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Interesting Itineraries: Anguilla & St. Barth’s


Looking for a little inspiration? Check out our Sample Itineraries page, where you’ll find trip ideas from across the globe. For the next couple of weeks, I’ll be highlighting different destinations, mostly in the context of a honeymoon or romantic getaways, to give you an in-depth look at the kind of experience you can expect out of that part of the world.

Today, I’m featuring two of my favorite Caribbean island: Anguilla & St. Barth’s. I visited both of these destinations earlier this year and was recently asked to put together a high-fashion honeymoon. Naturally, these two see-and-be-seen destinations were the first ones that came to mind. The perfect 8-day itinerary might look something like this:

Day 1: Fly into St. Martin, catch the 20 minute ferry ride to Anguilla

Day 2: Enjoy your first day exploring the resort: snorkel, paddle board, and take a stroll down the two unique beaches that flank the property

Day 3: Take in the scenery and culture on a tour of the island of Anguilla

Day 4: Get lost on a deserted island – the staff will prepare you a picnic lunch and take you out to an island all to yourself.

Day 5: Fly from Anguilla to St. Barth’s – arrive in time to catch the sunset and cocktails at Hotel Christopher

Day 6: Relax on the beaches of Eden Rock before an evening of shopping in downtown Gustavia

Day 7: Pack a picnic basket and explore one of the island’s twenty beaches

Day 8: Wheels up to St. Martin, where you’ll catch your flight back home


Lindsey Epperly

My name is Lindsey Epperly and I’m a travel consultant and owner of Epperly Travel, a national affiliate of Century Travel. I’m most passionate about building lifelong relationships with my clients and suppliers, discovering the globe in a way that makes me a better agent, and celebrating with my team when we reach a new milestone. One of our core values at Epperly Travel is to create fun and celebrate constantly – and I’m fortunate to be in a career that allows me to do just that. I’m proud to announce my recent achievements: landing a spot on Wendy Perrin’s WOW List as their Caribbean expert, being nominated for Virtuoso’s Rising Star Award and receiving a place on Jezebel Magazine’s Trailblazing Ten list.

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