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Three Ways to Sail in Naples
Explore Naples with our yacht charters and boat rentals suited for all experience levels. From bareboat options for seasoned sailors to skippered and fully crewed experiences, plus license-free boats for beginners, we offer the perfect vessel to discover Naples's beautiful waters your way.
Bareboat / Captain Optional
Ideal for experienced sailors seeking complete freedom and control for their Naples yacht rental experience.
•Complete control over sailing itinerary around Naples
•Privacy and intimacy for your group
•Opportunities to improve sailing skills in Naples's waters
•Cost-effective boat rental option for larger groups
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When planning a yacht charter in Naples, selecting the right type of boat is crucial to ensure your sailing experience aligns with your preferences, group size, and desired level of comfort. Here's a quick overview of the most popular boat types available for charter in Naples:
When planning your Naples yacht charter, choose from our premium fleet of sailing yachts, motor yachts, and luxury catamarans. Whether you prefer a crewed or bareboat charter experience, our professionally maintained vessels offer ideal options for every group size and sailing expertise. Discover competitive charter rates and top-quality amenities for your perfect sailing vacation in Naples.
What license do I need to rent a boat in Naples, Florida?
Florida doesn't require a boating license for most rentals, though some boats may need a captain's license or safety certification depending on size and type. For detailed licensing requirements and international credentials, visit our comprehensive licensing guide.
How much does it cost to charter a yacht in Naples during peak season?
Sailboat charters in Naples range from $2,500-$5,000/week in low season and $4,500-$8,000/week in high season. Catamarans run $5,000-$10,000/week (low) and $9,000-$18,000/week (high), while motor yachts start at $8,000-$15,000/week (low) and $15,000-$35,000/week (high). We offer flexible payment with just 15% down and three installments, plus exclusive discounts on many boats.
When is the best time to go sailing in Naples?
The best sailing season in Naples runs from November through April, with calm seas, temperatures around 70-80°F (21-27°C), and gentle easterly breezes. Summer months bring warmer waters perfect for exploring the Ten Thousand Islands, Marco Island, and the gorgeous Gulf Coast beaches, though afternoon thunderstorms are common from June to September.
What additional costs should I expect when chartering a boat in Naples?
Plan for mandatory end-cleaning ($110-$550 depending on boat size), security deposits (or deposit insurance from $110-$385), marina fees at Naples Bay or nearby harbors (catamarans typically cost 50% more than monohulls), fuel, and any local permits. We offer Sealogy charter insurance worldwide to protect your deposit and provide peace of mind.
Does Borrow A Boat offer flexible cancellation and payment options for Naples charters?
Yes! Select boats in Naples offer extended free cancellation periods pending confirmation, and we provide a unique 3-installment payment plan requiring just 15% down payment. This makes it easier to secure your dream sailing vacation on the Southwest Florida coast without paying everything upfront.
Can I find any type of boat charter in Naples through Borrow A Boat?
Absolutely! We operate worldwide and can source any professionally chartered boat in Naples, even if it's not yet in our database. Whether you're an experienced sailor looking for bareboat, need a skippered charter, or want a fully crewed luxury experience for your family, couple's getaway, or corporate incentive, we'll find the perfect boat for exploring Naples Bay, the Everglades, and beyond.
What services does Borrow A Boat offer to make my Naples charter easier?
We've partnered with trusted providers to handle every detail: airport transfers from Southwest Florida International Airport, Sealogy charter insurance for deposit protection, and professional skipper options. Our team helps coordinate everything so you can focus on enjoying Naples' stunning sunsets and pristine waters.
What are the best sailing routes and attractions around Naples?
Naples offers incredible cruising to the Ten Thousand Islands mangrove maze, pristine Keewaydin Island beaches, upscale Marco Island, and the protected waters of Rookery Bay. You'll enjoy world-class fishing, dolphin watching, and spectacular Gulf of Mexico sunsets, with easy access to both secluded anchorages and vibrant waterfront dining at Naples Bay or Fifth Avenue South.
