Quick Route Overview
This five-day route is built for boutique-minded travelers who want a small hotel, a rental car and long stretches of empty sand rather than a packed activity schedule. You will cover the west end, the east end fishing villages, the tiny capital and one full day on the water. The pace is deliberately slow: two anchor activities a day, afternoons free for swimming.
Anguilla has no cruise-ship crowds, no high-rises and no direct international flights. You fly into St. Maarten (SXM) and cross by ferry, which is why Day 1 is a soft landing instead of a sightseeing push. The island is only 16 miles long, so nothing on this itinerary is more than a 30-minute drive.
- Duration: 5 days / 4 nights
- Best season: Late July to mid-August for peak summer heat, calm water and the Anguilla Summer Festival; December to April for the driest weather and highest prices
- Base: Meads Bay — walkable to six restaurants and 15 minutes from the ferry dock
- Transit: Rental car (about US$45–65 per day in summer) plus a couple of short shuttle boats
Day 1: West End Landing — Maundays Bay and Shoal Bay West
Morning
Public ferries leave Marigot, St. Maarten, for Blowing Point roughly every 45 minutes from about 7:30am to 6pm. The crossing takes 25 minutes and costs around US$20–25 one way including the departure levy. Faster private shuttles from the SXM airport area run about US$65–75 and save you a taxi across St. Maarten.
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Book your rental car before you arrive and have the agent meet you at Blowing Point. You will need a temporary Anguilla license — US$25, issued on the spot, valid three months. And remember: they drive on the left.
Afternoon
Head straight to Shoal Bay West for a late lunch at Trattoria Tramonto, where pasta and fish plates run US$22–30 and the water out front is usually glassy. Then drive five minutes to Maundays Bay, park at the north end public access path and claim the sand beyond Cap Juluca's loungers. Every beach in Anguilla is public below the high-water mark, no matter how grand the hotel behind it.
Skip the resort bars here. A US$28 cocktail is not how you want to start the week.
Evening
Sunset from Maundays Bay is the best on the west side, with St. Martin's silhouette going purple behind the boats. Drive 10 minutes to Meads Bay for dinner at Blanchards Beach Shack, where burgers, fish tacos and rum punch land around US$20–26 per person. It closes by 9pm, so eat early.
Finish with a barefoot walk down Meads Bay — it is dark, quiet and completely safe.
Route Efficiency Tip: Everything today sits within 12 minutes of Blowing Point. Do not drive east on arrival day; you will burn an hour in the car when you could be swimming.
Day 2: Shoal Bay East and the East End Villages
Morning
Leave Meads Bay by 9am for the 25-minute drive east to Shoal Bay East, the island's postcard beach. Park in the public lot beside Uncle Ernie's and walk left along the sand until the loungers thin out. Chair-and-umbrella sets run US$10–15 each, and the snorkeling off the rocks at the eastern point is the best on the island.
Grab breakfast on the way. The Johnny cake and saltfish counter at E's Oven in South Hill opens early and costs about US$8–12 for a full plate.
Afternoon
Lunch at Mango's Seaside Grill or Uncle Ernie's, both right on the sand, with grilled lobster or ribs at US$20–30. Then drive 10 minutes to Island Harbour, a working fishing village with a small pier, painted boats and zero commercial gloss.
If Scilly Cay is open — it has been intermittent since the storms, so call ahead — the shuttle boat from the dock plus a grilled lobster lunch is the day's splurge. Otherwise walk the pier and drive up to Fountain Cavern National Park, where Amerindian petroglyphs sit behind a locked gate; access is by arrangement with the Anguilla National Trust.
Evening
Time it so you are back on Shoal Bay East for sunset, when the light hits the reef and the whole bay turns copper. Dinner at Hibernia in Island Harbour is worth the drive back east: an eclectic menu, mains US$30–42 and a genuinely warm welcome from the owners. It is small, so reserve a day ahead.
If your visit lands on a Sunday, swap dinner for Gwen's Reggae Grill Sunday barbecue on Shoal Bay East — US$25–35, live music, wrapped up by early evening.
Route Efficiency Tip: Shoal Bay East and Island Harbour are 10 minutes apart. Do both in one loop instead of two separate trips; the east end is the longest drive on your itinerary.
Day 3: The Valley Heritage and Crocus Bay by Boat
Morning
Start in The Valley, the island's tiny capital, around 9:30am. Wallblake House, a 1776 plantation house and the oldest standing structure in Anguilla, opens on weekday mornings for tours (free, donations welcome). Pair it with the small historical society museum nearby and Devonish Art Gallery on the same block.
Mid-morning snack at Ken's BBQ roadside stand — BBQ chicken with rice and peas for about US$10–14 — is a better use of money than any café in town.
Afternoon
Drive 10 minutes to Crocus Bay for lunch at da'Vida, where fish and chips and ceviche plates run US$22–32 and the deck hangs over the water. Then walk down to the jetty and take Calvin's little boat across to Little Bay, a two-minute hop costing about US$10 round trip.
Little Bay is a pocket cove under a limestone cliff with a knotted rope for climbing and excellent snorkeling. Bring water shoes; the entry is rocky and there is no shade after 2pm.
Evening
Drive to Sandy Ground for sunset over Road Bay, where the boats sit at anchor and the beach bars switch on. A rum punch at Elvis' Beach Bar costs US$8–12 and the live music is genuinely local, not a staged tourist show.
Dinner at Veya (mains US$38–48, a treehouse-style room above the sand) or Roy's Bayside Grill for something simpler at US$28–38. Both need a reservation in high season.
