Planning a trip to Anguilla? This is the guide we wish we’d had.
Anguilla has a reputation for being one of the most expensive islands in the Caribbean — and while that’s not entirely wrong, it’s also more accessible than most people think. In this travel guide, we’re covering everything you need to know to plan your own Anguilla trip, whether you’re staying for a few days or making it the centerpiece of a longer Caribbean island hop.
Here’s what we cover:
🌍 Anguilla Basics — what to know before you go
📅 When to Visit — dry season, shoulder season, and what to avoid
✈️ Getting There — flights into Anguilla and the ferry from Sint Maarten
⛴️ Ferry Guide — Calypso Charters vs. the public ferry, what to expect
🛂 Entry & Exit Requirements — passports, visas, and departure tax
🚗 Getting Around — rental cars, taxis, and driving on the left
🪪 Anguilla Driver’s License — yes, you need one (here’s how it works)
🏨 Where to Stay — luxury resorts, boutique hotels, and midrange options
💰 Budget & Costs — realistic daily budgets for every type of traveler
💵 Currency & Tipping — USD, Eastern Caribbean dollars, and service fees
🏖️ Beach Hopping — Shoal Bay East, Meads Bay, Rendezvous Bay & more
🍹 Best Beach Bars — Gwen’s Reggae Grill, Blanchard’s Beach Shack & more
🍽️ Where to Eat — from local breakfast spots to iconic dinners out
🏝️ More Things to Do — private island day trips, Scilly Cay & more
🔒 Safety — US State Department rating and tips
🧳 What to Pack — beach vacation essentials and what to leave at home
We traveled to Anguilla as the final stop on a five-night island hopping trip across Sint Maarten, St. Barth, and Anguilla — and it left the biggest impression of the three. This guide is built from real, firsthand experience, so you can plan your trip with confidence.
📍 Anguilla, British West Indies
🔗 Resources
Book Calypso Charters → https://fave.co/4w10mbR
Book Andy’s Auto → https://fave.co/4fEZzXB
Book Arawak Beach Club → https://fave.co/3Rz169V
📖 Chapters
00:00 Anguilla Travel Guide
00:34 Anguilla Facts to Know
01:18 When to Visit Anguilla
02:16 Day Trip, Split Stay, or Full Vacation?
03:29 How to Get to Anguilla by Plane
05:03 How to Get to Anguilla by Ferry
06:25 Arrival, Entry Requirements & Departure Tax
07:55 Getting Around Anguilla & Top Areas
09:01 Renting a Car & Driving in Anguilla
10:49 Must Know: Anguilla Drivers License
11:31 Where to Stay – Luxury vs Budget
14:08 Anguilla on a Budget & Costs
15:54 Currency & Tipping in Anguilla
17:05 The BEST Anguilla Beaches
18:33 Must Visit Beach Bars in Anguilla
20:20 Dining & Restaurants
22:44 More Things to Do in Anguilla
24:47 Anguilla Safety
25:22 What to Pack for Anguilla
📺 Watch More
https://youtu.be/othZjCRowOs
https://youtu.be/O7n9lw1YwV0
https://youtu.be/ZCv7PZVtauA
https://youtu.be/0A1A-3Gue7Q
https://youtu.be/U5JZGcXZbZk
Full Anguilla Playlist: https://www.youtube.com/playlist?list=PLs8O7YGRTMQNVSXjCvtycOieE70T5Qn1n
Full St Martin/St Barth/Anguilla Playlist: https://www.youtube.com/playlist?list=PLCwmaBa-xOH4
📚 Read More
All Caribbean Blog Posts: https://tinyurl.com/ucaft65r
All Resorts Guides, Reviews, and Room Tour Blog Posts: https://tinyurl.com/2fde9ke6
📸 Gear
Full gear list: https://stellainparadise.com/whats-in-our-camera-bag/
Amazon Storefront: https://a.co/d/0785iAUG
🎧 Music
Epidemic Sound – Get one month free!
https://share.epidemicsound.com/fqneui
📲 Follow Us
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