Find deals on 49 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.

Collection of sand dollars found on Mile Isle
Much loved
Vanishing Mile Isle Beachcomber Tour
Hilton Head Island, South Carolina, United States
5.0 (81)
2 hours, 30 minutes
from $429
Likely to sell out
Much loved
90-minute Private Dolphin Tour In Hilton Head Island
Hilton Head Island, South Carolina, United States
5.0 (420)
1 hour, 30 minutes
from $319
Much loved
Pontoon Boat Rental In Hilton Head Island
Hilton Head Island, South Carolina, United States
4.6 (25)
2 to 6 hours
from $287
Sunset, Fun set!
Large Group (7-15 People) Private Hilton Head Sunset Tour
Hilton Head Island, South Carolina, United States
5.0 (11)
2 hours
from $575
Private sunset cruise on Hilton Head Island by Island Head
Likely to sell out
Much loved
Private Hilton Head Sunset Boat Cruise (up To 14 Passengers)
Hilton Head Island, South Carolina, United States
5.0 (59)
2 hours
from $597
Much loved
2-hour Private Hilton Head Dolphin Watching Cruise
Hilton Head Island, South Carolina, United States
5.0 (270)
2 hours
from $379
Checking us out!
Likely to sell out
Much loved
Private Hilton Head Sunset Dolphin Tour
Hilton Head Island, South Carolina, United States
4.9 (16)
1 hour, 30 minutes
from $379
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)
2 hours
from $477
Much loved
Private Hilton Head Dolphin Tour
Hilton Head Island, South Carolina, United States
5.0 (20)
1 hour, 30 minutes
from $329
Tubing on Hilton Head Island with Island Head!
1 Hour Private Tubing Trip
Hilton Head Island, South Carolina, United States
5.0 (21)
1 hour
from $272
Much loved
2-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.7 (28)
2 hours
from $319
4-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.7 (14)
4 hours
from $551
5-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.5 (10)
5 hours
from $636
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)
3 hours
from $543
Private Sunset Sail in Hilton Head Island, SC
Likely to sell out
2 Hour Private Dolphin Sunset Sail At Shelter Cove
Hilton Head Island, South Carolina, United States
5.0 (4)
2 hours
from $434
Private Hilton Head Dolphin Watching Tour With Waterfront Dining Stops
Hilton Head Island, South Carolina, United States
5.0 (6)
2 hours, 15 minutes
from $414
3-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
4.6 (7)
3 hours
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)
2 hours
from $409
6-hour Private Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
5.0 (1)
6 hours
from $752
22 Ft. Luxury Pontoon Private Hilton Head Boat Rental
22 Ft. Luxury Pontoon Private Hilton Head Boat Rental For 2 Hours
Hilton Head Island, South Carolina, United States
5.0 (2)
2 hours
from $325
Two Hour Large Group Dolphin Tour
Hilton Head Island, South Carolina, United States
5.0 (3)
2 hours
from $595
Hilton Head Luxury Pontoon Rental For 2 To 8 Hours
Hilton Head Island, South Carolina, United States
5.0 (13)
2 to 8 hours
from $315
3 Hours Private Family Fishing Excursion Up To 6 Guests
Hilton Head Island, South Carolina, United States
5.0 (2)
3 hours
from $495
2 Hour Hilton Head Boat Rental With Vip Fireworks Viewing
Hilton Head Island, South Carolina, United States
5.0 (10)
4 hours
from $625
Much loved
Private Dolphin Boat Tour In Hilton Head Island
Hilton Head Island, South Carolina, United States
4.9 (15)
1 hour
from $400
Sunset Fireworks Sail on Hilton Head Island, South Carolina
2.5 Hour Private Sunset Fireworks Sail
Hilton Head Island, South Carolina, United States
5.0 (1)
2 hours, 30 minutes
from $521
Private Charters In Hilton Head
Hilton Head Island, South Carolina, United States
5.0 (1)
2 hours
from $895
4 Hour Private Hilton Head Boat Rental 24 ft. Luxury Pontoon
4 Hour Private Hilton Head Boat Rental 24 Ft. Luxury Pontoon
Hilton Head Island, South Carolina, United States
5.0 (1)
4 hours
from $675
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)
2 hours
from $399
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)
2 hours
from $529
Enjoying a dolphin day sail on Hilton Head
2 Hour Private Dolphin Day Sail
Hilton Head Island, South Carolina, United States
New (NaN)
2 hours
from $380
Savannah Hilton Airport (sav) To Hilton Head Island - Roundtrip Private Transfer
Savannah, Georgia, United States
New (NaN)
1 hour, 40 minutes
from $429
22 ft. Luxury Pontoon Private Hilton Head Boat Rental for 3 Hours
22 Ft. Luxury Pontoon Private Hilton Head Boat Rental For 3 Hours
Hilton Head Island, South Carolina, United States
New (NaN)
3 hours
from $475
Center Console Boat Rental In Hilton Head Island
Hilton Head Island, South Carolina, United States
New (NaN)
2 hours
from $368
Island Head Pontoon Boat Rental on Hilton Head Island
2-hour Hilton Head Pontoon Boat Rental
Hilton Head Island, South Carolina, United States
New (NaN)
2 hours
from $309
5 Hour Private Hilton Head Boat Rental 24 ft. Luxury Pontoon
5 Hour Private Hilton Head Boat Rental 24 Ft. Luxury Pontoon
Hilton Head Island, South Carolina, United States
New (NaN)
5 hours
from $775
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