Anguilla Travel Planning & Itineraries
By Bobby Atwal, TICO-registered travel advisor (Fora Travel), Toronto · Updated
Anguilla is a 26-km sliver of limestone with 33 beaches, no cruise ships, no casinos, no high-rises and no hurry. It's where the Caribbean's best sand meets its best food — beach shacks and Michelin-trained chefs on the same mile of coast — and where the resorts (Four Seasons, Cap Juluca, Malliouhana, Zemi) are built to disappear into the landscape rather than dominate it. Getting there takes an extra hop; that hop is the filter that keeps it quiet.
Free advisor planning includes Fora Reserve hotel perks at no extra cost — or use our AI planner to pace your Anguilla days, pick the right neighbourhoods, and build a route that makes sense.
Anguilla at a glance
- Best time to visit
- December to April is peak — dry, 27–29°C, breezy, and the villas and top resorts book out for Christmas and February a year ahead.
- How long to stay
- Five to seven nights. The travel day each way is long enough that a long weekend doesn’t make sense; a week lets you do a boat day, a west-end beach hop and still have slow days.
- Budget
- Anguilla has no budget tier — it's priced as a luxury island. Mid-range: $500–800 USD/day (a boutique like Frangipani or a villa share, a rental car, beach-shack lunches).
- Getting there from Canada
- There are no nonstops from Canada. The classic route is YYZ → St.
Planning Your Anguilla Trip
Best Time to Visit
December to April is peak — dry, 27–29°C, breezy, and the villas and top resorts book out for Christmas and February a year ahead. May to June is the sweet spot: same beaches, 30% off, and the island's restaurants are still open. Late August to October is the catch: many restaurants and some resorts close for the season and it's the core of hurricane risk — Irma in 2017 is still a reference point. November reopens everything and is excellent value.
Budget Overview
Anguilla has no budget tier — it's priced as a luxury island. Mid-range: $500–800 USD/day (a boutique like Frangipani or a villa share, a rental car, beach-shack lunches). Luxury: $1,500–3,000+/day (Four Seasons, Cap Juluca, Malliouhana, Zemi Beach House, or a staffed villa on Shoal Bay). Dining runs $80–150/person at the good tables. This is a destination where booking through an advisor pays for itself in upgrades and resort credits.
Getting There
There are no nonstops from Canada. The classic route is YYZ → St. Maarten (SXM) on Air Canada, WestJet or Sunwing (~4.5h), then a 20-min shared or private boat from the Blowing Point ferry terminal, or a 7-min flight on Anguilla Air Services. Your resort will arrange the sea transfer (~$75–100/person shared, ~$500+ private) and meet you at SXM — it's smoother than it sounds. Alternatively connect via Miami or San Juan to Anguilla's own airport (AXA).
Getting Around
Rent a car — there's no public transport and taxis are expensive. You drive on the left, roads are quiet, and nothing is more than 25 minutes away. A temporary Anguilla driving permit (~$25) is issued with the rental. Most resort guests still rent for two or three days to beach-hop: Shoal Bay East, Meads Bay, Rendezvous Bay and Sandy Ground are each worth a morning.
Common Anguilla planning mistakes
Not booking the boat transfer in advance
Arriving at SXM without a confirmed sea transfer means a scramble. Have your resort or advisor book the meet-and-greet and boat before you fly.
Visiting in September
Much of the island closes late August to October. If you want the restaurants and the full resort experience, go November to early July.
Expecting nightlife
A beach bar with live reggae on a Sunday is the peak. If you want clubs and casinos, that’s the St. Maarten side; Anguilla is for early nights and early swims.
Underestimating costs
Nearly everything is imported and priced for a luxury clientele. Budget realistically, or make lunch the beach-shack meal and dinner the splurge.
Anguilla Neighbourhoods
Meads Bay
A mile-long crescent of powder sand with the island’s densest cluster of great hotels — Four Seasons, Malliouhana, Frangipani — and Blanchards and Jacala for dinner. — best for: honeymoons, foodies, first-timers
Shoal Bay East
Routinely called one of the world’s best beaches: two miles of blinding white sand, a reef for snorkelling, and Gwen’s and Uncle Ernie’s for lunch. Zemi Beach House anchors the east end. — best for: beach days, families, snorkellers
Maundays Bay & Cap Juluca
The Moorish-white Belmond Cap Juluca resort curves around a perfect protected bay facing St. Martin — the single most photographed stretch on the island. — best for: romance, calm water, splurges
Sandy Ground
The island’s harbour village and nightlife, such as it is — Elvis’ Beach Bar, Johnno’s live music, the Sunday-afternoon scene. Casual guesthouses. — best for: music nights, boat trips, a looser vibe
Rendezvous Bay
A long, sweeping, often-empty beach looking across to St. Martin’s hills, home to CuisinArt and the legendary Dune Preserve beach bar. — best for: long walks, sunset drinks, space
Anguilla Food & Drink
Blanchards
The restaurant that put Anguilla on the food map — refined Caribbean-American on the beach. ~$90–130/person. Their casual Beach Shack next door does lobster rolls and frozen drinks for lunch.
