Anguilla Travel Guide: Things to do on Anguilla Trips, Best Time to Visit, and More! 

Are you looking for a laidback, luxury vacation where you can escape the chaos and crowds of more popular destinations? If so, an Anguilla trip may be just what you’re searching for. 

This little Caribbean island is a lavish yet private getaway that you’ll never forget. And in our Anguilla travel guide, we’re going to help you plan your Anguilla trip and enjoy the trip to the fullest.

Below, you’ll learn what attracts the world’s most famous celebrities to this mellow sanctuary and why it belongs on your bucket list. We’ll cover the best time to go to Anguilla, where to stay in Anguilla, and of course, things to do in Anguilla along your journey. 

You’ll have a clear roadmap of the next steps for planning your Anguilla trip in just a few minutes. First, where is the island of Anguilla, exactly?  

Where is the Island of Anguilla?

The island of Anguilla is a small, picturesque Caribbean island located in the northeastern Caribbean Sea. It is part of the Leeward Islands and is situated to the east of Puerto Rico and the British Virgin Islands, and to the north of Saint Martin. 

Despite its relatively small size and population (less than 15,000 people live here), Anguilla is a unique and diverse destination, where you’ll experience stunning natural beauty, vibrant culture, and a welcoming community. 

The island’s white sandy beaches, turquoise waters, and warm climate make it an ideal vacation spot for travelers looking to relax and unwind in a truly idyllic setting. But is vacationing in Anguilla right for you? 

Should You Visit Anguilla? Why an Anguilla Trip Belongs on Your Bucket List

You’ve likely got a few destinations in mind for your luxury getaway. What makes Anguilla the premier choice? There’s no question – this hidden gem belongs on your bucket list. It was ranked the #1 Caribbean Island in “Travel and Leisure’s World’s Best Awards,” for four straight years for a reason.

Anguilla is home to some of the most stunning beaches in the Caribbean (33 of them, to be exact). Some of these beaches are considered to be top choices in the world, each having its own character and charm. From the iconic Shoal Bay Beach with its powdery white sand and crystal-clear waters, to the secluded Little Bay Beach accessible only by boat, there’s a beach for every taste and preference.

What’s more, the cuisine you’ll encounter here is a food lover’s paradise. You’ll eat a unique blend of Caribbean and international cuisine. From fresh seafood and local specialties like conch fritters and johnnycakes to gourmet dining experiences at some of the island’s top restaurants.

And for those who travel to experience unique cultures, Anguilla will not disappoint. The island boasts a rich history that is celebrated through various events and festivals throughout the year. From the annual Anguilla Summer Festival, featuring music, food, and dance, to the Heritage Collection Museum, which showcases the island’s history and heritage, there’s plenty to explore and discover. We’ll talk more about all the things to do in Anguilla later on.

Maybe you are hoping that vacationing to Anguilla can serve as an opportunity to disconnect and unwind. With its laidback vibe, tranquil setting, and abundance of wellness activities, this Caribbean island is a perfect pick. From yoga classes on the beach to spa treatments at one of the island’s luxurious resorts, there are plenty of ways to find inner peace and hit the reset button.

But, anytime you’re traveling to a foreign destination you want to be able to enjoy peace of mind. So – is Anguilla safe for tourists?

Is Anguilla Safe for Tourists?

You don’t need to stress about your safety or well-being in this hidden gem. The island has a low crime rate. And the safety of this island is actually one of its biggest draws.

As a matter of fact, Anguillans are known for their warmth and hospitality, and visitors to the island often comment on how friendly and welcoming the locals are. From the moment you arrive, you’ll be greeted with open arms and made to feel at home.

What is the Best Time to Go to Anguilla for a Vacation?

when to visit anguilla

To make sure you truly get the experience you’re craving, you should plan your trip around the best time to go to Anguilla – which is typically between December and April. This is the island’s “dry” season. Throughout these months you can expect sunny, warm weather with average temperatures around 80°F. 

