Anguilla by Private Boat: An Island-Hopping Itinerary for a Day on the Water

There is a particular kind of day that only exists on a private boat. No queue at the dock, no fixed schedule, no captain watching the clock for a group of forty. Just you and up to nine of your people, a stretch of glass-clear Caribbean water, and a coastline that keeps offering one more bay worth stopping for.

This is the day we love hosting most: a slow, loose-limbed island-hop from Saint-Martin across to Anguilla. Here is how a full day on the water can unfold – and where a native captain’s local knowledge turns a good route into an unforgettable one.

Our Axopar 37 Suntop are designed for fast and confortable island-hopping.

Why Anguilla Rewards a Private Boat

Anguilla sits low and long, a thin ribbon of white sand and limestone just a short crossing from Saint-Martin. It is famous for two things: beaches that seem almost too pale to be real, and a laid-back, unhurried character that makes the island feel like a secret you have been let in on.

The catch is that Anguilla’s best places are not clustered together. They are scattered along 33 beaches and several small offshore cays, spread across both ends of the island. A shared tour has to pick a couple of highlights and stick to them. A private boat charter to Anguilla lets you string them together on your own terms – linger where the water is best, and leave when you are ready.

How the Day Starts

Most private days begin on the Saint-Martin side, where your captain will meet you at the dock and walk you through the plan. From there, the crossing to Anguilla is short and usually calm: a quick stretch of open water, then the island rising into view, flat and sun-bleached against the sky.

Because the boat is yours for the day, the first decision is one you get to make. Do you want to head straight for a quiet anchorage and swim before anyone else is out there? Or make your way down the coast, stopping wherever the water looks too good to pass?

A Sample Anguilla Island-Hopping Itinerary

Think of this as a menu rather than a script. Your captain will shape the route around the wind, the tide, and whatever mood the group is in.

1. Sandy Ground and Road Bay

The main harbor village on Anguilla, Sandy Ground is a lively, sociable first stop. Road Bay’s beach is calm and kid-friendly, and the strip behind it holds some of the island’s best-known beach bars. Anchor here if you want an easy start, a swim in sheltered water, and a taste of local life before the day opens up.

2. Crocus Bay and Little Bay

As you move west, Crocus Bay offers a gentle curve of sand and a dramatic cliff backdrop. Just around the point is Little Bay – a tiny, cliff-bound cove that many visitors never see, because it is easiest to reach by boat. The snorkeling here is excellent, with rocky ledges, reef fish, and the kind of clear water that makes a mask almost unnecessary. This is exactly the sort of spot a private day makes possible.

3. Sandy Island and Prickly Pear

Off the northwestern coast lie two postcard cays. Sandy Island is a small, low ring of sand with a few palms and a beach bar that appears at lunchtime. Prickly Pear is a bit larger, with calm shallows and a restaurant right on the sand. Either one makes a perfect midday pause: step off the boat onto the beach, swim, eat, and let the afternoon slow down.

4. Meads Bay and the West End

Anguilla’s west end is where the island shows off. Meads Bay is a long, wide sweep of white sand backed by elegant beach bars and restaurants – the kind of place where a lunch can stretch into a whole afternoon. If your group wants a more polished, upscale stop in the itinerary, this is where it belongs.

5. Shoal Bay East and Rendezvous Bay

On the eastern and southern sides, Shoal Bay East is the beach people photograph first: powdery sand, gentle turquoise gradients, and a handful of casual beach bars. Rendezvous Bay curves for nearly two miles, offering calm water and wide-open views back toward Saint-Martin – a beautiful, sheltered place to swim late in the day.

What Makes a Private Day Different

A shared tour shows you Anguilla. A private charter lets you live it at your own pace.

• Your itinerary, not a template. Want three beach bars and no snorkeling? Two anchorages and a long lunch? It is your call.
• Room for your group. Up to ten guests means the boat feels like your own – not a crowd.
• A captain who knows the water. Local knowledge decides where the wind and tide are kindest on any given day, which is the difference between a nice stop and the right one.
• No wasted time. You skip the dock queues and the group logistics, and spend your hours where they count.

Practical Tips for Island-Hopping by Boat

• Start early. Leaving Saint-Martin in the morning gives you the calmest water and the quietest beaches.
• Bring reef-safe sunscreen, a hat, and a light layer. The Caribbean sun is strong, and a warm afternoon breeze can surprise you.
• Pack light and waterproof. A dry bag for phones and cameras, and shoes you do not mind getting wet for beach landings.
• Keep the plan flexible. The best days often come from changing course toward the bay that looks too perfect to skip.
• Ask about a sunset add-on. Ending the day on the water as the sun drops behind the island is the kind of finish people remember for years.

Ready to Plan Your Day?

Anguilla is best understood from the water – one bay at a time, at your own speed, with the people you came to travel with.

Everything here is a starting point. From where do you want to start the day? What do you want to do? Tell us, and Captain Elliot and the Paper Boat Charter team will shape a private day charter across Saint-Martin, Anguilla, and St. Barth around exactly that. With up to ten guests, a bespoke itinerary, and a native captain who knows these islands, your day on the water is yours to design.

Ready to experience Anguilla from the water? Discover our private boat charter packages and plan your perfect day.

Book your private day charter and let’s make your dream real.