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Best Caribbean Charters to Book Now | Luxury Sailing

Are you dreaming of sun-soaked islands and crystal-clear waters? A Caribbean yacht charter offers a...

Are you dreaming of sun-soaked islands and crystal-clear waters? A Caribbean yacht charter offers a unique way to explore these stunning destinations. Yachting combines luxury with the thrill of adventure, giving you access to secluded beaches and vibrant marine life. In this guide, we will cover the essentials of booking the best Caribbean charters.

We have years of experience in the yacht charter business, and we’re here to provide all the information you need. We’ll help you choose the right yacht and know what to expect for a perfect Caribbean charter. Let’s explore the world of Caribbean yachting together.

Relax and unwind on the deck of the Ohana power catamaran as you explore the beautiful Bahamas, a popular choice for Caribbean charters.
The Bahamas dream of crystal-clear waters and endless horizons from aboard the Ohana.

What are Caribbean charters?

Ever wished for a vacation where you cruise crystal-clear waters, explore hidden islands, and set your own pace? A Caribbean yacht charter makes that dream a reality.

Imagine this: You set sail on a private yacht, discovering secluded coves and vibrant towns. Charters offer a unique way to experience the Caribbean, and there are different yacht types to fit your style.

  • Motor Yachts: luxurious and powerful, ideal for relaxation and enjoying top-of-the-line features.
  • Power Catamarans: spacious and stable, with plenty of room for families and friends to spread out and soak up the sun.
  • Sailing Catamarans: Experience the thrill of sailing with the comfort of a wide layout. These are perfect for exploring the Caribbean with a crew to handle the sailing for you.
  • Sailboats: For adventurous travelers who enjoy sailing. These charters typically come with a captain or crew to guide you.

Why choose Caribbean charters? Escape the Ordinary

Dreaming of a vacation unlike any other? A Caribbean yacht charter offers a memorable way to explore the islands, all on your own terms. Here’s why a charter might be the perfect fit for you:

  • Privacy Paradise: Relax on your private yacht with endless turquoise waters. Escape the crowds and unwind in pure serenity.
  • Craft Your Dream Adventure: Unlike staying at a single resort, a charter lets you design your ideal travel plan. Visit hidden coves, bustling towns, or famous beaches—you pick the destinations!
  • Unlock Hidden Gems: With a private yacht, you can reach secluded spots that are hard to reach on larger cruises. Explore secret beaches and pristine reefs.
  • Something for Everyone: Whether you want a quiet beach or an adventurous snorkel, a charter meets all desires.

Where to Set Sail: Picking Your Perfect Caribbean Charters Destination

The Caribbean has many islands ready to be explored. Here’s a glimpse at some popular destinations, each offering something unique for your dream charter:

The British Virgin Islands:

Scenic view of Anegada Beach in the British Virgin Islands with crystal-clear water, palm trees, and chairs. Explore the Caribbean with Caribbean Charters.
Relax on the shores of Anegada Beach in the British Virgin Islands.
  • Known for: its breathtaking beaches, calm sailing conditions, and relaxed atmosphere.
  • Island Features: Lush green mountains, secluded coves, and crystal-clear waters teeming with marine life.
  • Activities: Explore coral gardens, relax on pristine beaches, or visit charming island towns for local culture.
  • Cuisine: Fresh seafood takes center stage, with lobster, and conch, featured prominently in dishes.

St. Lucia:

A majestic view of Gros Piton, a volcanic peak in St. Lucia, a Caribbean island. Explore the beauty of the Caribbean with Caribbean Charters.
Towering over the Caribbean Sea, Gros Piton is a volcanic peak that is a UNESCO World Heritage Site.
  • Known for: dramatic volcanic peaks, lush rainforests, and luxurious resorts.
  • Island Features: volcanic black sand beaches, cascading waterfalls, and hidden coves perfect for snorkeling.
  • Activities: hike through rainforest trails, soak in therapeutic mud baths, or sail along the scenic coastline.
  • Cuisine: St. Lucian cuisine is a delicious blend of African, French, and Indian influences. Sample local dishes like smoked marlin or curried goat.

