St Croix offers some of the most memorable boat tours and cruises in the Caribbean. With its calm waters, stunning coastlines, and intriguing shipwrecks, it’s a perfect spot for sailors and landlubbers alike. We particularly like the Live Music Sunset Sail because it combines relaxing coastal views with lively entertainment and a friendly vibe. Imagine bobbing on a catamaran, sipping complimentary rum punch as the Caribbean sun dips below the horizon—what’s not to love? For a more hands-on experience, the Sunset Sail aboard the Tall Ship Denis Sullivan offers a chance to help raise sails and learn about maritime history, making it ideal for families or curious travelers. And history buffs will appreciate the Private Sailing Tour of Pirate Waters and Shipwrecks, which takes you into the bay where pirates once plied their trade—perfect for those who want more than just pretty scenery.
If you’re thinking about your options, St Croix’s boat tours run the gamut from romantic sunset sails to educational pirate history trips and convenient port shuttles. Whether you’re after a relaxing evening, a family-friendly adventure, or a private charter, there’s something here for everyone.
Quick Overview
Our list highlights five top boat experiences in St Croix. The Live Music Sunset Sail offers a relaxed, music-filled cruise with stunning coastal views [], perfect for unwinding after a busy day. The Sunset Sail aboard the Tall Ship Denis Sullivan combines a classic sailing experience with the opportunity to help out with the sails, all for a good cause []. For those interested in history and adventure, the Private Sailing Tour of Pirate Waters and Shipwrecks provides a rich narrative of pirate lore and shipwreck sites []. If you prefer quick, budget-friendly transport, the Frederiksted Cruise Ship Port Shuttle makes exploring Christiansted simple and affordable []. Finally, for total convenience, the Private Transfer from St.Croix Cruise Port to Hotels guarantees a smooth start or end to your trip [].
1. Live Music Sunset Sail
Rating: 5.0/5 (285 reviews)
Price: $70.00 per person
Duration: Approximately 2 hours 30 minutes
Location: St Croix, US Virgin Islands
For about $70, the Live Music Sunset Sail provides a relaxing cruise along St Croix’s coast while enjoying live Caribbean music and free rum punch. The boat is a comfortable catamaran that gently floats past Frederiksted’s historic waterfront and the Sandy Point National Wildlife Refuge, offering a wonderful view of the island’s natural beauty. The atmosphere is laid-back, making it perfect for couples celebrating a honeymoon or anniversary, or friends wanting a memorable evening. Children are welcome, which makes it a versatile outing for families as well.
What makes this tour stand out is the combination of gentle sailing, live local music, and the chance to unwind as the sun sets. The reviews highlight the crew’s attentive service and the quality of the music, often described as “phenomenal.” Many travelers note that it’s an ideal way to end a busy day on island, and the relaxed environment encourages meeting fellow travelers. At just over two and a half hours, it’s a manageable and enjoyable experience that offers great value for the price.
Bottom Line: The Live Music Sunset Sail is a fantastic choice for those seeking a mellow, musical evening with fantastic views and friendly company.
2. Sunset Sail Aboard the Tall Ship Denis Sullivan
Rating: 5.0/5 (9 reviews)
Price: $55.00 per person
Duration: About 2 hours
Location: St Croix, US Virgin Islands
If you’re after a more traditional sailing experience with a touch of history, the Sunset Sail aboard the Tall Ship Denis Sullivan is a perfect pick. This tall ship, modeled on classic schooners, offers a chance to connect directly with the sea—whether that’s helping hoist the sails or just soaking in the views. The experience feels more immersive, especially since all proceeds support the World Ocean School’s educational programs. That means your ticket isn’t just a fun outing but also supports maritime learning.
Guests rave about the crew’s friendliness and the opportunity to get involved, whether steering the ship or simply watching the sunset from deck. The ship’s design and the crew’s knowledge make this sail a memorable voyage for all ages, from kids to seniors. Compared to more commercial cruises, it offers a quieter, more hands-on experience that emphasizes environmental awareness and maritime heritage.
Bottom Line: For an authentic sailing adventure that highlights community support and maritime culture, this tall ship cruise is hard to beat—especially at only $55.
