Find deals on 42 top-rated, price matched, things to do close to $500+ around Hilton Head Island and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.

Sunset with Island Head
Private Sunset Cruise
Hilton Head Private Sunset Cruise For Up To 14 Passengers
Hilton Head Island, South Carolina, United States
4.9 (12)
from $529
Enjoy a 2 hour private charter with Island Head. This boat is driven by captain. It is a 25ft custom boat that holds up 14 passengers. Come cruise the water ways of Hilton Head Island.
2 Hour Private Charter (up To 14 Passengers)
Hilton Head Island, South Carolina, United States
5.0 (9)
from $477
If you're looking for sand dollars, this is the tour for you!
Likely to sell out
Much loved
Vanishing Mile Isle Beachcomber Tour
Hilton Head Island, South Carolina, United States
5.0 (85)
from $429
Much loved
90-minute Private Dolphin Tour In Hilton Head Island
Hilton Head Island, South Carolina, United States
5.0 (430)
from $299
Sunset, Fun set!
Likely to sell out
Large Group (7-15 People) Private Hilton Head Sunset Tour
Hilton Head Island, South Carolina, United States
5.0 (11)
from $575
Tubing on Hilton Head Island with Island Head!
1 Hour Private Tubing Trip
Hilton Head Island, South Carolina, United States
5.0 (21)
from $272
Much loved
2-hour Private Hilton Head Dolphin Watching Cruise
Hilton Head Island, South Carolina, United States
5.0 (270)
from $299
Pontoon Boat Rental In Hilton Head Island
Hilton Head Island, South Carolina, United States
4.6 (25)
from $287
3 Hours Private Family Fishing Excursion Up To 6 Guests
Hilton Head Island, South Carolina, United States
5.0 (3)
from $495
4-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.7 (14)
from $551
Two Hour Large Group Dolphin Tour
Hilton Head Island, South Carolina, United States
5.0 (3)
from $385
Private Daufuskie Island History And Artisian Tour
Hilton Head Island, South Carolina, United States
5.0 (1)
from $585
Likely to sell out
Much loved
Private Hilton Head Sunset Dolphin Tour
Hilton Head Island, South Carolina, United States
4.9 (17)
from $379
Much loved
Private Hilton Head Dolphin Tour
Hilton Head Island, South Carolina, United States
5.0 (20)
from $329
Much loved
2-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.7 (28)
from $319
Water ski adventure day on Hilton Head with Island Head! We offer wake boards, water skis, tubing, and kneeboards.
Private Water Ski Adventure Day (3 Hours)
Hilton Head Island, South Carolina, United States
5.0 (2)
from $543
Private Hilton Head Dolphin Tour With Waterfront Dining Stop
Hilton Head Island, South Carolina, United States
5.0 (6)
from $414
5-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.5 (10)
from $636
3-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.6 (7)
from $435
Private Water Ski, Wakeboard, Knee Board, Tubing, Adventure Day with Island Head on Hilton Head Island, SC
Private Water Ski Adventure Day (2 Hours)
Hilton Head Island, South Carolina, United States
5.0 (1)
from $409
6-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
5.0 (1)
from $752
Hilton Head Luxury Pontoon Rental For 2 To 8 Hours
Hilton Head Island, South Carolina, United States
5.0 (13)
from $315
Morning Beaufort River Tour
Hilton Head Island, South Carolina, United States
5.0 (3)
from $260
Family Kayak HILTON HEAD fun at it's best!
2 1/4 Hour Private Kayak Hilton Head Dolphin Nature Experience
Hilton Head Island, South Carolina, United States
5.0 (7)
from $450
2 Hour Hilton Head Boat Rental With Vip Fireworks Viewing
Hilton Head Island, South Carolina, United States
5.0 (10)
from $625
Much loved
Private Dolphin Boat Tour In Hilton Head Island
Hilton Head Island, South Carolina, United States
4.9 (15)
from $300
7 Hour Ultimate Lowcountry Day Up To 6 Guests
Hilton Head Island, South Carolina, United States
5.0 (1)
from $985
Picture Perfect
Likely to sell out
Much loved
2-hour Private Hilton Head Sunset Cruise
Hilton Head Island, South Carolina, United States
5.0 (240)
from $359
Private sunset cruise on Hilton Head Island by Island Head
Much loved
Private Hilton Head Sunset Boat Cruise (up To 14 Passengers)
Hilton Head Island, South Carolina, United States
5.0 (61)
from $597
Tubing And Dolphins Up To 6 Guests
Hilton Head Island, South Carolina, United States
New
from $475
Likely to sell out
Private Disappearing Island Dolphin Tour
Hilton Head Island, South Carolina, United States
New
from $379
Private Sunset And Fireworks Dolphin Tour (6 People Max)
Hilton Head Island, South Carolina, United States
New
from $475
Private Dolphin And Nature Tour Of Hilton Head
Hilton Head Island, South Carolina, United States
New
from $265
5 Hour Ultimate Lowcountry Day: Up To 6 Guests
Hilton Head Island, South Carolina, United States
New
from $745
Island Head Pontoon Boat Rental on Hilton Head Island
2-hour Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
New
from $309
Tubing And Dolphins With Up To 12 Guests
Hilton Head Island, South Carolina, United States
New
from $695