Anguilla Travel Guide: Your Key to an Unforgettable Trip
This Anguilla travel guide is designed specifically for first time visitors, with everything you need to know before you go. The guide includes what to do and where to eat. It also covers when to visit, how to get around, and typical costs. I’ve also included all of my practical Anguilla tips for tourists.
I spent six weeks living and working on the island of Anguilla in the British Virgin Islands, which gave me a perspective most travelers don’t get. Instead of just hitting the highlights, I made it my goal to see and do as much as possible and ended up experiencing nearly everything the island offers. I visited every major beach, ate across the island, handled everyday logistics like groceries and transportation, and tried out tons of local recommendations.
This guide brings those firsthand insights together in one place. Whether you’re deciding if the island is right for you, mapping out logistics, or wondering what to know before going to Anguilla, you’ll find it all here.
Anguilla Travel Guide Overview (TL;DR)
- Best for: travelers who want beautiful beaches, standout food, and a chill, uncrowded environment
- Not ideal for: people looking for nightlife, packed itineraries, or a party scene
- Ideal trip length: 4 to 5 days for a first visit
- Cost level: expensive compared to many other Caribbean destinations
- Food: the Anguilla food scene is incredible, considered the best food in the Caribbean
- Getting around: renting a car is the best option
Is Anguilla Worth It?
If you’re researching Caribbean islands, whether Anguilla is worth it comes down to the kind of trip you want. It’s not a party destination. Anguilla is quiet, slow, and more low-key. Think long beach days, incredible meals, and relaxed evenings rather than packed itineraries or nightlife.
Part of what makes it stand out is what it doesn’t have. There’s no major cruise port, so you won’t get waves of day visitors, and even in peak season it doesn’t feel crowded. The beaches are the main draw, with soft white sand, clear water, and perfect snorkeling conditions, plus excellent restaurants right on the coast. The food scene is also a highlight, ranging from casual beach shacks to upscale spots that rival fine dining anywhere.
The vibe is calm and refined. Nightlife exists, but it’s mostly beach bars, live music, and dinners that wind down before midnight. You won’t find clubs or all-night parties anywhere on the island. Compared to other Caribbean destinations, it feels less commercialized than Aruba or the Bahamas and more understated than St. Barts. If you want a peaceful, high-quality escape, Anguilla is hard to beat, but if you’re looking for constant activity, it may feel too slow.
Best Time to Visit Anguilla
Choosing the best time to visit Anguilla depends on what matters most to you: weather, price, crowds, or sea conditions. The island is warm year-round, but there are clear differences depending on the season.
Peak Season (December–April)
This is the most popular time to visit and for good reason. The weather is sunny, humidity is lower, and rain is minimal. It’s also the most expensive period, and restaurants often require reservations.
Sea conditions are typically calm and ideal for swimming and boating. This is the perfect time to spend your days listening to music at a beach bar and snorkeling off the beach.
Shoulder Season (April-July)
Late spring and early summer offer a strong balance of good weather and lower prices. The island is quieter without feeling completely deserted.
Off Season & Hurricane Season (July-November)
Late summer through fall overlaps with hurricane season in Anguilla. Weather becomes less predictable, beaches are empty, and prices drop.
Many popular restaurants and resorts close during this time of year, which means you would miss out on a lot of the highlights and charm of Anguilla. Unless you just want the cheapest trip possible I would not recommend visiting during this period.
How Many Days Do You Need in Anguilla?
Anguilla has a ton to offer beyond just its beaches. It’s possible to visit as a day trip from St. Maarten, but you need at least a few days in Anguilla to truly appreciate the island. Depending on the type of trip you’re looking for these are my recommendations for how long you need in Anguilla:
3 days – quick luxury getaway (1 beach day, 1 boat day, 1 day exploring the island)
4–5 days – ideal first-time trip, enough time to explore without being rushed or missing out on highlights of the island (1-2 beach days, 1 boat day, 2 days exploring)
6–7 days – full experience, slower pace, great for those who want to see the island and have time to be lazy on the beach (3 beach days, 1-2 boat days, 2-3 days exploring)
***Want to skip the planning? Jump to Anguilla sample itineraries***
How to Get to Anguilla
If you’re researching how to get to Anguilla, you’ll quickly learn it requires extra planning. There are several options, so picking the best one for your travel style and budget is important.
