HIGH ADVENTURE SAILING TRIP
From St. Thomas to St. John & St. Croix or the British Virgin Islands*
Trade the campground for a 50’ blue-water sailing yacht and turn “summer camp” into a true ocean expedition. Antillean Yacht Charters now offers a 5-night High Adventure trip designed for Scout troops, youth groups, and adventurous families who want to explore the U.S. and British Virgin Islands under sail.
Trip at a Glance
• Duration: 5 nights / 6 days
• Route: St. Thomas ➝ St. John ➝ British Virgin Islands (BVI)
• Group Size: 2–12 guests
• Typical Crew: Mix of adults and youth/Scouts
• Price: $14,500 total per group
• Includes: Captain, fuel, meals, non-alcoholic beverages, and the yacht Antillean
One flat rate for your entire crew – no per-person pricing to calculate.
Who This Trip Is For
This High Adventure itinerary is built for:
• Scout troops & youth groups
• Ideal for 2–6 adult leaders and a crew of Scouts or youth participants
• Flexible configurations such as:
• Up to 2 adults + 10 youth for a total of 12, or
• Up to 6 adults + 6 youth (max 12 guests total)
• Families & friends who want a more adventurous, hands-on sailing experience
• Groups who want to sail, snorkel, hike, and learn seamanship, not just “go on a boat ride”
We’ll work with you ahead of time to confirm the exact mix of adults and youth for your crew.
Highlights of Your High Adventure Week
Over five nights, you’ll live aboard Antillean, a 50’ Beneteau sailing yacht based on Water Island, St. Thomas. Each High Adventure trip is customized to weather, experience level, and group goals, but a typical week can include:
• Blue-water sailing between St. Thomas, St. John, and St. Croix
• Inquire about the BVI as there are additional fees*
• Snorkeling coral reefs, sea turtle hangouts, and historic wrecks
• Beach landings & hikes to scenic overlooks and hidden bays
• Night anchoring in protected coves with incredible star-filled skies
• Hands-on seamanship:
• Basic sail handling and line work
•. Helming under supervision
•. Navigation discussions and safety at sea
• Island time: Optional shore time at classic harbors and beach towns
Every crew is different. Some want to log as many miles as possible; others want more time in the water. Captain Matthias will help you strike the right balance.
Sample High Adventure Itinerary (Outline)
Day 1 – St. Thomas Departure
• Board Antillean in St. Thomas / Water Island
• Safety briefing, boat orientation, stow gear
• Short shake-down sail to a protected anchorage
• Swim, snorkel, and first night aboard
Day 2 – St. John National Park
• Sail along the north shore of St. John
• Snorkel reefs and underwater trails
• Optional hike to scenic overlooks
• Navigation or seamanship session in the evening
Day 3 – Option to cross to St Croix
• Morning passage across to the St Croix (weather-dependent)
• Fishing focused sailing during crossing
• Snorkeling, beach time, and exploring ashore
Day 4 – Island-Hopping & Adventure Day
• Sail between islands, practice sail trim and helming
• Snorkel or free-dive suitable sites
• Team-building games or challenges on board or ashore
Day 5 – Return Toward St. John / St. Thomas
• Sail back toward U.S. waters
• Final swim and snorkel stop
• Closing reflections and group photos aboard
Day 6 – Disembarkation
• Breakfast on board
• Pack up and return to St. Thomas / Water Island
• Disembark and travel home
Exact stops will vary based on weather, sea conditions, and any local regulations at the time of your trip.
What’s Included
Your $14,500 High Adventure package covers:
• 5 nights / 6 days aboard Antillean
• Professional captain – Captain Matthias Bitterwolf
• All meals on board are cooked by guests (breakfast, lunch, and dinner)
• Fuel & standard operating costs
• Use of the yacht’s standard gear and amenities
• On deck sleeping (hammocks available)
What’s not typically included (can be clarified with Captain Matthias when booking):
• Airfare or travel to/from St. Thomas
• Any required customs/immigration fees for the BVI
• Optional excursions, souvenirs, or meals taken ashore
• Gratuity for crew
Safety & Supervision
Safety is the top priority on every High Adventure trip.
• Antillean is a commercially licensed, professionally maintained vessel
• Captain Matthias holds a U.S. Coast Guard license and has extensive experience in the Virgin Islands
• All participants receive a full safety briefing on lifejackets, man-overboard procedures, and movement around the boat
• Youth crews must be accompanied by appropriate adult leadership and follow their organization’s safety guidelines
If you’re planning a Scout-specific High Adventure, we’ll work with your unit leadership to align with Scouting safety and supervision requirements.
Packing & Preparation
Once your reservation is confirmed, you’ll receive a suggested packing list tailored to this High Adventure trip, including:
• Recommended soft luggage, bedding and/or camping sleeping pad
• Sunscreen or bug spray and a thermos and your own first aid kit
• Clothing and footwear for boat life and hiking
• Snorkel gear vs. what’s provided onboard
• Identification for travel
• Cash as most places don’t accept credit cards
How to Book Your High Adventure Trip
Ready to start planning?
1. Check dates & availability with Antillean Yacht Charters.
2. Confirm your group size and adult/youth mix.
3. Reserve your week with a deposit.
4. Complete any required forms from your organization (if applicable).
Call or Email to Get Started
Phone: +1 (340) 998-5106
Email: AntilleanCharters@gmail.com
Book Online
[Book Your High Adventure Trip]
For Scout Leaders & Youth Group Organizers
If you’re a Scoutmaster, youth pastor, or program director:
• This High Adventure sail can serve as a capstone experience for older youth
• We can emphasize leadership, teamwork, and seamanship skills
• You’ll have direct contact with Captain Matthias to plan in advance
Use our contact details to start the conversation about your crew’s needs and goals.