Private charters to Anguilla from St Martin / St Maarten

Private boat charters to Anguilla from St Maarten & St Martin

Discover Anguilla by private boat from St Martin & St Maarten. Known for its white-sand beaches, crystal-clear water, and relaxed island atmosphere, Anguilla is one of the most popular private boat day trips in the Caribbean.

With a short crossing from St Maarten, you’ll have time to swim, relax, enjoy lunch ashore, and explore some of the region’s most beautiful coastline at your own pace.

Full-day and half-day private charters available.

Prefer to ask first? You can also reach us by email or WhatsApp.

Aerial view of private boat charter in Anguilla with clear turquoise water

Choose the right Anguilla charter

Full-day Anguilla charters

A complete day on the water with time to visit multiple beaches, swim, and enjoy Anguilla at a relaxed pace.

Explore full-day options →

Half-day Anguilla charters

A shorter, more focused trip with time for one or two stops. Best suited to guests with limited time and flexible expectations.

Explore half-day options →

Why Anguilla is different

Anguilla offers a very different experience compared to St Maarten. The beaches are quieter, the water is exceptionally clear, and the overall pace is more relaxed.

Because it’s a separate island, the day includes a short crossing and arrival formalities, but the reward is access to some of the most beautiful coastline in the region.

For most guests, it’s one of the standout experiences of their trip.

Guests looking for a day built around restaurants, shopping, beach clubs, and time ashore may also wish to consider a private charter to St Barts.

Why guests choose Anguilla

Crystal-clear water

Anguilla is known for some of the clearest water in the Caribbean, making it one of the most popular destinations for swimming, relaxing, and enjoying time on the water.

Spectacular beaches

From long stretches of white sand to smaller bays accessible by boat, Anguilla is often chosen by guests who want to spend time ashore as well as on the water.

Relaxed island atmosphere

The pace is slower, quieter, and less crowded than many Caribbean destinations, making it ideal for guests looking for a more laid-back day.

Beach restaurants and lunch stops

Many guests choose Anguilla specifically for the opportunity to enjoy lunch ashore before continuing their day on the water.

A true island escape

Unlike staying around St Martin, the crossing creates the feeling of visiting a completely different destination while still remaining close enough for an easy day trip.

Is an Anguilla charter right for your group?

Often best for:

  • beach lovers
  • couples
  • families
  • clear-water enthusiasts
  • relaxed travellers
  • guests who want time ashore
  • full-day experiences
  • visitors looking for a true island escape

You may prefer St Maarten if:

  • you want a shorter trip
  • snorkelling is your main priority
  • you only have half a day available
  • you want maximum flexibility

Explore St Maarten charters →

You may prefer St Barts if:

  • restaurants and shopping are important
  • you’re looking for a longer premium day
  • beach clubs are a priority
  • you want time in Gustavia

Explore St Barts charters →

Small private boat anchored in a quiet Anguilla bay with white sand beach and clear water

Based on the island. Here to help.

Local experts

Based in St Martin / St Maarten

Direct support

Speak to someone who knows the boats

7 days a week

Flexible help before and after booking

We help you choose the right charter based on your group, your timing, and how you want to spend your day — whether that’s a half-day trip, a full-day charter, or a relaxed sunset cruise.

Why book your Anguilla charter through EXPLR.SX?

Local knowledge

We live and work in St Martin and know which boats, routes, and experiences work best for different groups.

Trusted operators

We only work with trusted local captains and charter operators that we know personally.

Availability checked for you

No need to contact multiple operators. We check availability and recommend the most suitable options based on your dates, group size, and budget.

One point of contact

From your first enquiry until the day of your charter, you’ll deal directly with EXPLR.SX for guidance and support.

Reserve with a deposit

Secure your charter with a deposit online. The remaining balance is paid directly to your captain on the day.

Still deciding?

Choosing the right private boat charter is often less about the boat itself and more about the experience you’re looking for.

Anguilla is ideal for guests who prioritise beaches, clear water, and a relaxed island atmosphere, while St Maarten and St Barts offer very different styles of day trip.

