Anguilla Island Hopping Day — Full Day Adventure from St. Maarten

Overview: Anguilla Island Hopping Day

Start your day exploring the Caribbean’s stunning waters and unspoiled islands with this oneday plan. On the water by morning and dining ashore by early evening, this itinerary blends marine adventure, culture, and great food to create a memorable St. Maarten experience. It is feasible for stayover travelers based in a hotel, villa or resort on the Dutch or French side and visitors by yacht. For cruise visitors, it is unlikely your time on island allows to fit in this cruise – see the Private Anguilla Charter day instead.

Best Days to Do This Day Plan

This day tour is available Tuesday to Friday, the days when the departing Lambada sails to Prickly Pear Cays . Booking well in advance is strongly recommended, especially in high season (winter), and check the cruise ship schedule> — busy port days can affect ground transport and local traffic.

What to Bring and Important Tips

Make sure you carry your passport (required for Anguilla entry), sun protection, swimwear, a towel, and a light coverup. Prebook your Lambada day sail and dinner reservations to secure your spot, as tours fill up early during the busy winter months.

8:00 AM — CheckIn at Aqua Mania Adventures

Begin your exciting day at Aqua Mania Adventures located in <Simpson Bay Resort’s> marina. Checkin starts around 8:00 AM, giving you time to meet the crew, ensure your passport is ready for customs, and get briefed on the day’s sail. The Lambada catamaran departs promptly after checkin and heads out past the lush Dutch coastline toward the open Caribbean.

9:30 – 11:00 AM — Sailing to Prickly Pear Cays

Settle into your sailing adventure as the catamaran glides over calm turquoise waters toward Prickly Pear Island. The journey gives you breathtaking views of St. Maarten’s shoreline and the wide seascape beyond. Feel the breeze, grab a fresh drink from the open bar, and anticipate the first island stop.

 11:00 AM – 12:00 PM — Snorkeling, Beach Time at Prickly Pear Cays

On arrival at Prickly Pear Cays, drop anchor for snorkeling and swimming in clear, warm water. The reefs here are ideal for spotting tropical fish while floating among coral formations. If you prefer lounging, enjoy the soft white sand and panoramic views that make this uninhabited cay a true Caribbean gem.

2:00 – 1:30 PM — Lunch Onboard

Return to the Lambada for a buffetstyle Caribbean lunch served on deck. Savor grilled chicken, ribs, salads, Johnny Cakes and more while you relax under the sun. The open bar continues during lunch, letting you sample tropical beverages as you recharge for the afternoon’s adventure.

1:30 – 3:30 PM — Mead’s Bay, Anguilla

After lunch, the catamaran sails north to Anguilla’s Mead’s Bay, one of the island’s most beloved beaches. Swim in clear waters, lounge with a drink in hand, or snorkel along the shoreline’s gentle reefs. This second stop lets you experience seaside life on Anguilla without leaving the rhythm of your boat day.

3:30 – 4:45 PM — Return Sail to St. Maarten

As the afternoon winds down, the Lambada points back toward Simpson Bay. Enjoy the return sail with music and refreshing island breezes. Arrive back at Aqua Mania Adventures’ marina around 4:45 PM, giving you time to change or stroll along the marina before dinner

 5:00 – 7:00 PM — Dinner at Beirut in Simpson Bay

Cap off your day with dinner at Beirut Sxm, a popular Lebanese restaurant just a 5 – 10 minute walk from the marina. Enjoy flavorful mezze, grilled specialties, and refreshing beverages while recounting the day’s highlights. Dinner timing lets you avoid peak hours and relax after a full schedule of islan.

Transportation Tips:

Buses run frequently along the Philipsburg–Maho line and stop near Pelican Key for walks to the marina; however, evening buses are less frequent. Taxis are available at major resorts and key areas like Philipsburg’s Emmaplein and the Courthouse, and they can be faster and more flexible for return transfers after dinner.

Suggested One Day and Multi Day Itineraries on VisitStMaarten.com

After completing this memorable day trip, you may also enjoy these real itineraries featured in the Visit St. Maarten itinerary blog:

• Cruise Visitor Highlights — Best Shore Excursions in a Day (ideal for limited port time)

• Island Explorer — Five Day Adventure Around St. Maarten St. Martin

• Seven Day Caribbean Discovery — Complete St. Maarten Experience