The best things to do in Anguilla fit neatly into five days. A good Anguilla itinerary mixes beach days with one boat day and plenty of time doing nothing. Spend day one settling in at the beach below the villa, day two on a boat to Prickly Pear Cays or Sandy Island, day three exploring the West End beaches at Meads Bay and Rendezvous Bay, day four in Island Harbour with lunch at Scilly Cay, and day five slow at the villa pool. Five days is also our minimum stay, and about the right length to see the island without rushing.
If you are visiting Anguilla for the first time, this guide to Anguilla covers what to prioritize. Anguilla is a small Caribbean island, 16 miles long and 3 miles wide, so you can drive around the island in a few days. Below is the day-by-day plan we suggest to guests, a list of more things to do if you stay longer, and how a typical day at the villa actually unfolds, hour by hour.
Things to do in Anguilla: the 5-day itinerary at a glance
| Day | Plan | Where |
|---|---|---|
| Day 1 | Arrive, groceries, first swim, sunset at the villa | Shoal Bay East |
| Day 2 | Boat day with snorkeling and lunch on a cay | Prickly Pear Cays or Sandy Island |
| Day 3 | West End beaches, sunset dinner | Meads Bay, Rendezvous Bay |
| Day 4 | Fishing village, island lunch, quiet beach | Island Harbour, Scilly Cay, Savannah Bay |
| Day 5 | Nothing planned, pool and beach | Villa Okeanos |
| Extra days | Reef snorkeling, a kayak trip, a spa day, heritage | Crocus Bay, Little Bay, The Valley |
Day 1: Arrive and slow down at Shoal Bay East
Land at Clayton J. Lloyd International Airport (AXA), with direct flights from Miami and several US cities, or fly into Princess Juliana International Airport (SXM) on St. Maarten and take the ferry ride or a private boat across, paying the departure tax at the terminal. Our arrival guide covers both routes. The villa is 4.5 miles from the airport and 8 miles from the Blowing Point ferry terminal. Pick up groceries on the way in, or ask us to provision the villa.
Then drive down to Shoal Bay East, 2 to 3 minutes from the villa, for a first swim. In June 2026 it was ranked the best beach in North America. If you want a first rum punch on the sand, Uncle Ernie’s has served one in the middle of the beach since 1984 (it is closed on Tuesdays). Have a drink by the pool as the light fades and keep dinner simple.
Day 2: Boat day to Prickly Pear Cays or Sandy Island
Some of the clearest water in Anguilla is offshore, so take a boat for at least one day. It is the classic choice among Anguilla excursions. Prickly Pear, Anguilla’s pair of offshore cays about 20 minutes north of the island by boat, has restaurants, beach chairs and snorkeling gear. Sandy Island, Anguilla’s tiny sand island off Road Bay, is about a 10 minute boat ride from Sandy Ground. The island has several charter companies, including Calypso Charters, Tradition Sailing Charters and Fun Time Boat Charters. Book a day or two ahead, pack a dry bag and your snorkel gear, and plan on lunch on the sand out there.
Finish in Sandy Ground, the island’s liveliest village, for dinner and a drink by the water.
Day 3: The West End beaches
Drive to the West End for a different side of the island. Swim at Meads Bay, one of the 2026 top-ranked beaches in North America and home to Malliouhana, with the Four Seasons Resort on the point next door, and walk the long, quiet sand at Rendezvous Bay, with lunch at Sunshine Shack, a beach bar on the sand. Music fans may know the Dune Preserve here, home of the Moonsplash festival each March. Stay for sunset, then dinner on the West End. See the best beaches in Anguilla for more options.
Day 4: Island Harbour and Scilly Cay
Island Harbour is the fishing village just along the coast from the villa. On Wednesdays and Sundays, wait on the pier for the boat to Scilly Cay, a family-run, electricity-free restaurant on its own little island, for a long lunch. On other days, eat at Falcon’s Nest by the wharf, where the fishermen bring in the catch, including lobster. On Friday nights, Lime Keel House is the place for live music in Island Harbour.
In the afternoon, find the remote sand of Savannah Bay, Anguilla’s least developed beach. History lovers should save The Valley for an extra day (see below). Our list of restaurants near Shoal Bay East covers dinner.
Day 5: Do nothing, on purpose
The mistake guests make is booking something every day. Keep the last full day empty: the pool, the beach, a late lunch, and one more sunset.
What else is there to do in Anguilla if you have more time?