These guides can help you decide which option best suits your group.

→ Compare the two most popular private boat day trips from St Maarten.

→ What makes Anguilla different, who it’s best suited to, and whether the crossing is worth it.

→ Compare time, comfort, and how you travel between islands.
→ The easiest, most enjoyable private boat experiences for first-time visitors to St Maarten.

→ This guide explains what really matters when choosing the right size private boat charter.

Important to know before you go

Crossing time

The crossing from St Martin to Anguilla typically takes around 20–25 minutes each way depending on sea conditions and departure location.

Customs and immigration

Most private boat charters require customs and immigration clearance on arrival. Applicable fees are normally paid separately unless specifically stated otherwise.

Passport required

Anguilla is a separate British Overseas Territory. All guests must carry valid identification and travel documents required for entry.

Weather matters

Although the crossing is usually straightforward, routes and timings may occasionally be adjusted based on weather and sea conditions.

Full-day charters are usually best

While half-day trips are available, most guests find a full-day charter provides the best balance between crossing time, beach time, lunch ashore, and relaxation.

A typical private boat charter to Anguilla

Depart St Maarten

Meet your captain and board your private charter at the agreed departure marina.

Cross to Anguilla

Enjoy a scenic crossing of approximately 20–25 minutes depending on conditions.

Explore beaches and bays

Visit beautiful locations such as Meads Bay, Rendezvous Bay, Shoal Bay, Sandy Island, Prickly Pear, or other destinations depending on your itinerary.

Lunch and time ashore

Many guests choose to enjoy lunch at one of Anguilla's beachfront restaurants before continuing their day.

Relax and return

Spend the afternoon swimming, cruising, and enjoying the water before returning comfortably to St Maarten.

How much does a private charter to Anguilla cost?

Private charters to Anguilla typically start from around $1,100+ for a full-day experience, with pricing varying based on the boat, group size, itinerary, and level of comfort you’re looking for.

Because Anguilla involves an international crossing, larger boats are often recommended, particularly for guests prioritising comfort.

We’ll recommend the most suitable options based on your dates, group size, and budget before any payment is required.

Prefer to ask first? You can also reach us by email or WhatsApp.

How booking works

We check availability first — you only pay once your charter is confirmed.

Step 1 — Tell us your plans

Share your dates, group size, and what you’re looking for

Step 2 — We recommend options

We match you with the best available boats for your group

Step 3 — Reserve with a deposit

Balance paid directly to your captain on the day

Before you book

Anguilla charters involve a short international crossing, so timing, weather conditions, and customs clearance all play a role in how the day is structured.

While the crossing is usually straightforward, it’s important to allow enough time to fully enjoy the experience — which is why full-day charters are generally recommended.

We’ll confirm all details clearly before you book, including timing, departure point, and what’s included.

Private boat charter to Anguilla from St Martin turquoise water view
Turquoise waters of Anguilla

What guests say about booking with EXPLR.SX

Real feedback from guests who trusted EXPLR.SX to plan their time in St Martin & St Maarten — from private boat charters to island day trips.

“Everything was thoughtfully organised from start to finish, especially travelling with two young children. We felt completely looked after on the day, and the experience was both safe and unforgettable. Communication was excellent throughout, which gave us real peace of mind.”
Chelsey
USA
• Private Boat Charter
March 2026
“EXPLR.SX is a great choice when planning experiences in St Maarten. Everything was well organised, flexible, and easy to arrange, even when the weather changed. Communication was quick and helpful throughout, and we enjoyed both of our trips.”
Helene
Canada
• Private Boat Charter
April 2026
“Everything felt easy and smooth from booking through to the day itself. The experience was well planned but still flexible, which made it perfect for our group. We had an amazing time in Anguilla and would highly recommend it.”
Kristen
USA
• Private Boat Charter
April 2026
“An incredible day on the water and one of the highlights of our trip. Everything was perfectly organised, with great attention to detail throughout — including an amazing meal and thoughtful care for dietary requirements. The whole experience felt effortless.”
Stefani
USA
• Private Boat Charter
April 2026
“The highlight of our two weeks in St Maarten. We were a large group with kids and everything was incredibly smooth and completely stress-free. Communication was excellent and we felt looked after from start to finish.”
Marcus
USA
• Private Boat Charter
September 2025
“Very professional and reliable from start to finish. The whole day was easy, well organised, and a lot of fun — exactly what we were hoping for.”
Sara
USA
• Private Boat Charter
January 2026

Common concerns

Most guests have similar questions before booking.