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Naples offers sailors an extraordinary blend of dramatic coastal scenery, ancient history, and Mediterranean charm that's best experienced from the water. With Borrow A Boat, you can explore the stunning Gulf of Naples, cruise past Mount Vesuvius, and discover hidden coves along the Amalfi Coast while enjoying crystal-clear waters and world-class Italian hospitality. Whether you're planning a romantic getaway or a family adventure, chartering a boat in Naples opens up a world of unforgettable experiences along one of Italy's most breathtaking coastlines.
Flexible Booking That Works for You
We understand that travel plans can change, which is why we offer free cancellation up to 30 days before departure on select boats. You can secure your dream Naples charter with just a 15% down payment and spread the remaining cost across three convenient installments. Plus, our exclusive discounts make sailing the Italian coast more accessible than ever.
The Perfect Boat for Every Sailor
From experienced sailors seeking a bareboat sailboat to first-timers wanting a fully-crewed catamaran, we can source any professionally chartered boat to match your needs. Our fleet in Naples includes everything from nimble sailboats perfect for couples (starting around $150/day) to spacious motor yachts ideal for groups (from $500/day), and luxurious catamarans for families seeking comfort and stability (typically $400-800/day). Whether you're planning an intimate escape or a celebration with friends, we'll find exactly what you need.
Year-Round Sailing with Peak Season Perfection
Naples enjoys excellent sailing conditions from April through October, with July and August offering the warmest waters and most reliable winds. Popular routes include the spectacular journey to Capri and the Blue Grotto, the stunning Amalfi Coast with stops in Positano and Ravello, and day trips to the islands of Procida and Ischia. Spring and fall provide quieter anchorages and pleasant temperatures, making them ideal for sailors who prefer a more relaxed pace.
Seamless Support from Start to Finish
Our local partnerships ensure your Naples charter runs smoothly from the moment you land. Book convenient airport transfers to get from Naples International Airport to your marina hassle-free. Need a professional skipper to show you the best anchorages and local secrets? We'll connect you with experienced local captains who know these waters intimately. Protect your adventure with comprehensive charter insurance from Sealogy for complete peace of mind.
Gateway to Italy's Most Iconic Coastal Treasures
Your Naples charter puts you at the center of some of the Mediterranean's most celebrated destinations. Sail to the glamorous island of Capri for upscale dining and the famous Faraglioni rocks, explore the colorful cliffside villages of the Amalfi Coast, or anchor in secluded bays accessible only by boat. The combination of ancient Roman ruins, volcanic landscapes, and turquoise waters creates a sailing experience unlike anywhere else in the world.
Gateway to paradise islands and pristine Gulf waters
Perfect for:
Island Hopping
Wildlife Viewing
Beach Anchorages
Calm Waters
Essential information
Information type
High and low season
Description
Peak season runs from December through April when snowbirds arrive and prices reach their highest. Summer months from June to September offer lower rates but bring afternoon thunderstorms and higher humidity. Shoulder seasons of November and May provide excellent value with pleasant weather.
Best months to book:
November, December, March, April
Information type
Marinas, ports and mooring
Description
Naples Bay Resort Marina and Naples City Dock offer full-service facilities in the heart of downtown with easy access to restaurants and shopping. Bayview Park Boat Ramp provides public access while Crayton Cove offers protected mooring. The Gordon Pass leads to the Gulf of Mexico and numerous anchorages throughout the Ten Thousand Islands.
Best places to stay:
Naples Bay Resort Marina, Crayton Cove, Marco Island marinas
Information type
Wind & weather
Description
Naples enjoys gentle Gulf breezes averaging 8-12 knots (Beaufort 3-4) with calm morning conditions ideal for cruising. Winter months bring cooler, drier air with occasional cold fronts, while summer features sea breezes and afternoon thunderstorms. The protected Gulf waters and barrier islands provide excellent sailing conditions year-round.