Route Efficiency Tip: The Valley, Crocus Bay and Sandy Ground form a 10-minute triangle in the island's centre. Run them in one line and you will never backtrack.
Day 4: Sandy Island, Rendezvous Bay and a Long Lunch
Morning
Be at the Sandy Ground jetty by 10am for the shuttle boat out to Sandy Island, a sliver of sand and palms 10 minutes offshore. The boat is about US$10–15 round trip per person and the island's restaurant takes walk-ins for lunch.
Alternatively, book a day charter to Prickly Pear Cays with GB Express or a local operator (roughly US$70–95 including boat and lunch) if you want the best snorkeling in the territory.
Afternoon
Back on the main island by 2pm, drive 10 minutes to Rendezvous Bay — a two-mile arc of sand with St. Martin on the horizon and almost nobody on it. Garvey's Sunshine Shack at the eastern end does rum punch for around US$10 and grilled plates for US$15–25, cash only.
Fair warning: there is very little natural shade along Rendezvous Bay and no lifeguards. Bring an umbrella or rent a chair from Garvey's.
Evening
Stay for sunset, then drive 15 minutes back to Meads Bay for dinner at Straw Hat (mains US$30–42, seasonal fish, a solid wine list) or Jacala for a fancier beachfront meal.
End with a nightcap at SandBar on Meads Bay, where the crowd is a mix of locals and villa guests and the music stays at conversation level.
Route Efficiency Tip: Sandy Ground, Rendezvous Bay and Meads Bay sit in a neat westbound line. Park once at each and walk — none of these beaches needs a second visit by road.
Day 5: Meads Bay Slow Morning and Departure
Morning
Keep the last morning empty on purpose. Swim at Meads Bay before 8am, when the water is flat and the beach is yours, then have breakfast at Blanchards Beach Shack or the café at your hotel.
If you have energy, walk 10 minutes north over the rocks to Long Bay, an undeveloped surf beach with no facilities at all. It is a sharp contrast to the manicured resorts behind you.
Afternoon
Check out by 11am — most small hotels are flexible, so ask — then drive west toward Blowing Point. Fill the tank first; petrol stations cluster in The Valley and there is nothing near the ferry. The drive from Meads Bay takes 15 minutes.
Allow 90 minutes between the ferry dock and your flight from SXM, plus the taxi across St. Maarten, which runs US$25–35 to the airport.
Evening
If your flight is late, spend the afternoon at Maundays Bay or Sandy Ground rather than sitting at the dock. The last reliable public ferry leaves Blowing Point around 6pm, so confirm the schedule the day before — it shifts with the season and the weather.
Route Efficiency Tip: Do not attempt a beach stop on departure day unless your ferry is after 3pm. West end roads are slow and the boat will not wait.
Getting Around Anguilla
Rent a car. There is no realistic alternative for a five-day boutique trip — taxis charge per person, and a round trip to Shoal Bay East can cost more than a day's rental. Summer rates at local agencies run US$45–65 per day for a compact, and you want the collision waiver.
Public minibuses leave from The Valley's east and west terminals for about US$2–3, but they run on no fixed timetable, stop early and barely operate on Sundays. Fine for a cheap daytime hop into town; useless for beach-hopping.
Driving is on the left, roads are narrow with no streetlights outside The Valley, and goats have right of way. Avoid driving after dark on your first two nights until you know where the potholes are. Walking between bays is not realistic — there are no sidewalks and the distances are longer than they look on a map.
Estimated Daily Budget Breakdown
| Travel Style | Accommodation | Food & Drink | Transit & Sights | Total / Day |
|---|---|---|---|---|
| Budget Backpacker | US$85–110 (guesthouse in The Valley or South Hill) | US$45–60 | US$25–35 (minibus, one shared boat) | US$155–205 |
| Comfortable Mid-Range | US$190–280 (beach club studio, Meads Bay) | US$90–120 | US$55–75 (rental car, ferry, Little Bay boat) | US$335–475 |
| Boutique Splurge | US$550–900 (Malliouhana, Frangipani, Zemi Beach House) | US$180–260 | US$80–130 (bigger car, private charters) | US$810–1,290 |
All figures are in US dollars, which is what you will actually pay — the East Caribbean dollar is pegged at EC$2.70 to US$1. Note that Anguilla adds a 12% government accommodation tax plus a service charge that is not always built into quoted room rates.
Frequently Asked Questions
Do I need to book the ferry and rental car in advance?
The car, yes. Summer fleets are smaller and agencies such as Andy's, Junie's and Bassman regularly run out of automatics. The public ferry from Marigot does not take reservations — buy your ticket at the dock. Private shuttles like Funtime and GB Express do take bookings and are worth it if you land after 4pm.
How much cash should I carry?
US dollars are accepted almost everywhere. Cards work at hotels and most sit-down restaurants, but beach shacks, boat shuttles, taxi drivers and Calvin's Little Bay boat are cash-only. Carry US$150–200 in small bills and you will never be stuck.
Is peak summer actually a good time to visit?
July and early August are hot at 30–32°C, the water is bath-warm, and the Anguilla Summer Festival brings boat races at Sandy Ground and J'Ouvert in The Valley. Rates drop 30–40% after mid-August. The trade-off is hurricane season: September and October carry real risk, and a number of restaurants close for the whole stretch.
What should I skip?
Dolphin Discovery and the big resort buffets both cost far more than they deliver. Fountain Cavern is genuinely interesting but frequently locked, so do not build a day around it. And avoid planning a Shoal Bay East day on a Sunday in low season — half the beach bars shut.
