Private boat charter to Anguilla from Simpson Bay
Simpson Bay is a convenient Dutch-side departure area for private boat charters to Anguilla, particularly for guests staying around Simpson Bay, Pelican Key, Beacon Hill, Maho and nearby resorts.
Selected private boats operate from the Simpson Bay and lagoon area, making it possible to begin your Anguilla day close to many of the island’s main hotels, villas and tourism areas.
A full-day Anguilla charter can combine beautiful beaches, swimming, snorkelling and a relaxed lunch ashore, with the exact route shaped around the boat, sea conditions and your group.
Quick answer
Simpson Bay can be an excellent departure area for Anguilla if you are staying around Simpson Bay, Pelican Key, Beacon Hill, Maho or elsewhere on the Dutch side.
It works particularly well for:
guests staying around Simpson Bay, Pelican Key, Beacon Hill and Maho
couples and families wanting a convenient Dutch-side departure
full-day private Anguilla charters
groups interested in beaches, swimming, snorkelling and lunch ashore
guests for whom a suitable private boat is available from the Simpson Bay or lagoon area
Simpson Bay and Cole Bay are very close geographically. In practice, the right boat, route, comfort level and exact meeting point often matter more than whether a charter is described as departing from Simpson Bay or Cole Bay.
Private charter overview
Convenient Dutch-side departure
Practical for Simpson Bay, Pelican Key, Beacon Hill, Maho and nearby resorts
Selected private boats
Different group sizes, boat styles and comfort levels may be available
Full-day Anguilla experience
Beaches, swimming, snorkelling and time for lunch ashore
Why depart from Simpson Bay for Anguilla?
One of Simpson Bay’s main advantages is convenience for guests staying in one of the island’s busiest accommodation and tourism areas.
If you are staying around Simpson Bay, Pelican Key, Beacon Hill, Maho or nearby Dutch-side resorts, departing locally can avoid an unnecessary drive across St Maarten before the charter begins.
Selected private boats operating from the Simpson Bay and lagoon area can suit couples, families and groups planning a relaxed full-day Anguilla experience.
Depending on the charter, the exact meeting point may be at a marina, dock or other confirmed location around Simpson Bay and the lagoon rather than directly on Simpson Bay beach.
For an Anguilla day, the decision should ultimately be based on the right boat, route and overall experience for your group rather than simply choosing the departure point that appears closest on a map.
Is Simpson Bay convenient for where you're staying?
Simpson Bay is particularly convenient for guests staying around:
Simpson Bay
Pelican Key
Kim Sha
Beacon Hill
Maho
nearby Dutch-side hotels, villas and resorts
It may also be practical for guests staying around Cupecoy, depending on traffic, the exact meeting point and the charter available for your date.
Guests staying elsewhere can still find Simpson Bay worthwhile when a particular boat is especially well suited to their group.
For a full-day Anguilla charter, the right boat, comfort level and itinerary can matter more than saving a short drive before departure.
What does an Anguilla charter from Simpson Bay usually look like?
Your exact meeting point and departure instructions will be confirmed before your charter.
Because several marinas and departure areas sit around Simpson Bay and the lagoon, you should not assume that charters leave directly from Simpson Bay beach.
Once onboard, the day follows the itinerary and type of charter you have chosen, with the captain taking weather and sea conditions into account.
Entry procedures are completed as required before the Anguilla portion of the day begins.
Private trips normally allow a more relaxed pace than shared excursions, although exact stops cannot be guaranteed in advance because conditions on the water can change.
Departure and return times depend on the specific charter, and your confirmed schedule will be provided before the day.
Which parts of Anguilla can you visit?
The exact itinerary depends on the boat, sea conditions, entry formalities and the kind of day you want.
Depending on the route, private Anguilla charters may include areas such as:
Meads Bay
Sandy Island
Rendezvous Bay
Shoal Bay
Little Bay
Crocus Bay
other swimming, snorkelling or beach stops
Not every charter visits the same places, and trying to include every possible stop is rarely necessary.
