Caribbean
Anguilla
4 days
Anguilla, Long Weekend
Thirty-three beaches, no cruise ships, no casinos, and not much to do. Which is entirely the point.
- beach
- luxury
- foodie
$9.99
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Plate 01
Somewhere worth the climb
Travel creator & itinerary curator
Personalized trips,
without the stress.
From the best places to stay to can’t-miss experiences, I create travel plans that help you make the most of every destination. You tell me the vision. I handle the details.
- of trips planned
- Hundredsof trips planned
- of content views
- Millionsof content views
- destinations charted
- 31destinations charted
Ready when you are
Pre-made itineraries
Pick a country, download the plan, go. Every day mapped out, every booking that needs doing early flagged, and costs written as real ranges instead of a fantasy number.
$9.99
Browse the shop
Built around you
Custom trip planning
For the trip that doesn’t fit a template, a proposal, a birthday, six friends who can’t agree, or three countries in two weeks. You give me the vision; I handle every detail underneath it.
$99
Start my trip
The shop
Plans you can follow, for $9.99.
Every guide is the whole trip in one place: the experiences worth the flight, where to sleep, where to eat, what it actually costs, and a route map showing how it fits together. Instant PDF download, yours to keep offline.
Region
Style
31 shown
Custom planning · $99
Three steps between you and the plan.
From international adventures to quick weekend trips, I design vacations that match your travel style, your budget, and the way you like to move. You tell me the vision. I handle the details.
- 01
You tell me the vision
One form, about ten minutes. Your dates, your budget, who you’re travelling with, and how you actually like to move, slow mornings or first ferry out.
- 02
I chart the course
I work out the routing, which town to sleep in each night, what needs booking weeks ahead, and where the money is genuinely worth spending.
- 03
You get the plan
A clean guide built to read on your phone at an airport gate. Experiences, stays, places to eat and a route map. One round of changes included, so it ends up right.
What you get
In every plan
- A full guide to the whole trip, built around your dates and budget
- Where to stay each night, with two or three options at your price point
- Restaurant picks that fit how you actually eat, not a tourist top-ten
- Everything that needs booking in advance, in the order it needs booking
- Realistic costs per day, so the budget survives contact with the trip
- Routing and transfer times, so you’re never guessing how long a drive takes
- One round of changes after you read it
What it isn’t
Not included, on purpose
- Booking or paying for anything on your behalf. You book direct, in your own name
- Flights, hotels or tours as a package, and no commission taken from either side
- Travel insurance, visas or entry paperwork, though I’ll tell you what you need
- Being your rep on the ground. I’m a planner, not an agency
You book everything yourself, in your own name, at the price you can see. That means no markup, no commission steering the recommendations, and if something goes wrong you’re the customer, not me on your behalf.
Three ways to work together
Pick the one that fits.
A quick question and a three-country trip shouldn’t cost the same. Nothing is charged until we’ve both agreed the trip is one I can plan well.
The Consult
$29
You’ve mostly decided. You just want a second opinion.
- Best for
- One destination, a handful of questions
- Turnaround
- 2 working days
- Written answers to everything you ask about one destination
- Where to base yourself, and which areas to avoid
- A shortlist of what’s genuinely worth booking ahead
- An honest read on whether your budget matches the trip
No day-by-day plan and no bookings researched for you.
Start with ConsultThe Trip Plan
Most booked
$99
The whole trip, built around you.
- Best for
- One country, up to about two weeks
- Turnaround
- 5–7 days
- A full guide to your trip. Experiences, stays, food, routing
- Two or three places to stay at your price point, per base
- Everything that needs booking ahead, in the order it needs doing
- Realistic day-by-day costs, so the budget survives the trip
- One round of changes after you read it
You book everything yourself, in your own name.
Start with Trip PlanThe Grand Tour
$249
For the trip that has a lot riding on it.
- Best for
- Several countries, groups, or a trip that matters
- Turnaround
- 7–10 days, priority
- Everything in The Trip Plan, across multiple countries
- Inter-island and cross-border routing worked out properly
- Group logistics, different budgets, arrival times and appetites
- Milestone planning: proposals, birthdays, anniversaries
- Two rounds of changes, and I stay reachable while you travel
Still no bookings taken on your behalf. That never changes.
Start with Grand TourWorth it if
- You know roughly where and when, but the planning keeps stalling
- It’s a trip that matters, a proposal, a milestone, a first big one together
- You’re moving between several places and the logistics have got complicated
- A group that can’t agree, and someone needs to decide
Probably not, if
- You want the cheapest possible flight-and-hotel bundle
- You want someone to hold your booking money
- You already have the trip planned and want it checked, just email me instead
If a ready-made plan would do the job, buy one of those for $9.99 instead. I’d rather you spent less and got the right thing.
