Dispatch № 12Spring 2026
Hilton Ahead
№ 01Request an Itinerary

Tell us about your trip.

Three minutes of questions. One business day until we send back a real quote. No obligation, no sales pitch, and we will tell you if a consultant isn't worth it for your trip size.

Trip estimator

Rough budget for your Hilton Head trip.

A starting-point range based on 400+ trips we've booked. Not a quote. The real one comes after you fill out the itinerary form.

Estimated total trip spend
$5,320($3,724 to $7,182)
Our fee
$800(~15% of total)
Get a real quoteOr book a 30-min call ↗
Already decided?

Pay your itinerary fee directly.

For returning clients and referred guests. $95 discovery session (credited toward your itinerary), $450 flat itinerary, or a $500 trip-planning deposit applied to your final invoice. Secure checkout powered by Stripe.

№ 04FAQ

Questions we hear most.

How much does a Hilton Head itinerary cost?
The flat-fee custom itinerary is $450, delivered within 5-7 days and with revisions included. A $95 discovery session is also available and credits toward your itinerary if you proceed. Full-service group trips are billed as a percentage of trip spend, agreed up front.
How quickly will I hear back after submitting the form?
One business day for a real quote with scope and pricing. Same-day for active clients. If your trip is within a week, flag it in the message and we will prioritize.
Do you charge kickbacks or commissions?
No. Every fee is flat or percentage-based and agreed up front. We do not take commissions from villa companies, restaurants, or tour operators that affect your rates. Sponsorship income is separate from client work and publicly disclosed.
Can you book villas, dinner reservations, and tee times for me?
Yes. Full-service bookings include villa selection and contracts, Harbour Town and Palmetto Dunes tee times, S-tier restaurant reservations, charters, spa appointments, and airport transfers. Itineraries-only include specific recommendations and booking instructions for you to execute.
What kinds of Hilton Head trips do you plan?
Family vacations, golf trips, couples getaways, wedding weekends, corporate outings, Thanksgiving and spring break weeks, and RBC Heritage weeks. We also handle winter long-stay trips for snowbirds. If the trip is larger than six travelers, flag it on the form.
Is the discovery session worth it before the itinerary?
It is if you want to think through your trip out loud before committing. The $95 fee credits toward the $450 itinerary, so the only real cost is your time. If you already know what you want, skip the call and go straight to the itinerary request form.
Do you plan Bluffton and Palmetto Bluff trips too?
Yes. Bluffton and Palmetto Bluff are a 20-25 minute drive off-island, and we plan trips that split time between Hilton Head and Bluffton regularly. Palmetto Bluff is on our S-tier recommendation list for anniversaries and high-stakes weekends.