The Ultimate Guide to Anguilla

The dreamy, secluded Caribbean island of Anguilla is pure paradise. Think powdery white-sand beaches, crystal-clear turquoise water, and some of the most luxurious (yet laid-back) resorts in the world. Need I say more?

Kenny and I first visited this stunning island for our babymoon when I was pregnant with our first, and we instantly fell in love. Since then, we’ve come back as a family, and it’s become one of my absolute favorite destinations in the Caribbean. Anguilla is that perfect mix of chic and serene, with five-star resorts, incredible food, and a vibe that’s equal parts luxe and family-friendly, too! If you’re planning a trip to this Caribbean gem, you’re in the right place. Here are all of my Jetset-approved tips, tricks, and recommendations to help you plan the Anguilla vacation of your dreams.

 

When is the best time to visit Anguilla?

Peak season in Anguilla is from December to April when the weather is absolutely perfect! This makes it an ideal Spring Break destination for families, as the temperature usually ranges from upper 70’s to 85 degrees during this time, making it a lovely escape from cold winter. With peak season does come a heftier price tag, so keep this in mind as you are planning your trip.

If you want to save a little bit of money but still experience great weather, I recommend visiting between May and early August. Stay away from September through November as most businesses (including the resorts!) close down for hurricane season.

Kenny and I visited in March the first time we visited, and again in March as a family, and although it was definitely a bit windy at times, the sun was always shining and there was no rain, both times!

How can I get to Anguilla?

From the U.S., the fastest and easiest way to get to Anguilla is on a direct flight from Miami via American Airlines (MIA to AXA). Before American started flying direct to Anguilla’s Clayton J. Lloyd International Airport, U.S. tourists would need to either fly via private jet to the island or fly into St. Maarten and take the 20-minute ferry ride over to Anguilla. This is still a very popular option if you have better flights into St. Maarten from your home. The ferry from St Maarten is easy (30 mins) so that’s a good option too but I prefer to fly into AXA!

JETSET TIP: Be sure that you have some cash when you travel to Anguilla as we used cash for all of our taxis and found cash handy for tips! And there is also a $28 departure tax when you leave by plane or boat. Most places on the island accept both USD (U.S. Dollars) and ECD (Eastern Caribbean Dollars). We didn’t exchange any $ and used USD the whole trip. 

What is the best way to get around in Anguilla?

Although Anguilla is a relatively small island, walking won’t be the best choice. There are also no forms of public transportation, so cars, bikes, and scooters are your only options. Kenny and I found that taxis were the easiest way to get around for us, which I’d recommend, since it’s such an easy-to-get-around island (and the resorts made getting cabs super easy), but you can also rent a car for your stay if you want a little more freedom to explore. It’s also really popular to rent a Moke for the day or a few days to explore.

Just remember that, because Anguilla is a British overseas territory, they drive on the left side of the road! It’s also important to note that most of the roads in Anguilla aren’t paved, and there are very few street signs on the island. So, if you do choose to drive yourself, make sure you are comfortable doing so under all of these conditions.

 

Where are the best places to stay in Anguilla?

Anguilla is a relatively small island at just 16 miles long and three miles wide. Unlike many of its neighboring Caribbean islands, Anguilla has no shopping malls, cruise ships, casinos, or high-rise hotels, which gives it a more remote, secluded, exclusive vibe. Unless you want to book a VRBO or local bed and breakfast, you will have a total of only about 15 or so different hotels to choose from!!

The Best Luxury Resorts in Anguilla 

Ultra Luxe : the best of the best

Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca is an ultra-luxe Belmond hotel located on the south side of the island. With four beautiful restaurants, a cocktail lounge and bar, a five-star spa, the most beautiful white sand beach, and a gorgeous infinity pool overlooking the azure waters, Cap Juluca is architecturally stunning at every corner. The 70 guest rooms that make up the Cap Juluca resort are housed inside 15 white stucco villas that feel very Santorini-meets-Caribbean. The hotel is spread across 180 acres on the best beach in Anguilla – Maunday’s Bay, with its picture-perfect crescent-shaped white-sand beach and dreamy aqua water!