Some groups prefer a beach-focused day with plenty of time ashore, while others want more swimming, snorkelling and time exploring by boat.
The best route is usually the one that suits the conditions and gives your group enough time to actually enjoy Anguilla.
Who does an Anguilla charter from Simpson Bay suit best?
Guests staying around Simpson Bay, Pelican Key, Beacon Hill and Maho
Couples looking for a relaxed full-day Anguilla experience
Families wanting beaches, swimming and time ashore
Groups wanting a convenient Dutch-side departure
Guests interested in combining swimming, snorkelling and lunch in Anguilla
Visitors who would prefer not to travel across St Maarten before their charter
Groups for whom a suitable private boat is available from the Simpson Bay or lagoon area
Guests who value the right boat and experience more than the exact marina name
What to know before booking
Valid travel documents are required for entry into Anguilla
Immigration and customs fees apply and vary by charter
Your exact meeting point depends on the boat and is confirmed before departure
Departures are from marinas, docks or other designated meeting points around the Simpson Bay area.
Routes and stops depend on weather and sea conditions
Full-day charters are normally the appropriate format for Anguilla
Boat capacity, shade, seating and onboard facilities vary
Lunch arrangements differ and are normally paid separately
Not every charter includes the same beaches or snorkelling stops
Balance-payment terms depend on the specific charter
We help narrow down the options based on your group size, comfort preferences, budget and preferred type of day
Simpson Bay or Cole Bay for Anguilla?
Simpson Bay and Cole Bay are very close geographically, and both can be convenient for guests staying on the Dutch side of St Maarten.
Simpson Bay may be particularly convenient if you are staying around:
Simpson Bay
Pelican Key
Kim Sha
Beacon Hill
Maho
Cole Bay may offer access to a different or wider choice of private boats, depending on your date, group size and preferred charter style.
The better option usually depends on:
which boats are available
the exact meeting point
your group size
the Anguilla route
boat comfort and facilities
your budget
your accommodation
weather and sea conditions
Because the two areas are so close, there is normally little reason to decide between Simpson Bay and Cole Bay before comparing the actual charter options.
A boat departing a few minutes farther away may be much better suited to your group than the nearest available option.
Simpson Bay or a French-side departure for Anguilla?
French-side departure points such as Marigot, Nettle Bay and Anse Marcel can also be very convenient for Anguilla, particularly when you are already staying nearby.
Simpson Bay may make more sense if you are staying on the Dutch side or if a suitable boat available there is a better fit for your group.
The best departure point depends on more than crossing distance. We also consider:
where you are staying
which boats are available
your group size
the Anguilla route
comfort and onboard facilities
your budget
weather and sea conditions
There is no single departure point that is automatically best for every Anguilla charter.
How booking works
Tell us your dates
Let us know your preferred date and group size
We confirm availability
We check suitable Simpson Bay and nearby options and guide you clearly
Reserve with a deposit
Secure your booking online, balance paid according to the terms of your charter
Common questions
Do we need passports for a private charter to Anguilla?
Yes. Anguilla is a separate territory, so valid travel documents are required for all passengers.
The exact documentation required can depend on nationality and immigration status. We will explain what passenger information is needed for the charter, but each guest remains responsible for travelling with the correct documents.
How long is the trip from Simpson Bay to Anguilla?
The journey time varies depending on the boat, route, departure point and sea conditions.
It is better not to choose a charter based only on an estimated crossing time. Boat design, comfort, conditions and the overall itinerary can have a much greater effect on the day than a small difference in journey length.
Can we choose where to stop in Anguilla?
A private charter allows more flexibility than a shared excursion, and your preferences can normally be discussed when planning the day.
However, the final route remains subject to weather, sea conditions, entry procedures, timing and the captain’s judgement.
Not every beach or offshore stop will be practical on every charter.
