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Travel to The Caribbean

A world that is as vibrant under the water’s surface as it is above it. Welcome to the Caribbean. This collection of more than 7,000 islands (10% of which are inhabited) is believed by many to be paradise. (Especially if you’re a water lover and want to spend hours wasting away the day on beautiful beaches!).  But traveling to the Caribbean one time, doesn’t mean you can check it off your bucket list. Each island is distinct, whether that’s noted through its food, activities, luxury resorts or the special ‘finds’ in the local markets.  Beach-goers, scuba divers, snorkelers, sailors, fishermen, hikers and golfers alike will all have one thing in common after visiting the Caribbean – they’ll each be anticipating their return.

Not all trips to the Caribbean are created equal


Our travel designers have scouted the best hotels, tours and guides to help you avoid common pitfalls while maximizing your time in the Caribbean.  Which experience would you prefer?

A crowd of tourists...
or a quiet moment?
An ugly surprise...
or comfort in a foreign land?
A tourist trap...
or authentic cultural interactions?

Don't wait. The best options disappear quickly.


Travel is an investment in yourself, and it’s not worth the gamble to compromise the experience you’ve been dreaming about. Every day you wait, means another traveler is taking an option off the table.   


For example: 

  • The most authentic lodging is offered by small boutique properties with local character.  However, the charm of a small property means the limited number of rooms quickly sell out.    

  • Tour guides will make or break your trip.  When you have an exceptional guide, it can be life-changing.  When you have a mediocre guide, it’s a missed opportunity.  The best guides are booked well in advance.  Travelers who wait will only find left over talent available closer to the travel date.

When To Book?

Jan-Mar, Holidays: 8-12 months prior

Apr-Dec. 6 months prior

When To Go?

Peak Season

Jan, Feb, Mar, Holidays

Off-Peak Season:


Average Cost of a Trip to the Caribbean

Starting at Pricing:


Good:  $250 per day, per person*
Better:  $500 per day, per person*
Best:  $800 per day, per person*


*Ballpark pricing is based on an annual analysis of industry costs including transfers, tours, meal allowances and lodging








british virgin islands

cayman islands



dominican republic




puerto rico

st. barths

st. kitts & nevis

st. lucia

st. martin

st. vincent & grenadines

turks & caicos

u.s. virgin islands

Feeling Overwhelmed?

We offer worry free, expert travel advice. While many travel websites rely on computer algorithms and artificial intelligence, our expertise comes from our first-hand knowledge.  

There is nothing "artificial" about our intelligence.  We listen. Get to know you.  And then design an amazing trip that's all your own.  

Once you experience working with our travel designers, you will wonder why you wasted all that time traveling another way.

need a second opinion?

Already have an itinerary? Our experts are happy to offer an honest assessment.

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