This resort is a destination in itself, and caters to honeymooners, babymooners, and anyone looking for a secluded, private, perfect and pristine beach getaway. We returned here with our little ones and it was definitely baby-friendly as well (especially the beach and the ability to walk out from our room to the beach! so baby-friendly) but i would imagine it a bit too ‘romantic’ and quiet for older kids who might prefer the more bigger bustling scene of the Four Seasons. 

 

Want to book Belmond Cap Juluca with an expert luxury travel agent who specializes in Anguilla specifically?

Book with me directly! Email [email protected] with your preferred dates, and I’ll personally get back to you with the best available rates and VIP amenities, just for being a VIP Jetset reader.

Perks may include:

Complimentary daily breakfast

Resort credit

Free room upgrades (when available)

Early check-in / late check-out

Insider VIP access through our trusted connection with the resort

Your stay will be booked directly through our preferred partner program, giving you the best possible experience – with luxury touches you won’t find when booking elsewhere.

Malliouhana

Malliouhana has a storied, glamorous past as being the first luxury resort on Anguilla! It oozes old school glamour, and is one of my favorite places to stay!!! Every corner of this dreamy hotel is chic & colorful and the decor is one of my favorites of any hotel, ever. It’s SO unique, SO freaking perfect, easily one of the most beautiful hotels in the Caribbean.

Link to my cover up here!

Between the beach club, which felt like a total Caribbean paradise and somewhere we could have spent a week, and the infinity pools, which were some of the most stunning pools (and cabanas) I’ve ever seen, this hotel was dreamy! It felt a little more casual than the Cap Juluca, but that’s not to say it was less high end, just a little less opulent and glam, more effortlessly cool. 

Malliouhana with kids

I was surprised at how kid-friendly Malliouhana is, one of the beautiful big infinity pools at the resort is family-friendly (the other is reserved for adults) and given that we were there around spring break time, there were lots of other families! (but also not toooo many that it felt too crowded!). I loved the kids club here, too (it’s huge and amazing! located right above Leon’s beach club on the beach.

The only thing to note about Malliouhana vs Cap Juluca with little ones is that Malliouhana is located on the cliff and getting to the beach, etc, takes a lot of walking / navigating jaggier rocks etc. it’s not as easy of a beach entrance as the Cap Juluca rooms on the beach. However, I would say that my toddler liked this pool better than Cap Juluca’s, and the kids club is better here at Malliouhana too!

The rooms at Malliouhana

All the rooms here are GORGEOUS. We loved the Turtle Cove villa, perfect for a family looking for a 2-bedroom villa in Anguilla. I mean, these views cannot be beat!

  

Want to book The Malliouhana in Anguilla with a luxury travel agent who specializes in Anguilla specifically?

Book with me directly and I’ll make sure your trip is ultra-special, at zero cost to you! Email [email protected] with your preferred dates, and I’ll personally get back to you with the best available rates and VIP amenities that my team can get you, just for being a VIP Jetset reader.

Perks may include:

Complimentary daily breakfast

Resort credit

Free room upgrades (when available)

Early check-in / late check-out

Insider VIP access through our trusted connection with the resort

Your stay will be booked directly through our preferred partner program, giving you the best possible experience – with luxury touches you won’t find when booking elsewhere.

Luxe

Four Seasons Resort and Residences Anguilla

The Four Seasons in Anguilla is a great option for families, groups and couples looking for a buzzy, modern vibe and a stunning oasis in Anguilla. The FS used to be a Viceroy and was recently converted to an FS. It is the largest resort on the island. Four Seasons Resort and Residences Anguilla feels like a home away from home, and offers a wide variety of accommodations ranging from one bedroom guest rooms to one, two and three bedroom Residences to five bedroom stand alone Villas – making it an especially great spot for families and groups. The vibe here is much more bustling (and crowded) than Malliouhana or Cap Juluca, but many families prefer that as they feel like their kids can be wild and right at home with the other families on property!

Also FS Anguilla arguably the best sunset on the island! I’d recommend heading to their sunset lounge to catch a sunset whether or not you’re staying there! That’s one of the best things about Anguilla, people often hop around to check out the other resorts for lunches, happy hours, and what not.

Want to book The Four Seasons in Anguilla with a luxury travel agent who specializes in Anguilla specifically?

Book with me directly! Email [email protected] with your preferred dates, and I’ll personally get back to you with the best available rates and VIP amenities, just for being a VIP Jetset reader.