3. Private Sailing Tour of Pirate Waters and Shipwrecks
Rating: 4.5/5 (23 reviews)
Price: $175.00 per person
Duration: About 2 hours
Location: St Croix, US Virgin Islands
History buffs and curious explorers will find the Private Sailing Tour of Pirate Waters and Shipwrecks fascinating. Starting at Salt River Bay, where pirates once traded and fought, this private tour takes you to key sites like Columbus Cove, home to the wreck of Pirate Jean Martel’s ship, and the remains of two Dutch ships sunk in 1650. The tour includes beverages and admission to notable sites, making it a comprehensive package.
What’s special about this tour is its private nature—it’s perfect for groups, families, or romantic getaways. The guide, Captain Stan, is highly praised for his wealth of knowledge and engaging storytelling. The stops include historic fort sites like Fort Christiansvaern, which hosted multiple battles, and shipwreck sites with vivid stories of piracy, conquest, and shipwrecks. The tour is more than just a boat ride; it’s an educational journey that transports you back in time.
Bottom Line: If you love history, pirates, and private experiences, this tour offers a rich, personalized adventure with plenty of storytelling and exploration.
4. Frederiksted Cruise Ship Port Shuttle to Christiansted
Rating: 0/5 (No reviews)
Price: $27.00 per person
Duration: 20-30 minutes
Location: St Croix, US Virgin Islands
For travelers arriving by cruise ship, the Frederiksted Cruise Ship Port Shuttle makes it simple to visit Christiansted, a lively town filled with colorful buildings, historic sites, and waterfront restaurants. The shuttle departs from Molly’s Tropical Boutique, taking just about 20-30 minutes to reach the heart of Christiansted, making it an affordable and convenient way to explore.
While it doesn’t offer an in-depth tour, this shuttle is ideal for those who want to see the town without hassle or extra expense. Once there, you can stroll cobblestone streets, visit Fort Christiansvaern, or browse local shops. It’s a straightforward, practical option for cruise passengers who want to maximize their time ashore without the need for organized tours.
Bottom Line: This port shuttle is a cost-effective way to explore Christiansted if your time is limited and you want a straightforward transfer.
$27.00 per person
5. Private Transfer from St.Croix Cruise Port to St.Croix Hotels
Rating: 0/5 (No reviews)
Price: $176.38 per person
Duration: About 30 minutes
Location: St Croix, US Virgin Islands
If comfort and convenience are your priorities, the Private Transfer from St.Croix Cruise Port to Hotels guarantees a smooth start or end to your trip. Instead of waiting in long lines for a taxi or shared shuttle, you’ll be greeted by a professional driver in a clean vehicle, ready to take you directly to your accommodation.
This service is especially useful if you’re traveling with luggage or arriving late at night. It’s a simple, no-hassle option that ensures you’re transported in comfort and style. While it’s more expensive than shared shuttles, the door-to-door service might be worth it if you value time and convenience over cost.
Bottom Line: For a stress-free, private ride between the port and your hotel, this transfer offers peace of mind and a comfortable trip.
$176.38 per person
How to Choose Your Perfect Boat Tour in St Croix
Picking the right boat experience depends on what kind of day you want. If you’re after a relaxed evening with good music and stunning sunset views, the Live Music Sunset Sail is your best bet. For a hands-on sailing experience with an educational twist, the Tall Ship Denis Sullivan offers something unique. History lovers should consider the Pirate Waters and Shipwrecks tour, which dives into the island’s fascinating pirate past.
Budget travelers or cruise passengers can opt for the Frederiksted Port Shuttle or the Private Transfer, which provide practical ways to get around without breaking the bank. Think about your interests—whether that’s sailing, history, or simply enjoying the scenery—and choose accordingly. Booking early is recommended, especially for the more popular sunset and private tours, to ensure availability.
Final Thoughts
St Croix offers a range of boat tours suited to many interests and budgets. For a relaxing, music-filled sunset, the Live Music Sunset Sail is a top pick. History enthusiasts will love the Pirate Waters and Shipwrecks tour, full of stories and exploration. And if you’re arriving by cruise, the Port Shuttle helps you get into town easily.
No matter which experience appeals most, these tours give you a chance to see the island from a different perspective. To make the most of your trip, consider booking early—these tours tend to fill up, especially in peak season. With so many great options, you’re bound to find a boat tour that makes your time in St Croix truly memorable.