Traditional Sailing Adventure to Anguilla’s Prickly Pear Cays

Imagine drifting on a beautifully restored Caribbean cargo sloop, soaking up the sun, and watching dolphins and flying fish leap alongside your boat. For about six hours, you’ll cruise to the Prickly Pear Cays, a picture-perfect pair of islands off Anguilla’s coast, with plenty of opportunities for snorkeling, swimming, and relaxing on white sandy beaches. The tour, costing around $644 per person, is well suited for those craving an authentic, laid-back day on the water, with a sprinkle of history and local flavor thrown in.

What makes this experience shine? First, the sailing on a traditional, retired cargo vessel is a delight for anyone who appreciates maritime history and the romance of old-school sailing. Second, the all-inclusive food, drinks, and snorkeling gear mean you can simply relax and enjoy without fussing over extra costs—freeing you to savor every moment.

The one thing to keep in mind is that while the tour is quite immersive and fun, it’s not for those with shellfish allergies or serious nut allergies, as the lobster lunch is a highlight, but also a potential issue for some. It’s best suited for travelers who enjoy social, scenic days on the water with a touch of adventure and comfort—perfect for families, couples, or groups of friends wanting an authentic Caribbean experience.

Key Points

• Authentic Sailing: Cruising on a historic Caribbean sloop offers a genuine maritime experience.
• All-Inclusive Comfort: Food, drinks, snorkeling gear, and beach chairs are provided, making it a hassle-free day.
• Beautiful Destinations: Prickly Pear Cays boast stunning beaches, clear waters, and vibrant coral reefs.
• Engaging Crew: Guides and crew are praised for their knowledge, friendliness, and attentiveness.
• Family Friendly: Suitable for most travelers, including kids, with enjoyable activities and relaxed pace.
• Limited Spots: Small group sizes (max 12) ensure personalized attention and a cozy atmosphere.

An In-Depth Look at the Sailing Adventure in Anguilla

The Start: A Historic Vessel with a Personal Touch

From the moment you step aboard, you’re transported to a different era. This is not just any boat—it’s the last surviving Caribbean sloop of her kind, a vessel with a story of trade, rum smuggling, and maritime resilience. As you settle into the deck, the captain offers a quick safety briefing along with tales of the boat’s past, which adds a layer of authenticity and charm.

We loved the way the crew makes you feel like part of their maritime family. One reviewer, Matthew, notes, “The entire crew is so knowledgeable and accommodating. They treated us like family during our entire charter.” The relaxed and friendly atmosphere helps you unwind and appreciate the scenery, the history, and the crew’s enthusiasm.

The Sailing Experience: A Balance of Relaxation and Engagement

The tour kicks off with a cheerful start—morning mimosas or fresh orange juice in hand—as the captain explains the boat’s history and what to expect. The sailing itself is a highlight; with the sails hoisted, you glide smoothly over the water, watching for turtles, flying fish, and dolphins. During migration season, whales might even make an appearance, adding to the magic.

Help raise the sails if you’re feeling energetic, or simply sit back with a cocktail in hand and take in the panoramic views. We found the experience to be beautifully slow-paced, allowing plenty of time to soak in the scenery and relax. The small group size means everyone gets personal attention, and the crew ensures safety and fun go hand in hand.

The Prickly Pear Cays: A Beach Lover’s Paradise

After about three hours of sailing, you arrive at the Prickly Pear Cays, a relatively untouched stretch of white sand beaches and vibrant coral reefs. Here, snorkeling gear is provided, and the reef is teeming with marine life—perfect for both beginners and more experienced snorkelers.

Guests frequently praise the clarity of the water and the variety of fish seen below. As one guest put it, “Snorkeling the reef was incredible, with so many colorful fish swimming around.” Swimming and floating along the shore are also popular, with guests searching for shells or just enjoying the gentle waves.