Perks may include:

Complimentary daily breakfast

Resort credit

Free room upgrades (when available)

Early check-in / late check-out

Insider VIP access through our trusted connection with the resort

Your stay will be booked directly through our preferred partner program, giving you the best possible experience – with luxury touches you won’t find when booking elsewhere.

Quintessence, Relais & Chateau

This boutique hotel is elegant and secluded, giving you the perfect oceanfront escape! Children 12 and younger are not allowed at this property, making this a great adults getaway option. Between Quintessence’s private nature and the unmatched attentiveness of the staff, you’ll feel as if you’re the only guest there! Their amazing concierge and 24/7 butler service add to the already opulent and intimate nature of the hotel. Not only does it have an amazing restaurant called Julian’s (more on this below!), it also boasts an extensive art collection that has been perfectly curated by the hotel’s owner.

Frangipani Beach Resort Anguilla

Frangipani Beach Resort is an intimate resort hosting just 19 rooms and one four-bedroom villa – but don’t let its size fool you! This resort is a cult FAVORITE, and has a fitness center, bike rentals, a spa, water sports, boat tours, and a super popular (and deliiiish) beachfront restaurant called Straw Hat. It’s also located on dreamy Mead’s Bay (the same beach as Malliouhana!), which is the best area to stay on the island. There’s also a great boutique on property that you should stop by whether or not you choose to stay here! It’s great for some island boutique shopping and resort wear. 

Contact [email protected] to book -this hotel only accepts bookings via email and I can help get you the best rate! 

Aurora Anguilla Resort and Golf Club

Aurora is a great option for families – it even has a water park!! The vibe is more ‘big resort’ than the others on this list. Aurora Anguilla Resort and Golf Club has comfortable rooms, a relaxing spa, and dining options with locally-sourced ingredients, AND a nine and an 18-hole golf course with sweeping views of the Caribbean ocean! So if you are a vacation golfer, this is the place to be (in your Kenny Flowers golf gear, of course!).

Where are the best places to eat in Anguilla?

There’s something about fresh island food that I just love. My top rec no matter where you dine in Anguilla is to order Anguilla’s famous Johnny Cakes (basically bread meets donut, amazing) and tons of fresh lobster!!

Something to know: You WILL need reservations!!! I recommend making them before your trip!

Blanchard’s

This restaurant is a great spot for dinner! We loved it so much on our most recent trip that we went twice. Prices range from $30 – $65 USD per plate, and there are tons of incredible dishes on the menu (including vegan, vegetarian, and gluten-free options!). Highly recommend the jerk chicken, the wedge salad, and definitely save room for dessert and order a carrot cake and the cracked coconut!!! My favorite.

Straw Hat

We loved eating at Straw Hat! It’s casual, delicious, and so fresh! Located in the Frangipani Beach Resort and serves breakfast, lunch, and dinner seven days per week (reservations are highly encouraged for dinner!).

Veya Restaurant

At Veya, you can dine in a “treehouse” and enjoy some amazing Anguillan seafood while you listen to live music! We loved it here. I prefer it for a romantic trip since it’s a taxi ride away, and a little more romantic vs the beach restaurants which cater more to families.

The Cap Shack

We ate at The Cap Shack so many times during our week in Anguilla. Located on the Cap Juluca resort property, you can go whether you’re staying there or not. I am obsessed with the lobster roll and Kenny loved the poke bowl too!!! Plus it has the BEST pina colada on the island and the views are insanely beautiful.

Sharky’s Restaurant

Sharky’s Restaurant is loved by both tourists and locals! The vibrant color scheme of the private-home-turned-restaurant will certainly catch your eye, but once you are inside, the delicious food and inviting atmosphere are what will keep you coming back.

Jacala

If you need a mid-day break, head to Jacala for a French-inspired lunch! This place is so good, even Martha Stewart declared it as her favorite in all of the Caribbean!

Uchu 

Another Cap Juluca restaurant that is worth a visit is Uchu. Even if you aren’t staying at Cap Juluca, I highly recommend that you come here for lunch to enjoy its beautiful atmosphere! The restaurant was buzzing at lunch of groups coming from other hotels to check out the Belmond. But it still felt intimate!

Julian’s

Julian’s is a tropical French bistro known for its romantic atmosphere and incredible wine list. Sadly, I couldn’t put their wines to the test this time, but this place is definitely going to be first on our list when we come back!