Flights
Direct Flights – Direct flights to Anguilla are limited and expensive. The Anguilla airport (AXA) is very small and frequently has delay issues. I would only recommend this option if you have a large budget.
Through St. Maarten – This is by far the most common and cost effective option for getting to Anguilla. You’ll land at Princess Juliana International Airport (SXM) then take the ferry to Anguilla. This option will save you money on flights, but will require a bit of extra time and planning.
NOTE: a $36 departure tax must be paid upon leaving St. Maarten or Anguilla.
Ferries from St. Maarten to Anguilla
Public – The public ferry from St. Maarten to Anguilla runs every hour and does not require prior booking. After leaving the airport you’ll take a shuttle to the Marigot Ferry Terminal, on the French side of the island. There you’ll board the ferry, arriving in Anguilla in about 30 minutes.
NOTE: The public ferry often does not accept cards. In this case you will have to pay in cash after boarding the Ferry. Make sure you have cash before boarding.
Semi-Private – The private ferry terminal is located just a few steps from SXM. These transfers do require prior booking, which can be easily done online. After leaving the airport you’ll walk over, show your passport, and board the ferry. Once onboard you’ll enjoy a 20-30 minute ride with drinks included (yes even beer and rum punch) There are two main companies for semi-private ferry transfers
Calypso Charters – $75 USD per adult one-way or $150 round trip. Children (2-11) are approximately $40 one-way/$80 round trip, with infants under 2 riding free. Book here
Fun Time Charters – $150 USD per adult round trip Book here
Clearing Customs
As with any international destination, you’ll need to clear customs when you arrive at SXM. At peak times lines can be rather long (1+ hours), so give yourself plenty of time to make your transfer. Upon arrival at the Anguilla port you’ll go through customs a second time, then you can take a taxi to your accommodation (available at the taxi stand right outside).
All things considered, I would allot at least 2 hours from landing in St. Maarten to arrive at your stay in Anguilla. In the peak season and weekends it may take even longer.
Where to Stay in Anguilla
With the island being so small, no matter where you stay you’ll never be more than 30 minutes from everything you want to see and do. That said, choosing your type of accommodation can drastically change the vibe of your trip. Chain hotels aren’t really a thing in Anguilla, so your options are a resort, a boutique hotel, or an Air BNB.
Where to Stay by Accommodation Type
Resorts
Resorts are obviously the most luxurious and expensive option, but if it’s within your budget, Anguilla offers some of the best resorts in the Caribbean.
Aurora Anguilla – This is where I stayed during my 6-weeks in Anguilla and I absolutely loved the property. The staff goes above and beyond for guests and its location on Rendezvous Bay is postcard worthy. It’s more family friendly than the other resorts and Aurora has the only golf course on the island!
Four Seasons – The Four Seasons is located on Meads Bay Beach and has a more modern, trendy aesthetic. It’s known for the picturesque Sunset Lounge and is perfect for those looking to get great photos.
Cap Julaca – The Cap Julaca, on Maunday’s Bay, features gorgeous Moroccan inspired architecture. The property feels fresh and airy. This is the ideal option for couples.
Boutique Hotels
Boutique Hotels fall somewhere in between, you get the feel of a more private and unique stay without the resort price tag. They are scattered all over the island, and can be found on every stretch of beach.
Vacation Rentals
Rentals are another fantastic option in Anguilla. While they offer a less upscale experience, you get the benefit of a completely private accommodation. Great deals can be found on both Airbnb, VRBO, and other third-party sites like Expedia or Booking.com.