The brief · $99
Tell me everything.
Ten minutes here saves a week of back and forth. There are no wrong answers. “I don’t know yet” is a useful answer too.
Nothing is charged when you send this. I read it, tell you honestly whether I’m the right person for the trip, and we go from there.
Who’s planning
Hi. I’m Ian.
I’m a travel creator and itinerary curator who designs personalized, stress-free trips. From the best places to stay to can’t-miss experiences, I create travel plans that help you make the most of every destination.
After planning hundreds of trips and creating content viewed by millions, I’ve learned what truly makes a trip unforgettable. Every itinerary is built from real experience. I personally visit destinations, test activities, and handpick recommendations so you can travel with confidence.
Have me plan yours · $99The whole idea
“You tell me the vision.
I handle the details.”18°07′N 77°18′W
How I plan
Four rules.
- 01
A plan you can hold in your head
A good itinerary fits on a phone screen at a gate with bad wifi. If you need three apps and a group chat to follow it, it has failed at the only job it had.
- 02
Room left in the day
The most common planning mistake is fitting in everything. I leave gaps on purpose. The afternoons you don’t plan are usually the ones you talk about afterwards.
- 03
Money, honestly
Every cost is written as a range, and the ranges are real. I’d rather tell you a trip needs more than you hoped than have you find out at the airport.
- 04
No commission, no steering
I take nothing from hotels or operators. You book direct, at the price you can see. That’s what keeps a recommendation worth reading.
Questions
The things worth knowing before you buy.
Buying an itinerary
What do I actually get for $9.99?
A PDF with the whole trip written out: general tips for the country, a route map, every experience worth your time, where to sleep and why there, where to eat, how long each transfer takes, and what it realistically costs. It’s built to read on a phone and to print if you’d rather have paper.
How is it delivered?
Instantly. You’re taken straight to a download page after payment, and Stripe emails you a receipt with a link back to it. Nothing to wait for and no account to make.
Can I use it offline?
Yes. That’s the point of a PDF. Download it before you fly and it works with no signal, which is when you tend to need it most.
How current is the information?
Every plan carries the date it was last checked, on the page and in the PDF. Because prices and opening hours drift, costs are always written as ranges rather than exact figures, and each plan ends with six things to confirm yourself before you travel. Treat it as a well-researched route, not a live booking system.
Can I share it with the people I’m travelling with?
Of course, share it with everyone on the trip. Just don’t resell it or post it publicly.
Custom planning
What happens after I send the brief?
I read it and reply within one working day, usually sooner. If it’s a trip I can plan well, I’ll say so and send a payment link. If it isn’t. Wrong region, wrong budget, or you’d genuinely be better off with a $9.99 plan. I’ll tell you that instead.
When do I pay?
Only after we’ve both agreed the trip is one I can do properly. Sending the brief costs nothing and commits you to nothing.
How long does it take?
Five to seven days from the point we agree the brief. If you’re flying sooner than that, say so in the brief and I’ll tell you honestly whether it’s doable.
Do you book anything for me?
No, deliberately. You book everything yourself, in your own name, at the price you can see. I take no commission from any hotel or operator, which is what keeps the recommendations worth reading. And if something goes wrong, you’re the airline’s customer, not mine.
What if the plan isn’t right?
One round of changes is included as standard. Tell me what’s off and I’ll rework it. Most plans need a nudge somewhere. That’s normal, not a failure.
Do you only do the Caribbean and Central America?
That’s where the ready-made plans are, and where I’m strongest. For custom trips, ask me anyway. If it’s somewhere I can’t plan to the standard I’d want, I’ll tell you rather than take the money.
Money and the small print
Can I get a refund?
Ready-made itineraries are non-refundable once the PDF has been downloaded, because at that point you have the whole product. If a download fails or you were charged twice, email me and I’ll sort it the same day. Custom planning is refundable in full up until I start work.
What currency are prices in?
US dollars. Your bank may add its own conversion fee on top, which is outside my control.
Are you a travel agent?
No. I sell travel plans, not travel. I never take custody of your booking money, never act as an agent for an airline or hotel, and never resell anyone’s inventory. You remain the direct customer of everyone you book with.
Still wondering something?
Ask me directly. I answer my own email and I’d rather talk you out of the wrong trip than sell you one.
Email ianalsopp@gmail.comStop describing the trip. Start booking it.
Grab a ready-made plan for $9.99, or hand me the whole thing and get a trip built around exactly what you want.