How dangerous is sailing in the Caribbean?

When planning a sailing holiday, you must consider your safety and that of your loved ones. The Caribbean is among the most beautiful destinations in the world to visit for a holiday. It has lots of attractions and activities, and sailing is always a tourist favorite. Generally, sailing in the Caribbean is perfectly safe and fun. Of course, some risks arise with every holiday destination, but we have mitigated most of them to ensure you have the best experience. Weather Issues Managing the weather can be tricky as it's an unpredictable natural phenomenon. The best time to sail in the Caribbean is from November to July. The safest month, when you are unlikely to experience hurricanes, is June. May is also a good month, so you could plan your visit around this time. Safety Features Our vessels have the latest navigational and communication devices. Even during fair weather, you can experience unforeseen hurdles. That is why we have ensured that all of our boats are ready to face any unexpected circumstances. Experienced Personnel The people handling our boats and yachts are among the best in the business. They are primarily locals with lots of experience. They are knowledgeable about the local waters, ensuring that you remain safe and comfortable throughout your trip.

What is the best time to go to Caribbean?

If you plan to go on holiday in the Caribbean, it is good to know the best times to visit so that you can get the most out of your holiday. You don't want to arrive when the weather is poor, meaning you can't fully experience the region's breathtaking beauty. Plan your travel dates in line with the most popular seasons. May, June, and November These are some of the best months to visit the Caribbean. During this time, mild sunshine makes it easy to sunbathe and relax. Temperatures range from 68 to 77 degrees. There are fewer tourists as it's not the peak season, so you can enjoy boat rides and other water activities at low prices. There are occasional showers, but rain shouldn't stop play. February to May These are the driest months in the Caribbean but also the busiest with tourists flocking from Europe. There are plenty of festivals at this time of year, like the Holetown Festival, Bequia Regatta, and some sailing festivals. The weather is generally dry and hot, with temperatures reaching up to 86 degrees. The calm sea is ideal for swimming, sailing, snorkeling, and other water activities. Water visibility in the clear sea can be up to 45 meters deep, making it the best time to dive and experience marine life.

What licenses do I need to charter a boat in the Caribbean?

Most Caribbean destinations require an internationally recognized sailing license for bareboat charters. Check our detailed licensing guide for specific requirements by island. Alternatively, hire one of our professional skippers if you don't have a license.

How much does it cost to charter a boat in the Caribbean?

Prices vary by season and boat type. Sailboats range from $300-500/day in low season to $450-700/day in high season. Catamarans cost $500-800/day in low season and $750-1200/day in peak season. Motor yachts start at $800/day and can exceed $2000/day during peak periods.

When is the best time to sail in the Caribbean?

The prime sailing season is December through April, with temperatures around 82°F (28°C) and steady trade winds of 15-20 knots. You'll enjoy clear skies, calm seas, and perfect conditions for visiting attractions like the Baths in BVI or the Tobago Cays Marine Park.

What additional costs should I expect for a Caribbean charter?

Beyond the charter fee, budget for: mandatory end-cleaning ($150-600), security deposit (or insurance $150-400), marina fees (typically $50-150/night, 50% higher for catamarans), and local cruising permits. We offer flexible payment plans with just 15% down payment.

What support services do you offer in the Caribbean?

We provide comprehensive services including airport transfers , provisioning, and charter insurance . Our local partners ensure smooth check-in/out and 24/7 support throughout your charter.

Can I cancel my Caribbean charter booking?

Select boats offer extended free cancellation periods pending confirmation. We also provide a unique 3-installment payment plan and exclusive discounts on many Caribbean charters. Specific cancellation terms are clearly outlined during booking.

Do you offer crewed charters in the Caribbean?

Yes! We provide bareboat, skippered, and fully crewed options across the Caribbean. Whether you're an experienced sailor or first-timer, we'll match you with the perfect boat and crew. We can source any professionally chartered boat, even if not yet in our database.

Luxury Yacht Charter in the Caribbean

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Three Ways to Sail in Caribbean

Explore Caribbean 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 Caribbean's beautiful waters your way.

Bareboat / Captain Optional

Ideal for experienced sailors seeking complete freedom and control for their Caribbean yacht rental experience.

•Complete control over sailing itinerary around Caribbean
•Privacy and intimacy for your group
•Opportunities to improve sailing skills in Caribbean's waters
•Cost-effective boat rental option for larger groups

Show all bareboat rentals in Caribbean

Skippered / Captain Mandatory

Perfect for those seeking a balance of freedom and expert guidance while enjoying a boat rental in Caribbean.