Where to Stay by Area:
Meads Bay – for upscale dining and luxury convenience
Shoal Bay – for beach time and snorkeling
Rendezvous Bay – for long beach walks, calmer vibe, and views of St. Maarten
Sandy Ground – for bars, live music, and a more casual atmosphere
Island Harbour / East End – for a more local, quieter feel
Do You Need a Car in Anguilla?
For most visitors, yes. Transportation is essential, and renting a car is by far the easiest way to explore the island. It’s also much more cost effective for stays longer than a day. That said, it isn’t the only option. Some travelers find that taxis or Mokes are a better option for them.
Renting a Car
Renting a car in Anguilla is by far the easiest way to explore. It’s the cheapest option, especially for multi-day rentals, and gives you complete freedom. Jeeps are the most popular rental, but they are usually more expensive and pretty beat up (the one I rented had every single light on when I got it and the company said that was normal…) For the most cost effective and comfortable choice I’d get an SUV for the duration of your visit.
Taxis
Taxis in Anguilla are available but expensive for frequent use. Expect to pay $30 or more to get anywhere. Typically the drivers will give you their card when they drop you off to call them back when you’re ready to be picked up. Many only accept cash so don’t forget to hit an ATM if you decide to take a taxi.
Mokes
Mokes are the mini jeep/ golf cart hybrids you’ll see all over pinterest and google image searches of Anguilla. While they’re undeniably adorable, they’re very expensive to rent. Getting one to drive around will run you $150+ a day. If getting the experience and pictures is a priority, I’d recommend doing an hourly rental then switching to a standard car.
Driving Tips
Keep in mind, they drive on the left side of the road in Anguilla. When booking a car make sure you ask for one with a left-hand driver’s seat (an American car) and request an automatic transmission, unless you really want to drive a stick shift around town.
You’ll need a temporary drivers license to rent a car, which can be easily purchased through the car rental companies. They cost $15 for 3-days and $30 for a month.
The roads are decent but can be narrow and bumpy in spots. Traffic is typically light and Google Maps is reliable for directions around Anguilla.
My best advice is to spend your first day in Anguilla just driving around without a set destination. You’ll get a feel for the culture, stop into little places that catch your eye, and see all of the breathtaking beaches. The main road across the island is a loop, so it’s hard to get too lost.
How Expensive Is Anguilla?
Many travelers ask, is Anguilla expensive? In short, yes. The island caters to high-end tourism, so Anguilla prices are generally higher than elsewhere in the Caribbean. You also have to consider that everything has to be imported and often brought by boat from St. Maarten, making average costs even higher. The total cost of travel to Anguilla depends heavily on accommodation and dining choices.
Accommodation Costs
Luxury properties dominate the market. I would argue the resorts are worth it if they’re within your budget, but staying in a luxury accommodation is not a requirement. You can absolutely have the trip of a lifetime while staying in a more budget friendly place.
Food & Dining Costs
Excellent but pricey, even for casual meals. You can expect dinners to cost at least $40 per person, even at more laid back spots. To cut down on food costs you can make a grocery run (my go to grocery stores were Best Buy and Limin) for breakfasts and lunches, then eat out for dinners. The stock at the grocery stores can get low at times, but they have all the basics.
Transportation Costs
Renting a car for the duration of your stay is by far the most cost effective option for getting around. Taxis add up incredibly quickly and Mokes are aesthetic but pricey.
Things To Do in Anguilla
There are plenty of things to do in Anguilla, but most activities in Anguilla revolve around beaches, food, and the ocean.
Beaches
You would be hard pressed to find a “bad” beach in Anguilla. While the entire coast line is stunning, these are the “must-see” spots.
Rendezvous Bay – A long stretch of fluffy white sand with a view of St. Maarten across the water.
Shoal Bay – Anguilla’s most famous beach, consistently ranked among the world’s best beaches. It’s also one of the best places to snorkel from the beach.
Sandy Ground – This bay is lined with beach bars (my absolute favorite being Elvis Beach Bar) and is a bit less upscale than other areas. It’s perfect for a casual beach day.
Mead’s Bay – This is the most luxury option. The beach is lined with restaurants and several beach clubs.