St. Kitts:

Aerial view of Brimstone Hill Fortress, a UNESCO World Heritage Site on St. Kitts Island in the Caribbean.
Brimstone Hill Fortress: A UNESCO World Heritage Site, this formidable fortress offers stunning views of the Caribbean Sea.
  • Known for: its rich history, scenic beauty, and vibrant culture.
  • Island Features: Picturesque beaches, rolling hillsides, and Brimstone Hill Fortress, a UNESCO World Heritage Site.
  • Activities: hike Mount Liamuiga, visit Brimstone Hill Fortress or relax on golden sand beaches.
  • Cuisine: St. Kitts offers a delightful mix of Caribbean and European flavors. Don’t miss trying local specialties like steamed conch and St. Kitts sugar cake.

Leeward Islands:

Relaxing scene of a docked boat on a beautiful beach in Antigua with turquoise water, white sand, and palm trees.
Set sail for paradise in Antigua, where the beaches are pristine and the water is crystal-clear.
  • Island Chain Highlights: Known for its sailing conditions, and a relaxed atmosphere.
  • Features: lush green mountains, secluded coves with pristine beaches, and calm seas ideal for first-time sailors.
  • Activities: Explore coral reefs, relax on uncrowded beaches, or visit island towns for local life.
  • Cuisine: Fresh seafood takes center stage, with local dishes featuring lobster, conch, and island fish.

St. Martin (French side) & Saint Maarten (Dutch side):

Aerial view of Fort Louis Marina in Marigot, Saint Martin, with docked sailboats and motorboats.
Fort Louis Marina bustles with activity, offering a perfect starting point for exploring the Caribbean by boat.
  • Island Highlights: Diverse culture, duty-free shopping, and stunning beaches.
  • Features: The island has a French side (St. Martin) and a Dutch side (Saint Maarten), offering a unique blend of European and Caribbean influences. Relax on pristine beaches with calm waters on the French side, or explore the lively shops and casinos on the Dutch side.
  • Activities: Hike Pic du Paradis, shop in Philipsburg, or lounge on family-friendly beaches.
  • Cuisine: Enjoy French cafes and bistros on the French side, or indulge in Dutch specialties like stroopwafel (syrup waffles) on the Dutch side.

St. Vincent and the Grenadines:

Photo of a colorful church perched on a hilltop overlooking the blue ocean in St. Vincent and the Grenadines. Explore the Caribbean with Caribbean Charters.
Experience the lush rainforests, beautiful beaches, and clear waters of St. Vincent and the Grenadines.
  • Island Chain Highlights: Picturesque islands, secluded bays, and a relaxed atmosphere.
  • Features: The Grenadines are a collection of smaller islands, many of which are empty, offering a true escape. Explore hidden coves with white-sand beaches and crystal-clear waters.
  • Activities: hike to waterfalls on St. Vincent, kayak in secluded bays, or relax on pristine beaches.
  • Cuisine: Fresh seafood is a staple, with lobster, conch, and local fish featured prominently in dishes.

Selecting the Ideal Caribbean Charters for Your Ultimate Getaway: How to Choose?

Selecting the right yacht for your Caribbean charter is essential for an enjoyable trip. Here’s a simple guide to help you make an informed decision:

  • What: Determine the type of yacht that suits your needs.
  • Where: Consider your destinations. Some yachts are best for shallow waters and secluded coves; others are best for open-sea voyages.
  • When: Think about the time of year for your charter. Peak seasons offer vibrant activities and events, while off-peak seasons provide quieter, more private experiences. Different yachts may offer better experiences, depending on the season.
  • How: Assess your group’s size and preferences. Larger groups may need more space and amenities, while smaller groups might prefer a cozier, more intimate setting. Also, consider the level of crew service you want.