Jacala
French-Caribbean in an open beach pavilion — the lobster salad and the crème brûlée are the orders. ~$80–110/person. Reserve a front-row table at sunset.
Gwen’s Reggae Grill
Grilled lobster, ribs and rum punch under sea-grape trees on the best beach in the Caribbean. ~$30–45/person. Sunday afternoon has live reggae.
Veya
Treehouse-style dining in the hills above the harbour — Moroccan-spiced shrimp, jerk-spiced tuna, a serious wine list. ~$90–120/person. Book early in season.
Dune Preserve
Bankie Banx’s driftwood beach bar, built from boat wrecks — rum punch at sunset and live music at the Moonsplash festival in March. The island in one place.
Day Trips from Anguilla
Sandy Island & Prickly Pear Cays
10–30 min by boat (half day)Tiny offshore sandbars with a beach-bar lunch (grilled lobster and crayfish) and shallow turquoise snorkelling. Boats leave from Sandy Ground; Sandy Island is 10 minutes, Prickly Pear 30.
Little Bay & Scilly Cay
15–20 min from the east endLittle Bay is a cliff-ringed cove reached by rope or boat with turtles and rays; Scilly Cay is a one-restaurant islet off Island Harbour where you wave for the boat and eat lobster all afternoon.
St. Martin / Sint Maarten
25-min ferry from Blowing PointThe French side — Marigot market, Grand Case’s restaurant row, Orient Bay — is a 25-min ferry away. A fun contrast day, especially for food.
Beach-hop the west end
All within 20 minNot a trip, a plan: Rendezvous, Cove Bay, Maundays and Shoal Bay West in one slow day with a car, a cooler and no agenda. This is what Anguilla is for.
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A Sample Anguilla Itinerary
Here’s a flavour of what our AI planner builds. Generate your own personalized Anguilla itinerary in 60 seconds — free.
YYZ → SXM → boat → Meads Bay
- •Morning flight to St. Maarten
- •Met at SXM, 20-min boat to Blowing Point
- •Check in on Meads Bay, first swim
- •Sunset dinner at Jacala
Shoal Bay East
- •Morning on the island’s best beach
- •Snorkel the reef
- •Lobster lunch at Gwen’s
- •Lazy afternoon, resort dinner
Boat day: Prickly Pear & Sandy Island
- •Sail out from Sandy Ground
- •Snorkel and swim at Prickly Pear
- •Grilled crayfish lunch on Sandy Island
- •Sunset rum punch at Elvis’ Beach Bar
West-end beach hop
- •Rendezvous Bay walk at sunrise
- •Maundays Bay swim
- •Lunch at Blanchards Beach Shack
- •Sunset at Dune Preserve, dinner at Veya
Little Bay → departure
- •Boat to Little Bay for turtles
- •Final swim on Meads Bay
- •Boat back to SXM
- •Afternoon flight home
Anguilla Travel FAQ
How do I get to Anguilla from Canada?
Fly nonstop to St. Maarten (SXM) from Toronto, then take a 20-minute boat across — your resort or advisor arranges the meet-and-greet and sea transfer. Total door-to-door is about 7 hours.
Is Anguilla worth the extra cost over other islands?
If beaches, food and quiet are your priorities, yes — nowhere else in the Caribbean combines all three at this level. If you want nightlife, budget options or an all-inclusive, look elsewhere.
Which resort should I choose?
Four Seasons for families and facilities, Cap Juluca for pure romance, Malliouhana for classic style, Zemi Beach House for Shoal Bay access. All four are properties where advisor perks — breakfast, upgrades, credits — are significant.
How many days do I need?
Five to seven nights. The travel day each way is long enough that a long weekend doesn’t make sense; a week lets you do a boat day, a west-end beach hop and still have slow days.
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