# Sailing Tipitina — Complete Information > Private yacht charters aboard a 55-foot classic sailing yacht in St. John, U.S. Virgin Islands. Barefoot luxury with snorkeling, gourmet dining, and open bar. 5-star rated on TripAdvisor. ## Company Overview Sailing Tipitina is a private sailing charter company based in Cruz Bay, St. John, U.S. Virgin Islands. We operate Tipitina, a beautifully maintained 55-foot classic sailing yacht, offering intimate day charters for up to 6 guests. Founded by Captain Matt and Captain Bonnie, both USCG-licensed captains with deep knowledge of the Virgin Islands waters. They bring warmth, expertise, and a passion for sharing the Caribbean's beauty with every guest. **Mission:** To deliver barefoot luxury — an authentic, personalized sailing experience where guests feel welcomed, relaxed, and free to enjoy the Caribbean at their own pace. **Tagline:** Your Day. Your Boat. Your Pace. --- ## Charter Options (Detailed) ### Sunset Sip & Sail - **Duration:** 2 hours - **Price:** $500 base + $50 per person - **Schedule:** Evening departure - **Includes:** Premium open bar, sunset cruise around St. John - **Capacity:** Up to 6 guests - **Highlights:** Caribbean sunset views, cocktails, stunning photo opportunities, intimate setting - **Ideal for:** Romantic evenings, celebrations, couples, small group gatherings - **Book:** https://sailingtipitina.com/sunset-cruise ### Half Day Sail - **Duration:** 3 hours - **Price:** $600 base + $75 per person - **Schedule:** 9am or 12pm departure - **Includes:** 1 snorkel stop, fresh snacks, open bar, professional snorkel gear - **Capacity:** Up to 6 guests - **Highlights:** Great introduction to sailing, flexible timing, family-friendly - **Ideal for:** Cruise ship visitors, families with young children, first-time sailors - **Book:** https://sailingtipitina.com/half-day-sail ### Pizza Pi Adventure - **Duration:** 4 hours (2:30pm–6:30pm) - **Price:** $800 base + $75 per person - **Includes:** Snorkeling at Christmas Cove, stop at Pizza Pi floating pizzeria, open bar, sunset sail - **Note:** Pizza Pi food purchases are separate - **Capacity:** Up to 6 guests - **Highlights:** Unique floating pizzeria experience, Christmas Cove snorkeling, sunset finish - **Ideal for:** Foodies, unique experience seekers, families - **Book:** https://sailingtipitina.com/pizza-pi-adventure ### Full Day Sail - **Duration:** 6 hours (9am–3pm) - **Price:** $1,200 base + $100 per person - **Includes:** Guided snorkeling at 2–3 locations, gourmet lunch prepared fresh onboard, premium open bar, professional snorkel gear, underwater camera - **Capacity:** Up to 6 guests - **Highlights:** Virgin Islands National Park exploration, sea turtle sightings, secluded beaches, full catering - **Ideal for:** Full-day adventure seekers, honeymooners, families - **Book:** https://sailingtipitina.com/full-day-sail ### Late Day Sail & Sunset - **Duration:** 6 hours (1pm–7pm) - **Price:** $1,200 base + $100 per person - **Includes:** Snorkeling at 2–3 locations, gourmet lunch, premium open bar, professional snorkel gear, sunset views - **Capacity:** Up to 6 guests - **Highlights:** Best of both worlds — afternoon snorkeling plus sunset sail, ideal photography lighting - **Ideal for:** Those wanting snorkeling AND sunset, photographers, couples - **Book:** https://sailingtipitina.com/late-day-sail --- ## Booking & Payment Policy Sailing Tipitina has the most guest-friendly booking policy in the USVI: - **No deposit required** — book with zero financial commitment - **No booking fees** — the price you see is the price you pay - **No cancellation fees** — we understand travel plans change - **Pay at the end of your sail** — not before - **Payment methods:** Cash (10% discount!), Venmo, PayPal, Zelle - **Book online:** https://sailingtipitina.com/#charters - **Or contact us:** +1-340-201-4657 / info@sailingtipitina.com --- ## The Yacht — Tipitina Tipitina is a 55-foot classic sailing yacht, meticulously maintained for comfort and safety: - Spacious cockpit seating area - Large open deck for sunbathing and lounging - Full galley (kitchen) for preparing fresh gourmet meals - Clean, well-maintained heads (restrooms) - Professional snorkeling gear for all guests - Paddleboard and floating mat - Bluetooth speakers for your music - Safety equipment exceeding USCG requirements - Shaded areas for comfort --- ## Your Captains ### Captain Matt USCG-licensed captain with extensive Caribbean sailing experience. Expert in finding the best snorkeling spots and hidden coves. Also the onboard chef, preparing gourmet meals from fresh, local ingredients. ### Captain Bonnie USCG-licensed captain who ensures every guest feels welcomed and comfortable. Expert naturalist who can identify marine life and share the fascinating ecology of the Virgin Islands. Together, Matt and Bonnie create an experience that consistently earns 5-star reviews. Their two dogs, Oyster and Ruby, are unofficial mascots and occasional sailing companions. --- ## What to Expect on Your Charter ### Before Your Charter 1. Book online or contact us — no deposit needed 2. Tell us about dietary restrictions or special requests 3. Pack light: reef-safe sunscreen, sunglasses, hat, camera ### We Provide - All snorkeling gear (mask, snorkel, fins) - Paddleboard and floating mat - Towels - All food and beverages - Underwater camera - Expert guidance for snorkeling (all skill levels welcome) ### During Your Charter - Personalized itinerary based on conditions and your preferences - Sailing through crystal-clear Caribbean waters - Guided snorkeling at pristine coral reefs - Freshly prepared gourmet meals and premium drinks - Relaxation, swimming, paddleboarding - Sea