Caribbean travel for the whole family, planned by a local.
No two people in a family want the same thing from a trip. The kids want the pool, the teenagers want wifi, grandma wants a proper sit-down dinner, and you just want five quiet minutes with a drink in your hand. I plan around all of it: the right property, the right mix of activities, and a little carved-out time for the parents too, because you deserve a trip as much as anyone else in the group. Let's just say I'm basically part family therapist, part travel planner at this point.
I'll bring the rum. You bring the whole crew. Let's talk!
Different ages, different needs...
one trip that works.
The Rum & Roots Family Menu
The Full Pour
Every detail of your trip handled, from first idea to final boarding pass. Accommodation, transfers, dining, activities, experiences: all of it researched, booked, and managed on your behalf.
Served Neat
The core foundations of your trip, locked in: accommodation, transportation, and the experiences worth booking in advance. Dining, free days, and everything in between? Yours to fill in on your own terms.
Pick Your Proof
You've chosen the destination but don't want to spend hours going down social media or AI rabbit holes to find the right place to stay. Let me handle it. Three hand-picked hotels or villas, a genuine insider take on each, and booking handled once you've chosen.
On The House
You already know which hotel you want. Book through me at the same rate as going direct through the hotel, with the added benefit of perks like complimentary upgrades, early check-in, and welcome amenities at select properties. No planning fee.
The Blend
Not every family fits neatly into one package. If that's you, let's build something custom around exactly what you're after.
Every trip is different. Every traveller is different. Pick the package that's right your family.
Every trip is different. Every traveller is different. Pick the package that's right for your family.
The Full Pour
Every detail of your trip handled, from first idea to final boarding pass. Accommodation, transfers, dining, activities, experiences: all of it researched, booked, and managed on your behalf.
Served Neat
The core foundations of your trip, locked in: accommodation, transportation, and the experiences worth booking in advance. Dining, free days, and everything in between? Yours to fill in on your own terms.
Pick Your Proof
You've chosen the destination but don't want to spend hours going down social media or AI rabbit holes to find the right place to stay. Let me handle it. Three hand-picked hotels or villas, a genuine insider take on each, and booking handled once you've chosen.
On The House
You already know which hotel you want. Book through me at the same rate as going direct through the hotel, with the added benefit of perks like complimentary upgrades, early check-in, and welcome amenities at select properties. No planning fee.
The Full Pour
This is the full concierge experience. Accommodation, transfers, dining reservations, activities — every single detail researched, booked, and managed on your behalf.
Every detail, handled. Every moment, considered. All you have to do is show up.
In short
What I do to get you there
- Research and shortlist every property, restaurant, and experience against your specific needs, your pace, and your non-negotiables
- Negotiate directly with properties and suppliers where possible to secure the best rates and applicable perks
- Source and book experiences, dining, and activities through trusted operators and contacts I know personally
- Handle every email, negotiation, and special request with suppliers so your inbox never sees any of it
- Coordinate payments and chase confirmations across every booking so nothing slips through
- Build your full itinerary with every detail documented and ready to go
- Stay available throughout your trip for any last minute requests or support you need along the way
Most popular
What you get
- Complimentary consultation call (up to 1 hour)
- A custom trip proposal tailored to your vision, travel style, and budget
- Two rounds of revisions
- Every booking confirmed, documented, and organised into a full itinerary accessible via the Fora app
- Optional pre-departure call
- In-destination support throughout your trip
- $150 USD per day of travel
- 3-day minimum required
Served Neat
I lock in the core foundations of your trip: accommodation, transportation, and the experiences worth booking in advance. Dining, free days, and everything in between? Those are yours to fill in however you like.
The essentials, expertly handled. The rest, yours to savour.
In short
What I do to get you there
- The same planning process as The Full Pour, but with research and coordination scoped to accommodation, transportation, and core experiences.
What you get
- The same end-to-end planning experience as The Full Pour, but your proposal is only scoped to accommodation, transportation, and core experiences.
- Dining reservations and day-to-day activity planning are not included. Those are yours to explore on your own terms.
