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Anguilla Itineraries...
Driving To All Corners of the Island


Jump down to the itineraries.

Before we moved to Anguilla in 2008, my Dad and I would spend hours before we hopped on that plane south. We'd pour over our old Anguilla map, creating itineraries by marking our must-see's for each day on the map. From east to west, we'd plan out our exploratory driving tours (leaving a few days for just lounging by the pool or sea, of course!).

Our original map
anguilla map

It seems that we aren't the only ones who plan our days like this. Over the years, many Anguilla-Beaches.com readers have emailed me, asking for our best suggested itineraries for a morning, an afternoon, or for the entire day.

Here they are!

Using The Itineraries

Before driving these mapped-out routes, here are a few tricks to know...

Map-Based Anguilla Itinerary Tips

  • Each itinerary breaks into "two levels." "Must Sees" are the essentials and "Get Adventurous" are for travelers who want to explore more deeply (often over rougher roads).
  • If one of the "levels" doesn't appeal to you, just "untick it" from the white panel. The corresponding set of pins will disappear from the map.
  • Follow the pins to reach favorite beaches, scenic views, hikes and restaurants.
  • For more information about points of interest on your route, click the pins on the map or the points listed in the white panel.
  • Use the + and - to zoom in and out.
  • Grab and drag the map to see more.
  • Want to change the style of the map to satellite or terrain view? Scroll to the very bottom of the white panel to "Base Map" and and click on the the drop down menu icon (located far right).
  • Note: While these maps work well on tablets, they are still "buggy" on phones. Google is aware of the issue and they're working on fixing it. You also need internet connection to view these maps (whether you're browsing on a desktop computer, laptop, tablet or mobile device). An offline version that lets you track your progress on a smartphone as you move through each itinerary is not yet available from Google. I will keep you updated. :-)


Itinerary #1: The East End

First up is a tour of the often unexplored East End. Less developed than the West End, this part of Anguilla is rich in untouched natural beauty and wild coastlines, and is home to a historic, charming, working fishing village.

Charming Island Harbour
island harbour itinerary anguilla

Part 1: The Must-See's

This route starts at Le Bon Pain, a local bakery where Bernard, the owner, makes the best croissants on the island. Start your morning with breakfast here.

Proceed to "The Point" of Shoal Bay East (via an hidden, unknown path). A special photo opp, spend some time walking the beach. Go for a swim and and then, back in the car!

From there, it's over to Island Harbour, the quintessential Anguilla fishing village.

Looking up at Windward Point
windward point drive

End up at Nat's (Palm Grove), the place for a fresh and tasty crayfish lunch!

Part 2: For The Adventurous

For the adventurous, the following drive-and-hike tour takes you over more rugged terrain. It culminates with a mild-to-moderate exertion "trek" to the peak of Windward Point.

No sherpas needed, but watch the cacti! This is not a flip-flop walk (sneakers highly recommended). Your special reward is magnificent 360° view from the top of Windward Point.

Start with a drive over the rocky Harbour Ridge Road, affording magnificent views from Island Harbour to Scrub Island.

Retrace the ridge road partly back, taking a left at the first opportunity to picture-perfect Captain's Bay. On most days, this a "look-but-don't-swim" beach (currents and rip tide).

Now for a drive to the easternmost point reachable by car. Follow the "Route To Windward Point" beyond the eastern end of the beach, until it becomes impassable.

Sneakers on, and armed with water, wind your way up to the very top of Windward Point. Glorious views in all directions await.

On your way down, either head back to the car or walk around the base this Anguillian mini-mountain to reach THE most eastern point of mainland Anguilla.

Once you're back in the car, head out to Nat's for those well-deserved crayfish!

Scrub Island seen from the top of Windward Point
scrub island anguilla

Click here for more on Anguilla's East End.

Happy exploring!

Click here for the map-based itinerary, or click the image below....

anguilla map itineraries

More Itineraries

The West End
This itinerary highlights all of the must-see's, such as Barnes Bay and Shoal Bay West, and the tucked away stuff, like West End Bay, Sherricks and one of the most charming Caribbean cottages. With a few stops for lunch and rum punches along the way, this itinerary covers all of the West End, from Maunday's Bay to Anguillita Island.

The Middle of the North Shore
The center of Anguilla's northern coastline is dotted with picture-perfect coves, magical caves and many local spots to grab a tasty bite to eat. This in depth itinerary doesn't miss a thing and includes terrific vantage points, and points out historic sites, too.

Romantic Anguilla
From the privacy, to the tranquility, to the fine-dining and romantic restaurants, Anguilla is for lovers. This itinerary takes you through Anguilla's most romantic restaurants and to, arguably what is the sweetest cove for love birds.

Please let me know how you like these itineraries. Would you like more? What routes would you like to see? Special activities (ex., birdwatching)? How can I make this more useful for you?

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