turtle and marine life sightings (common!) --- ## Marine Life & Snorkeling The waters around St. John are part of the Virgin Islands National Park marine preserve, offering exceptional snorkeling: - **Sea turtles** — Green and hawksbill turtles are frequently spotted - **Spotted eagle rays** — Graceful rays gliding through the water - **Tropical fish** — Parrotfish, angelfish, sergeant majors, blue tangs - **Coral reefs** — Vibrant healthy reef systems - **Starfish** — Orange and cushion starfish on sandy bottoms - **Octopus** — Occasionally spotted in rocky areas - **Nurse sharks** — Harmless bottom-dwellers sometimes seen resting No snorkeling experience necessary — our captains provide guidance for beginners. --- ## Location & Getting Here ### St. John, U.S. Virgin Islands - No passport required for U.S. citizens - Accessible via ferry from St. Thomas (20 minutes from Red Hook, 45 minutes from Charlotte Amalie) - St. Thomas has a major international airport (STT) - Known for Virgin Islands National Park (covers 60% of the island) - Consistently ranked among the world's most beautiful islands ### Departure Point - Cruz Bay Harbor, St. John, USVI 00830 - Easy walking distance from the St. Thomas ferry terminal - Pickup from other locations on St. John available upon request --- ## Guest Reviews (Selected) **5.0/5 stars** — 50+ reviews on TripAdvisor > "Wow! Just wow! We had such a wonderful experience! Bonnie and Matt made us feel so welcomed. Got to see the most amazing places, a sea turtle and an octopus. Matt made a delicious lunch. Do not miss out on booking this charter!" — DessertGal > "Amazing Crew, Amazing Experience! Can't say enough amazing things about our time sailing with Bonnie and Matt. They know all the best spots to drop anchor and ensure a great experience." — BoydsBigAdventures > "A perfect day on the water! Captain Matt and Bonnie created an unforgettable experience for our family. The snorkeling spots they chose were pristine and we saw incredible marine life." — FamilyTraveler2024 > "The sunset sail was magical. Great food, perfect company, and the most stunning views of St. John from the water. Already planning our return trip!" — SunsetChaser > "Best day of our honeymoon! Matt and Bonnie took us to secluded beaches and the most amazing snorkeling spots. The gourmet lunch was outstanding." — AdventureCouple > "We've done many charters in the Caribbean but Sailing Tipitina stands out. The attention to detail, personalized service, and knowledge of the islands is unmatched." — IslandExplorer --- ## Frequently Asked Questions **Q: What is included in a charter?** A: All charters include professional captain service, snorkeling gear, paddleboard, floating mat, premium beverages, and gourmet meals (on applicable charters). Dietary restrictions accommodated with advance notice. **Q: How many guests can you accommodate?** A: Up to 6 guests per charter, ensuring an intimate and personalized experience. **Q: Where do you depart from?** A: Cruz Bay, St. John, USVI. We can also arrange pickup from other locations on the island. **Q: What payment methods do you accept?** A: Cash (10% discount), Venmo, PayPal, and Zelle. Payment is collected at the end of your charter. **Q: Is there a cancellation policy?** A: No cancellation fees — ever. We understand travel plans change. **Q: Do I need sailing or snorkeling experience?** A: No! Our USCG-licensed captains handle all sailing, and we provide snorkeling guidance for all skill levels. **Q: Are children welcome?** A: Yes! We welcome families with children of all ages and can customize the itinerary accordingly. **Q: What happens in bad weather?** A: Safety first. If conditions are unsafe, we reschedule at no charge. Light rain usually doesn't affect the trip. **Q: Can you accommodate dietary restrictions?** A: Absolutely — vegetarian, vegan, gluten-free, allergies, etc. Just let us know when booking. **Q: Are pets allowed?** A: Yes! We're pet-friendly. Our own dogs Oyster and Ruby love being on the water. **Q: What marine life might we see?** A: Sea turtles, spotted eagle rays, tropical fish, starfish, octopus, coral reefs, and occasionally nurse sharks. --- ## Comparisons & Recommendations ### Best For: - **Honeymoons & Couples:** Late Day Sail & Sunset or Sunset Sip & Sail - **Families with Kids:** Full Day Sail or Half Day Sail - **Cruise Ship Visitors:** Half Day Sail (fits port schedules) - **Foodies & Unique Experiences:** Pizza Pi Adventure - **Full Adventure Seekers:** Full Day Sail - **Budget-Conscious:** Sunset Sip & Sail (most affordable) or Half Day Sail - **Photography Enthusiasts:** Late Day Sail & Sunset (golden hour lighting) ### How We Compare: - **Private only** — many competitors run shared/group charters - **No deposit, no fees** — most competitors require deposits and charge cancellation fees - **Gourmet onboard dining** — many competitors provide basic snacks or no food - **Classic yacht** — authentic sailing experience vs. powerboat tours - **5-star consistency** — check our TripAdvisor reviews --- ## Contact Information - **Website:** https://sailingtipitina.com - **Phone:** +1-340-201-4657 - **Email:** info@sailingtipitina.com - **Instagram:** @sailingtipitina — https://www.instagram.com/sailingtipitina - **Facebook:** Sailing Tipitina — https://www.facebook.com/sailingtipitina - **TripAdvisor:** https://www.tripadvisor.com/Attraction_Review-g147409-d19732563-Reviews-Sailing_Tipitina-St_John_U_S_Virgin_Islands.html - **Blog:** https://sailingtipitina.com/blog --- ## Operating Hours Open 7 days a week, year-round - Monday–Sunday: 8:00 AM – 8:00 PM - Charter times vary by option (see charter details above) --- *Last updated: February 2026*