best. vacation. ever.

Customized Caribbean Trip Planning

Sound familiar?

You want an unforgettable Caribbean vacation, and an all-inclusive resort is NOT the vision you have in mind. This time it has to be a different kind of tropical travel experience.

You've envisioned the whole thing: warm days in the Caribbean somewhere off the beaten path, outside of the been-there-done-that spots. A place where you and your travel guests can leave the world behind.

You're looking for a place that sidesteps the crowds and cookie-cutter resorts and you know that what you want is out there. But you're no closer with your travel plans than you were two months ago!  

You do a ton of work looking at resort websites and reading everything you can find on TripAdvisor, but you’re simply not seeing the results and frankly, you just don't have the time to put all the pieces together.

You're not convinced a 'traditional' travel agent can you help you. But you wish someone would just guide you. Someone with the inside track who knows (no, really knows) the places you're dreaming of.

the struggle is real

what if we could make Planning your trip super-easy (and fun)?

How awesome would it feel to finally ditch the trip planning struggle? To have the inside scoop on everything you need to know about the most extraordinary experiences in the Caribbean.

Instead of hours and hours of research, confusing online information, and sheer frustration, you can relax and finally enjoy the details of creating the dream vacation you want and one that you and your travel guests will talk about years from now.

Sounds almost too good to be true, Right? It isn't.


Custom caribbean trip planning

Created for sophisticated, culturally curious travelers who crave a customized and personalized travel experience in the Caribbean...without the stress.

Lodgings You'll Love

We vet, recommend, and book accommodations that you'll love and are available for your travel dates whether you prefer a luxe hotel, an inn full of character or the seclusion of a private property or a private island.

Unforgettable experiences

Whether you're a "see-it-all" type of traveler, or you prefer a more leisurely pace, we curate and book tailor-made activities, private tours, day trips and authentic experiences (that the average traveler knows nothing about!).

Exceptional Food

From delicious local, island specialties to world-class gourmet dining, the Caribbean offers a mélange of cuisine to satisfy your every whim. We advise on where to go (and secure reservations, when needed) with your preferences and priorities in mind.

Work with a seasoned Caribbean destination expert to design a trip that takes you and the traveling companions you choose--whether it's one, two, or ten--to extraordinary places throughout the Caribbean.

Seamless Logistics

Unsure of how to get from Point A to Point B? We arrange in-destination transportation (private transfers, car rentals, helicopters, boats, private drivers). Anything and everything can be arranged.

A Tailor-Made itinerary

Everyone's idea of a dream trip is different and we're happy to design yours. Your trip is designed to fit into your schedule and will be tailored exactly to who you are and what you want to do. Nothing we do is off-the-shelf.

Peace of Mind

Sometimes the most rewarding trips are the ones where you can just let go, knowing you're in good hands. You'll have unlimited and honest travel advice on everything from climate to tipping. We have your back and are here to help you every step of the way.

without a doubt, this will be...

The trip you'll talk about (excitedly) for years.

You'll explore and enjoy specially-arranged visits with friendly and knowledgeable locals, and throughout your trip, you'll stay in top accommodations. Simply select your destination and decide when you'd like to go. We'll take care of the rest.

We specialize in these Caribbean DestinationS:

Anguilla | Grenada | Nevis | Saint Lucia


How much does trip planning cost?

We Advise. you book. 

Essential Trip Planning

Prefer to DIY your Caribbean adventure? Get expert guidance and trusted recommendations from a seasoned advisor to craft your perfect Caribbean getaway with ease.


  •  A 30-minute 1-on-1 trip planning session. 
  • A personalized trip summary with up to 2 - 3 Caribbean hotel/resort recommendations based on your style and budget
  • Activity suggestions for your destination
  • Your accommodation confirmed and booked on your behalf (optional).
Planning Fee: $150

We Advise. We Plan. We book. 

