st thomas boat charters

Bring Your Whole Crew on the Water

Planning a celebration, corporate event, family reunion, or group adventure with more than six people? Don’t let group size limit your Virgin Islands sailing experience. Our large group sailing charters accommodate up to 18 guests through our coordinated multi-boat fleet system. Instead of settling for a crowded commercial tour or splitting your group across different times, we can sail multiple boats from our fleet, creating a unified experience where your entire group shares the same adventure across the beautiful waters between St. Thomas and St. John.

Departing from Sapphire Beach, the boats sail in formation, anchor together at each location, and follow the same itinerary throughout the day. At swimming stops, snorkeling sites, and beaches, your entire group comes together to share the experience. It’s the perfect solution for bachelor and bachelorette parties, corporate team building, extended family vacations, wedding party celebrations, milestone birthdays, or any occasion where you want your whole group to experience the magic of sailing the Virgin Islands together.

Ideal For Group Events and Celebrations

Bachelor and Bachelorette Parties

Make your bachelor or bachelorette party legendary with a day of sailing, snorkeling, and celebrating in paradise. The multi-boat format works perfectly for these parties – the group stays together for swimming and beach activities while having comfortable space during sailing segments. Bring your crew, enjoy the open bar, snorkel pristine reefs, visit secluded beaches, and create memories that’ll be retold at the wedding and for years after. We’ve hosted countless bachelor and bachelorette parties and know how to make your celebration special while keeping everyone safe and having a blast.

Friends’ Group Vacations

Traveling to St. Thomas with a large friend group? A sailing charter becomes the centerpiece activity that brings everyone together. Rather than splitting into smaller activities or dealing with the logistics of separate bookings, one large group charter gets everyone on the water together. Whether you’re college friends reuniting, longtime friend groups on annual trips, or neighborhood friends on vacation together, sailing the Virgin Islands as a group creates stories you’ll retell for years.

Milestone Birthday Celebrations

Turn a milestone birthday – 30th, 40th, 50th, or beyond – into an adventure. Invite your closest friends for a day of celebration on the water. The large group format means you can bring everyone who matters rather than limiting to a small handful. Toast the birthday honoree at sunset, snorkel together, share laughs on pristine beaches, and create new memories to mark this life milestone. We can incorporate special touches like birthday decorations, champagne toasts, or coordinating with a birthday cake.

Wedding Parties and Bridal Events

Celebrate your wedding party with a day on the water before the big day. Whether it’s the entire wedding party together, a bridesmaids’ day out, a groomsmen adventure, or both parties joining forces, sailing the Virgin Islands creates bonding and relaxation before wedding festivities. The beautiful setting provides fantastic photo opportunities. Your wedding party in swimsuits and sunglasses sailing the Caribbean makes for great pre-wedding content and memories! Consider scheduling your large group charter as a destination wedding activity that brings both wedding parties together in a relaxed, fun setting.

Trip Details

Duration: Customizable

Departure: Sapphire Beach, St. Thomas, USVI – easy to find with convenient parking available

Sailing Area: Waters surrounding St. Thomas and St. John, including views of the Virgin Islands National Park

Included: Professional captain and crew, beverages (including rum punch, beer, wine, and soft drinks), light snacks, all safety equipment, Snorkeling Gear

Group Size: With multiple vessels we can accommodate up to 18 people

What to Bring: Sunscreen, camera, light jacket for the breeze, and your sense of adventure!

Our Reviews

      EXCELLENT  
   Based on 134 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Simon Nold 
 
 
 
 Trustindex verifies that the original source of the review is Google. This is perfect for small groups. Kendal was an awesome captain that really gave us a great sailing experience. Full of knowledge of the local area and had great snorkeling spots. Would recommend to  anyone who is looking for that smaller intimate sailing experience!
  
 
      Posted on Google  
   
   Jenn Douglas 
 
 
 
 Trustindex verifies that the original source of the review is Google. Our sailing trip with Captain Kendall was absolutely unforgettable! ⛵🌊

From the moment we set out, his incredible experience and deep knowledge of sailing made us feel confident and safe on the water. You can immediately tell how passionate he is about the island and about sailing—he shared so many interesting insights that made the entire trip feel like both an adventure and a learning experience.

It was my first time sailing, and I’ll admit the waves made me a little nervous at first. But Captain Kendall’s great sense of humor quickly eased my anxiety and had us all laughing and enjoying the ride. His calm confidence made the whole experience even better.