Are Anguilla customs and immigration fees included?
This varies between boats and charter options.
Some prices include certain entry fees, while others list them separately or collect them before departure.
We will explain the applicable fees clearly when recommending an option so you can compare the real overall cost.
Where can we stop for lunch in Anguilla?
Lunch is commonly arranged at one of Anguilla’s beachfront restaurants.
The most suitable restaurant depends on the route, availability, group preferences and where the boat can conveniently stop.
Lunch is normally paid directly to the restaurant unless the charter description specifically states that it is included
Where do private boat charters depart in Simpson Bay?
Although described as departing from Simpson Bay, private charters normally leave from a marina, dock or other designated meeting point in the wider Simpson Bay and lagoon area rather than Simpson Bay beach itself. Your exact departure location depends on the boat and will be confirmed before your charter.
Is Simpson Bay better than Cole Bay for Anguilla?
Neither departure area is automatically better.
Simpson Bay may be especially convenient for nearby hotels and resorts, while Cole Bay may provide access to a different or wider choice of boats.
Because the areas are close together, it is normally better to compare the actual boats, facilities, route and price rather than choosing based on the departure name alone.
Is Simpson Bay better than Marigot, Nettle Bay or Anse Marcel for Anguilla?
That depends on where you are staying and which boats are available.
Simpson Bay can make sense for guests staying on the Dutch side, while French-side departures may be more convenient for guests already staying around Marigot, Nettle Bay, Grand Case, Cul-de-Sac or Anse Marcel.
The right boat, comfort level, route and overall value normally matter more than choosing the geographically closest departure.
What happens if the weather or sea conditions are not suitable?
The captain and operator will assess the weather and sea conditions before departure.
Routes may be adjusted if necessary, and in some cases the charter may need to be postponed, changed or cancelled for safety reasons.
The applicable weather policy depends on the specific charter terms and will be explained before booking.
Which boat should we choose for an Anguilla charter from Simpson Bay?
The best boat depends on your group size, budget, comfort expectations and the type of day you want.
Some guests prefer a smaller, faster motorboat, while others prioritise shade, seating, space, stability or onboard facilities.
We compare the available Simpson Bay, Cole Bay and nearby options and explain which ones genuinely make sense for your group.
Choose the right experience
Anguilla private charters
→ Clear water, beautiful beaches and relaxed private day trips from St Maarten.
Full-day private charters
→ Complete days on the water with time to explore and relax.
Half-day private charters
→ Shorter private experiences around St Martin with swimming and coastal stops.
Private transfers to Anguilla
→ Direct private transportation between St Maarten and Anguilla.
St Barts private charters
→ Premium island experiences combining boating, restaurants, and time ashore.
Not sure which Simpson Bay option fits your Anguilla day?
Tell us your date, group size and the kind of day you have in mind.
We can narrow down the available Simpson Bay and nearby options based on your budget, comfort preferences and what is available for your date.
We’ll also tell you honestly if a boat departing from Cole Bay, Marigot, Nettle Bay, Anse Marcel or another departure point would make more sense for your group.
You do not need to know which boat to choose before contacting us.
What guests say about booking with EXPLR.SX
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Related guides
Most guests have similar questions before booking.
You may also find these guides useful:
→ Compare Cole Bay with Simpson Bay, Marigot, Nettle Bay, Anse Marcel and Philipsburg.
→ Explore the different private charter experiences available from Simpson Bay.
→ Understand typical charter prices, fees and additional costs.
→ Compare the two ways of travelling to Anguilla from St Maarten.
Based on the island. Here to help.
Based in St Martin / St Maarten
Speak to someone who knows the boats
Flexible help before and after booking
EXPLR.SX is based in St Martin / St Maarten and helps visitors navigate the many private charter options available across the island. Rather than asking guests to compare dozens of operators themselves, we help identify the most suitable option based on group size, destination, comfort level, budget and availability.