Boat Trips & Island Hopping
Boat tours of Anguilla and the surrounding islands are offered by various companies and I would absolutely add one to your itinerary. Many include snorkeling stops, open bars, and even meals on board. Popular stops include Sandy Island and Prickly Pear, which are both incredible for seeing ocean life.
Unforgettable Experiences
Scilly Cay – This is a tiny island in Island Harbor. Spend the day here eating delicious lobster and drinking “The Strongest Rum Punch” on the island. To get there, go to the end of the Island Harbor and wave at the island until the small ferry boat comes to get you (yes I’m serious, there’s no way to book ahead) the boat ride is $5 round trip and can be added to your bar tab. Double check their as they typically only open on certain days of the week.
Sandy Island – Another island day trip off the coast of Sandy Ground. Sandy island features a gorgeous beach with cabanas and chairs for rent. To get there, go to their stand in the middle of the Sandy Ground beach to catch the boat over, it’s $40 round trip per person.
Scuba Diving – As a certified diver this was a must do for me and I think anyone visiting Anguilla should try it. I went through Scuba Shack, they offer experiences for both certified and first time divers. The sea life around the island is unbeatable, you have to see it to believe it.
Ship Wreck – There is a ship wreck right on the beach in Sandy Ground that makes for an amazing photo op and a quick sidequest. To get there, stop at Backstreet Scenic Village Vista Viewpoint above Sandy Ground. From there head down the rock trail just to the left of the view point. After about 5 minutes of walking you’ll find yourself down on the beach right next to the shipwreck!
Anguilla Arch – The Anguilla Arch is absolutely worth seeing in person, though I would recommend having a car to get there. On the way you’ll head down a dirt road before coming to a small shack next to the arch. It’s $5 cash to get over to the view point. The man who runs the spot has been doing it for years and is full of fun facts about Anguilla.
Pro tip: Ask him for directions to the secret beach… it’s the most beautiful place I’ve ever seen
Water Sports
Many of the resorts offer a variety of activities included in your stay like fishing, sailing, snorkeling, paddleboarding, kayaking etc. If your accommodation doesn’t include these things It’s absolutely worth checking out guided experiences around the island. Sandy Ground and Shoal Bay are hotspots for tours and rentals.
You may notice a lack of food pictures… that is because 90% of the time my phone does not eat first…
Where to Eat in Anguilla
The food scene in Anguilla is world famous, and for good reason. While you can find top-notch spots for all kinds of cuisine, I’d recommend sticking primarily to Caribbean dishes, especially seafood. When in Rome do as the Romans do, right?
Breakfast
Mill house – A casual spot for breakfast, brunch, and good coffee. The Johnny Cake Eggs Benedict is an absolute must-try
Yves Coffee – A cute little cafe offering lattes, matcha, pastries, and breakfast sandwiches
Straw Hat – While they’re famous for their dinner, I think they do breakfast even better.
Lunch
Blanchard’s Beach Shack (aka my fav spot) – Right next to the main Blanchard’s Restaurant is this walk up food shack with chairs and umbrellas for rent. They have everything from tacos and burgers to ice cream and rum punch pitchers. The mahi bites are definitely pricey, but they’re worth every penny when paired with their cilantro lime sauce. All of the menu options are fantastic and I found myself going back again and again.
Tasty’s – A casual spot with a view overlooking Sandy Ground. They’re famous for their seafood salad, but I personally go for the chicken wrap. I also tried out their breakfast and it did not disappoint.
Da vida – Beachside restaurant with a variety of lunch options including a caesar salad pizza that’s just as good as it sounds (be sure to add jerk chicken or shrimp on top!)
Dinner
Leon’s – Head here on a Friday night for live music and dancing! They have a wide range of menu options but the Rock Shrimp appetizer is my number one. Also try out their passion fruit rum bucket.
