Cheap Flights to Anguilla

Anguilla overview

The main gateways to this Edenic island are Puerto Rico, St. Maarten/Martin, Antigua and St. Kitts. Canadian travellers generally fly to St. Maarten and then take a ferry ride to Anguilla, which takes about 20 minutes. Just 25km long and less than 5km wide (at its widest point), the island is located to the north of the Leeward Islands in the Eastern Caribbean. Its beaches - 33 in total, and all public - are considered among the best in the world. 

The island is known as the Wreck Diving Capital of the Caribbean. The Spanish galleon, El Buen Consejo, lies off its shores and there are nine ships under the waves that a wide variety of marine life dash and dart about. A double reef system (rich in soft and hard corals), and a lack of strong currents make Anguilla ideal for scuba diving and snorkelling. 

Anguilla attracts a discerning type of traveller. Hotels here are world-class and resorts the last word in luxury. Small wonder that Anguilla is a favourite with the Hollywood A-list. While the celebs are probably not searching as hard for cheap flights to Anguilla as the rest of us, the island has a range of affordable accommodation and welcomes all travellers. 

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Anguilla climate

Anguilla’s climate is like a slice of heaven. The skies are sunny and clear year round with an average temperature of 27 C. The gentle trade winds and the warm, extremely swimmable ocean temperatures keep the heat down. September and October are the rainy months, but the rain is usually light and sporadic.

When to fly to Anguilla

With temperatures that rarely dip below 26 degrees Celsius (80F) there's no bad time to visit Anguilla, but when it's winter elsewhere - mid-December to mid-April - that's when most travellers take cheap flights to Anguilla. 

Peak Season: 

The middle of December to the middle of April is high season, when travellers escape the winter weather at home. 

Off Season: 

Low season coincides with hurricane season in the Caribbean, June through November. Anguilla frequently gets hit with tropical storms and hurricanes. If you are willing to take your chances with the weather, you could score big with savings on flights and accommodation.

Getting around Anguilla

Anguilla is a tiny island, just 25km long and less than 5km wide, and there is no public transportation system. Renting a car allows visitors maximum independence. There are several agencies on the island including Thrifty and Island Car Rentals. You'll need a valid driver's licence and a temporary local permit from the rental agency that costs about $20 (US). Visitors can also rent bicycles and mopeds. 

A delightful side trip is taking the ferry to St. Martin/Sint Maarten. Catch the ferry at Blowing Point. It chugs to Marigot. Pack your passport and remember that there's a departure tax of about $5 (US) ($13 EC), children under 12 go free.

Anguilla insider information

  • Wallblake House is the only surviving plantation-era house on Anguilla. The entire complex, including the kitchens, stables and workers' quarters still stand, giving a fascinating glimpse into 18th-century life on the island. It's open Monday, Wednesday and Friday between 10am and 2pm. 
  • Cheapflights.ca's pick of the beaches are Mead's Bay and Shoal Bay. They're two of the finest Caribbean beaches we've had the pleasure to lie on.
  • Six nearby islands belong to Anguilla too. They are Scrub Island, Sombrero, Dog Island, Sandy Island, Prickly Pear and Anguilliate.
  • The Summer Festival takes place in early August each year. Dancing, competitions, fairs, costumes, parades, beach picnics and boat races make this an unmissable event. If you're taking cheap flights to Anguilla at this time, try to be up for the J’Ouvert Mornin’ - Sunrise Street Jam. It starts at 5am, a daybreak jam through the streets to commemorate emancipation. 
  • The cuisine is a fusion of European, American and Caribbean flavours. Unsurprisingly, the seafood - local crayfish, lobster, grilled Snapper, Swordfish and Mahi Mahi - is a specialty.

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