If you’re heading to the Caribbean for a summer escape, a winter-sun break, a family holiday or a honeymoon, one thing’s certain: your trip will start at the airport. After a long flight, warm weather and that familiar wave of tropical air, the only thing you’ll want is to get to your resort, villa or cruise ship smoothly. That’s where airport transfers make a huge difference.
At My Holiday Taxi, we help holiday travellers book safe, reliable and stress-free airport pickups across popular sunshine destinations, starting in the Caribbean and expanding globally — destination by destination. Whether you’re travelling to Jamaica, Barbados, the Dominican Republic or any of the region’s stunning islands, here’s how to choose the right airport transfer for your holiday.
1. Understand How Caribbean Destinations Work
Caribbean holidays are incredibly destination-based. Most visitors stay at all-inclusive resorts, beachfront hotels, villas and Airbnbs, family guesthouses, honeymoon suites or join cruises.
That means airport transfers vary depending on:
- island layout
- airport location
- tourism infrastructure
- road networks
- resort zones
- peak travel seasons
Examples:
- Jamaica → Montego Bay, Negril, Ocho Rios
- Dominican Republic → Punta Cana
- Barbados → strong villa + resort coastline
- St. Lucia → hilly, longer transfers from airport
Knowing this helps you pick a transfer that matches your holiday style.
2. Book Before You Fly
Caribbean travellers almost always benefit from pre-booking transfers — especially during:
- summer holidays
- winter sun peak (Dec–March)
- Easter & spring break
- cruise season
On-arrival taxi ranks can be:
- unpredictable
- cash-based
- priced by negotiation
- limited at peak times
- stressful with kids/luggage
Pre-booking solves this instantly — especially for families, couples, groups, villa guests and returning residents.
3. Choose the Right Vehicle for Your Group
Different groups need different transfer styles:
- Families: space, car seats, calm transitions
- Couples: privacy, comfort, honeymoon vibes
- Groups: larger vehicles + extra luggage
- Cruise travellers: port logistics
- Villa guests: remote or private locations-
At My Holiday Taxi, we offer options for all of the above because holiday travellers are not one-size-fits-all.
4. Check What’s Included
A good Caribbean airport transfer should include:
- full route pricing
- luggage
- air-conditioning
- reasonable driver waiting time
- Avoid services that add:
- baggage fees
- airport surcharges
- after-hours charges
- surprise cash extras
Transparent pricing = less holiday stress.
5. Make Sure Villas, Resorts & Ports Are Supported
Hotels are easy. Villas, Airbnbs and cruise ports aren’t always supported by generic transfer sites. Look for services that support:
- villa districts
- private addresses
- ports & marinas
- boutique hotels
- off-resort accommodations
Caribbean villa holidays are growing fast — especially in Barbados, Jamaica, St. Lucia and Turks & Caicos — and they require flexibility.
6. Safety & Licensing Matter
Licensed drivers and insured vehicles are essential in Caribbean tourism. look for:
- background-checked drivers
- proper tourism licences
- insured vehicles
- air-conditioning
- safe driving standards
Every My Holiday Taxi partner meets these requirements, and we vet new destinations before launching.
7. Don’t Forget Cruise Transfers
The Caribbean is one of the world’s most iconic cruise regions. If you’re cruising from:
- Montego Bay
- Ocho Rios
- Miami
- Fort Lauderdale
- San Juan
- Barbados
…airport-to-port transfers save hours of hassle.
Cruise travellers always pre-book — timing matters.
8. When to Book Transfers for Caribbean Holidays
As a guide:
- Peak season: 3–8 weeks before flying
- Shoulder season: 2–4 weeks
- Last-minute: book before takeoff if possible
Families usually book first → couples next → groups last. Holiday travel rewards early planning.
At My Holiday Taxi, we make airport transfers for Caribbean holidays easier, safer and more stress-free — so you can start enjoying your trip the moment you land.