One of the highlights was the delicious home-cooked lunch he prepared for us—seriously amazing flavor! 🍽️ And the wildlife sightings were incredible. We saw beautiful, colorful fish and even two baby turtles swimming nearby, which felt like such a special moment.

If you’re looking for an authentic, fun, and memorable sailing experience, Captain Kendall is the one to go with. Highly recommend! 🌴🐢
  
 
      Posted on Google  
   
   Jennifer Elkins 
 
 
 
 Trustindex verifies that the original source of the review is Google. BOOK IT!! After our experience I would trust Captain Kendall with my life.  Experience beyond comprehension.  Good company. Delicious lunch. Great snorkeling spots.    Don't miss this opportunity everyone!
  
 
      Posted on Google  
   
   mo gatto 
 
 
 
 Trustindex verifies that the original source of the review is Google. Absolutely perfect day spent with Kendal. He was captain, chef, bartender, lifeguard  and entertainment.  I have no idea how he did all that without ever breaking a sweat!  The boat was well equipped with everything needed for a day of sailing, snorkeling, eating and drinking.  Kendal is an extremely skilled sailor.  He navigated unusual Caribbean winds and weather with ease. Watching him solo the boat ( even picking up the mooring ball while simultaneously controlling the helm and sheets) was nothing short of amazing.  He put extra effort into getting us to the best snorkeling locations and to make sure we had a great sail in between.  Like I said…an absolutely perfect day.
  
 
      Posted on Google  
   
   V H 
 
 
 
 Trustindex verifies that the original source of the review is Google. We looked for the best day trip on the water and found it here. Captain Kendall was a wonderful host, guide, history teacher, cook, beverage server and overall safe keeper for the passengers. Lots of hats! The boat is well equipped and clean. If you’re looking around for a high value excursion, this is for you!
  
 
      Posted on Google  
   
   Marianne Langlois 
 
 
 
 Trustindex verifies that the original source of the review is Google. Spend the day sailing with Kendall who has years of experience. He shared the history of the many islands. He took us to private bats for snorkeling and prepared a very filling lunch. Highly recommend if looking for a day trip
  
 
      Posted on Google  
   
   Cari Grundman 
 
 
 
 Trustindex verifies that the original source of the review is Google. What a great day!! Tommy the captain and Kayla, his first mate, were delightful and so easy to plan our day trip with. They picked us up in the 40’ Beneteau promptly at 9 am.
The boat was clean and well maintained. Tommy is knowledgeable and confident at the helm and made even the first time sailor feel right at home! We sailed to 3 blissful coves, Lovongo, Scott and Christmas where anchor was dropped and off we went snorkeling. All equipment was supplied. The locations were picture perfect and empty (due to being off season!) A lunch of grilled chicken, pasta salad and watermelon was provided and plenty of rum punch, painkillers and tequila.
Tommy is a wealth of knowledge about the islands, their history, and fun facts. The 6 hr day flew by and we’d definitely book with Tommy and Virgin Island Day Sailing again!!
  
 
      Posted on Google  
   
   Robyn Calhoun 
 
 
 
 Trustindex verifies that the original source of the review is Google. We had the BEST day ever sailing and snorkeling with Kendall.  This is our 1st visit to St Thomas and our 1st time to book with VI Day Sailing.   We have traveled to many places and taken similar trips but this one was by far the best!   Kendall took us to the best spots to snorkel, cooked a delicious lunch and made sure all our needs were met.
  
 
      Posted on Google  
   
   Colleen Wise 
 
 
 
 Trustindex verifies that the original source of the review is Google. Mark is a great captain and Rusty is a great first mate! They’re both very friendly, accommodating and knowledgeable. The drinks were perfect and the food was delicious. It was really fun to go ocean sailing, I highly recommend it!
  
 
      Posted on Google  
   
   Alan C 
 
 
 
 Trustindex verifies that the original source of the review is Google. Captain Mark and Rusty did a great job
We had a great day of sailing and snorkeling Michelle even got a great video of herself swimming with the turtles.
Lunch was absolutely delicious
Highly recommend this trip
  
 
  
  
 
     Verified by Trustindex  Trustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more

Planning Your Large Group Charter

Booking Process

Booking a large group charter is straightforward but requires more advance planning than smaller charters. Contact us with your group size, preferred dates, and general vision for your charter. We’ll discuss options, explain the multi-boat coordination, answer questions, and provide detailed pricing. Once you’re ready to proceed, we’ll secure your boats with a deposit and begin detailed planning. As your date approaches, we’ll finalize group distribution, confirm dietary needs, coordinate any special elements, and ensure every detail is perfect.

