Choosing Simpson Bay tours by the day you want
Simpson Bay tours work most clearly when compared by destination, time aboard or on the road, and departure location. A full catamaran day to Prickly Pear is different from a short sunset cruise, while an island drive is a way to see the Dutch and French sides from land. Decide which experience matters first, then compare what comes with that particular product.
Staying in Simpson Bay does not put every departure at your doorstep. The half-day island tour starts at the cruise port in Philipsburg, and the coastal catamaran day sail starts at a marina in Philipsburg. Other sailing and evening options start in the Simpson Bay area. Include the journey to the meeting point in your plans, with the transport guide as a starting point.
Island and boat outings
The Prickly Pear sail includes lunch and snorkeling gear. For a port departure, consider the guided island tour with transportation.
Hand-picked tours, booked through GetYourGuide and Viator. Prices are indicative starting prices in US dollars (as of November 2026). Tap a tour for live availability and the current price in your currency.
Trimaran sailing and snorkeling
- Snorkeling masks and fins
- Gourmet sandwich lunch
- Drinks and snacks
A sailing outing with time for snorkeling.
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Catamaran outing from Philipsburg
- Snorkeling equipment
- Paddleboards
- Lunch on board
A day on the water with equipment for swimming and paddling.
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Prickly Pear day sail
- Lunch on board
- Snorkeling gear
- Port fees
Sail to Prickly Pear in Anguilla on a day cruise.
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Island outing with hotel pickup
- Driver and guide
- Air-conditioned vehicle
- Unlimited beer, wine and soft drinks
Confirm that your accommodation is eligible for pickup.
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Simpson Bay sunset sail
- Open bar
- Warm snacks
An evening on the water with refreshments.
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Guided island tour from the cruise port
- Transportation included
- Guide included
- One drink
A guided outing starting at the Philipsburg cruise port.
Check availability →Compare sailing, sunset and island drives
Match a Prickly Pear day, a trimaran sail, a coastal catamaran or a guided island drive to your available time and departure location.
Half a day or a full day
The 4.5-hour island tour includes transportation, a guide and one drink, with meals separate. It starts at the cruise port, so it can make sense for passengers planning a land outing from Philipsburg. Visitors staying in Simpson Bay need to account for the road journey there. The shore excursion page explains the port setting and the need to plan around a ship’s own schedule.
For a longer sailing outing from Simpson Bay, the trimaran cruise takes 5.5 hours and includes snorkeling masks, fins, swimming noodles, a sandwich lunch, drinks, snacks and fruit. The boat is a trimaran. If the boat type itself is part of your decision, compare it with the catamaran options from Philipsburg rather than treating every sailing excursion as a catamaran trip.
Island tours on land
An island drive suits visitors who want a guided road outing instead of time aboard a boat. The hotel-transfer option takes 300 to 360 minutes and includes a driver-guide, an air-conditioned vehicle and drinks, including beer, wine and soft drinks. Confirm the specific accommodation for pickup. That service concerns the excursion transport, rather than arranging a place to stay.
The cruise-port half-day and the hotel-pickup drive solve different starting-point needs. Compare those needs before comparing the length of the outing. A port meeting is convenient for the right ship arrival, while an accommodation pickup can simplify the beginning and end of a day based on land. Avoid fitting another fixed appointment directly against either return.
Prickly Pear by catamaran
The 7.5-hour Prickly Pear catamaran cruise leaves from the Billy Folly Road area of Simpson Bay. Its inclusions are the day cruise, onboard drinks, lunch aboard, snorkeling gear and port fees. Hotel transfers are separate. This is the long boat day in this comparison, so leave space for reaching the marina before boarding and returning to your accommodation afterward.
Prickly Pear is part of Anguilla’s marine-park setting, rather than an island of Sint Maarten. Its destination also distinguishes it from Pinel and Tintamarre on the French side. If an Anguilla beach package is your main interest, compare the separate Anguilla day-trip arrangements, where boat transfers, land transfers and taxes are explained for those products.
Sunset and coastal sailing
The 2-hour evening cruise from the Simpson Bay marina area includes an open bar and warm snacks. It suits a day when the main plan is elsewhere and you want a shorter time on the water afterward. The sunset page compares it with the 1.5-hour alternative. Choose these for an evening cruise, while snorkeling belongs with the daytime sailing options.
The 5-hour coastal catamaran sail from Philipsburg includes a skipper, snorkeling equipment, paddleboards, a floating mat, lunch, drinks and light snacks, with a restroom aboard. Its starting point matters as much as those extras when staying in Simpson Bay. Choose the shorter journey to the boat only if that also gives you the route and activities you want.
Private or shared, and time for watersports
A shared sailing or island outing works when its published route already suits your day. For an adaptable land route or a private Anguilla package, continue to private tours. Pickup arrangements and group pricing vary by product, so a private booking should be compared on its actual route and inclusions rather than the label alone.
Snorkeling is the water activity built into several sailing choices here. Use the snorkeling guide if equipment and time in the water matter more than boat type. Leave flexibility for weather, and keep an alternative land plan rather than relying on a boat departure to fill an irreplaceable gap in your itinerary.
Questions about your visit
Which excursion starts at the cruise port?
The 4.5-hour guided island tour starts at the cruise port in Philipsburg and includes transport and one drink. Simpson Bay is a different starting area; allow for reaching the port if you are staying there.
Is lunch included on every trip?
Inclusions differ. The Prickly Pear cruise and the trimaran sailing outing include lunch. The half-day port island tour excludes meals, while the evening cruise provides warm snacks. Compare the relevant product instead of extending one meal arrangement to all outings.
Can I choose a shorter evening trip?
The 2-hour sunset cruise leaves from the Simpson Bay marina area with an open bar and warm snacks. It is a compact evening outing, so it serves a different purpose from the longer daytime sailing routes.