Island Roots Charters Introduces New Multi-Trip and Multi-Boat Savings for 2026
Looking for a way to save a few bucks on your “bucket list” Virgin Islands vacation in May 2026 and beyond? We have two new offers you’ll be excited about.
First, a little background: various large groups and families have been asking us about booking two (or three) tandem charters at once, or adding a second trip during their stay. So we're making both options an official part of some new discounted offerings starting now (as of May 2026). These new discounted trips are built around the idea of being able to include as many guests as possible and experience the best destinations throughout the U.S. and B.V.I. on their (often once in a lifetime) Caribbean vacation. We’re excited to extend this offering to make it easier and more financial approachable. Allowing guests to enjoy the Virgin Islands in ways that help more people “check all the boxes” on their tropical holiday!
Book Two Trips, Get 10% Off The Second
Book any two Island Roots Charters trips during your stay in the Virgin Islands and receive 10% off your second trip.
The combinations are perfect for guests who want to do a full day BVI charter and then come back for a trip focused on the USVI — two completely different experiences on two different days. Others use this offer to book a daytime family charter and return later in the week for a Golden Hour sunset snorkel, adults only this time maybe??? The options are endless when you know you’ve got two trips instead of just one.
We built these savings around feedback from guests who have done both a St. John day trip and a BVI excursion in the same vacation and came away saying it was the best travel decision they could make. If you have ever wanted to really make the most of your time in the Virgin Islands, this is the golden ticket.
Applies to base charter rates only. Excluding holidays.
Get a Discount When You Book Multiple Boats — Perfect For Booking Large Groups
Book more than one boat for your charter and receive 5% off each boat — this is one of the best specials available for groups planning a Virgin Islands celebration or reunion in 2026.
Island Roots operates three WorldCat powerboats that can accommodate up to 36 passengers across the fleet. Chartering multiple boats at once is ideal for wedding parties, milestone birthdays, multi-family vacations, and large groups of friends traveling together. Each boat has its own space, its own cooler, and its own experience — all while the whole group travels together, stops at the same spots, and shares the day.
This has been our most requested arrangement over the past year. We're formalizing it now so guests can plan around it.
May 2026: A Few Spots Still Available
For those who don’t like to plan far in advance — book a trip for this month (May, 2026). We still have a few openings left. The weather is warm, the water is clear, and it’s not too crowded. Last minute trips don't usually come with savings; this one does. Pair your impulses with these deals and a May trip to the Virgin Islands becomes a more affordable way to experience what the Virgin Islands has to offer.
A Travel Deal Hack To Pay Even Less For Your Virgin Islands Trip
Booking directly with Island Roots by phone, text, or email means you can avoid any online booking fees and taxes that third-party platforms add on top. It also means you get to talk through the trip with us before you commit — which is always our preference. We can help you figure out which combination of charters makes the most sense for your group and build an itinerary tailored to what you actually want to do.
All discounts apply to base charter rates only. Excluding holidays.
Call or text: 340.643.5000