I recently returned from a one week vacation in Anguilla, a British island in the Caribbean just North of St. Maarten/St. Martin. It was my fifth time visiting, but the first time actually staying on the island. The previous four times were day trips from St. Maarten on private charters. We would tell the captain where we wanted to go and he would take us there. From those prior visits I had a decent idea of how good the dining scene was as well as all the beautiful white sand beaches.

Here is a recap of my trip in the event that you vacation to Anguilla. There are many things a new or even seasoned Anguilla visitor might not know about.

The first thing you should know about Anguilla is there is no direct way of getting there unless you have a private plane. So unless you are ballin’ like that you will most likely be flying into St. Maarten. The other possibility is that you are already on a nearby island. Assuming St. Maarten is your departure point, which for most it is, you can either take a short flight, a private boat charter from multiple companies right across from the airport or leave out of Marigot, the French Capital, on the public ferry. The flight is over $200 and while taking the public ferry from Marigot may be cheaper you still have to hire a taxi to drive you around the island and then wait for the ferry which runs on the hour. My suggestion for the money is the private boat charter. We use Funtime, which picks you up from the airport, takes you to the dock, processes your information, takes you directly to customs from the water, a Funtime employee takes your passport and gets it stamped for you before you continue on to Anguilla. Once there, they unload your luggage and you can take a taxi to your resort or private villa.

As you can see the first day will usually be a long one. You will probably arrive in the late afternoon in time to shower, change and decide what’s for dinner. Since we stayed in a villa I decided to just lay low and explore my new home for the week.

The morning of day two I woke up refreshed and ready to explore. Sand Castle Villa is located on Limestone Bay on the North side of the island in The Valley. From prior visits I knew that Little Bay was the next bay over and it had a beautiful private beach and a fun rock that you could swim to and jump off. I found the trail off our road, climbed down the wall with rope that locals have left to assist in getting down the wall, swam out to rock, climbed up it and jumped a few times. Brian, Lauren and I also made 11-22-11 with rocks which has become a tradition on every vacation. For dinner we dined at Veya which is located on the road to Sandy Ground. Amazing food and atmosphere and somewhere I would consider a must try.

We decided go to Shoal Bay West on day three, which is on the south west end of the island. Shoal Bay East is the more well know and famous beach, but Shoal Bay West is equally as nice in my opinion. White sand, calm water, and a nice casual restaurant called Trattoria Tramonto. We ate lunch there and spent most of the day relaxing before heading home. We went to dinner at Sandbar, a local tapas restaurant that my family had eaten at before on prior trips and said was great. The prices here are very reasonable and the view of Crocus bay is perfect. After dinner we went to Elvis’ Beach Bar, a local watering hole and boat bar. This is usually where you will find the party so make sure to stop in and get the low down for the week.

This trip marked my first time spending Thanksgiving away from home. It was certainly different as being on a tropical island doesn’t give you that fall Thanksgiving feeling we are used to here in the states. Day four started off exploring the East end of island. We went to Shoal Bay East, bought fresh Crayfish and a Slippery Tail Lobster from a local fisherman right off the boat, climbed a coconut tree at Gwen’s to make some coconut risotto for dinner the following night and had Thanksgiving dinner at Jacala overlooking Meads Bay. After dinner we had drinks at Viceroy which is a simply amazing resort and another must visit location.

The agenda for day five was to meet up with my local friend Jill and go hiking on the north east end of the island where she lives. We went from Seafeathers Bay to Mimi’s Bay and found an amazing underground water cave that I climbed down to and then swam in. It was crystal clear, calm and had twenty foot ceilings, but you would never know it was there unless you looked hard and climbed down steep sharp coral. My friend Jill was amazed that something this cool was right there and she had never found it or heard about it from other friends. After our hike we headed to Little Bay for a snorkel, jumped off the rock again and climbed into a bat cave. I also got to finally try Jill’s Surf Ski which is a high performance kayak that is long and narrow and requires tremendous balance. My first 15 minutes was spent constantly flipping over, but slowly I got the hang of it to where I could ride without falling constantly. On the way home we stopped at Davida on Crocus Bay for some apps and then made dinner at the villa. The menu was quite possibly the best home cooked meal of recent memory. 14 Crayfish and 1 Slippery Tail Lobster grilled with mango butter, coconut risotto, grilled roasted red peppers, grilled pineapple and cinnamon salted plantains. Needless to say we all encountered a food coma and didn’t go out afterwards.

For day six we decided to go to Meads Bay and hang out at Straw Hat, a nice, quaint, little beach bar. I decided to dig a hole for my nephew Beckett to play in but after a while I decided I had a better idea. Below is a picture of my handy work. We made dinner reservations at Dolce Vita in Sandy Ground. This is another exceptional dining experience that I highly recommend. I got fresh Red Snapper de-boned table side and every other dish at the table was simply amazing. We finished out the night at Pump House for some live Reggae and drinks.

On the morning of day seven we woke up to the first sign of bad weather. A break in the rain allowed us to head out and explore the far East end of the island. Once you reach a certain point the developed part of the island ends and you enter an area of total rugged dirt roads. After driving for at least twenty minutes we reach Nat’s Place, which we were told to look for. It’s the only place you will find out there and on this day it was closed. From there we continued heading East to see just how far we could go. By now the rain had started again and turned into a downpour. Luckily we were driving a Jeep Wrangler Unlimited with 27” off-road tires or we would have been stuck. We tried to wait out the storm so we could get out of the Jeep and hike up to the tower which was indeed the furtherest point, but it never did let up so we headed back to the villa where it rained the remainder of the day and night.

The last day arrived, but that didn’t mean the fun was over. After packing we headed back to St. Maarten the same way we came, but instead of just sitting in the airport like most other people there is a better option. If you don’t check any bags you can just get a taxi from the dock directly to the end of the runway where you will find Sunset Beach Bar and Driftwood Boat Bar. Wear your bathing suit, get a few final drinks, watch your plan land and bring a change of clothes to put on before leaving. Then you can catch a taxi back to the airport. If you do need to check bags however, you can still hit the bar/beach, just come over earlier. The airport opens at 10am so you could check any luggage and then use the rest of the day to do whatever you want.

I hope you find this post useful if you are going to Anguilla. It’s not a matter of it I would come back, but when I will be back.

Travel Tips:

• Funtime Charters located directly across from the airport will take you from St. Maarten to Anguilla and does customs for you. The ride takes about 40 minutes total and costs $65 one way/$130 round trip.
• A taxi to most resorts or villas will cost you about $50 one-way.
• There is a mandatory $20 departure tax when leaving Anguilla so have cash.
• Estimate about $200 additional to cover your transportation to and from, departure tax and tips for drivers and porters.
• Most beaches that have restaurants will not charge you for chairs or umbrellas if you dine with them.
• To drive you are supposed to get a temporary drivers license which costs $20.
• Their currency is the EC and is fixed at $1 = $2.68 EC so just say dollars and they will convert it for you.