Lunchtime consists of a delicious Caribbean lobster lunch—a treat that many reviewers, including Jake, say is a highlight. The lobster is grilled to perfection, and the meal is served with local beverages, all included. You’ll also find plenty of beach chairs and shade, making it easy to relax, sip on a rum punch, and enjoy the scenery.

Return Journey and Sweet Endings

On the way back, the open bar remains available, featuring a variety of drinks, from tropical cocktails to soda and water. To satisfy sweet cravings, fresh watermelon and chocolate chip cookies are served—a simple but thoughtful touch that keeps the mood light and cheerful.

Many travelers mention how friendly and attentive the crew is, making sure everyone is comfortable and having fun. We loved the way the crew keeps the atmosphere lively and relaxed, creating a perfect balance of adventure and leisure.

The Value and Practicalities

While $644 per person might seem steep at first glance, it’s important to consider what’s included: a six-hour sailing adventure, snorkeling equipment, lobster lunch, all drinks, and the unique experience of sailing on a historic vessel. Compared to other excursions that might charge extra for food or equipment, this all-inclusive setup provides excellent value for a full day of entertainment, relaxation, and culture.

Booking in advance (about 27 days ahead on average) is recommended, as the tour is popular, with a maximum of 12 travelers ensuring a personal experience. It starts promptly at 9:00 am from Sandy Ground, and transportation to the meeting point isn’t included, so plan accordingly.

Considerations

• The tour may be canceled if minimum passenger numbers (6) aren’t met, but full refunds or alternative dates are offered.
• The lobster lunch is a highlight, but those with shellfish allergies should be cautious.
• The tour isn’t recommended for travelers with severe nut or shellfish allergies.
• The small group size fosters intimacy but also means spots fill up quickly.

Who Will Love This Tour?

This sailing adventure is ideal for those who enjoy authentic maritime experiences, appreciate good food and drinks, and want a relaxed day on the water with a touch of history. Families, couples, and groups of friends looking for a memorable, scenic day will find this tour a perfect fit.

Final Thoughts

This traditional sailing trip in Anguilla offers more than just a boat ride; it’s an immersion into Caribbean culture, history, and natural beauty. The crew’s friendliness, the authentic vessel, and the stunning landscape combine to create a memorable experience that appeals to those seeking a balance of adventure and leisure.

If you value good value for money, authentic storytelling, and beautiful scenery, this tour ticks all those boxes. It’s a great way to see Anguilla from a different perspective—on the water, with the wind in your hair, and a lobster lunch in your belly. Whether you’re a seasoned sailor or a first-time snorkeler, you’ll leave with a smile and stories to tell.

Frequently Asked Questions

Is this tour suitable for children?
Yes, many reviews mention bringing young kids along; the relaxed pace and family-friendly activities make it suitable for children.

What should I bring?
Bring sun protection, a hat, sunglasses, and possibly a reef-safe sunscreen. Towels and swimsuits are provided, and snorkeling gear is included.

Is lunch really included?
Yes, a Caribbean lobster lunch, along with beverages and snacks, are included in the price.

What if the weather is bad?
The tour requires good weather, and if canceled due to poor weather, you’ll be offered a different date or a full refund.

Are drinks unlimited?
Yes, the open bar includes unlimited drinks during the trip, from cocktails to soft drinks.

How many people are in each group?
The maximum group size is 12, offering a personal and friendly atmosphere.

Do I need to book in advance?
Yes, booking about 27 days ahead is recommended, especially during peak season.

Can I help with sailing the boat?
You’re welcome to help raise the sails if you like, or simply relax and enjoy the views.

Are there any dietary restrictions?
Please inform the tour provider of any dietary requirements at booking; the lobster lunch is a highlight but may not suit everyone.

What is the start time?
The tour begins promptly at 9:00 am from Sandy Ground.

This sailing adventure in Anguilla offers a perfect mix of history, scenery, and leisure. If you’re after a hands-on, authentic Caribbean experience that leaves you relaxed and full of stories, this tour is well worth considering.