I have a little rule when planning a trip: the number of potential shoe-wearing opportunities must be directly proportional to how excited I get. A city break might offer a solid three-shoe rotation (boots for walking, heels for dinner, trainers for the journey). But a multi-country, sun-drenched, glamorous adventure? We’re talking next-level shoe strategy, and my wanderlust is officially off the charts.
For ages, I’ve dreamt of a trip that combines pure relaxation with a whirlwind of new cultures—waking up to a new horizon without having to pack and unpack my suitcase every day. It felt like a fantasy, until I stumbled upon the perfect solution: a Caribbean cruise. And not just any cruise. A voyage so glamorous it would make my most fabulous heels feel right at home.
(Disclaimer: My travel daydreams are currently being fueled by the amazing team at Trip2escape. As you know from my Bruges trip, their parent brand VAQQY travels are wizards at trip planning, and they’ve done it again!)
A Floating Palace on the Sea
The ship for this dream trip is the MSC Divina, and honestly, she’s a destination in her own right. Inspired by the timeless elegance of Sophia Loren, the ship is dripping with the kind of glamour you read about in novels. I’m already picturing it: descending one of the glittering Swarovski crystal staircases, feeling like a golden-age movie star. My red carpet heels would finally have their moment!
From a real stone piazza to a breathtaking Infinity Pool that melts into the sea, every detail is designed for decadent relaxation. It’s the kind of place where you can spend your days at sea simply enjoying the beauty of your surroundings, with a different spot for every pair of poolside sandals in your luggage.
A Wardrobe for a World of Wonders
The real magic of this trip is the itinerary. It’s a perfectly curated journey through the heart of the Caribbean’s most vibrant destinations. My packing list is already writing itself:
- Ocho Rios, Jamaica: The home of lush rainforests and cascading waterfalls. This stop calls for practical but stylish waterproof espadrilles, perfect for exploring Dunn’s River Falls before heading to a beachside bar for a cocktail.
- Cartagena, Colombia: I’ve swooned over photos of Cartagena’s colourful colonial streets. Wandering through this living piece of history demands comfortable-yet-chic leather sandals that can handle the cobblestones while still looking perfect for that impromptu photo op.
- Puerto Limon, Costa Rica: The call of the wild! This is the place to break out the sturdy walking shoes for an eco-adventure, exploring the incredible biodiversity of the rainforest. Pura Vida!
- Oranjestad, Aruba & Isla de Roatan, Honduras: White sand, turquoise water… these are the days for minimalist flip-flops and bare feet. It’s all about soaking up the sun and finding the perfect palm tree to relax under.
Planning Your Own Glamorous Getaway
I know that planning a multi-stop trip can feel overwhelming, but this is where I let you in on the secret. The experts at Trip2escape have bundled this entire dream trip into one seamless package. They handle all the details so you can focus on the important things (like finalizing your shoe selection!).
The offer is incredible value and includes practically everything:
- Return Flights from the UK
- A 1-night pre-cruise stay in a 4* Miami hotel (perfect for acclimatizing!)
- The 11-night, full-board cruise on the stunning MSC Divina
- All gratuities, taxes, and fees are taken care of.
They have several dates available, with prices starting from £1399 per person* for January 2026, which is fantastic for a trip of this scale.
If a winter escape filled with glamour, sunshine, and a world of new experiences sounds like your kind of fairytale, I can’t recommend this enough.
You can find all the details for this incredible Caribbean cruise package right here.
For any specific questions or to get your adventure on the calendar, you can reach the friendly team by calling 0207 167 9788 or dropping an email to info@trip2escape.com.
So, what do you think? Which of these sunny destinations would you be most excited to step out in? Let me know in the comments below
