Week in Anguilla
Who: Couples, Honeymoons and Families

7 Days

From $2,680pp

A Week in Anguilla

Ollie is here to help give you the inside track.

Anguilla still flies relatively under the radar but this is a Caribbean classic thanks to exceptional places to stay, beautiful beaches and arguably the best food in the West Indies. Combine all three and more in this week-long itinerary.

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When To Travel













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All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

Day 1: Arrive in the Caribbean

You will fly into Sint Maarten (Saint Martin), the Dutch/French island that's Anguilla's Leeward Islands neighbour, and on arrival you will be met and transferred to the ferry port for the 20-minute crossing to Anguilla.

You will be met off the ferry and transferred to your hotel, where you can enjoy a well-earned dinner. As this is a famously culinary destination, our detailed Dossier of the best places to eat and drink will come in handy tonight and throughout your stay.

Day 2: Anguilla

Time to get your bearings, which shouldn't take long as the island is only 15 miles long by three miles wide - hence the name 'Anguilla' (or eel in Spanish). Not a very flattering name, particularly given this over-sized sandbank is home to 33 of the most beautiful beaches in the Caribbean.

Again, our detailed Dossier recommends the finest of these, including the two miles of picture perfect fine white sand and hip beach bars that is Shoal Bay; or the gentle curve and pelicans of Meads Bay. Then there's the wilder, woollier Junk's Hole on the (even) less busy east coast.

Day 3: All Aboard

By now you'll have got a better understanding of this beautiful corner of the Caribbean, but today we've arranged for you to see Anguilla from the water on a sailing and snorkelling trip aboard a wonderful old school sloop.

After a swim (and possible turtle sightings) in the deliciously warm waters of Little Bay, enjoy an equally delicious lobster roll and rum punch lunch before sailing back to Sandy Ground.

Days 4–5: R&R

You should be suitably relaxed by now, and with our detailed Dossier on hand to recommend the finest of the many fine places to eat on the island, you will hopefully have discovered why Anguilla is rated as the culinary capital of the Caribbean.

Day 6: Paddle Board

All that wining and dining might not be doing the waistline much good, so it's time to work off some of the calories again on a morning guided paddle boarding tour.

Your guide will show you one of the island's secret lagoons and beaches that can't be reached by car, and you can really earn that beach shack lobster lunch. Again.

Day 7: Homeward Bound

Depending on the time of your flight today, you should be able to enjoy one last lazy morning and long lunch before you are transferred back to the ferry to Sint Maarten in time to check in for your flight home.

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

A Rough Idea of Price

While all of our holidays are completely tailor-made and prices will vary based on things like time of year and level of accommodation, we want to give you as good an idea of how much this itinerary will cost. All of the costs on our sample itineraries exclude international flights, however, ask us if you would like us to arrange your flights at our preferred rates. The below prices are based on two people sharing.

This Itinerary

If you would like to book the exact itinerary mentioned above, during mid-season and staying in our preferred room category at our preferred hotels. Ask us if you would also like us to arrange your international flights.



Bare Necessities

If you would like to pare back the above itinerary by travelling at non-peak times, staying in a standard room and removing some or all of the guided activities.



Bells & Whistles

If you are looking for something extra special and would like to stay in top room categories at some of the most luxurious hotels we work with, and add more activities and guiding.



Ollie is our expert for this itinerary and, as a seasoned traveller, has the inside track on the most memorable adventures.

Call us on 1-866-205-8369