With that said, you’re not the only one looking for the best time to go to Anguilla for a vacation. This dry season is also the busiest time in Anguilla. But as we’ve touched on already, even the busy season here is a more mellow experience than St. Barts or other more popular destinations.

However, if you’re looking for a quieter time to visit Anguilla, the shoulder season between May and August can also be a good option. During this time, the weather is still pleasant, although there may be occasional showers. Hotel rates and crowds tend to be lower, making it an ideal time to explore the island at a more relaxed pace.

Now – the one time we don’t recommend traveling to Anguilla is during September and October. This is considered the off-season for the island as its usually hammered by tropical storms and hurricanes. You could have your trip interrupted by travel restrictions or spend your vacation indoors – neither of which is ideal.

How to Travel to Anguilla for Tourists in the US or Elsewhere

Now that you know the best time to go to Anguilla, the question becomes how to travel to Anguilla for tourists in the US or elsewhere. Regardless of where you’re departing from, you’ll have two options:

  1. Book a flight to St. Maarten and take the 25-minute ferry ride to Blowing Point. This is typically the most cost-effective approach to getting to Anguilla. But, it is a bit more work and takes a while longer than the alternative.
  2. Book a flight directly to Anguilla’s Clayton J Lloyd International Airport. This airport only accommodates small aircraft, so you’ll have to consider getting a private jet

There are other options as well – like chartering a yacht and pulling into one of the marinas on the island that offer mooring and docking facilities. You can depart from many other Caribbean islands. This approach is undoubtedly more expensive but offers a unique experience where you can explore the island’s coastline and surrounding waters in a whole new way. 

Do You Need a Passport to go to Anguilla as a Tourist?

However you decide to travel to Anguilla, you’re probably wondering – do you need a passport to go to Anguilla? The answer is yes – unless you hold a British ID. The reason being this is a British-owned island. So, US travelers need a passport valid for at least six months beyond their date of entry into Anguilla.

And, it’s worth looking into the COVID-19 policies leading to your arrival. This island has strict policies and may require a negative PCR test, proof of health insurance, and other personal information. 

Where to Stay in Anguilla: Resorts, Hotels, and Other Options

Where to Stay in Anguilla

You’ve figured out how to travel to Anguilla. Now, it’s the point in our Anguilla travel guide when we get to talk about some of the more fun stuff: like where to stay in Anguilla. First, we want to talk about the two main towns and villages you’ll want to visit during your travels.

The Valley

This is the capital of Anguilla – and the main town on the island. It’s located smack dab in the center and is known for its unique colonial buildings. This is where you’ll find most of the island’s shops, restaurants, and other villages – along with government buildings. It’s worth a stop while vacationing to Anguilla as you’ll get to immerse yourself in the island’s culture in the Valley.

Blowing Point

Jutting off the west end of Anguilla is Blowing Point. As the name suggests, it’s quite windy in this small village. It’s also the main point of entry for visitors arriving by sea from St. Maarten. Here, you’ll discover a small marina and several beachfront resorts.

If you plan to take a day trip to another island, this is where you’ll go. You can charter fishing boats and sailboats at Blowing Point – which will be something we discuss shortly in our section on things to do in Anguilla.

Experience Anguilla as it Was Intended: From a Breathtaking Luxury Villa

travel guide to Anguilla

In terms of where you should actually book your accommodations, there are quite a few options – but a luxury villa is our recommendation. After all, you may not have another opportunity to visit Anguilla anytime soon. You want to enjoy it to the fullest and experience all it has to offer – and what better way than luxury villas in Anguilla?

At Insider Villas, we can help take all the stress off your plate as we work together to book your accommodations. This allows you to enjoy peace of mind so you can truly kick your feet up and relax. 

One great choice is the Shiloh Villa Estate. You’ll feel like you’re soaring over the world as this villa sits on the Caribbean coast. Here, you’ll enjoy breathtaking views, exceptional luxury, and five-star services. Whether you’re golfing or just kicking back in your private estate, you won’t be disappointed. It’s located just outside of Blowing Point in Rendezvous Bay, Anguilla – making all the things to do in Anguilla quite accessible. 

