Anguilla sits in some of the most spectacular water in the Caribbean. The sea around the island — coral-filtered, reef-sheltered, impossibly blue — is best experienced from the deck of a private boat. Whether you want a full day anchored off Sandy Island's sand bar, a fast crossing to St Barths for lunch, or a sunset cruise with a group, this guide covers every boat charter option available from Anguilla and what each one actually involves.
Charter Options at a Glance
Private Day Trip
Sandy Island · Prickly Pear · Full day
$2,000
Shared Group Trip
7–9 passengers · Per person
$200 / person
Island Transfer — St Maarten
Anguilla ↔ SXM · Private
$2,100
Island Transfer — St Barths
Anguilla ↔ SBH · Private
$2,600
Private Day Trip — Sandy Island & Prickly Pear
The private day trip charter is Anguilla's quintessential boat experience. Your group — up to 9 passengers — has the entire vessel to yourselves. You set the pace, choose the anchoring spots, and decide how long you stay at each.
Sandy Island
Sandy Island is a tiny, uninhabited sand bar sitting roughly a mile off Anguilla's west coast, visible from Sandy Ground. Surrounding it is a shallow turquoise lagoon and a coral reef with excellent snorkelling. A seasonal beach bar operates on the island — tables set directly in the sand, cold drinks, grilled fish. There is nothing else here. That's the point.
The crossing from Sandy Ground takes around 10 minutes by boat. Most private charters spend two to four hours anchored here before moving on — or staying for the entire day if the group prefers. The reef around the island is calm enough for easy snorkelling and shallow enough for children. Visibility in peak season (January–April) regularly exceeds 50 feet.
Prickly Pear Cay
Prickly Pear Cay sits further north-east, about 4 miles from Anguilla's north coast. It is larger than Sandy Island, with two distinct bays — Prickly Pear East and Prickly Pear West — each offering different reef conditions and depths. The eastern bay is calmer and better for snorkelling; the western bay has more open water and better for swimming.
A private charter can visit both Sandy Island and Prickly Pear in the same day — the boat moves between them while your group swims, snorkels, or simply drifts.
What's included: A captained private vessel, snorkelling equipment, cooler. Drinks and food are not included but you're welcome to bring whatever you like — the crew will keep drinks cold. The captain handles navigation, anchoring, and safety. You handle relaxing.
Shared Group Trip — $200 per Person
The shared group trip is designed for larger parties — minimum 7, maximum 9 passengers — travelling together. At $200 per person, it's the most cost-effective way to get on the water in Anguilla. The experience is the same as a private charter: Sandy Island, Prickly Pear, open water — your group has the boat.
This option suits family reunions, friend groups, wedding parties, or any group that wants a shared day-on-the-water experience. The per-person pricing also makes it easier to split costs across the group rather than splitting a flat charter fee.
Island Transfers — St Maarten & St Barths
Beyond day trips, a private boat is the fastest and most flexible way to move between Anguilla and the neighbouring islands. Both crossings are private — your group only, departure on your schedule.
Anguilla ↔ St Maarten (SXM)
~45–60 minutes crossing
$2,100
The St Maarten crossing is the most popular inter-island route from Anguilla. Most guests use it to connect with their flight at Princess Juliana International Airport (SXM) or to spend a day in Philipsburg or Grand Case without taking the ferry. The crossing is sheltered for the most part — sea conditions are generally manageable year-round.
The key advantage over the scheduled ferry: a private boat transfer departs exactly when you need it to. No queuing at Blowing Point, no fixed schedule, no sharing a vessel with 50 strangers. If you need to catch a 6am flight, the boat departs at 4am.
Anguilla ↔ St Barths (SBH)
~1.5–2 hours crossing
$2,600
St Barths (Saint Barthélemy) is 45 miles south-east of Anguilla. There is no scheduled ferry connection between the two islands — a private boat is the only sea route. The crossing takes 1.5 to 2 hours depending on sea conditions; the open Atlantic between the islands can be choppy in certain months.
The St Barths day trip is popular among guests staying at Anguilla's top resorts who want a change of scene: lunch at Le Sereno or Maya's, a morning at Gouverneur or St Jean beach, shopping in Gustavia — then back to Anguilla by evening. It is an exceptional day.
What to Do on a Full-Day Charter
A full day on the water around Anguilla typically runs 8–9 hours. A well-paced private charter itinerary might look like this:
Depart Sandy Ground
Board the vessel at Sandy Ground harbour. Your captain gives a brief safety overview. The cooler is stocked with ice; add your drinks.
Arrive Sandy Island
Anchor off the sand bar. Snorkel the reef, swim to the island, or sit on the back deck with a drink and do absolutely nothing. The island bar opens mid-morning.
Cruise to Prickly Pear
20-minute run north-east to Prickly Pear Cay. Different reef, different depth, quieter. Lunch on the boat — whatever you've brought, or the captain can source fresh lobster with advance notice.
Open water — swim, drift, explore
Some groups want a second snorkelling session; others prefer to simply anchor in calm water and swim off the back of the boat with a view of the island. Both are excellent options.
Return to Sandy Ground
Head back to the harbour as the light drops. Sunset from the water looking back at Anguilla's north coast is as good as it gets.
Practical Notes Before You Book
Book at least 48 hours in advance
The boat needs to be prepped and the captain confirmed. During peak season (December–April), book further ahead — availability fills quickly, especially around school holidays and Carnival week.
Bring reef-safe sunscreen
Anguilla's reefs are protected. Standard oxybenzone-based sunscreens damage coral. Reef-safe mineral sunscreen (zinc oxide or titanium dioxide) is recommended and increasingly required at ecologically sensitive sites.
Inter-island transfers require your passport
Crossings to St Maarten (French/Dutch territory) and St Barths (French collectivity) are international. You will clear customs on arrival. Keep your passport accessible — not buried in luggage.
Sea conditions vary by season
January–April brings the calmest, clearest water. May–November can have stronger swells, particularly on the open Atlantic side (relevant for the St Barths crossing). The captain monitors conditions and will advise if a route needs to be adjusted for safety.
A 50% deposit secures the booking
Boat charters are confirmed with a 50% deposit paid online. The remaining balance is payable on the day. If weather forces a cancellation, the deposit is fully refunded or applied to a rescheduled date.
Private Charter vs Shared Ferry to St Maarten
The public ferry from Blowing Point to Marigot runs several times a day at around $20–25 per person each way. It's the budget option. Here's how it compares to a private boat transfer:
| Factor | Public Ferry | Private Charter |
|---|---|---|
| Departure | Fixed schedule | Your schedule |
| Other passengers | Up to 50+ | Your group only |
| Luggage | Restricted, queuing | Load at your pace |
| Destination | Marigot only | Any SXM dock |
| Cost (group of 4) | ~$80–100 return | $2,100 one way |
For most resort guests, the ferry is fine for a casual day trip. The private charter earns its premium when timing matters — early-morning flight connections, groups with luggage, guests who value having the vessel to themselves, or anyone who has been on a crowded Caribbean ferry and would prefer not to repeat the experience.
Ready to Get on the Water?
Book an Anguilla Boat Charter
Private day trips from $2,000. Shared group trips at $200 per person. Island transfers to St Maarten and St Barths. All captained, all private, all on your schedule.
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