Choosing the right yacht ensures you get the most out of your Caribbean yacht charter experience. Our information is here to help you evaluate your options, ensuring a trip that matches your desires and expectations. Let’s explore how to find the perfect yacht for your adventure.

Choosing the Yacht Type for Your Next Caribbean Charters

REACH (Sailing Catamaran)

  • Considerations: The REACH sailing catamaran stands out for its size, layout, capabilities, and ideal usage. This model is perfect for long voyages and exploring multiple destinations.
  • Size and Layout: The 50-foot REACH catamaran has spacious cabins and a wide deck for a medium-sized group. The layout enhances both functionality and relaxation, making it ideal for family trips or group charters.
  • Features: The REACH catamaran offers excellent stability and speed, appealing to those who enjoy smooth sailing. Luxury amenities include a fully equipped kitchen, comfortable living areas, and outdoor lounging spaces.
  • Location Details: USVI/BVI
  • Operating Area:
    • Summer Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
    • Winter Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

RAPSCALLION (Sailing Catamaran)

  • Considerations: The RAPSCALLION sailing catamaran is flexible and fits many types of trips.
  • Size and Layout: The compact yet efficient design of the RAPSCALLION allows for easy maneuvering and docking. It comfortably fits smaller groups, making it perfect for intimate getaways.
  • Features: This model boasts a balance of speed and stability, ensuring a smooth ride. It offers cozy cabins, modern amenities, and a pleasant traditional sailing experience.
  • Location Details: USVI/BVI
  • Operating Area:
    • Summer Operating Area: Caribbean Windwards, Caribbean Virgin Islands (US)
    • Winter Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

    $11,000 - $11,000/ week + expensesCaribbean Virgin Islands (BVI) + 3 others

    6345.00 Ft

PROMISCUOUS (Sailing Catamaran)

  • Considerations: The PROMISCUOUS catamaran offers both comfort and adventure. Its distinct features make it suitable for various sailing conditions.
  • Size and Layout: With a generous size of 58 feet, the PROMISCUOUS provides ample space for guests. Its layout ensures comfort and functionality for long trips.
  • Features: The catamaran offers excellent stability, making it perfect for longer trips. Luxury amenities include spacious cabins, modern entertainment systems, and gourmet dining facilities.
  • Location Details: SXM ports are available with approval; add $4,000 (round trip, not each way). Preferred time after May 1st for charters out of the Virgin Islands.
  • Operating Area:
    • Summer Operating Area: Caribbean Virgin Islands (BVI)
    • Winter Operating Area: Caribbean Virgin Islands (BVI)

    $32,000 - $36,000/ week + expensesCaribbean Virgin Islands (BVI) + 1 others

    10558.00 Ft

M/Y QARA (Motor Yacht)

  • Considerations: The QARA motor yacht is a luxurious option ideal for high-speed travel and exploring multiple destinations.
  • Size and Layout: Its large size and layout provide comfort and privacy for short or long trips.
  • Features: QARA offers high speed, stability, luxury amenities, modern entertainment, lavish interiors, and spacious decks.
  • Location Details: Based in St. Croix, there is no delivery fee for week-long charters out of St. Thomas and BVI. They have 2023 and 2024 BVI permits!
  • Operating Area: US Virgin Islands

M/Y PRIME TIME (Motor Yacht)

  • Considerations: PRIME TIME is a versatile motor yacht designed for comfort and performance, suitable for various types of charters.
  • Size and Layout: Its size and layout maximize comfort and usability for small to medium groups.
  • Features: PRIME TIME offers modern amenities, including comfortable cabins, entertainment options, and outdoor relaxation areas. Its design provides a traditional motor yacht experience with modern comforts.
  • Location Details: Based from Tortola’s East End, near the airport
  • Operating Area:
    • Summer Operating Area: British Virgin Islands (BVI)
    • Winter Operating Area: British Virgin Islands (BVI)