Speaking of which, it’s time to talk about what to do in Anguilla along your journey!

What to do in Anguilla: Exploring, Playing, Sightseeing, Relaxing, Eating, and Other Things to do in Aguilla on Your Trip

In creating this Anguilla travel guide we’ve uncovered a diverse range of things you have to do. One of the big draws of this island is that it has something for everyone: from sightseeing to relaxing to adventuring, and of course, fine dining. Here’s some advice on what to do in Anguilla when planning your itinerary – starting with some activities for the adventurer within you:

Sports & Activities

  • Aurora International Golf Club: The Aurora International Golf Club is a picturesque 18-hole golf course located on the eastern side of the island. The course features stunning views of the Caribbean Sea & surrounding landscape while presenting a challenging but enjoyable experience for golfers of all levels.
  • Kitesurfing: We mentioned earlier that Blowing Point can be quite a windy ordeal – which is great for those who want to try kitesurfing! This is a unique way to take in the crystal-clear waters of Anguilla and the island’s surrounding scenery. Several kitesurfing schools on the island offer lessons and equipment rentals for all skill levels.
  • Prickly Pear Cay snorkeling experience: Prickly Pear Cay is a small uninhabited island located just off the coast of Anguilla, and it’s a popular spot for snorkeling and swimming. Visitors can take a boat tour to the island and explore its coral reefs and marine life.
  • Kayak to Anguillita: Anguillita is a small island located just off the coast of Anguilla, and visitors can take a guided kayak tour to reach it. The island is home to several stunning beaches and offers breathtaking views of the surrounding waters – all while getting some much-needed exercise to work off the drinks and food you’ll consume throughout your trip!
  • Guided coastline hike: Anguilla’s coastline is known for its natural beauty and stunning vistas. Guided hikes are available for visitors to explore the island’s rugged terrain and take in its picturesque views – while capturing some photos that are sure to leave your friends and family green with envy!
  • Cave tours: Anguilla is home to several limestone caves that are open for exploration. Visitors can take a guided tour to learn about the island’s geological history and explore its fascinating underground caves and formations.
  • Pickleball & tennis: Anguilla has several tennis and pickleball courts available for visitors to use. These activities offer a great way to stay active and enjoy the island’s warm weather.
  • Cycling trails: Anguilla has several cycling trails that wind through the island’s picturesque countryside and offer stunning views of the coast and surrounding landscape.
  • Fishing excursions: Anguilla’s clear waters are home to a variety of fish species, making it a great destination for fishing enthusiasts. Visitors can take a fishing excursion with a local guide and try their hand at catching a variety of fish species.
  • Boat racing & boat charter: Anguilla is known for its boat racing culture, and visitors can watch or even participate in one of the island’s boat races. Visitors can also charter a boat and explore the island’s coastline at their leisure, taking in its natural beauty and soaking up the sun.


  • Wallblake House: This historic plantation house in Anguilla dates back to the 18th century. It has been restored and is now open to visitors for a guided tour to learn about the history of the property and the island itself. The house features a collection of antique furniture and artifacts, and visitors can also explore the beautiful gardens and grounds surrounding the property.
  • Old Salt Factory and Pumphouse: This is another historic site in Anguilla that dates back to the island’s salt production era. The factory and pumphouse have been preserved and are now open to visitors, who can learn about the history of salt production on the island and see the original machinery and tools used in the process.
  • The Anguilla Arch in the southwest: This natural rock formation is located on the southwestern coast of the island – and it’s a truly captivating sight that you won’t regret making time for. The arch is made up of two large rock formations that have eroded over time, leaving a striking archway overlooking the ocean. Visitors can take a scenic drive to the arch and explore the surrounding area, which features stunning views of the Caribbean Sea and the neighboring island of St. Martin.

