Dispatch № 12Spring 2026
Hilton Ahead
№ 01Services

Everything we do for you, in one place.

Hilton Head is deceptively big. Twelve square miles of neighborhoods, three major resorts, five championship golf courses, and a hundred restaurants that range from white-linen to barefoot-on-a-deck. Here's how we sort it for you.

№ 02Pricing

Three tiers, priced up front.

No kickbacks from villa companies. No commission baked into your quoted rates. Pick the tier that matches your trip — and the tier-2/3 bookings include a transparent percentage on top so the harder work gets paid for. Heritage week, Wine & Food, snowbird leases, and ultra-premium stays use the application path.

Compass

A focused consultation for first-time visitors.

$295
  • 60-minute video consultation
  • Curated 3-villa shortlist with notes
  • Restaurant + tee-time reservation list
  • Neighborhood guide PDF
  • 30 days of email support
Ideal for

First-time HHI visitors, $5K-$10K trip budget.

Most popular
Charter

Full itinerary build with bookings handled end-to-end.

$895
+ 7% of net commissionable trip cost
  • Full custom itinerary build
  • 2 video planning calls
  • Lodging negotiation + booking
  • Restaurant, tee-time, and activity reservations
  • Trip-week text-line support
  • 60 days post-trip support
  • Welcome gift on arrival
Ideal for

Returning visitors, honeymoons, $10K-$25K trips.

Heritage

9-month lead planning for Heritage week, snowbirds, and ultra-luxury.

$2,500
+ 10% of net trip cost
  • Everything in Charter
  • 9-month lead planning for RBC Heritage / Wine & Food / snowbird leases
  • Private airport transfers
  • Pro-shop + tournament access (where available)
  • On-island concierge handoff
  • Dedicated planning lead
Ideal for

Heritage attendees, snowbirds, $25K+ trips.

A note on commission: the 7% (Charter) and 10% (Heritage) percentages apply only to commissionable bookings — villas, private clubs, restaurant packages where the supplier offers a referral fee. In practice, most of the percentage rides on supplier commission, so the client-side delta is small or nothing. Disclosed before booking, never hidden.
№ 03What we actually do

The five services, line by line.

01

Custom Itineraries

Day-by-day planning built around your group, your budget, and what you actually want out of the week. Golf heavy, kid friendly, quiet beach days, or some weird combination we figure out together.

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02

Villa & Resort Booking

From Sea Pines oceanfront villas to Palmetto Dunes and Forest Beach. We pick the right property for your group and negotiate the rate.

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03

Group & Family Trips

Weddings, reunions, corporate offsites, golf buddy trips. Coordinated lodging, transportation, dining, and activities for groups of 10 to 100.

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04

On-Island Concierge

Live support while you're here: last-minute boat charters, restaurant swaps, kid-sitter intros, bike deliveries to your door. One text, handled.

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05

Dining & Tee-Time Reservations

We hold the 7pm table at Skull Creek Boathouse and the 7am tee time at Harbour Town you can't get online. Relationships you can't fake.

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№ 04FAQ

Questions we hear most.

What services does Hilton Ahead actually book for clients?
Villa and resort lodging, Harbour Town and Palmetto Dunes tee times, S-tier dinner reservations, dolphin and fishing charters, private-car airport transfers, spa appointments, group dinners for weddings and corporate trips, and full-week family itineraries. We are based on the island and do most of this by a phone call, not a booking form.
How is pricing structured?
Three main options: a $95 discovery session (credits toward the itinerary), a $450 flat custom itinerary with revisions, and full-service trip planning billed as a percentage of trip spend for groups of 6+ or weddings. No kickbacks from vendors; every fee is agreed up front.
Can you get me a Harbour Town tee time?
Yes, if you stay inside Sea Pines Resort. Villa guests get 120-day tee-time priority at Harbour Town Golf Links. If you book the villa through us, we land the tee sheet. Public bookings are nearly impossible inside 60 days.
Do you handle wedding logistics?
Yes. Hilton Head wedding weekends are one of our core services. We coordinate group lodging across 8-12 properties, airport shuttles, welcome bags, rehearsal dinner venues, and a point of contact during the weekend itself. We are not the wedding planner, we are the travel operations team around them.
Do you plan Bluffton and Palmetto Bluff trips?
Yes. Bluffton and Palmetto Bluff sit 20-25 minutes off-island, and we regularly split trips between Hilton Head and Bluffton for couples and small groups. Palmetto Bluff is on our S-tier list for anniversaries and proposals.
How far ahead do I need to book?
Summer villas: 5-6 months out. October: 3-4 months. RBC Heritage week: 9-10 months. Winter: two weeks is fine unless it is a holiday. Spring break: 4-5 months. Dinner reservations at S-tier restaurants: 2-3 weeks lead time in summer, 1 week off-season.
What makes you different from booking direct with a resort?
We tell you which building to ask for, which room number to avoid, which restaurant disappoints on a Saturday, and whether a property is in-between renovation cycles. A resort cannot say "skip the Omni in May 2026, they are mid-renovation." We can, and do, in writing.
Do you offer on-island concierge once my trip starts?
For full-service clients, yes. Text-line support during your trip window for restaurant swaps, weather pivots, last-minute charter bookings, and anything else that comes up. For flat-fee itinerary clients, we handle pre-trip changes but the concierge line is not included.
An invitation

Tell us when you're coming.
We'll handle the rest.

Three minutes of questions. One business day until we come back with a quote. No sales pitch. The trip gets built for you, not for whatever the algorithm happens to be boosting this week.