Signature Trip Planning

Made for a customized trip in a single Caribbean destination with booked excursions and experiences tailored to your interests.

Here's what you can expect:

  • A comprehensive all-about-your trip planning session to understand what you want for your  Caribbean trip. 
  • A custom-designed overall itinerary  to match your interests and spending plan
  • Your accommodation and logistics (including round-trip airport transfers) confirmed and booked on your behalf.
  • Tours and excursions secured, booked and confirmed on your behalf.
  • Must-know travel advice including entry requirements, visa and passport info 
Planning Fee: $500

We Advise. We Plan. We book (& so much more)

Ultimate Trip Planning

Ideal for a curated freedom-filled, island-hopping escape, perhaps for a slightly larger group, packed with lots of island adventures and options, including:

  • Everything in the Signature Trip Planning service
  • A custom multi-leg itinerary for your group
  • Concierge-level planning, inclusive of dining reservations, spa bookings, etc.
  • VIP perks, amenities and exclusive access (where available)
  • In-destination trip support
  • Access to your personalized trip app
Planning Fee: starts at $850

Note: Custom Trip planning services do not include international air travel to OR from the Caribbean

Which type of planning is best for you?

side-by-side comparison

Compare TRIP Planning features


Number of travelers


up to 8

up to 12

1-on-1 consultation with a Caribbean destination expert 

Recommendations on accommodation, food & dining, activity & excursions and local transportation

Custom travel itinerary design

Hotel-only summary

Your tailor-made, curated itinerary delivered as a mobile app & PDF

PDF only


Your hotel, inn or villa confirmed & booked

Confirmed reservations & arrangements of all of your local transportation needs during your stay

Food/dining arrangements and restaurant bookings

Booking of curated tailored activities, excursions & experiences 

Up to two (2)

Handling of payments due for each trip component*

On-trip support

VIP access & experiences

Island-hopping & multiple daily itineraries

Planning & coordination of your special event or celebration

custom rate

Planning Fee




Why us?

The Caribbean is vast! And your travel options and destinations are endless. The challenge, however, is narrowing down your choices from a long, long list of possibilities. Where should you go? Which type of accommodation is the right one for you and your guests? (Because, what you see isn't necessarily what you'll get!).

Instead of playing the guessing game, talk to someone who can give you the answers you're looking for. 

No hassle. No fuss. Just need-to-know details and information so that you can make the right decision. Working with us is a completely different (and enjoyable) experience. Please get in touch, today.

the Experience

Here's what happens when you Contact us


You tell us what type of trip you're dreaming of (the more details the better!) and then schedule a 30-min phone call.


Chat with our travel planner to hear how we'll plan your trip (and see if we're a good fit).


If you decide to hire us, we start building your customized Caribbean itinerary and ultimately plan the trip you want.

sounds good, but...

Is custom trip Planning for me?

Custom Trip planning is perfect for you if:
  • You want to skip the crowds and the packaged all-inclusive options for your next trip (i.e. you tend to zig when everyone else zags).
  • You are looking for cultural immersion and/or authentic experiences that make you feel like you are part of the local landscape, not just someone visiting to take in the most popular tourist sights.
  • You prefer a smaller, luxury hotel or private property with a distinctive style and peaceful atmosphere for your Caribbean getaway.
  • You want and expect the best but are strapped for time and need someone to put all the pieces together for your Caribbean trip.
Custom Trip planning is not for you if:
  • You're planning a last-minute getaway. (Designing your custom trip takes time and requires several weeks to create an itinerary that reflects your interests and pace.)
  • You're searching for discount travel deals or you are budgeting significantly less than $500 / day per person for accommodation and activities/excursions during your trip.
  • You're arranging a trip for a large group or you're interested in a packaged or mass-market cruise ship tour.
  • You're uncomfortable providing us with credit card info for your bookings.

Ready to plan your trip to the caribbean?

Let's talk. Schedule your free appointment to chat with us, today.