness, customer service skills, and general capacity to deliver an outstanding yachting experience.

Convenience:

Since Anchor has direct connections to yacht and boat owners, we don't publish any vessels that have been sold through various intermediaries. You may get direct pricing and availability from Naples boat owners when you use Anchor's Yacht Rentals.

Make Your Yachting Experience Your Own:

You can design a unique Naples yachting experience when you rent a yacht from Anchor Rides. Our friendly staff will assist you in organizing extra activities or services for your trip. 

Call a live Charter Expert now!

A caring team is crucial because renting a yacht is a significant commitment. The foundation of Anchor Rides is delivering the finest possible customer service. Our team at Anchor Rides is at your side from beginning to end, ensuring that your Naples yacht rental experience is simple and enjoyable.

Naples Yacht Rental for Special Events

Looking to rent a yacht for a special event? Check out some of our most popular requests below:

• Bachelor and bachelorette partys 
• Celebrate birthdays
• Family gatherings
• Graduation party on a yacht!
• Birthdays aboard a yacht!

How Much Does a Yacht Rental in Naples Cost?

In Naples, a charter typically costs $2,200. Yacht rentals can range in price from $500 for a half-day to $15,000 to $20,000 for a full day. Everything depends on the boat's size and the year.

The cost to rent a yacht varies in Naples. The size of the yacht, the date you are renting it, and the length of time you want to rent it all must be taken into account when determining how much it will cost to rent a yacht in Naples. Budgeting is also important for any extra features or services you might want to include, such as caterers, jet skis, a DJ, or even a masseuse.

The average cost of a half-day boat hire in Naples is $500, whereas the average cost of a half-day yacht rental in Naples starts at over $1500. Per half-day, the average cost is $2200.00.

Choosing a boat, choosing your dates, and then examining the all-in price is the easiest method to find out how much your Naples boat rental will cost you.

With clear pricing offered by Anchor Rides, you can plan your journey knowing precisely how much it will cost. Visit our Naples Yacht Charters right away!

Yachting in Naples, FL

Naples, located on Florida's southwest coast, is ideal for yachting enthusiasts with its serene waterways and beautiful coastline. Known for its upscale charm and pristine beaches, Naples offers a luxurious yachting experience. On the deck of your yacht, enjoy the meeting of azure waters and white sands, with stunning views of the Gulf of Mexico. Discover Naples' allure and the promise of an unforgettable maritime adventure.

35' Sunsation

65' Mikelson

55' Prestige

100' Broward

84' Lazzara

51' Schaefer

72' Galeon

73' Sunseeker Manhattan

76' Sunseeker

Why charter a yacht in naples, fl, enjoy the beach at the naples pier, take a cruise or rent a boat, charter a yacht to marco island beaches, .css-1uazooj{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;width:100%;outline:2px solid transparent;outline-offset:2px;transition-property:var(--chakra-transition-property-common);transition-duration:var(--chakra-transition-duration-normal);font-size:1rem;-webkit-padding-start:var(--chakra-space-4);padding-inline-start:var(--chakra-space-4);-webkit-padding-end:var(--chakra-space-4);padding-inline-end:var(--chakra-space-4);padding-top:var(--chakra-space-2);padding-bottom:var(--chakra-space-2);padding:10px 16px;}.css-1uazooj:focus-visible,.css-1uazooj[data-focus-visible]{box-shadow:var(--chakra-shadows-outline);}.css-1uazooj:hover,.css-1uazooj[data-hover]{background:var(--chakra-colors-blackalpha-50);}.css-1uazooj[disabled],.css-1uazooj[aria-disabled=true],.css-1uazooj[data-disabled]{opacity:0.4;cursor:not-allowed;} .css-1pkhz46{font-size:var(--chakra-fontsizes-sm);font-weight:600;-webkit-flex:1;-ms-flex:1;flex:1;text-align:left;} how do i book a yacht on yachtlife .css-g5ledl{width:1em;height:1em;display:inline-block;line-height:1em;-webkit-flex-shrink:0;-ms-flex-negative:0;flex-shrink:0;color:currentcolor;vertical-align:middle;font-size:8px;}, when is my payment collected is it refundable.