Blanchard’s – This famous spot lives up to the hype. Go with a group and split a bunch of dishes so you can try a bit of everything. Their style is Caribbean mixed with southern dishes and it works beautifully. Reservations recommended
Mirabelle’s – Popular with a more local crowd this asian fusion spot is absolutely phenomenal. Another place I recommend splitting a bunch of things with a group. Reservations usually not necessesary
Veya – While their food is great, the vibe is what makes Veya a stand-out. The restaurant is built like a treehouse and they often have live acoustic music. Great for wine-lovers. Reservations needed
Sharky’s – Sharky’s is one of the most well known Anguillan restaurants. They are famous for their lobster stir fry which is served in a huge lobster shell. Make a reservation!
Beach Bars
Elvis Beach Bar– A classic beach bar in the best way possible. They often have live music and a jumbo screen to watch any sports you request. In way of food, their nachos are great and can even be topped with jerk goat for a local flair.
Bankie Banx – Anguilla’s most famous beach bar. This place is a hippie paradise built like a treehouse on Rendezvous Bay. You’ll find live Reggae music, interesting characters, and Jimmy Buffet even used to do pop-up concerts here. Right next to Aurora Resort.
Olas tacos – Chill spot in Shoal bay with good tacos, huge drinks, and chairs to lay out on the beach.
Madeariman – This is a classic beach bar that always has a good vibe without being too crowded
Sunshine Shack – A cool spot with a walk up bar and a grill on the beach. Made-to-order lobster may take a while to get but it’s worth the wait. Just a walk down the beach from Aurora Resort.
Cocktails & Apps
Savi Beach – Beach club by day, restaurant by night, Savi Beach feels extremely modern. Perfect place to get evening drinks before dinner, or even stick around for a full meal. If you stay for dinner, just trust me and get the Mahi Au Gratin.
SandBar – Every single dish at this tapas bar is fantastic and their drinks are even better. 5 minute walk down the beach from Elvis Beach Bar, so you can easily hit both in one night.
Sunset Lounge – Inside the Four Seasons, this place has the best sunset view on the island and creative cocktails. Try to get there before sunset time to get a good table
Local Eats
Criss Conch Shack – No frills and the best conch fritters I’ve ever had. Right next to Elvis Beach Bar.
Jelly BBQ – Classic Anguillan BBQ spot, the cheapest meal you’ll find on the island and still absolutely delicious. Truthfully, any roadside BBQ you see around the island is a solid lunch option.
Palm Grove Grill – A secluded spot on the beach on the far side of the island serving Anguillan BBQ and seafood. You’ll have to take some back roads to reach the restaurant so you’ll want a rental car.
E’s Oven – Hence the name, meals here are cooked in a huge stone oven inside the restaurant. Everything on the menu is simple and delicious.
What to pack for Anguilla
Packing for Anguilla is easier than 90% of destinations. Even in January the temperature never drops below 75 degrees and it’s sunny a majority of the time, with the exception of hurricane season of course. Almost everywhere has a casual dresscode, even the nicer restaurants.
I would pack comfortable and cool clothes for exploring; like jean shorts, tennis dresses, flowy skirts, etc. You want to be abe to go from lunch, to the beach, to the car, and then shopping without having to do 3 full wardrobe changes.
You’re going to be spending time on the beach, so don’t forget bathing suites and cover ups! You don’t need to worry about bringing your own towel, most hotels and beach clubs have towels available for guests or to rent.
For nights and dinners a sundress is the easiest choice for just about any establishment. The whole island has a very “come as you are” attitude, so don’t stress too much about being underdressed. If you want to spice up your outfits, I always think accessories and jewelry are the best way to do it when traveling.
Aside from clothes, I would recommend bringing sunscreen and any other toiletries you’ll want in your room and on the beach from home. They’re available on the island but selection is extremely limited and can be pricey.
Anguilla Itinerary: 1, 3, 5, and 7 day plans
If you’re trying to figure out how to structure your trip, these sample itineraries will give you a realistic idea of what your days might look like depending on how long you’re staying. Anguilla is best experienced at a slower pace, so don’t try to overpack your schedule.