- $150 USD per day of travel
- 3-day minimum required
Pick Your Proof
You've chosen the destination, but finding the right place to stay is the hard part. Let me take that off your plate. I do the searching, the vetting, and the honest shortlisting so you do not have to spend hours going down rabbit holes on social media reviews or AI tools.
Three hotels or villas, hand-picked. The honest insider take, included.
In short
What I do to get you there
- Research and shortlist accommodation against everything we discussed: your travel style, your budget, and your non-negotiables
- Apply years of Caribbean knowledge to each option, the kind of detail that only comes from genuine familiarity with these properties and this region
- Present each option with enough context that the decision feels easy, not overwhelming
- Handle the booking once you have decided, communicating your preferences and any special requests directly to the property
Planning fee: $200 USD flat fee. Each additional round of options is $200 USD.
What you get
- Complimentary consultation call (up to 1 hour)
- Three curated accommodation options (hotel or villa).
- If you'd like to see a second set of options after your first three, that's available as an additional round.
- An honest take on each: the vibe, the location, standout features, and any trade-offs worth knowing
- Booking handled once you've decided, with VIP perks unlocked at select properties
- A point of contact if anything needs adjusting before your trip
On The House
You already know which hotel you want to stay at. Before you book directly, let me handle it. Same rate, and at many properties, added perks included on top.
Your hotel, booked. Extra perks, included. No fee.
In short
What I do to get you there
- Book through my preferred partner network to access perks that are not available to the public or through third-party booking sites
- Handle the booking, communicating your preferences and any special requests directly to the property
Planning fee: None. You pay the cost of your stay, and nothing more.
What you get
- Your chosen hotel booked on your behalf at the same rate you would find booking directly, but with any VIP perks I can unlock at the property as well
- Perks can include: complimentary upgrades, early check-in, welcome amenities and resort credits
- Your booking confirmation and all relevant documents sent to you in one organised email
- A point of contact if anything needs adjusting before your trip
The Full Pour
This is the full concierge experience. Accommodation, transfers, dining reservations, activities — every single detail researched, booked, and managed on your behalf.
Every detail, handled. Every moment, considered. All you have to do is show up.
In short
What I do to get you there
Most popular
What you get
- Complimentary consultation call (up to 1 hour)
- A custom trip proposal tailored to your vision, travel style, and budget
- Two rounds of revisions
- Every booking confirmed, documented, and organised into a full itinerary accessible via the Fora app
- Optional pre-departure call
- In-destination support throughout your trip
- Research and shortlist every property, restaurant, and experience against your specific needs, your pace, and your non-negotiables
- Negotiate directly with properties and suppliers where possible to secure the best rates and applicable perks
- Source and book experiences, dining, and activities through trusted operators and contacts I know personally
- Handle every email, negotiation, and special request with suppliers so your inbox never sees any of it
- Coordinate payments and chase confirmations across every booking so nothing slips through
- Build your full itinerary with every detail documented and ready to go
- Stay available throughout your trip for any last minute requests or support you need along the way
- $200/day (3-4 travelers)
- $250/day (5–8 travelers)
- $300/day (9–10 travelers)
- 10+ travelers, let's talk
All fees quoted in USD and are per day of travel. 3-day minimum required.
Planning fees
Served Neat
I lock in the core foundations of your trip: accommodation, transportation, and the experiences worth booking in advance. Dining, free days, and everything in between? Those are yours to fill in however you like.
The essentials, expertly handled. The rest, yours to savour.
In short
What I do to get you there
Most popular
What you get
- The same end-to-end planning experience as The Full Pour, but your proposal is only scoped to accommodation, transportation, and core experiences.
- Dining reservations and day-to-day activity planning are not included. Those are yours to explore on your own terms.
- The same planning process as The Full Pour, but with research and coordination scoped to accommodation, transportation, and core experiences.
- $150/day (3-4 travelers)
- $175/day (5–8 travelers)
- $200/day (9–10 travelers)
- 10+ travelers, let's talk
Planning fees
All fees quoted in USD and are per day of travel. 3-day minimum required.
Pick Your Proof
You've chosen the destination, but finding the right place to stay is the hard part. Let me take that off your plate. I do the searching, the vetting, and the honest shortlisting so you do not have to spend hours going down rabbit holes on social media reviews or AI tools.