•Professional navigation and safety with local Caribbean expertise
•Local knowledge and recommendations for hidden gems in Caribbean
•Relaxed sailing experience in the beautiful waters of Caribbean
•No license required for your Caribbean yacht charter adventure

Show all skippered rentals in Caribbean

Fully Crewed

The ultimate luxury yacht charter experience in Caribbean with full professional service.

•Complete relaxation and comfort throughout your Caribbean boat journey
•Professional crew service tailored to your needs
•Gourmet dining experience featuring local Caribbean cuisine
•Personalized itinerary planning to explore the best of Caribbean

Show all crewed charters in Caribbean

Discover the Magic of Caribbean with a Boat Charter

The Caribbean offers a sailor's paradise with crystal-clear turquoise waters, steady trade winds, and over 7,000 islands to explore. From the vibrant culture of the British Virgin Islands to the secluded coves of the Grenadines, chartering a boat here opens up endless possibilities for tropical adventures, world-class snorkeling, and island-hopping experiences.

Why Book With Us?

Year-Round Sailing Paradise
The Caribbean boasts ideal sailing conditions throughout the year, with consistent trade winds and temperatures ranging from 75-85°F (24-29°C). The peak season from December to April offers perfect weather, while the summer months bring warmer temperatures and occasional afternoon showers, along with better deals on charters.
Flexible Booking Options
Plan your Caribbean escape with confidence using our flexible payment options, including a 3-installment plan with just 15% down payment. Select boats offer free cancellation up to 30 days before departure, and early bookers can enjoy exclusive discounts on peak season charters.
Your Perfect Boat Awaits
Whether you're dreaming of a luxurious catamaran in the BVI, a comfortable sailboat in Antigua, or a sleek motor yacht in St. Martin, we've got you covered. Prices start from $350/day for sailboats to $1,200/day for catamarans, with options for every group size and budget.
Seamless Local Support
Our Caribbean partners ensure a smooth sailing experience from start to finish. We arrange reliable airport transfers, connect you with experienced local skippers, and offer comprehensive charter insurance through Sealogy for peace of mind on the water.
Routes for Every Sailor
From the protected waters of the Virgin Islands to the adventurous passages between St. Vincent and the Grenadines, we'll help you plan the perfect itinerary. First-time sailors can enjoy easy island-hopping in the BVI, while experienced crews can tackle more challenging routes through the Windward Islands.

The Borrow A Boat Promise

We Make Boating in Caribbean Easy

Experience the ultimate yacht charter and boat rental in Caribbean with our seamless booking platform. From luxury vessels to affordable options, discover the perfect boat for your Caribbean adventure today.

Secure online payments: Book your Caribbean boat rental with confidence through our protected payment system, ensuring your transaction is safe and worry-free.
Avoid endless back-and-forth with brokers: Our streamlined platform connects you directly with verified boat owners in Caribbean, saving you time and hassle when booking your perfect vessel.
Book your charter within minutes: Our user-friendly system lets you secure your Caribbean yacht charter instantly, with immediate confirmation and all details at your fingertips.
Best offers on 1000s of boats: Choose from the largest selection of boat rentals in Caribbean, with competitive prices and exclusive deals on everything from sailboats to luxury yachts.

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Caribbean Yacht Charter Guide

Pristine waters, year-round sailing, and island-hopping paradise across multiple nations

Perfect for:

Island HoppingBeach LoversSnorkeling

Information type
High and Low Season
Description
Peak season runs December through April with premium rates and perfect weather. Low season offers better deals May through November but includes hurricane season.
Best months to book:
December, January, February, March
Information type
Marinas, Ports and Mooring
Description
Mix of full-service marinas and secluded anchorages throughout the islands. Most popular destinations offer mooring balls and modern facilities.
Best places to stay:
Rodney Bay Marina, Virgin Gorda Yacht Harbor, Port Louis Marina
Information type
Wind & Weather
Description
Steady trade winds and tropical climate provide ideal sailing conditions. Afternoon squalls common but brief.
Temperature & Winds:
75°F to 85°F, 15-20 knots, Beaufort 4-5
Information type
Required Licenses and Certifications
Description
Requirements vary by island nation but generally accept international sailing certificates. Some areas require local permits.
Best license to hold:
International Certificate of Competence, ASA 104 Bareboat Charter Certification

Currency: USD
Season: November - July

Sailing Conditions in Caribbean

The Caribbean is a premier sailing destination renowned for its consistent trade winds, crystal-clear waters, and over 7,000 islands spanning 1 million square miles. The prime sailing season runs from December to April, offering perfect conditions with steady winds and minimal rainfall. The region combines stunning tropical landscapes with excellent sailing infrastructure, making it a paradise for sailors seeking both adventure and relaxation.