1 Day in Anguilla (Day Trip from St. Maarten)
If you’re coming over from St. Maarten for the day, you won’t be able to see everything, but you can absolutely get a feel for what makes the island special.
Morning: Travel and arrival
- Take an early ferry from St. Maarten to maximize your time (earliest at 8:30am)
- Clear customs and grab a taxi or rental car
- Head straight to Shoal Bay or Meads Bay
Midday: Beach and lunch
- Set up at the beach and plan to stay for a few hours
- Swim, relax, and snorkel if you’re at Shoal Bay
- Grab lunch right on the beach
Afternoon: Light exploring
- Stop at a second beach if you have time
- Or head to Sandy Ground for a more casual beach bar vibe
Late afternoon: Head back
- Return to the ferry terminal with buffer time
- Take an evening ferry back to St. Maarten (latest at ~5pm)
3 Days in Anguilla
Three days is the minimum I’d recommend if you want to actually experience the island beyond just one beach.
Day 1: Arrival and settling in
- Travel to Anguilla and check in
- Head to Rendezvous Bay or Meads Bay for a relaxed afternoon
- Explore a bit on the way there and back
- Dinner at a nearby restaurant
- Optional drinks at Sunset Lounge or Savi Beach
Day 2: Shoal Bay and a full beach day
- Spend the morning at Shoal Bay
- Snorkel directly off the beach
- Stay through lunch (Olas Tacos or Medeariman)
- Optional stop at another beach on the way back
- Dinner at a casual spot or hotel
- End the night at Elvis or Bankie Banx if you want a night out
Day 3: Boat day and wrap up
- Take a boat trip to Sandy Island (quick trip over) or Prickly Pear Island (full boat tour)
- Spend the day snorkeling, swimming, and relaxing on the island you choose
- Return in the afternoon
- Grab an early dinner or head out depending on your travel plans
5 Days in Anguilla
Five days perfect for most first-time visitors. You’ll have enough time to see different parts of the island without feeling rushed.
Day 1: Arrival and settle in
- Travel to Anguilla and check in
- Drive around the island to get your bearings
- Dinner at one of my recommended restaurants
Day 2: Shoal Bay and Scilly Cay
- Morning at Meads Bay
- Swim, lay-out, and relax
- Head to Island Harbour and go to Scilly Cay for lunch
- Plan to stay a while and make it a full afternoon
- Dinner back near your accommodation
Day 3: Boat day
- Spend the day at Sandy Island (similar vibe to Scilly Cay) or Prickly Pear (catamaran tour there and back)
- Snorkeling, swimming, and a full day on the water
- Relaxed dinner afterward
Day 4: Shoal Bay and a nicer night out
- Breakfast at Millhouse
- Spend the day around Shoal Bay
- Move between the beach, lunch spots, and drinks
- Plan a nicer dinner and dress up a bit (aka a sundress and flip flops)
Day 5: Explore and head out
- Drive around the island without a set plan, catch-up on anything you still want to do
- Stop at the Anguilla Arch and any beaches that catch your eye
- Grab one last lunch
- Head to the ferry or airport
7 Days in Anguilla
With a full week, you can really settle into the pace of the island and not feel like you’re trying to fit everything in.
Day 1: Arrival and unwind
- Travel to Anguilla and check in
- Drive around to get your bearings
- Casual dinner by accommodation
Day 2: Shoal Bay
- Full day at Shoal Bay
- Swim, snorkel, and lunch on the beach
- Dinner at Leon’s
- Beach bar like Bankie Banx or Elvis if you’re up for it
Day 3: Scilly Cay and Island Harbour
- Head to Island Harbour
- Spend the day at Scilly Cay
- Dinner at Blanchard’s or Sharky’s
Day 4: Boat day
- Visit Prickly Pear on a catamaran tour
- Snorkel, swim, and spend the day on the water
- Casual dinner
Day 5: Meads Bay and sunset drinks
- Spend the day around Meads Bay
- Beach hop, have lunch, and grab drinks
- Cocktails at Sunset Lounge
- Dinner at Blanchard’s or Sharky’s
Day 6: Explore beyond the main spots
- Breakfast at Millhouse
- Visit the Anguilla Arch
- Drive the island loop
- Lunch at Jelly BBQ
- Stop anywhere that looks interesting
- Dinner at Mirabelle’s or somewhere you haven’t tried yet
Day 7: Slow morning and departure
- Final beach walk or swim
- Breakfast or brunch
- Head to the ferry or airport
Cultural Events, Festivals, and Carnival in Anguilla
Anguilla is usually pretty quiet, but if your trip lines up with one of the island’s festivals, the atmosphere completely changes. Music, boat racing, food, and community events are a big part of the culture here, and it’s a very different experience from a typical beach day.
