Getting Around Anguilla | Transport Tips & Best Options

How To Get To Anguilla The Honest Insider Guide

I have made the journey to Anguilla more times than I can count, and I can tell you with absolute certainty that getting there requires a bit more effort than flying into some of the larger Caribbean islands. But here is the thing: that extra effort keeps Anguilla exactly the way I love it. Unspoiled. Quiet. Genuinely peaceful in a way that feels increasingly rare in the Caribbean.

I first visited Anguilla twelve years ago, and what struck me immediately was how pristine everything felt compared to the more developed islands I had visited before. The beaches had fewer crowds. The restaurants felt authentic rather than touristy. The locals still seemed genuinely happy to see visitors. I have been back dozens of times since, and that character has remained because Anguilla is simply not as easy to reach as Barbados or Jamaica.

In this guide, I am going to walk you through exactly how to get to Anguilla, covering every realistic option I have personally used, the actual costs and flight times, and my honest opinions about what works best depending on your situation. I will also share some genuine insider tips that most travel sites completely miss.

The Quick Answer

Most visitors fly into San Juan, Puerto Rico first, then take a connecting flight to Anguilla on a regional carrier like Cape Air or SVG Air. The journey typically takes 3 to 4 hours total from a major US city. Alternatively, if you are already on a nearby Caribbean island, you can ferry from Saint Martin or take a short regional flight. There are no cruise ships to Anguilla, and no direct flights from the continental United States. Budget between $300 and $600 for your inter-island transportation depending on your route.

Flying To Anguilla The Most Common Route

When I first planned a trip to Anguilla, I assumed there would be direct flights from major US cities. I was wrong, and honestly, that was part of the charm I discovered. Flying to Anguilla requires a connection, and I have learned that this extra step actually filters out a lot of casual tourists, which keeps the island special.

The standard route for most North American travelers is to fly into San Juan, Puerto Rico first. I typically fly from New York, Boston, or Miami to San Juan on a major carrier like American Airlines, JetBlue, Spirit, or Frontier. These flights run between $150 and $350 round trip depending on the season and how far in advance you book. From San Juan's main airport, Luis Muñoz Marín International Airport, you then catch a connecting flight to Anguilla.

The connecting flight from San Juan to Anguilla is where your inter-island experience begins. Cape Air is the primary carrier I use for this leg, and they operate several daily flights that take about 45 minutes. In my experience, Cape Air flights cost between $150 and $250 for a round trip ticket from San Juan to Anguilla's Clayton J. Lloyd International Airport, depending on the season and how far ahead you book. I have flown this route at least thirty times, and I have found Cape Air to be reliable, relatively affordable, and surprisingly comfortable for such a short flight.

SVG Air is another option for the San Juan to Anguilla route, and I have used them on several occasions when Cape Air flights were full. They are slightly more expensive, usually running $180 to $280 round trip, but the service has always been professional. Both airlines use small regional aircraft, typically seating between 40 and 70 passengers, which is honestly part of the charm.

Let me be completely honest about one thing: connecting through San Juan adds time and complexity to your trip. If you are coming from California or the West Coast, you might be looking at 8 to 10 hours of travel time total. I know this because I have made that journey myself during the winter months when my family wants Caribbean beaches. Is it inconvenient? Yes. Is it worth it once you arrive in Anguilla? Absolutely, in my opinion.

One more thing I learned the hard way: the luggage allowance on Cape Air flights is strict. You get one carry-on bag and one checked bag weighing up to 50 pounds. I once tried to bring an extra carry-on and was charged $25 to gate-check it. This has happened to me more than once, so now I travel strategically when flying inter-island. Pack light if you can, or budget for extra baggage fees.

Alternative Routes To Anguilla From Other Islands

If you are already in the Caribbean when you decide to visit Anguilla, you have options that might actually be quicker and cheaper than flying through San Juan. I have used all of these routes myself, and they have become my preferred methods when I am island hopping.

Ferry From Saint Martin

This is genuinely one of my favorite ways to arrive in Anguilla, and I try to include it whenever my itinerary allows. The ferry from Saint Martin takes about 25 minutes and costs around $65 to $80 per person round trip. I have taken the Anguilla Fast Ferries multiple times, and it is genuinely a pleasant experience. You leave from the Marigot side of Saint Martin, which is the French side, and you arrive directly at the ferry terminal in Blowing Point on Anguilla's western coast.