Wind Conditions

•Eastern Caribbean experiences reliable trade winds from November to June, typically Force 4-5 (11-21 knots) from the northeast to east
•Windward Islands (Grenada, St. Vincent, St. Lucia) receive stronger winds, often Force 5-6 (17-27 knots), with acceleration zones between islands
•Leeward Islands (Virgin Islands, St. Martin, Antigua) enjoy moderate winds, typically Force 3-5 (7-21 knots), ideal for casual sailing
•Western Caribbean (Jamaica, Cayman Islands) experiences lighter winds, Force 2-4 (4-16 knots), with occasional northerly winter fronts
•Hurricane season from June to November can bring variable conditions and requires careful planning

Sea State

•Eastern Caribbean sees Atlantic swells of 3-6 ft (1-2 m) on windward coasts
•Protected leeward coasts typically experience calmer waters of 1-3 ft (0.3-1 m)
•Passages between islands can have choppy conditions with waves up to 8 ft (2.4 m)
•Western Caribbean generally has calmer seas, averaging 2-4 ft (0.6-1.2 m)
•Protected anchorages throughout the region offer flat water sailing opportunities

Temperature

•Air temperatures remain consistently warm year-round, ranging from 75°F to 85°F (24°C to 29°C)
•Water temperatures vary seasonally from 75°F to 83°F (24°C to 28°C)
•Coolest period is December to February, with temperatures around 75°F (24°C)
•Humidity levels are higher during summer months, May to October

Tides and Currents

•Tidal ranges are generally minimal, typically 1-2 ft (0.3-0.6 m)
•The Caribbean Current flows westward through the region at 0.5-1 knots
•Stronger currents of 2-3 knots can be found in passages between islands
•The Antilles Current north of the Greater Antilles flows eastward at 1-2 knots
•Local currents around islands can be significant, especially in channels

Best Sailing Areas for Different Skill Levels

•Beginners: British Virgin Islands (BVI) offer protected waters, easy navigation, and numerous anchorages. St. Vincent's Grenadines and St. Martin's Simpson Bay provide gentle conditions and short passages
•Intermediate: Windward Islands (Martinique to Grenada), Puerto Rico's Spanish Virgin Islands, and US Virgin Islands offer more challenging conditions with longer passages and varying wind strengths
•Advanced: Eastern Caribbean passages between major island groups, Dominica to Guadeloupe route, and offshore passages to Western Caribbean destinations (Cuba, Jamaica, Cayman Islands) present challenging conditions and complex navigation

Best Time to Rent a Boat in Caribbean

The Caribbean offers year-round sailing opportunities across 7,000 islands featuring crystal-clear waters, steady trade winds, and diverse cultures. From the Virgin Islands to the Windward Antilles, sailors find protected anchorages, vibrant coral reefs, and well-equipped marinas. The region's reliable easterly winds and numerous line-of-sight navigation routes make it particularly appealing for both novice and experienced sailors.

High Season (December to April)

Pros & advantages: Steady northeast trade winds of 15-20 knots provide ideal sailing conditions throughout the Lesser Antilles; Low humidity and minimal rainfall create perfect conditions for island hopping between St. Martin and Grenada; Peak season for beach bars, restaurants, and marine facilities, especially in popular spots like the BVIs
Cons & disadvantages: Charter rates can be 50% higher than low season, particularly during holiday weeks in the Virgin Islands; Popular anchorages in places like The Bight at Norman Island often reach capacity by early afternoon; Advanced reservations required for most marinas and mooring balls, especially in the Spanish Virgin Islands

Shoulder Season (May to July)

Pros & advantages: Moderate trade winds of 10-15 knots perfect for family cruising around the Leeward Islands; Reduced charter rates and greater availability of preferred vessels for island exploration; Less crowded anchorages in prime locations like the Tobago Cays and Les Saintes
Cons & disadvantages: Increasing chance of afternoon squalls, particularly when sailing near Dominica and St. Lucia; Temperature rises to 85-90°F (29-32°C), making midday sailing more challenging without steady winds; Some beach restaurants and facilities begin reducing hours as tourist numbers decrease

Low Season (August to November)

Pros & advantages: Lowest charter rates of the year with potential savings of 30-40% on bareboat charters; Warm water temperatures of 84°F (29°C) perfect for swimming and snorkeling adventures; Excellent deals on flights and marina fees throughout the entire Caribbean basin
Cons & disadvantages: Hurricane season peaks in September, requiring flexible planning and comprehensive insurance coverage; Variable wind conditions ranging from dead calm to sudden squalls around mountainous islands; Many facilities operate on reduced schedules, particularly in smaller islands like Bequia and Mayreau

For the optimal combination of sailing conditions and amenities, plan your Caribbean charter during the high season between December and April, when steady trade winds and perfect weather prevail. Shoulder season (May-July) offers an excellent balance of good conditions and value, ideal for families and budget-conscious sailors. While low season presents the best deals, it requires more flexible planning and experienced sailing skills to handle variable conditions and potential weather disruptions. First-time charterers should strongly consider high or shoulder season, while experienced sailors can take advantage of low season savings with proper preparation.