Temperature & Winds:
65°F to 90°F, 8-12 knots (Beaufort 3-4)
Information type
Required licenses and certifications
Description
Florida does not require a boating license for yacht charters, but operators born after January 1, 1988 must complete a Florida-approved boating safety course and carry a Boating Safety Education ID Card. Charter companies typically require proof of sailing experience or certification. An ICC or ASA certification is highly recommended and often required by charter operators.
Best license to hold:
American Sailing Association (ASA) Certification, Florida Boating Safety Education ID Card
Currency:
USD
Season:
October - May
Sailing Conditions in Naples, Florida: Complete Guide for Yacht Charter & Cruising
Naples, Florida, situated on the Paradise Coast of Southwest Florida, offers exceptional year-round sailing opportunities in the warm waters of the Gulf of Mexico. This sophisticated coastal destination combines protected bays, pristine barrier islands, and access to the renowned Ten Thousand Islands, making it ideal for sailors of all experience levels. The prime sailing season runs from November through May, when conditions are most favorable, though summer months provide excellent opportunities for experienced sailors who can navigate afternoon thunderstorms. With consistent Gulf breezes, calm morning waters, and abundant anchorages, Naples delivers an unforgettable sailing experience along Florida's stunning southwest coastline.
Wind Conditions
•Naples Bay and Gordon Pass experience predominantly easterly winds during winter months (November-April), averaging 8-12 knots (Force 3), creating ideal conditions for leisurely cruising and learning basic sailing techniques. These protected waters see wind speeds increase to 10-15 knots (Force 3-4) during afternoon sea breezes.
•The Gulf of Mexico offshore areas from Naples typically experience stronger winds, averaging 10-18 knots (Force 3-4) during winter months. Spring months (March-May) can bring slightly stronger conditions with winds reaching 15-20 knots (Force 4-5), particularly during frontal passages.
•Summer months (June-September) feature lighter morning winds of 5-10 knots (Force 2-3) from the southeast, building to 12-18 knots (Force 4) by afternoon. Sailors must monitor for rapidly developing afternoon thunderstorms that can produce sudden wind shifts and gusts exceeding 25 knots (Force 6).
•The Ten Thousand Islands region south of Naples experiences similar wind patterns but with slightly reduced velocities due to the sheltering effect of mangrove islands. Winds typically range from 8-15 knots (Force 3-4), making this area particularly suitable for intermediate sailors.
•Keewaydin Island and the barrier island chain provide excellent wind shadow protection during easterly winds, while westerly winds create ideal sailing conditions along the island's Gulf side with steady 10-15 knot (Force 3-4) breezes.
Sea State
•Naples Bay and the inland waterways maintain calm conditions year-round, with wave heights rarely exceeding 1-2 ft (0.3-0.6 m). These protected waters are ideal for beginners and provide safe harbors during adverse weather conditions.
•Gulf of Mexico waters off Naples typically experience wave heights of 2-4 ft (0.6-1.2 m) during calm winter periods, increasing to 3-6 ft (0.9-1.8 m) during moderate wind conditions. The Gulf's relatively shallow continental shelf creates short-period waves that can be choppy.
•During frontal passages, particularly common from November through March, Gulf waters can build to 5-8 ft (1.5-2.4 m) with occasional higher sets. These conditions are best suited for experienced sailors in well-equipped vessels.
•Summer months produce generally calmer morning conditions with wave heights of 1-3 ft (0.3-0.9 m), though afternoon thunderstorms can temporarily create confused seas of 4-6 ft (1.2-1.8 m) with steep, short-period waves.
•The Ten Thousand Islands region offers exceptionally protected waters with wave heights typically under 2 ft (0.6 m), though tidal currents through passes can create standing waves and choppy conditions during peak flow periods.