PHILOTIMO (Power Catamaran)

  • Considerations: PHILOTIMO is powerful and stable, making it perfect for those seeking speed and comfort.
  • Size and Layout: The catamaran’s spacious design offers ample room and enhances functionality and relaxation.
  • Features: PHILOTIMO combines speed and stability, featuring luxury amenities like modern living spaces, gourmet kitchens, and ample lounging areas.
  • Locations Details: Available in BVI ONLY; November 2023 to August 2024
  • Operating Area:
    • Summer Operating Area: Caribbean Windwards, Caribbean Virgin Islands (BVI)
    • Winter Operating Area: Caribbean Virgin Islands (BVI)

    $32,000 - $38,000/ week + expensesCaribbean Virgin Islands (BVI) + 1 others

    6363.00 Ft

PERPETUAL BLUE (Sailing Catamaran)

  • Considerations: PERPETUAL BLUE is ideal for those seeking both adventure and luxury, with features for various sailing conditions.
  • Size and Layout: Its design provides ample space for guests, with a layout that ensures comfort and ease of movement.
  • Features: This catamaran offers excellent stability and luxury amenities, including comfortable cabins, modern entertainment, and outdoor spaces for relaxation.
  • Location Details: US/BVI
  • Operating Area:
    • Summer Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Leewards, Caribbean Windwards, Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
    • Winter Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Leewards, Caribbean Windwards, Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

Painted Pelican (Power Catamaran)

  • Considerations: Painted Pelican offers power and luxury, designed for travelers seeking both adventure and comfort.
  • Size and Layout: The catamaran’s spacious design ensures comfort and enhances functionality and relaxation.
  • Features: This power catamaran offers speed, stability, modern living spaces, gourmet kitchens, and outdoor lounging areas.
  • Location Details:  Nanny Cay Resort and Marina Tortola, British Virgin Islands
  • Operating Area:
    • Summer Operating Area: British Virgin Islands (BVI)
    • Winter Operating Area: British Virgin Islands (BVI)

Each of these yacht types offers unique benefits, catering to different preferences and needs. Selecting the right yacht ensures a memorable and enjoyable Caribbean charter experience tailored to your desires.

Set Sail on Your Dream Caribbean Charters Adventure: A Step-by-Step Guide

Ready to ditch the crowds and explore the Caribbean in style? Here’s a smooth ride through booking your memorable yacht charter with us:

  • Spark Your Inspiration: Let us know what tickles your fancy! Drop us a line about your ideal Caribbean escape. Are you dreaming of island hopping, diving with colorful fish, or simply soaking up the sun on secluded beaches? The more we know, the better we can tailor your dream vacation.
  • Chat It Up: We’ll schedule a personalized consultation to chat about your vision, answer any questions you have, and get to know your group. This is your chance to share your must-haves and hidden desires for your Caribbean adventure.
  • Find Your Perfect Yacht: Get ready to set your sights on stunning yachts! We’ll present a selection that matches your preferences, from luxurious catamarans to sleek motor yachts. Imagine yourselves relaxing on deck, enjoying breathtaking views, and creating lifelong memories.
  • Chart Your Course: Once you’ve found your ideal yacht, we’ll walk you through the contract and terms, ensuring everything is crystal clear. This is your chance to ask any questions and feel confident about setting sail.
  • Get Ready to Set Sail: We’ll provide a comprehensive pre-journey guide filled with helpful tips and information. This will cover everything from packing essentials to provisioning the yacht with delicious food and drinks.
  • Welcome Aboard! It’s finally here! Step aboard your private yacht and meet your friendly captain and crew. They’ll take care of everything, allowing you to unwind and begin your Caribbean paradise adventure.

Following these steps ensures a smooth and stress-free booking process for your Caribbean yacht charter. Plan carefully and communicate clearly for a memorable adventure.

