private boat CHARTERS

The Ultimate in Personalized Private Virgin Islands Sailing

Imagine a day on the water designed entirely around you. No fixed schedule, no sharing with strangers, no compromises on what you want to experience. Our private sailing charters departing from Sapphire Beach in St. Thomas offer complete freedom to create your perfect Virgin Islands adventure. Whether you’re planning a romantic proposal, celebrating a milestone with family, hosting clients, or simply want the intimacy and flexibility of having the boat to yourselves, a private charter transforms good into extraordinary.

With VI Day Sailing’s private charters, you’re not just booking a boat, you’re securing a dedicated crew, a floating platform for your celebration or relaxation, and the flexibility to explore the pristine waters between St. Thomas and St. John exactly as you envision. Want to anchor at a secluded beach for hours? Done. Prefer to visit multiple snorkeling spots? Absolutely. Need to coordinate specific timing for a surprise proposal? We’ll make it perfect. This is sailing the Virgin Islands on your terms.

Why Choose a Private Sailing Charter?

Complete Privacy and Intimacy

The boat is exclusively yours. No other guests, no strangers in your photos, no adjusting your plans to accommodate others’ preferences. This privacy is invaluable for couples seeking romance, families wanting quality time together, or groups celebrating special moments. You can relax completely, be yourselves, and create genuine memories without any outside distractions.

Personalized Service and Attention

Your dedicated captain and crew focus entirely on your group. They get to know your preferences, adjust to your comfort level, share knowledge about locations that interest you, and ensure every detail meets your expectations. This personalized attention elevates the entire experience, making you feel truly cared for rather than just another booking.

Perfect for Special Occasions

Some moments deserve a perfect setting. Private charters excel for proposals, honeymoons, anniversaries, milestone birthdays, family reunions, celebrations of life –  or any celebration where you want everything just right. We can help coordinate special touches – decorations, champagne, specific music, photography timing, or whatever makes your occasion memorable. The privacy ensures your special moment remains intimate and genuine.

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Private Charter Options

Private Sunset Cruise

An intimate private sunset cruise is one of St. Thomas’s most romantic experiences. Departing from Sapphire Beach in the late afternoon, you’ll sail the waters between St. Thomas and St. John as golden light transforms the seascape. Perfect for proposals, anniversaries, or simply celebrating each other, a private sunset charter creates magic. Choose your departure time, select your route, and enjoy champagne or cocktails as the Caribbean sky puts on its nightly show – just for you. Typical duration: 2 hours

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Full Day Private Adventure

The full day private charter is our most popular option for good reason – it provides time to truly experience everything the Virgin Islands offer without any rushing. Depart Sapphire Beach mid-morning and spend 6-8 hours exploring the best of St. Thomas and St. John. Visit multiple snorkeling locations, each offering different marine life and reef formations. Stop at secluded beaches accessible only by boat. Enjoy a catered lunch at a scenic anchorage. Swim, sail, relax, explore – all at your preferred pace. The full day format lets the experience breathe, creating those spontaneous moments that become favorite vacation memories. Typical duration: 6-8 hours

Book the FULL DAY ADVENTURE

Extended Private Experience + Sunset

For those who want the ultimate Virgin Islands sailing day, the extended private charter combines full day exploration with a sunset finale. Spend the day snorkeling, swimming, and discovering the islands’ beauty, then remain on the water as other boats return to harbor. As the sun begins its descent, we’ll position perfectly for sunset viewing, providing champagne and appetizers while you watch the sky transform. Return to Sapphire Beach under early stars, tired in the best possible way, with a day’s worth of incredible memories. This is the charter people talk about for years. Typical duration: 8-10 hours

Book FUll day + sunset cruise

We can Accommodate Larger Groups – up to 18 People!

Private charters work for groups from two to larger parties. Intimate couples find the exclusivity perfect for romance. Families appreciate having the boat to themselves. Friend groups celebrate together without outsiders. The key is ensuring everyone has comfortable space. When contacting us, let us know your group size and we’ll recommend the appropriate vessel for your needs.

Frequently Asked Questions

A private charter means the boat is exclusively yours. You choose the departure time, customize the itinerary completely, control the pace of activities, and enjoy total privacy with just your group. No sharing with strangers, no predetermined schedule that can’t be adjusted, no compromises on what you want to experience. It’s your boat, your day, your way. The crew’s attention is focused entirely on your group, and we can incorporate special requests and personal touches impossible on shared tours.