Three hotels or villas, hand-picked. The honest insider take, included.
In short
What I do to get you there
Most popular
What you get
- Complimentary consultation call (up to 1 hour)
- Three curated accommodation options (hotel or villa). If you'd like to see a second set of options after your first three, that's available as an additional round.
- An honest, informed take on each option: the vibe, the location, standout features, and any trade-offs worth knowing before you decide
- Booking handled once you have chosen, with VIP perks unlocked at select properties
- A point of contact if anything needs adjusting before your trip
- Research and shortlist accommodation against everything we discussed: your travel style, your budget, and your non-negotiables
- Apply years of Caribbean knowledge to each option, the kind of detail that only comes from genuine familiarity with these properties and this region
- Present each option with enough context that the decision feels easy, not overwhelming
- Handle the booking once you have decided, communicating your preferences and any special requests directly to the property
On The House
You already know which hotel you want to stay at. Before you book directly, let me handle it. Same rate, and at many properties, added perks included on top.
Your hotel, booked. Extra perks, included. No fee.
In short
What I do to get you there
Most popular
What you get
- Your chosen hotel booked on your behalf at the same rate you would find booking directly, but with any VIP perks I can unlock at the property as well
- Perks can include: complimentary upgrades, early check-in, welcome amenities and resort credits
- Your booking confirmation and all relevant documents sent to you in one organised email
- A point of contact if anything needs adjusting before your trip
- Book through my preferred partner network to access perks that are not available to the public or through third-party booking sites
- Handle the booking, communicating your preferences and any special requests directly to the property
Client snapshots
"Taylor is simply the best! Not only does she know her stuff, but she anticipates needs, is so responsive, and is so fun to work with. She had us so excited for the trip prior and has us dying to go back after. She had the sweetest care package waiting for us on arrival with some thoughtful touches that let me know she truly was listening to every detail during our planning process. I’m a type A mom, and Taylor never made me feel silly or high maintenance for my questions and wanting to plan the best trip for my family. Can’t wait to work with her again."
Destination: Barbados, April 2026
Package: The Full Pour
Details: Stay at Beach View Hotel
The Bergers
Client snapshots
"Taylor is simply the best! Not only does she know her stuff, but she anticipates needs, is so responsive, and is so fun to work with. She had us so excited for the trip prior and has us dying to go back after. She had the sweetest care package waiting for us on arrival with some thoughtful touches that let me know she truly was listening to every detail during our planning process. I’m a type A mom, and Taylor never made me feel silly or high maintenance for my questions and wanting to plan the best trip for my family. Can’t wait to work with her again."
The Bergers
Destination: Barbados, April 2026
Package: The Full Pour
Details: Stay at Beach View Hotel
What happens next
Fill out the form on my Contact page and select a time that works for your complimentary consultation call.
We'll spend up to an hour talking through your trip, your wishlist, and everything I need to get started.
Within 24-48 hours of our call, I'll send over your planning agreement and planning fee invoice (if applicable).
The moment I have your signed contract and payment, I get to work. Timelines for proposals, revisions, and bookings vary by package and will be clearly outlined in your contract.
We'll have an optional (but recommended) pre-departure call to walk through every detail before you go. Then it's time to celebrate. Two-four weeks after, I'd love to connect for a quick call and hear how everything went while the memories are still fresh.
Consultation call
Contract & planning fee
Planning & collaboration
Pre-departure through post-event
Submit your enquiry
What happens next
Fill out the form on my Contact page and select a time that works for your complimentary consultation call.
Submit your enquiry
We'll spend up to an hour talking through your trip, your wishlist, and everything I need to get started.
Consultation call
Within 24 hours of our call, I'll send over your planning agreement and planning fee invoice (if applicable).
Contract and planning fee
The moment I have your signed contract and payment, I get to work. Timelines for proposals, revisions, and bookings vary by package and will be clearly outlined in your contract.
Planning & collaboration
We'll have an optional (but recommended) pre-departure call to walk through every detail before you go. Then it's time to celebrate. Two-four weeks after, I'd love to connect for a quick call and hear how everything went while the memories are still fresh.