Fine Dining

    • Eventide, Rendezvous Bay: Experience a variety of fresh seafood dishes, including locally caught fish and shellfish, as well as a selection of meat and vegetarian options. The restaurant is also known for its inventive cocktails and extensive wine list.
    • Kitchen Table, Rendezvous Bay: This fine dining restaurant features contemporary cuisine with Mediterranean influences, and the restaurant prides itself on using fresh, locally sourced ingredients. The open kitchen and beautiful ocean views make for a unique and memorable dining experience.
    • Bankie Banx’s Dune Preserve, Rendezvous Bay: This is a one-of-a-kind beach bar and restaurant located featuring a variety of Caribbean and international dishes. The rustic, laid-back atmosphere is perfect for relaxing and taking in stunning ocean views.
    • Breezes, Merrywing Bay: Breezes is a high-end seafood restaurant located at the luxurious Four Seasons Resort on Merrywing Bay. The menu features a variety of fresh seafood dishes, as well as meat and vegetarian options. The restaurant’s beautiful setting and elegant atmosphere make for a dining experience you won’t soon forget.
    • D Richard’s, Aurora International Golf Club: This restaurant creates contemporary Caribbean cuisine with international influences and is the perfect way to finish up 18 holes.
    • Straw Hat Restaurant, Meads Bay: Located on the beautiful Meads Bay, the menu features a variety of fresh seafood dishes, as well as meat and vegetarian options. The laid-back atmosphere and stunning ocean views make this a combination of fine dining and sightseeing.
    • Jacala, Long Bay Village: Jacala is a fine dining restaurant located on the picturesque Long Bay Beach. The menu features French-inspired cuisine with Caribbean influences, and the wine list is one of the best in Anguilla – perfect for complimenting the cuisine itself.
    • Veya Restaurant, North Hill Village: Right in the heart of the charming North Hill village you’ll enjoy a unique fusion of Caribbean, Indian, African, Asian, and Mediterranean cuisine in a treehouse setting. The menu changes regularly to feature seasonal ingredients, and the wine list is updated frequently as well. And, there is live music most nights.
    • Elvis’s Beach Bar, Sandy Ground: Here, you’ll enjoy a truly local and authentic experience – with grilled fish, ribs, and lobster. The casual setting and live music make for a fun and lively atmosphere, and the food is always fresh and flavorful.
    • Kens BBQ, The Valley: For a more casual and family-friendly atmosphere, try Ken’s flavorful and delicious BBQ dishes. The menu features classic Caribbean favorites, including jerk chicken and pork, and guests can enjoy their meal while soaking up the local culture and atmosphere.
  • Authentic Anguillan cooking class: this could have been included in our list of things to do in Anguilla – but since you’ll end up eating what you prepare, we figured it was most fitting to put it here. Local chefs guide you through the process of preparing traditional dishes using fresh and locally sourced ingredients. From creating mouth-watering stews and soups to grilling fresh fish and meat, the class provides an immersive experience that showcases the flavors of the island – so you can recreate the experience back home with friends and family.

More Tips for Maximizing Your Anguilla Trip to the Fullest

visit Anguilla

Before we bring our Anguilla travel guide to a close, we want to provide a few more tips for maximizing your trip to the fullest. 

First, cars are driven on the opposite side of the road here compared to here in the US – you’ll drive on the left side. And in terms of currency, you’ll want to find an exchange center and convert your currency to XCD – which is the eastern Caribbean dollar (EC for short). The exchange rate is EC $2.7:$1 USD.

We also encourage you to prepare for your Anguilla trip by picking up a universal travel adaptor. The last thing you want is to scramble to find a way to charge your devices during your trip – this is a time to kick back and relax.

Closing Thoughts on Our Anguilla Travel Guide

That concludes our Anguilla travel guide. We hope what you’ve learned today helps you set out with confidence in planning your Anguilla trip and enjoying it to the fullest. After reading this, it’s clear why vacationing in Anguilla is a bucket-list-worthy experience. From all the things to do in Anguilla to the fine dining, the sightseeing, and the relaxing – there is something for everyone here. 

So, what are you waiting for? Put this plan in motion and start by booking your luxury villa for your Anguilla trip today!


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