We accommodate groups from intimate couples (perfect for proposals or anniversaries) to larger parties for family reunions, corporate events, or friend celebrations. The exact capacity depends on the vessels used, but we ensure everyone has comfortable space and the charter doesn’t feel crowded. When you contact us, let us know your group size and we’ll recommend the perfect boat(s) for your private charter.

Absolutely! That’s the beauty of a private charter. Want to spend the entire day snorkeling at multiple reefs? Prefer beach hopping? Have specific locations you want to visit? Planning a proposal and need perfect timing? Celebrating an anniversary and want a romantic atmosphere? We’ll create an itinerary tailored exactly to your vision. We offer recommendations based on weather, sea conditions, and our experience, but the final decisions are yours.

We strongly recommend booking as far in advance as possible, especially for peak season dates (December-April), weekends, holidays, or if you require a specific date for a special occasion like a proposal or anniversary. Popular dates can book months ahead. That said, we sometimes have last-minute availability – if you’re already in St. Thomas or need something soon, contact us and we’ll do our best to accommodate. Earlier booking simply ensures you get your preferred date and gives us more time to coordinate any special requests.

Private charters represent a higher investment than shared tours because you’re reserving the entire vessel exclusively for your group. However, for groups of 4-6+ people, when you divide the charter cost among participants, the per-person price often approaches shared tour rates while offering dramatically superior service, customization, and privacy. For special occasions where privacy and personalization matter, many guests find the value well worth the investment. Contact us for specific pricing based on your group size, desired duration, and any special requests.

We provide beverages and food appropriate to your charter length as part of the package. However, private charters offer flexibility for special requests. Want specific wines or champagne? Dietary restrictions requiring particular foods? A birthday cake for a celebration? Special cocktails? Let us know your preferences and we’ll accommodate. In some cases, we can coordinate with local restaurants for catered meals, or you can bring items that have special meaning for your occasion.

A private sunset sail is one of the most romantic proposal settings imaginable. The natural beauty of the Caribbean, the intimacy of having the boat to yourselves, the magic of golden hour light, and the ability to coordinate perfect timing all combine to create an unforgettable moment. We’ve coordinated many proposals and can help with details like timing, positioning the boat for the best backdrop, providing champagne for the celebration, and even working with photographers if you want the moment captured professionally. We’ve yet to receive a “no” during a proposal on one of our charters!

Let us know about any mobility concerns when booking so we can ensure the vessel we assign can accommodate your needs safely and comfortably. We want everyone in your group to fully enjoy the charter. Our crew is experienced in assisting guests with various needs, and the private nature of your charter means we can adjust activities and pace to ensure everyone participates at their comfort level.

Absolutely, families with children are very welcome. The private charter format actually works wonderfully for families because you can customize activities to different age levels and take breaks whenever needed. We have safety equipment for all ages, and the private nature means you don’t worry about your children disturbing other guests. Many families tell us their private charter was the highlight of their Virgin Islands vacation because it brought everyone together for a shared adventure.

We monitor weather closely and prioritize your safety and enjoyment. If conditions are unsuitable for sailing, we’ll contact you to discuss options – rescheduling to another day during your visit, modifying the itinerary to more protected waters, or providing a full refund if rescheduling isn’t possible. The Caribbean generally offers predictable weather, but we maintain flexibility to ensure the best possible experience. For private charters booked far in advance, we work with you to find alternative dates if weather becomes a concern.

Yes! Private charters can include music tailored to your preferences. Want a specific playlist for your celebration? Prefer particular genres? Planning a proposal and need the perfect song at the right moment? Let us know your musical preferences and we’ll arrange it. We can create whatever atmosphere you’re envisioning.

Yes, we regularly host corporate groups for client entertainment, team building, and business meetings in a unique setting. The private charter format works excellently for corporate purposes. It’s impressive enough to wow clients, intimate enough for genuine relationship building, and the beauty of the Virgin Islands creates positive associations with your company or team. We can customize duration, activities, and catering to match your corporate objectives. Contact us to discuss how a private charter can support your business goals.

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up to 6 guests – PRIVATE SUNSET SAIL FROM $695
7 to 12 guests – click here
up to 6 guests – PRIVATE FULL DAY FROM $1260
7 to 12 guests – click here
more than 12? click here
  • Customizable Options
  • Open Bar & Snacks
  • Snorkeling Equipment
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