You may also find these guides useful:

→ How conditions are handled and your options.

→ Understanding deposits, communication, and what to check before booking.

→ When to book — and when last-minute still works.

→ How to avoid common mistakes when booking.

→ The calmest routes, easiest crossings, and best options for guests worried about seasickness.

Frequently asked questions

For many visitors, a private boat charter to Anguilla becomes the highlight of their trip. Anguilla is known for its white-sand beaches, exceptionally clear turquoise water, and relaxed atmosphere. Unlike St Maarten, where many attractions are concentrated around the coastline, Anguilla feels like a true island escape. Guests often choose Anguilla because they want time ashore, beautiful beaches, beachfront restaurants, and a slower pace. If beaches and clear water are your priorities, Anguilla is often the best private boat day trip from St Maarten.

The crossing between St Martin and Anguilla typically takes around 20–25 minutes each way depending on weather conditions, departure location, and the type of boat. Most guests find the crossing relatively straightforward, especially on calm-weather days. Larger boats generally provide a more comfortable ride if sea conditions become choppy.

 

Anguilla charters involve an international crossing, customs and immigration procedures, additional fuel consumption, and generally require larger boats than many local St Maarten trips. The experience also includes access to one of the Caribbean's most desirable island destinations. While pricing is typically higher than a local St Maarten charter, many guests feel the additional beaches, scenery, and island experience justify the difference.

Customs and immigration fees are usually charged separately unless specifically stated otherwise for a particular charter. Fees vary depending on nationality, age, and local regulations. We'll always explain any applicable charges before you confirm your booking so there are no surprises.

Yes. Anguilla is a separate territory and valid travel documents are normally required for entry. Requirements can vary depending on your nationality and immigration status, so guests should ensure they have the necessary documentation before travelling. If you're unsure, contact us before booking and we'll help point you in the right direction.

Absolutely. Many guests choose Anguilla specifically because they want to spend time on the island itself. Depending on your itinerary, you may visit beaches, enjoy lunch at a beachfront restaurant, explore different bays, or simply relax ashore before continuing your day on the water.

A half-day Anguilla charter focuses on a smaller number of locations and less time ashore. Because the crossing itself takes time, many guests find a full-day charter offers a much better overall experience. Full-day charters provide more flexibility, more beach time, more swimming opportunities, and a more relaxed pace throughout the day.

It can be, particularly for guests with limited time or those staying close to a suitable departure point. However, because Anguilla involves an international crossing, most visitors find that a full-day charter provides significantly better value and allows enough time to fully enjoy the destination. We generally recommend full-day trips whenever possible.

Safety always comes first. Captains monitor weather and sea conditions carefully and may adjust routes, departure times, or itineraries if necessary. If conditions are considered unsafe for the crossing, rescheduling or alternative arrangements may be discussed depending on the circumstances and operator policies. We'll always keep you informed and help coordinate the best available solution.

Yes. Private charters offer far greater flexibility than shared tours. While weather and sea conditions always influence the final route, many charters can include a combination of beaches, bays, snorkelling stops, swimming locations, and lunch ashore. We'll help design the day around your priorities and recommend an itinerary that works well for your group.

Tell us what you have in mind

Tell us your date, group size, and what you’re looking for, and we’ll guide you to the best available Anguilla charter.

Reserve your date with a deposit. Balance paid on the day.

Plan your day

We’ll reply with available options and next steps.
No payment required.

We’ll help you choose the best option for your dates.

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to Anguilla?

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Check availability

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