Future Adventures

The Journey: Departing from Crown Bay, located in the heart of downtown St. Thomas, US Virgin Islands, we will begin our journey to the seldom explored west end of St Thomas. Visiting the Mermaid's Chair, Brittany Beach and Botany Bay, we will then continue around the north shore and make our way to Magens Bay. We will spend a few days exploring the best of St Thomas before turning our attention to the world famous destinations of St. John. First stop will be for an afternoon and evening adventure in Cruz Bay, STJ. We will then continue our circumnavigation of the island before returning to Crown Bay, St. Thomas at the end of the week. Enjoy one of the top 10 beaches in the world at Trunk Bay with the amazing underwater snorkeling trail is definitely a bucket list stop. Hiking Rams Head and having tacos and drinks from a floating booth at Lime Out in Coral Bay is also a must do. Coral Bay is known as the OG community of real locals on St. John. We will then make our way to Lameshur Bay where we will snorkel with Green Sea Turtles, hike the Reef Bay Trail to visit the site of the 1,500+ year old petroglyphs and make our way to the ruins of a 1700s era sugar plantation. This trip will be heavily focused on snorkeling, hiking and outdoor adventures. Friends joining this intimate cruise will need to be physically capable of multiple long hikes with challenging terrain and good swimmers given the focus on snorkeling remote sites with limited access for vessels.

The Natural Beauty of the US Virgin Islands

See St. Thomas and St. John like never before. Sailing, snorkeling and hiking focused. 10/18/25 - 10/26/25 (0 Cabins Available - Full Boat)

10/18/25, 8:00 PM

10/25/25, 1:00 PM

The Journey: Departing from Nanny Cay Marina on Tortola's southern shore, you will be greeted by a long line of beautiful islands. Norman, Cooper, and Virgin Gorda welcome you to the start of your journey as you slip lines and head north through the Caribbean's most famous sailing grounds. We will spend a few days enjoying the North Gorda Sound as well as a few more anchored up at White Bay, JVD. Join us for the best restaurants and beaches that the beautiful British Virgin Islands has to offer. Connect with Jason ( Jason@IslandBoyIslandGirl.com ) for help scheduling the exact flights in and out of the islands. The airport at Beef Island, Tortola (EIS) is the easiest as it is already in the BVIs, but you can also fly into St Thomas (STT) but you will have to transfer islands and clear customs which can be time consuming and costly. Dinners will be at Hendo's on JVD, Saba in Gorda Sound, Scrub Island Resort, Pirates Bight on Norman Island and one more yet to be determined. Sailing vacations do not get any better and more luxurious than the BVIs in January!

The Opulent BVIs

Spend a week in the BVIs enjoying the best sailing, beaches and food that JVD,Virgin Gorda and the British Virgin Islands have to offer. 1/17/26 - 1/24/26 (0 Cabins Available - Full Boat)

1/17/26, 9:00 PM

1/24/26, 3:30 PM

The Journey: While final details of the specific islands that we will visit are still being firmed up, a classic Saronic Gulf itinerary will typically include stops at Aegina, Poros, Hydra and Spetses. With opportunities to visit sites like the Temple of Aphaia, The Temple of Poseidon or the Bouboulina Museum, these calm sailing waters and historical islands are a world class destination and some of the best sailing grounds in the world.

The Greek Isles

Experience Sailing the Saronic Gulf of Greece via Athens! 8/29/26 - 9/5/26 (1 Cabin Remaining)

8/29/26, 9:00 PM

9/5/26, 2:00 PM

The Journey: The usual travel plan is to sail each morning for a few hours to a new anchorage or mooring field and then to explore islands, reefs, beaches and beach bars into the afternoons and evenings. This plan is completely customizable depending on the preferred activities of the group. Browse some of the other trips in both the Future Adventures section as well as the Past Adventures section to get a feeling for the various types of options. Sailing in the Abacos tends to be more beach bars & restaruants every night, where sailing in the US Virgin Islands tends to be more meals on boats with amazing reef snorkels and National Park hikes. The BVIs are some of the premiere sailing grounds with world class restaurants each night while the Exumas are a mix of breath-taking anchorages on remote islands alone followed by luxurious stops at places like Staniel Cay and Highborne Cay.

Build Your Dream Trip

Pick the Area and Let Jason customize a Plan. Dates are flexible.

Island Boy Island Girl