Once you confirm your reservation, your broker will process your payment.

• If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
• If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
• If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.

Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.

Why is there a 3% credit card convenience charge?

Are my payment details saved on the app, what if your servers get hacked is my payment information really safe.

Welcome Aboard!

Naples nantucket yacht charters, the premium provider for luxury yachting, the world's finest luxury performance & cruising yachts.

Welcome to Naples Nantucket Yacht Group

Is it your desire to cruise the Gulf waters of Naples, The Keys, Southwest Florida, Cape Cod, Nantucket Sound, Martha’s Vineyard, Newport or the Hamptons on the finest yachts with a professional attentive crew?

Congratulations! You found us!

Welcome to Naples Nantucket Yacht Group , your premium provider for luxurious yachting. We pride ourselves on our yachts, but most of all our people and the services we provide.

View the information here on our website and call or email us for more information. Our loyal customers have become our best sales team.

Offering 3-hr yacht cruises, half-day (4 hours), full-day (8 hours) & multi-day charters.

Our latest offerings, luxury yachts available for charter, yachts 100'+.

Sunseeker 131

Available for Charter in The Bahamas, Windward Islands, Leeward Islands, US Virgin Islands & British Virgin Islands

Ocean Alexander 114

Available for Charter in St. Petersburg & Tampa, FL | Winters in The Bahamas

Horizon 110

Available for Charter in Fort Lauderdale, Summers in Nantucket & Multi-Day Charters to The FL Keys, The Bahamas & The Northeast

Hatteras 100

Available for Charter in Bahamas Feb – May & Northeast U.S. June – Oct

YACHTS 50' - 100'

Ocean Alexander 98

Available for Charter in the Northeast US

Sunseeker 95

Available for Charter in Tampa, St. Petersburg & Sarasota, FL | Winters in Naples, FL & The Bahamas

Available for Charter in the Northeast U.S.

Sunseeker 92

Available for Full-Day Charter in Cabo San Lucas, Mexico

YACHTS 28' - 50'

Available for Charter in Naples Year Round for 3 Hr Sunset Cruises, Half- and Full-Day Charters, & Multi-Day Charters to The FL Keys & Captiva Island

Cruisers Yachts 38

Available for Charter in Naples Year Round for 3 Hr Sunset Cruises, Half- and Full-Day Charters

Available for Charter in Naples Year Round

Boston Whaler 28

LUXURY, FLEXIBILITY...ALL FUN!

Multi-day charters, full-day & half-day charters, 3-hr sunset yacht cruises, special occasions, charter optional add-ons.

Learn more about the optional add-on services we offer for making your charter the most memorable, hassle-free experience possible.

• VIP Ground Transportation
• Private Jet Service

VIP CHARTER LOYALTY PACKAGES

Charter more often, score big deals.

Frequent guests of ours have a chance to earn discounted rates applied toward their future charters just by doing what they love – enjoying time well spent on the water on our fleet of luxury performance and cruising yachts – and coming back for more!

Our VIP charter loyalty packages include great benefits such as:

• 15% off standard yacht charter rates
• 10% off standard ground transportation rates
• 1 complimentary 3-hour sunset cruise on our 68′ Prestige or larger yacht

LUXURY YACHTS AVAILABLE FOR FRACTIONAL OWNERSHIP

A Few Kind Words From Our Friends

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Head office.

850 Central Ave Suite 110 Naples, FL  34102

239.331.6868

[email protected]

• Fractional Ownership
• Yacht Management

Our Leadership

• Bill Charbonneau Founder & Principal
• Jacquie Charbonneau Director of Operations

Ⓒ 2024 Naples Nantucket Yacht Group. All Rights Reserved.

