Caribbean group travel

Twenty-two people. One set of dates. Nobody mad at you.

I plan Caribbean and cruise travel for families and groups going somewhere together on purpose. Reunions, milestone birthdays, anniversaries, destination weddings. You pick the reason and the people. Everything after that is mine.

Start your group See what I handle

The part nobody warns you about

Someone in the family always ends up organizing it.

It is usually whoever is best at it, which is a poor reward for being good at things.

So you are collecting passport numbers out of a group chat. Your aunt wants a balcony and your brother wants the cheapest cabin on the ship. Four people have not paid. The deposit is due Friday and the airline just moved one flight.

Then you finally get there and spend the trip you planned answering questions about the trip you planned.

That whole job is the thing I take off you.

A real group, on paper

The complexity is the product.

A family trip is a set of moving parts with deadlines attached. This is what one looks like before I touch it.

Thirty years of my working life has been running programs with hard dates and too many stakeholders. Same work. Better weather.

Group ledger St. Lucia / 7 nights
24travelers, ages 4 to 81
7households, each paying separately
4departure cities, one arrival window
11dietary, mobility, and medical notes
3payment plans running on different dates
1set of dates everybody had to agree on
1person holding all of it

That last line is the problem.
Right now it is you. It does not have to be.

What I handle

The unglamorous half. All of it.

  • 01Room blocks and cabin holdsSpace secured early, at a group rate, before your dates sell out.
  • 02Deposit and payment schedulesReminders go to each household from me. You never chase your cousin for money.
  • 03Rooming lists and manifestsNames, passports, birthdates, bedding. Collected once, used everywhere.
  • 04Split billing across householdsDifferent budgets in the same group without anyone comparing receipts.
  • 05Flights from four citiesArrivals grouped tightly enough to share transfers.
  • 06Access and dietary needsCarried to every hotel, ship, restaurant, and tour operator. Once.
  • 07Group dining, excursions, transfersHeld at the size you actually are, on the days that suit the group.
  • 08One person on call during the tripWhen a flight cancels at eleven at night, they call me.

Tell me the occasion and roughly how many.

Start your group
Twelve people, different ages, different budgets, different ideas about a vacation. She made everyone happy and I did not have to manage a single thing.

Dana K.Caribbean group cruise

Trip types

Reasons families end up on a plane together.

Caribbean cruise ship at sea
Best first group

Group cruises

Everyone eats the same food and wakes up at the same island regardless of what they paid. Budget stops being a conversation.

Caribbean beach and shoreline
Most requested

Reunions and milestones

Sixtieth birthdays, fortieth anniversaries, the first time the whole family has been in one place since the funeral.

Caribbean resort view
High stakes

Destination weddings

Your guests get planned for properly. Blocks, budgets, transfers, and arrival times handled while you deal with the wedding.

Start on a ship.

Most first groups should be a cruise. Space is held on a small deposit, unsold cabins release back without penalty, and the price range on one ship is wide enough that a tight budget and a generous one can travel together without either party noticing.

Resorts and villas work beautifully too. They carry contracts with real teeth, which is worth taking on once we know how your particular group fills.

Trish, Caribbean travel advisor

Who is planning this

Thirty years of things that could not slip.

Army Signal Corps, then three decades running large technology programs with hard dates and more stakeholders than anyone wanted. Budgets, dependencies, contingency plans, and the person everyone calls when something moves.

Twenty-four travelers across seven households is that same work. I have never met a rooming list that scared me.

On the Caribbean specifically, I will tell you when an island is wrong for what you want, which one to pick instead, and which resort is living on its stock photography. You get the real read before you commit the family to it.

Independent advisor. Hosted by WorldVia Travel Group. IATA accredited.

Start your group

Tell me about the people.

Four questions is enough to start. I come back within one business day with real questions and a sense of what is possible on your dates.

  1. You send this form. Takes about a minute.
  2. I reply within one business day with what your dates and party size actually open up.
  3. We talk for thirty minutes if it looks like a fit. Free, and there is nothing to sign.

If you do not know your numbers yet, say so. Most people do not this early.

Reply within one business day. Your email stays with me.

I told Trish our budget, our travel style, and that we hated touristy nonsense. She came back with an itinerary designed specifically for us. Best trip of our lives. Michelle R. / Belize

Group travel intel, once a month.

Sailing dates worth holding, resorts that handle large families well, and what to book how far out.

Start your group