Temperature
•Naples enjoys a subtropical climate with warm temperatures year-round. Winter months (December-February) see daytime air temperatures ranging from 70-78°F (21-26°C), with nighttime lows of 52-60°F (11-16°C), creating comfortable sailing conditions with minimal need for foul weather gear.
•Spring and fall shoulder seasons (March-May and October-November) offer ideal sailing temperatures with daytime highs of 78-86°F (26-30°C) and evening temperatures of 62-72°F (17-22°C). These months provide the most comfortable conditions for extended cruising.
•Summer months (June-September) bring hot, humid conditions with daytime temperatures of 88-92°F (31-33°C) and high humidity levels. Morning sails are most comfortable, with afternoon heat requiring sun protection and adequate hydration.
•Gulf of Mexico water temperatures range from 68-72°F (20-22°C) during winter months, warming to 78-82°F (26-28°C) in spring and fall, and reaching peak temperatures of 84-88°F (29-31°C) during summer. These warm waters make swimming and water activities enjoyable throughout the year.
•The sailing season experiences minimal temperature variation between day and night during summer months, while winter evenings can be 15-20°F (8-11°C) cooler than daytime highs, requiring light layers for sunset cruises.
Tides and Currents
•Naples experiences mixed semi-diurnal tides with an average tidal range of 2-3 ft (0.6-0.9 m). Spring tides can reach ranges of 3.5-4 ft (1.1-1.2 m), while neap tides typically show ranges of 1.5-2 ft (0.5-0.6 m). These moderate tidal ranges require attention to depth when anchoring in shallow areas.
•Gordon Pass experiences strong tidal currents reaching 2-3 knots during peak ebb and flood, with maximum currents occurring approximately 2 hours after high and low tide at Naples Bay. Navigating this pass during slack tide or favorable current is recommended for less experienced sailors.
•The Ten Thousand Islands region features numerous tidal creeks and passes where currents can reach 2-4 knots during spring tides. Local knowledge or detailed chart study is essential for safe navigation, as these currents can significantly impact vessel handling.
•Naples Bay itself experiences moderate tidal currents of 0.5-1.5 knots, with strongest flows near Gordon Pass and in the main channel. These currents are generally manageable for all skill levels but should be considered when maneuvering in tight quarters.
•The Gulf of Mexico coastal waters show minimal current influence except near inlets and passes. Longshore currents typically flow southward at 0.5-1 knot, though wind-driven currents can temporarily reverse this pattern during strong northerly winds.
Best Sailing Areas for Different Skill Levels
•Beginners should focus on Naples Bay, particularly the northern bay areas near Moorings Bay and Venetian Bay. These protected waters offer consistent light winds, minimal current, calm sea states, and plenty of room to practice basic sailing maneuvers. The bay provides excellent learning conditions with easy access to marinas and services.
•Intermediate sailors will enjoy exploring Keewaydin Island's leeward waters, the southern sections of Naples Bay extending toward Gordon Pass, and day trips to Marco Island. These areas offer more challenging wind conditions, moderate currents, and the opportunity to practice coastal navigation while maintaining reasonable proximity to protected harbors.
•Advanced sailors can venture into the Gulf of Mexico for offshore passages, explore the intricate channels of the Ten Thousand Islands wilderness area, and navigate challenging Gordon Pass during various tidal and wind conditions. The 40-mile passage south to the Dry Tortugas or north to Sanibel Island provides excellent blue-water experience, while the Ten Thousand Islands offer exceptional gunkholing and navigation challenges through shallow, unmarked waters requiring superior boat handling and navigation skills.
•Gordon Pass, the primary inlet connecting Naples Bay to the Gulf, can experience challenging conditions with waves of 3-5 ft (0.9-1.5 m) when wind opposes tidal current. Timing passage during favorable conditions is essential for safety.