How Far in Advance to Book

Large group charters require significantly more advance booking than smaller charters because we need to coordinate multiple vessels and crews. We strongly recommend booking:

3-6 months ahead for groups of 12+, especially during peak season (December-April)
2-3 months ahead for groups of 7-12 during peak season
1-2 months ahead for groups of 7-12 during off-season
Immediately for last-minute needs – we’ll check availability but cannot guarantee multiple boats on short notice

Corporate events, bachelor/bachelorette parties, wedding groups, and family reunions often have fixed dates requiring even more advance planning. Book as early as possible to secure your preferred date. Contact us today!

Frequently Asked Questions

For groups of 13-18 guests, we coordinate two boats from our fleet that sail together as a coordinated convoy. Your group is divided across boats, but both boats depart together, sail together, anchor together, and follow the same itinerary throughout the day. The captains maintain constant radio communication coordinating timing and activities. At every stop – swimming, snorkeling, beaches – everyone comes together. While sailing, you’ll see the other boats in your group nearby. It’s a coordinated group experience using multiple vessels to accommodate larger numbers while maintaining comfort and personalization.

Yes, in virtually every way. Commercial party boats pack 50+ guests (often strangers) onto one vessel, creating crowded conditions, long lines for equipment, competition for shade and space, and generic one-size-fits-all itineraries. Our multi-boat charters give your group exclusive use of all vessels, with no strangers, customized itinerary, personal attention from crew, comfortable space, authentic sailing experience, and all the flexibility of private charters. The per-person price is often similar but the experience is dramatically superior. You get quality over crowding.

We accommodate groups up to 18 guests using our coordinated multi-boat charter system. Groups of 12 or fewer fit comfortably on a single boat for a private charter. Groups of 13 to 18 use two boats sailing together. Each boat maintains a maximum amount of guests for comfort, ensuring everyone has space to move around and enjoy the sailing experience without feeling crowded.

Large group charters require deposits to secure multiple boats and crews. Specific cancellation terms are detailed in your booking agreement, but generally we work with groups to find solutions if circumstances change. Weather-related cancellations receive full refunds or flexible rescheduling. For guest-initiated cancellations, policies vary by timing and circumstances. Contact us to discuss your specific situation. We’re reasonable and work to find fair solutions when plans change.

Yes, large group charters are fully customizable just like a standard private charters. Choose your departure time, select destinations based on your group’s interests (more snorkeling, beach time, or sailing), adjust pacing, incorporate special elements for celebrations, and control the experience. Want your bachelor party to visit specific spots? Need your corporate event timed around specific schedules? Celebrating a birthday and want certain touches? We’ll customize everything. The multi-boat format doesn’t reduce flexibility, it simply scales our personalized service to larger groups.

Large group charters cost more in total than single private charters because we’re coordinating multiple boats and crews. However, when calculated per person, large group charters often represent excellent value, typically less per guest than many land-based group activities while providing a more memorable experience. The price includes exclusive use of multiple boats, professional crews for each vessel, all equipment, food, beverages, customization, and coordination. For corporate events, the per-person investment often compares favorably to catered functions while providing significantly more impact. Contact us for specific pricing based on your group size, desired duration, and any special requests.

Large group sailing charters are excellent for corporate events and team building. The shared adventure naturally builds camaraderie as colleagues experience challenges together and create positive shared memories. The beautiful setting impresses clients and creates positive associations with your company. The multi-boat format naturally creates smaller conversation groups while maintaining overall team cohesion. We’ve hosted numerous successful corporate events, client entertainment outings, team retreats, and incentive trip activities. The informal atmosphere on the water facilitates authentic connection that’s difficult in office settings, while the impressive experience demonstrates investment in your team or clients.

BOOK ONLINE NOW!

Up to 12 Guests can Book Direct HERE sunset sail or full day

we can accommodate groups up to 18 people! contact us today

Open Bar & Snacks
Snorkeling Equipment
2 Boats = Twice the Fun!