Guests ask us for the “Anguilla briefing” every high season. Not the glossy pitch, the one that stops them from making the same three mistakes.
Here it is, roughly the version we send by voice note the day someone tells us they are thinking about a first trip.
Anguilla is not “St Barth but cheaper”
Every year someone books Anguilla expecting a quieter version of St Barth. It is quieter, but it is not St Barth. Different island, different mood, different rules.
- Language: English, driven by British Caribbean history.
- Currency: East Caribbean dollar officially, US dollar in practice everywhere.
- Vibe: no yachts jockeying for the same anchorage, no scene. Restaurants sit on the sand, not on cliffs.
- Nightlife: essentially none, unless you count live music at Elvis at Sandy Ground.
If you want a party, base in St Martin. If you want to stop having conversations for a week, this is the island.
The arrival fee catches everyone
Anguilla charges a fee at arrival (roughly $20 per adult) and a departure tax (about $28 per adult), both payable in cash. Neither is on your ferry ticket. Neither is refunded.
Bring small bills. USD is fine. First-timers who arrive on the ferry from Marigot without cash spend twenty minutes hunting for a working ATM at Blowing Point. Skip that.
Where to base yourself
We covered the beaches in detail on our Anguilla page. The short version for a first visit:
- Meads Bay if you want the classic postcard with calm water most days. Blanchards and Straw Hat within walking distance. Malliouhana at one end.
- Rendezvous Bay if you want the biggest, quietest stretch, and the sea stays flat even when the wind is up.
- Shoal Bay East if you want the whitest sand of the three, and you do not mind being further from the “town” restaurants.
Do not base at Blowing Point just because that is where the ferry lands. Blowing Point is a port, not a destination. Twenty minutes down the road is a different island.
Book restaurants before you land
The Anguilla shortlist of restaurants is small. Blanchards, Veya, Straw Hat, Da Vida, Uncle Ernie for lunch. A few more, but not many.
They fill up in high season, and several give priority to hotel guests. If you land in December without reservations, you will be eating in your resort every night. Nothing wrong with that if the resort is Cap Juluca. Everything wrong with it if you spent an hour choosing a boutique inn.
We hold tables in advance. That is the first thing our guests forget they need us for.
Getting there is not the ferry
Most first-timers assume “ferry from Marigot” is the only option. Not really.
- Public ferry from Marigot to Blowing Point works. Runs roughly every 45 minutes, $28 one way, cash preferred. It is fine for solo travellers and couples with light luggage. It is a bad idea for four adults with big suitcases at 4pm on a Sunday.
- Private speedboat costs more but the customs is pre-cleared, the crossing is 15 minutes, and you skip the queue on both sides. For families and small groups it usually works out cheaper than four separate ferry tickets plus stress.
- Direct flights land from Antigua, San Juan, and St Thomas. Worth checking if your international routing already goes through one of those hubs.
- Helicopter from SXM in 8 minutes. Not cheap, occasionally the right answer.
More detail in our St Martin to Anguilla ferry guide.
What to actually book in advance
For a first trip in high season (December to April), the order we book things in:
- Villa or hotel. The good ones sell out first, especially over Christmas and February.
- Two or three restaurant nights. Not all of them. Leave two evenings loose.
- The crossing. Private if you have the group, ferry if it is just the two of you.
- A driver for arrival day and departure day. Optional in between.
- A boat day. Sailboat or catamaran with a captain. This is what most guests say was the best thing they did all week.
What not to bother with
- Renting a car for the whole stay unless you like driving. Taxis are metered, drivers know everyone, and the whole island is 16 miles long.
- A packed schedule. The island is designed for the opposite. Two things a day is plenty.
- Bringing a lot of clothes. You will wear a swimsuit at 11am and something linen at 8pm and that is it.
When to go
High season is December through April: dry, warm, the trades keep it comfortable. Prices peak, so do the crowds, but the Anguilla version of a crowded beach is empty by any other standard.
Shoulder season (May, June, October, November) is our recommendation for a first visit. Water is warmer, prices soften, the island slows down. Weather is mostly kind.
Hurricane season (July to September) is not off-limits. Most days are perfect. We keep the plan flexible and reschedule around any storm that shows up on the forecast a week out. Guests who come in August usually get their whole itinerary, just shifted.
When to let someone else plan it
If reading this made you want to start a spreadsheet, do the spreadsheet. It is a small island, and you can figure it out.
If reading this made you want to close the tab and think about something else, tell us your dates. We book the villa, hold the tables, arrange the crossing, and send you the plan.
Anguilla is one of the three islands we cover. See also our full Anguilla guide and St Martin to St Barth day trips if the trip is bigger than one island.