TLS AFFILIATED PRO
Personalized Caribbean vacation plans from Toby, plus practical tech, smart-home products, travel gear, and photography picks to help you travel smarter.
Personalized plans from $49 for 1–2 travelers Compare plans
TOBY’S PRODUCT PICKS
Explore everyday tech, smart-home products, and travel essentials.
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Compare up to 3 picks by their intended use. Open each recommendation for shopping details; confirm specifications and current prices with the retailer.
STRAYHORN VISUALS · PHOTOGRAPHY BY TOBY
Bring a little island life home. Explore photographs of Caribbean shores, tropical color, and moments by the sea.
Shop prints & digital downloadsView the full collection, available print formats, download licenses, and current prices on Picfair.
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A PLAN FOR YOUR PEOPLE
Personalized research and an editable planner, with one revision included. Planning fees are separate from flights, accommodation and other travel costs.
COUPLES & SOLO TRAVELERS
$49 USD · 1–2 people
Normally delivered within 3 business days after payment and receipt of your details.
MAKE ROOM FOR EVERY AGE
$89 USD · 3–5 people
Secure Stripe checkout. Email your brief separately to confirm availability and delivery date. Your personalized planner is delivered by email after payment and receipt of your trip details.
GET EVERYONE ON THE SAME PAGE
From $149 USD · 6+ people
For girls’ trips, family reunions, bachelorette parties and retreats. Stripe checkout is $149 USD. Email your brief separately to confirm scope, final quote and delivery date before payment. Your personalized planner is delivered by email.
Personalized plans and tier worksheets are delivered by email. You book and pay travel providers directly. Childcare availability is confirmed with providers; the cost tracker records reimbursements and does not send payments.
A GETAWAY THAT FEELS LIKE YOU
Get a personalized travel plan with recommended flights and accommodations, a day-by-day itinerary, restaurant and activity suggestions, transportation information, direct booking links, and one revision after delivery.
The Duo: $49 for 1–2 travelers. Family Pack: $89 for 3–5 travelers. Group/Retreat: from $149 for 6 or more travelers, with a confirmed quote before payment. Duo plans are normally delivered within three business days. Family and group delivery dates are confirmed before payment. Planning begins after payment and receipt of your trip details. One revision is included.
You make reservations and payments directly with travel providers. TLS Affiliated Pro provides research and planning assistance; it does not book travel or guarantee third-party prices, availability, or services.
Compare the three planning tiers
Get a personalized travel plan with recommended flights and accommodations, a day-by-day itinerary, restaurant and activity suggestions, transportation information, direct booking links, and one revision after delivery.
The Duo: $49 for 1–2 travelers. Family Pack: $89 for 3–5 travelers. Group/Retreat: from $149 for 6 or more travelers, with a confirmed quote before payment. Duo plans are normally delivered within three business days. Family and group delivery dates are confirmed before payment. Planning begins after payment and receipt of your trip details. One revision is included.
You book and pay travel providers directly. Planning does not include reservations or third-party travel costs. Group/Retreat plans start at $149; request a confirmed quote before payment.
A few details to start something good.
ONE STEP CLOSER
Here’s your starting point for a personal travel plan.
Your brief is ready. It has not been sent. Email it when you’re ready to start a conversation.
Email my trip detailsDuo checkout is $49 USD for 1–2 travelers. Email your brief separately. Planning begins after payment and receipt of your details.
You can also download your brief to keep a copy and attach it to your email.
Opens your email app for review. Planning starts after payment and your trip details are received. For Group/Retreat, confirm your quote before payment.
PLAN IT YOUR WAY
Download a TLS planner and build a trip around your dates, budget, and pace.
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BEFORE YOU BOOK. BEFORE YOU BUY.
Practical guides for the choices behind a great trip or a useful purchase.
Choose a base, build a realistic budget, and leave room to enjoy the trip.
Read the Jamaica guideCARIBBEAN TRAVEL · 4 MIN READCompare a resort stay with an independent trip before you book.
Read the Dominican Republic guidePRODUCT BUYING · 4 MIN READCheck compatibility, subscriptions, and privacy before adding to cart.
Read the buying guideMEET TOBY
I’m Toby, the creator of TLS Affiliated Pro. I create personalized Caribbean vacation plans around your dates, interests, and budget. I also research and share practical technology, smart-home products, travel gear, and photography equipment to help you make more confident purchases.
Have a question? Send me a message. I’ll respond within 48 hours.
Contact Toby