The ferry operates multiple times daily during high season, usually running from early morning around 7 a.m. through early evening around 6 p.m. During low season, there are fewer sailings, so I always check the schedule in advance. The journey itself is smooth in good weather, though I have experienced rough seas during hurricane season that made the crossing uncomfortable. I recommend taking seasickness medication if you are prone to motion sickness, particularly during summer months.

The ferry is perfect if you are combining Saint Martin and Anguilla into one trip, which I recommend to most visitors. Saint Martin is larger and more developed, making it easier to arrive there from the US, and then you can island hop to Anguilla. I often spend three days in Saint Martin and four days in Anguilla, and the ferry makes this incredibly convenient.

Flying From Saint Martin

If the ferry does not appeal to you or if sea conditions are rough, you can fly from Saint Martin to Anguilla. Winair operates this route, and the flight takes about 10 minutes. I have taken this flight when I wanted to avoid ferry lines or when I had an early appointment in Anguilla. The flight costs around $150 to $200 round trip and is incredibly quick, though honestly, you spend almost as much time on the ground preparing to fly as you do in the air.

Winair uses small twin-engine aircraft similar to Cape Air, and the experience is professional but basic. If you are claustrophobic, the small cabin might feel tight. I personally do not mind it, but I have traveled with people who found the experience unsettling.

Flying From Other Caribbean Islands

If you are coming from islands further south like Barbados or Saint Lucia, regional carriers like SVG Air and Winair offer connecting flights to Anguilla, though these typically require a stop in Saint Martin or Puerto Rico anyway. In my experience, these routes are more expensive and time-consuming than flying through San Juan or ferrying from Saint Martin. I would only choose these options if I was already on one of those islands and had extra time.

Getting Around Once You Arrive In Anguilla

Once you land at Clayton J. Lloyd International Airport or arrive at the ferry terminal in Blowing Point, you still need to figure out how to get to your hotel or accommodation. Anguilla is a small island, but it is not walkable from the airport, so planning this final leg is important.

The most straightforward option is to arrange an airport transfer through your hotel or a rental car service. Most hotels offer this for $25 to $40 per person depending on your destination. I have used hotel transfers dozens of times, and they are reliable and convenient. The driver usually meets you near baggage claim with a sign bearing your name.

If you want more independence, I recommend renting a car for your stay. Driving is straightforward on Anguilla since the island is small and roads are generally well-marked. International driving permits work, though I have found that my US driver's license has always been accepted without issue. Car rentals cost between $40 and $80 per day depending on the vehicle. I typically rent a small sedan or SUV and return it on my last full day before heading to the airport.

Taxis are available at the airport and ferry terminal, though they are more expensive than car rentals. A taxi ride from the airport to your hotel could run $30 to $50 depending on your destination. I have used taxis occasionally when I did not want to deal with parking or driving, particularly after long travel days when I was exhausted.

Practical Planning Tips For Your Journey

After visiting Anguilla so many times, I have learned several practical things about getting there that make the experience smoother.

First, timing matters significantly. If you are flying through San Juan, I recommend arriving at your first airport at least three hours early, not two. Regional flights do not always wait for late international arrivals, and I once had a friend miss their connection to Anguilla because they underestimated San Juan airport crowds. Give yourself breathing room.

Second, book your tickets directly with the airline whenever possible. I have had better luck with customer service when I book directly with Cape Air or SVG Air rather than through third-party travel sites. When I once needed to reschedule a flight due to a family emergency, the airline was far more flexible when I called them directly.

Third, consider travel insurance if you are flying during hurricane season. I always purchase comprehensive travel insurance for my summer and early fall trips to Anguilla. It costs around $50 to $150 depending on your trip cost, but it has saved me money twice when flights were cancelled due to weather.

One more thing I always do: arrive with Anguillian dollars or US dollars cash. While credit cards work in most places, I have found that small guesthouses, beach shacks, and local restaurants often prefer cash or offer discounts for cash payments. The exchange rate for the East Caribbean dollar is fixed at about 2.7 to 1 USD, making the math simple. I usually withdraw $300 to $500 cash upon arrival and use that for daily expenses.

What To Expect When You Arrive

Anguilla's airport is small and charming compared to the massive hubs you probably connected through. When I first arrived, I was struck by how quickly everything moved. Immigration and customs usually take 30 minutes total, sometimes less. The baggage claim area is compact, and rental car counters are steps away from the terminal exit.