An island light creative website.

(239) 206-9955

Personalize your Naples Experience on the water

We're your on the water concierge.

Our Mission

Our mission is to be your exclusive on the water concierge. 

With The Blue Dahlia you can personalize your Naples lifestyle on the water. We cater each custom designed package to fulfill your nautical needs. Explore the lavish Port Royal community, indulge yourself with champagne while enjoying Naples world famous sunsets in the background, cruise around to see Florida's tropical wildlife in their natural habitats and much more!

New Additions

Bow canopy shade.

Prolonged exposure in the Florida sun can cause a number of short term and long term issues. The Blue Dahlia can ensure that you are covered, literally!  The Blue Dahlia has a custom canopy shade that attaches to the bow and will keep you out of the sun but not out of the fun. The bow canopy can be utilized while beached up or at idle speeds.

Stern Canopy Shade

Party in the front, coverage in the back! The Blue Dahlia also has a Canopy Shade for the stern as well. This ensures that you stay safe from prolong sun exposure while driving in no wake zones or even hanging out at Keewaydin Island. 

The Cannon Salutation

This tradition began with the British Royal Navy and continues with the U.S. Navy. Cannons or guns are fired at sunset when the flag is taken down, as a sign of respect. In the days when ships were armed with cannons, it could take as long as twenty minutes to load and fire. When a ship emptied her guns in salute, she rendered herself powerless and showed they were no threat to nearby forts. Over time, this gesture became a sign of respect. Ask about our special pricing to customize your charter and fire the cannon for your special occasion. 

Copyright © 2020 The Blue Dahlia Private Charters - All Rights Reserved.

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Experienced sailors can bareboat  Island Dreams , our 31' Catalina, for a half day, full day, or overnight sail. Enjoy cruising along Naples' sugar white sandy beaches aboard a fun and easy-to-sail yacht. She is well equipped for your sailing needs.  Up to 6 guests are permitted. Island Dreams' equipment includes roller furling main and jib, color chart plotter, autopilot, VHF radio with RAM microphone in cockpit, bimini, and swim platform. She has raised stern rail seats and wide decks for maximum lounging area.

​If you feel your sailing skills are a bit rusty, you may want to take a captain aboard for part of your charter. This is a great way to brush up on your skills, take some pressure off while you orient yourself to the boat, and get some great local knowledge. ​​

Island Sailing - Naples, FL​​

Naples' Premier Sailing Charter Company

What is a bareboat sail?

Want to go sailing but don't want to pay the high costs of owning a sailboat? You can! We also offer a boat club (5 and 10-day packages). 

Send us your sailing resume, and we'll schedule a time to evaluate your sailing and navigational skills to ensure that you can set up the vessel and navigate through the channel and in the local sailing areas (Naples, Marco, Fort Myers, and Sanibel).  We'll show you how to set up Island Dreams and how to stow her away at the end of a sail (docking). For those using our packages, we look to complete all of the sails within a 12 month period and only accept ten boat club members at a time, to ensure availability.  Boat club members have priority over regular captained charters when scheduling.

What is the boat club?

Island Sailing Naples | 800 12th Avenue South, Naples, FL | [email protected] | 239.398.1483

• Captained Charters
• Bareboat/Boat Club
• Our Captains

​​​ Bareboat Prices:

Half day (4 hours):    $450

Full day (8 hours):    $700

Boat Club Packages:

• 5 full day sails:    $2,250 *
• 10 full day sails:  $3,750 * ​ ​

* Day sails only, not to be combined for multi-day sails

​​ Prices subject to change and do not include tax.

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• Text (910) 447-2456 Call (910) 447-2456

Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 14 yacht & boat rentals in naples, fl.

In addition to the best offers we have for boat and yacht charters in Naples, FL, see also options available for rent in these nearby locations:

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Rent a Boat in Naples, Florida with Sailo!