Five days covers the beaches. With a week or more, these are the other things to do in Anguilla we suggest to guests, all a short drive from the villa.
Snorkel the reefs at Crocus Bay and Shoal Bay East
Crocus Bay, on the north coast, has some of the best snorkeling on the island, with a reef formation covered in hard and soft corals and a wide mix of fish. Closer to home, the reef at Shoal Bay East sits just to the right of Elodia’s, and the water there is usually calm enough to snorkel from the beach. Little Bay, a small cove under the cliffs, has good snorkeling right inshore.
Take a kayak along the cliffs to Little Bay
Anguilla Watersports launches two-person glass bottom kayaks from Crocus Bay and runs guided kayak and paddleboard tours along the limestone cliffs to Little Bay. Through the clear hull you can watch fish, coral and sometimes a sea turtle below you. The Bayside bar at da’Vida on Crocus Bay also rents kayaks, paddleboards and snorkel gear, and the restaurant serves Anguillian lobster and crayfish.
Book a spa day at Zemi Beach House
The Thai House spa at Zemi Beach House, on Shoal Bay East, is set in buildings more than 300 years old that were built in Thailand, shipped to Anguilla in the 1980s and rebuilt overlooking the bay. It also has a hammam. Stay on for lunch at 20 Knots, the resort’s casual restaurant.
See a little heritage in The Valley
Wallblake House in The Valley, built in 1785, is a good first stop if you want to learn about the history of Anguilla. The Anguilla National Trust also runs heritage tours that include the Big Spring petroglyphs. Add a horseback ride on the beach at Cove Bay with Seaside Stables, or a round of golf at Aurora, the only course on the island, and you have a full second week.
A perfect day at Villa Okeanos, hour by hour
Early morning
The light comes up over the water and the house is quiet. Whoever wakes first makes coffee and takes it out to the balcony, and for about an hour nothing happens at all. If you want the beach to yourself, drive down now, while it is close to empty and the water is flat.
Late morning
Breakfast at the villa, usually, because the kitchen is right there and nobody wants to drive anywhere yet. After that the day splits. Some go back to the beach, some stay at the infinity pool.
The middle of the day
It is hot between noon and three, and the covered terrace is where everyone ends up. It has shade and a long table, and it is where a big group actually gathers.
Late afternoon
The wind picks up around four and the terrace gets comfortable again. Someone starts on dinner and someone else on drinks at the outdoor bar.
Evening
Sundowners at the bar, then dinner either at the long table outside or down at one of the beach places. After dark it is properly quiet up here. No road noise, no resort music. Guests mention that more than the pool or the view.
Tips for planning your Anguilla itinerary
- Rent a car. It is the best way to get around. Anguillians drive on the left, and roads are narrow, so take driving at night slowly.
- Mind the season. Hurricane season runs June to November, with the peak in September.
- Check opening days. Scilly Cay serves lunch on Wednesdays and Sundays, and many smaller places keep set days.
- Book boats and popular dinners ahead, especially from January to April.
- Time it with an event. Moonsplash in March, Festival del Mar at Easter and the Summer Festival around early August all change the feel of the island. See the best time to visit Anguilla.
Frequently asked questions
Yes, if you want quiet beaches more than nightlife. The island has 33 public beaches, and Shoal Bay East was ranked the best beach in North America in 2026. Add the reefs, the boat trips and some of the best food in the Caribbean, and these are the Anguilla things to do we would not skip.
A boat day. If you only book one thing, make it a trip to Prickly Pear or Sandy Island, with snorkeling on the way and lunch on the sand.
Five days is a good minimum. It gives you beach days, a boat day and time to explore both ends of the island. Villa Okeanos has a five-night minimum stay.
Anguilla is known for its beaches first: 33 of them, all public, with white sand beaches and turquoise water. Then boat trips to the offshore cays, reef snorkeling, kayaking at Crocus Bay, a spa day, beach bars and restaurants, boat racing in season, horseback riding, golf and a little history in The Valley.
Yes. Calm beaches and boat days suit children well. Read our guide to renting an Anguilla villa for families and groups.
You can visit on a day trip from St. Maarten, but you will see one or two beaches at most. Staying on the island is the way to see it properly.
Plan your days from Villa Okeanos
Villa Okeanos sleeps up to 11 on the ridge above Shoal Bay East, with an infinity pool and views to St. Martin. See the whole property, check which dates are open, or ask us to help plan your days.