Naples, Italy, positioned on the stunning Tyrrhenian Sea in the Campania region, offers sailors an extraordinary Mediterranean sailing experience with breathtaking views of Mount Vesuvius, access to the legendary Amalfi Coast, and gateways to the islands of Capri, Ischia, and Procida. The Gulf of Naples provides protected waters ideal for both novice and experienced sailors, with consistent thermal winds, numerous marinas including Mergellina and Marina di Stabia, and a rich maritime heritage dating back millennia. The combination of favorable sailing conditions, world-class cuisine, archaeological wonders, and dramatic coastal scenery makes Naples an exceptional year-round destination, though conditions vary significantly by season.
High Season (June to August)
Pros & advantages
•Consistent thermal winds of 10-20 knots from the northwest create ideal sailing conditions for exploring Capri, Sorrento Peninsula, and Amalfi Coast routes.
•Warm sea temperatures reaching 75-79°F (24-26°C) make swimming, snorkeling, and water activities particularly enjoyable at secluded anchorages and grottos.
•Extended daylight hours until 8:30 PM allow longer sailing passages and more time exploring coastal towns like Positano, Amalfi, and Ravello.
Cons & disadvantages
•Marina berths and mooring buoys around Capri and Positano require advance booking weeks ahead, with premium prices often exceeding €200 per night.
•Intense heat with temperatures reaching 86-90°F (30-32°C) creates uncomfortable conditions below deck, requiring early morning departures and air-conditioned cabins.
•Popular anchorages become extremely crowded with superyachts and charter boats, particularly at Capri's Marina Piccola and Ischia's Sant'Angelo, limiting anchoring space.
Shoulder Season (April to May and September to October)
Pros & advantages
•Moderate temperatures of 68-77°F (20-25°C) with comfortable sailing conditions and reliable maestrale winds averaging 12-18 knots for excellent passages to Pontine Islands.
•Significantly reduced crowds at marinas and anchorages mean easier berthing at competitive rates, with spontaneous reservations possible at Procida and Ischia.
•Sea temperatures remain pleasant at 64-73°F (18-23°C) in these months, while cultural events like Maggio dei Monumenti showcase Naples' maritime history.
Cons & disadvantages
Low Season (November to March)
Pros & advantages
•Marina rates drop by 40-60% at facilities like Marina di Stabia and Mergellina, making extended stays economical for experienced sailors.
•Authentic local experience with uncrowded anchorages and genuine interaction with Neapolitan maritime communities in working harbors like Pozzuoli and Baia.
•Experienced sailors enjoy challenging conditions with stronger winds of 15-25 knots and occasional gale systems perfect for testing seamanship skills.
Cons & disadvantages
For most sailors, the shoulder seasons of May and September offer the optimal balance of pleasant weather, manageable crowds, and authentic experiences while exploring Naples and the surrounding islands. High season suits families and beginners seeking guaranteed sunshine and calm conditions, despite higher costs and congestion at popular destinations like Capri. Experienced sailors comfortable with challenging conditions will find exceptional value and solitude during the winter months, though careful passage planning and proper equipment are essential for safe navigation in the Gulf of Naples year-round.
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September and October bring increased rainfall with occasional thunderstorms requiring careful weather monitoring and flexible itineraries when sailing the Amalfi Coast.
•Variable wind patterns during April and May can produce light air days under 8 knots, necessitating motoring between destinations like Sorrento and Salerno.
•Some seasonal restaurants and beach clubs on smaller islands close by late October, limiting dining options at remote anchorages around Ventotene.
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Unpredictable weather with frequent scirocco and libeccio winds bringing rough seas of 6-10 feet, making passages uncomfortable and potentially dangerous for beginners.
•Cold temperatures ranging from 46-59°F (8-15°C) and sea temperatures dropping to 57-61°F (14-16°C) require proper foul-weather gear and heating systems.
•Limited charter availability and reduced marine services as many operators close for winter maintenance, with fewer provisioning options in island communities.