You don’t need to plan your trip around these, but if your dates happen to overlap, they’re absolutely worth checking out.
Anguilla Summer Festival (Carnival)
- Late July through early August
- Around 10 to 14 days of events
- The biggest and most energetic time of year
This is Anguilla’s version of Carnival and easily the liveliest the island gets. Expect parades, music, boat races, beach parties, and events that go well into the night. The whole island gets involved, and there’s something happening almost every day.
If you’re worried Anguilla might feel too quiet, this is the one time of year that definitely won’t be the case.
Moonsplash Music Festival
- Typically March or early April
- Held at the Dune Preserve (Bankie Banx) on Rendezvous Bay
- Reggae-focused and more laid back
Moonsplash has a completely different feel than Carnival. It’s smaller, more relaxed, and centered around live music right on the beach. You’ll find a mix of locals and travelers, and it tends to go late without being chaotic.
Festival Del Mar
- Easter weekend
- Located in Island Harbour
- Focused on fishing and local culture
This is one of the more local events on the island and a great way to see a different side of Anguilla. Expect boat races, seafood, live music, and a really casual, community-focused atmosphere.
Anguilla Regatta
- Usually in May
- Celebrates traditional boat racing
Boat racing is a big deal in Anguilla, and this event is centered around it. Even if you’re not into sailing, it’s interesting to watch and gives you a better sense of how important the ocean is to the island.
Other Events Worth Knowing
- Anguilla Day (May 30) with celebrations across the island
- Anguilla LitFest in May with smaller cultural events
- Occasional food events and pop ups throughout the year
NOTE: If your trip doesn’t line up with any of these, you’re not missing anything essential. But if it does, they can add a completely different side to the island that most people don’t experience.
Is Anguilla Safe?
Overall, Anguilla is safe and feels calmer than many destinations. Concerns about crime in Anguilla usually relate to petty theft rather than violent incidents. Violent crime affecting tourists is rare. Basic precautions like locking doors and watching belongings are usually sufficient.
Solo travel is common, and daytime activities feel very safe. At night, roads can be dark, so driving cautiously is important.
I explored the island primarily by myself for the 6-weeks I was there and, aside from some standard cat-calling, I never felt nervous or unsafe.
Anguilla Travel FAQs
Is Anguilla worth it?
Yes, if you want beautiful beaches, standout food, and a peaceful, uncrowded Caribbean trip. If you want nightlife or a packed itinerary, it may feel too slow.
How many days do you need in Anguilla?
At least 3 days if you want to experience more than one beach. For most first-time visitors, 4 to 5 days is ideal.
Do you need a car in Anguilla?
For most visitors, yes. Renting a car is the easiest and most cost effective way to get around the island.
Is Anguilla expensive?
Yes. Anguilla is generally more expensive than many other Caribbean destinations, especially when it comes to hotels and dining.
Is Anguilla safe?
Overall, yes. It feels calmer than many destinations, and tourist concerns are usually limited to petty theft rather than violent crime.
Where should you stay in Anguilla for a first visit?
That depends on the kind of trip you want. Meads Bay is great for luxury and convenience, Shoal Bay is ideal for beach time and snorkeling, and Rendezvous Bay is better for a calmer vibe and long beach walks.