Sunshine Shack

If the name alone doesn’t bring a smile to your face, the vibes certainly will! Sunshine Shack is a local watering hole that is loved by everyone on the island. It is the perfect place to post up on a sunny afternoon!

Scilly Cay

Scilly Cay is actually a nearby private island that has been around for more than 35 years! In order to get over to this little gem of a restaurant/island paradise, just take the island’s ferry a few minutes east of the mainland. They are open for lunch on Wednesdays and Sundays, and the experience even includes a live reggae band! So cool!!

What are the best things to do in Anguilla?

Other than eating your heart out and soaking up the sun in your resort’s beach chairs, there are tons of fun things to do in Anguilla!

Ride a Horse on the Beach!

With Seaside Stables, you can check “ride a horse in the ocean” off of your bucket list! Whether you are an experienced rider or a new rider, you’ll love the tranquil experience of riding through the surf on top of a horse! We also did this through the Cap Juluca hotel if you’re staying there!

Cliff Jump and Snorkel at Little Bay

Little Bay is one of the most popular attractions on the island, but getting there can be an adventure in and of itself. Little Bay is really only accessible by boat, although you could hike down the trails or rent a kayak from da’Vida (located right around the corner) if you’re feeling really adventurous. Once you have arrived on the beach, I highly recommend snorkeling along the reef or jumping off of the famous rock (like Lebron James did!).

Paddle Board at da’Vida Bay & Restaurant

da’Vida Bay is a fantastic spot for swimming, snorkeling, and non-motorized water sports! Enjoy the water right in front of the da’Vida Restaurant, or head around the corner to Little Bay. If you get hungry, try their famous caesar salad pizza and frozen mojito!

Golf at Aurora Anguilla Resort and Golf Club

Looking for an awesome place to rock your new Kenny Flowers Country Club looks? This is it! Aurora Anguilla Resort and Golf Club is a premier signature golf course with the most gorgeous Caribbean backdrop.

Enjoy the Sunset at Sunset Lounge

It’s called Sunset Lounge for a very good reason! This restaurant/lounge at the Four Seasons is known as one of the best places to take in the sunset on the island. They are also known for their incredible cocktails! 

What should I pack for Anguilla?

I have a pretty extensive tropical vacation packing guide complete with all of the beach essentials on the blog already, but there are a few other looks I would recommend specifically for Anguilla!

Here’s what I wore in Anguilla

  

 

I wore this set basically every day – it’s so comfy and the perfect chic vacation cover up matching set.

shown here over my one-shoulder white jacquard bikini.

resort shirt linked here

my kids wore these matching suits in Anguilla – one of our favorite prints ever!

 

this yellow one piece is so perfect in Anguilla! And it’s sooo stretchy, flattering, and comfy. Ultra high-quality fabric – it’s a fav of mine.

WHAT MY KIDS WORE:

White terry polo linked here (true to size)

Striped linen boys pants linked here

 

Other things to pack for Anguilla

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One of my vacation go-to’s, always! So chic!

You may have seen me in this dress in Dubai as well. It’s one of my favs!

I love our Aruba suit because it is so stretchy!

The best villas to rent on Anguilla

Sandcastle Beach House

4 Bedrooms, Sleeps 8

This amazing luxury rental property in Anguilla is right on the beach and comes with its own complimentary Jeep wrangler for transportation, private pool, jacuzzi, chefs kitchen and kayaks/paddle boards. This is a great option for families or groups. Ask your host about getting private chefs on onsite massages. 

Sea Villa at Long Bay Villas: Privacy, 5-star service, butler, on secluded beach

For the most luxurious villa in Anguilla, look no further than this beachfront mansion. Featured on Netflix’s “The World’s Most Amazing Vacation Rentals” Season 2!

Check rates for your dates here.

Sand Villa at Long Bay Villas

Sister property to the above! Long Bay Villas was featured on Netflix’s “The World’s Most Amazing Vacation Rentals” Season 2 and is Anguilla’s largest and most private staffed, luxury property with ultimate beach access. 

Sand, Sea and Sky at Long Bay Villas can be rented individually or combined with each other and/or our sister property next door (same management team) Santosha Villa Estate Anguilla. Ideal for a family reunion, destination wedding or group retreat in Anguilla.

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