Planning a sailing vacation and looking for boat rentals in Naples, Florida? Enjoy the freedom of the open water on a private yacht charter in Naples, FL from Sailo. Rent a boat from Naples, FL from a couple of hours to a full day, to really explore Florida. With a licensed captain driving your boat rental in Naples, FL with, you’ll be able to relax and discover those hidden gems with your friends or family. Prefer to skipper your Naples yacht rental? Use our advanced filters to find your perfect bareboat charter on Sailo!

Our luxury boat rentals in Naples, FL private inventory

Explore the beauty of Florida state from Naples by a yacht charter. You’ll find boats to rent in Naples with Sailo, for the best choice. Set sail on one of our several elegant sailboats. You can also choose from numerous catamarans, available to charter. What better way to discover the shores of Florida than from the deck of a luxury motor yacht? Browse the available on Sailo for your ideal boating trip. You’ll also find 1 larger party boats, perfect for groups of 13 or more available in Naples, FL.

How to find the right yacht charter in Naples?

Wondering how to find the best yacht charter in Naples for a memorable experience on the water in Florida? We have created a set of advanced filters to help you navigate easily our database of Naples boat rentals and find the one for you. First pick a start date and then choose your trip duration. You can go for an extraordinary of 2, 4 hours or full day experience. Next, select the number of guests, the type of boat to rent in Naples, Fl and the price range you are comfortable with. The crew filter helps you narrow down the results to the boats with the captain included in the price, or bareboats that you’ll captain yourself. Choose the boat you want in Florida, to view more pics, read description and reviews. Message the owner if you have any questions or continue with your booking request.

How much does it cost to charter a yacht in Naples, FL?

Naples yacht charters for daily trips are available at an average of $1100 per day. Cheaper boats (sometimes with no captain included) may be rented for $250. Our luxury yacht charters in Naples, Florida may have price tags up to $6500, with crew, fuel, docking fees and other extras added to your budget.

What is Sailo’s cancellation policy for the Naples Bay boat rentals?

As long as the booking request hasn't been accepted by the boat owner, the renter can cancel the request without any charge. If the renter cancels after the booking request has been accepted, the booking will be subject to the terms of the cancellation policy in place for each boat. The renter should check the cancellation policy with the boat owner, as some of the professional operators have specific cancellation policies which supersede that of Sailo. Whenever a boat owner doesn't have a specific cancellation policy, Sailo's Standard Cancellation policy  will apply.

Because we love the ocean

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:

• Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
• Eco-friendly sunblock can help prevent damage to marine life
• buy local and sustainable food products

However long you’re sailing for, a little goes a long way.  Read more about responsible boating.

Popular sailing destinations in Florida:

• Miami yacht rentals
• Yacht charters in Fort Lauderdale
• Key West boat rentals
• Boat charters in Key Largo
• Yacht rentals in St. Petersburg, FL
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• Accessibility Statement
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• British Virgin Islands
• La Paz, Mexico
• Cabo San Lucas, Mexico
• Key Largo, FL
• St. Vincent and Grenadines

26° 08′ 57″ N / 081° 47′ 39″ W

Naples Boat Charters   is a sightseeing charter company owned and operated by Capt. Joey D Charters, Inc. The “ Sweet Dreamin'  “ (a 2018 24′ Key West 239) is docked at: Hyatt House Naples ( the Marina behind the Hotel ) 1345 Fifth Ave., So., Naples, FL 34102 Capt. Joey D will charter the "Sweet Dreamin"  UP TO SIX   ( 6 )  passengers for a private, narrated sightseeing charters around Naples Bay, Port Royal, Keewaydin and Marco Island and 2 hour private sunset charters.  Also offered are 5 hour lunch trips to Marco Island; wedding ceremony officiant at your venue or on the beach and, the releasing of ashes at sea. * We ALSO OFFER FISHING CHARTERS & BOAT RENTALS!  * PLEASE click  Services and Rates  to read more!