Which Boat to Charter in Caribbean?

When planning a yacht charter in Caribbean, 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 Caribbean:

Catamaran

Spacious, stable multi-hull vessels offering comfort and luxury for larger groups and families.

•Perfect for families and larger groups seeking stability and space
•Features spacious living areas with multiple cabins and large deck spaces
•Excellent stability and easy maneuverability for comfortable sailing

View 934 available catamarans for rent in Caribbean

Monohull Sailboat

Classic sailing vessels perfect for authentic maritime experiences, combining tradition with modern comfort.

•Ideal for traditional sailing enthusiasts and smaller groups
•Offers a more authentic sailing experience with excellent performance
•More affordable compared to catamarans and motor yachts

View 235 available sailboats for rent in Caribbean

Motor Yacht

Luxurious powered vessels combining speed, comfort, and high-end amenities for premium cruising experiences.

•Ideal for covering longer distances with speed and comfort
•Offers premium amenities and modern luxury features
•Perfect for exploring multiple destinations without wind dependence

View 91 available motorboats for rent in Caribbean

Speedboat

Agile, open boats designed for thrilling day trips and water sports activities.

•Ideal for exciting day trips and water sports
•Perfect for quick coastal exploration
•Easy to handle with great maneuverability

View 51 available speedboats for rent in Caribbean

Power Catamaran

Twin-hulled motor vessels offering exceptional space and stability with powerful performance.

•Combines catamaran stability with motorboat speed
•Spacious layout with excellent fuel efficiency
•Perfect for comfortable long-distance cruising

View 41 available power catamarans for rent in Caribbean

RIB

Rigid Inflatable Boats combining speed, safety, and versatility for dynamic water activities.

•Excellent for day trips and water sports
•Superior stability and safety in various conditions
•Perfect for coastal exploration and quick transfers

View 5 available RIBs for rent in Caribbean

Houseboat

Floating vacation homes offering a unique blend of comfort and water-based living.

•Perfect for those seeking a floating apartment experience
•Ideal for calm waters and peaceful harbor stays
•Offers home-like comfort with full living amenities

View 1 available Houseboat for rent in Caribbean

Gulet

Traditional wooden sailing vessels offering unique charm with modern comfort, ideal for luxury charter experiences.

•Traditional wooden sailing vessels with timeless charm
•Spacious deck areas perfect for entertaining and relaxation
•Comes with professional crew for a premium charter experience

No Gulet available in Caribbean, view other locations

Caribbean Yacht Charter FAQ

What licenses do I need to charter a boat in the Caribbean?
Most Caribbean destinations require an internationally recognized sailing license for bareboat charters. Check our detailed licensing guide for specific requirements by island. Alternatively, hire one of our professional skippers if you don't have a license.
How much does it cost to charter a boat in the Caribbean?
Prices vary by season and boat type. Sailboats range from $300-500/day in low season to $450-700/day in high season. Catamarans cost $500-800/day in low season and $750-1200/day in peak season. Motor yachts start at $800/day and can exceed $2000/day during peak periods.
When is the best time to sail in the Caribbean?
The prime sailing season is December through April, with temperatures around 82°F (28°C) and steady trade winds of 15-20 knots. You'll enjoy clear skies, calm seas, and perfect conditions for visiting attractions like the Baths in BVI or the Tobago Cays Marine Park.
What additional costs should I expect for a Caribbean charter?
Beyond the charter fee, budget for: mandatory end-cleaning ($150-600), security deposit (or insurance $150-400), marina fees (typically $50-150/night, 50% higher for catamarans), and local cruising permits. We offer flexible payment plans with just 15% down payment.
What support services do you offer in the Caribbean?
We provide comprehensive services including airport transfers, provisioning, and charter insurance. Our local partners ensure smooth check-in/out and 24/7 support throughout your charter.
Can I cancel my Caribbean charter booking?
Select boats offer extended free cancellation periods pending confirmation. We also provide a unique 3-installment payment plan and exclusive discounts on many Caribbean charters. Specific cancellation terms are clearly outlined during booking.
Do you offer crewed charters in the Caribbean?
Yes! We provide bareboat, skippered, and fully crewed options across the Caribbean. Whether you're an experienced sailor or first-timer, we'll match you with the perfect boat and crew. We can source any professionally chartered boat, even if not yet in our database.

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