Hear from Our Guests on their Caribbean Charters

Curious about what others are saying about their Caribbean charter adventures with us? See what our past guests have experienced:

REACH Guest Review

Total Perfection!

To say this was a trip of a lifetime would be an understatement. From your smiles each day to the amazing drink, snack and meals – all total perfection!

Life has been good to us to let us take this trip with you, but luck also played it’s hand at putting us on “Reach”.

I’m hopeful our paths will cross again with many cold drinks!
God bless you both



This was exactly the vacation that we needed! The perfect mix of activities and locations. You couldn’t have gotten more perfect mornings at each spot.

We really appreciated your local knowledge and sailing expertise. Thanks for a great first trip of many to the BVIs!

Zach Hagan
Baltimore, MD


Simply said, we had the best time imaginable. The Promiscuous is a nice boat, but Paul and Dani made it extraordinary! Their hospitality, knowledge of the BVI’s, professionalism, and personalities were incredible.

Paul managed the boat, took time to explain sailing, and got the boys involved. He planned the perfect itinerary for sailing and diving. Dani’s drive for happiness through food and service was unmatched by anyone I have ever met before.

They weren’t going to rest until our whole group of eight were satisfied. They made everything very simple for us. My wife and family can’t remember a vacation more rewarding.

We had some rain, but it was fine as the boys were diving, and Dani arranged a Spa Day for my wife.



Great time yachting around the BVI with our kind hosts Captain Ken & Julie of the Ruby One! Our group loved exploring Tortola, The Virgin Gorda Baths and Norman Island. Highlights included gourmet meals, comfy accommodations, tasty cocktails, and special family time.

Saba Rock, our favorite restaurant, is on a tiny island. Check out the upstairs bar and walk the grounds after dinner! The Ruby One is a beautiful yacht and we cannot recommend it enough!!

Maximizing Your Caribbean Charters Experience: Tips for a Smooth Journey

Your Caribbean yacht charter promises to be a memorable adventure. Here are some tips to help you get the most out of your trip:

  • Communicate with the Crew: Communicate clearly with the crew to ensure your needs and preferences are met. Share your travel plan preferences, dietary restrictions, and any special requests.
  • Be Flexible: Weather conditions and other factors may affect your plans. Stay open to changes and trust the crew’s expertise in navigating the best routes.
  • Respect Local Cultures: Be mindful of local customs and traditions. Show respect and appreciation for the cultures you encounter during your journey.
  • Stay Safe: Follow safety guidelines provided by the crew, especially when engaging in water activities. Use life jackets when necessary and be cautious in unfamiliar waters.
  • Pack Smart: Bring essentials and pack light. Remember that space on the yacht may be limited, so avoid overpacking.
  • Stay Hydrated: The Caribbean sun can be intense. Drink plenty of water and protect yourself from the sun with sunscreen, hats, and sunglasses.
  • Relax and Enjoy: Embrace the slower pace and enjoy the beauty of your surroundings. Take time to relax, unwind, and fully immerse yourself in the experience.

By following these tips, you’ll ensure a smooth and enjoyable Caribbean yacht charter. Your adventure awaits—let the journey begin!

FAQS | Caribbean Charters


The Caribbean calls out with turquoise waters, lush islands, and endless adventure. Caribbean charters offer a unique way to experience it all on your own terms. This reference has helped you explore the possibilities, from choosing the perfect yacht to crafting your dream travel plan.

Key Takeaways for Perfect Caribbean Charters:

  • Match Your Needs to the Yacht: Consider your group size, travel style, and desired amenities to find the ideal yacht for your adventure.
  • Plan Your Paradise: Choose the islands to visit, the activities you like, and the vibe you want for your trip.
  • Communicate for Success: Tell the captain or crew your preferences to tailor the experience to your group’s desires.

Ready to start planning your memorable Caribbean charters? Contact the CKIM Team today! We can answer any questions you have and help you find the perfect yacht and travel plan to turn your dream vacation into reality.

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