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2026 Activities Guide

Oceanfront Hilton Head Vacation Rental

This villa sits directly on the sand, you simply cannot get closer to the beach anywhere on Hilton Head Island.As you enter this single-level villa, you’ll be welcomed by an open-concept kitchen, dining, and living area. The kitchen features...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
The 10 Best Beach Canopies & Umbrellas for 2026

Beach canopies and umbrellas create shade, lower ambient temperatures and block UV rays on hot, sunny Summer days. Sitting under the canopy of a quality beach umbrella can make the difference between comfort and sweltering. When choosing an...

Renovated Townhouse Golf View Deck, Pool...

Summary:Water Oak 27The Space:Welcome to Water Oak 27 - your ideal hideaway on Hilton Head Island, SC! This striking condo is located within the gated community of Palmetto Dunes Oceanfront Resort, offering both privacy and convenience. This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
The 7 Best Fishing & Beach Carts for 2026

For families travelling to the beach, or fishermen carrying tackle/coolers, a beach cart can be the best purchase of your vacation. These carts feature extra-wide wheels to move across soft sand, even when loaded. Carts are often built for specific...

Nautical condo with a balcony, & AC - cl...

Summary:Bluff Villas 1716 - Nautical condo with a balcony, & AC - close to pickleball and tennis courts.The Space:Located at the tip of Sea Pines, this sunny and entirely-refreshed villa is ready to host you and your guests in the heart of South...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Private Lesson with Doug Weaver

Palmetto Dunes Golf Academy

Book online
$160.00 - $800.00

description: About Doug Weaver, Director of the Palmetto Dunes Golf Academy Golf Digest South Carolina Top-Ten Instructor. Doug Weaver is a former PGA Tour Pro, US Open record holder and recent Lowcountry Golf Hall of Fame member. His weekly TV...

Three Hour Beach Combing and Dolphin Nature Watch Tour
Book online
$375.00 - $415.00

description: *Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

2 Hour Hilton Head Guided Boat Tour

Bluewater Adventure - Hilton Head

Book online
$115.00 - $135.00

description: Rates - Adults - $135 - Children - $115 - Fireworks Tour every Tuesday night - $135 ___________________________________ Duration 2 hours ___________________________________ Guided boat tours offered daily! Adventure awaits...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

description: See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty...

SC Pimento Cheese Festival- Pimento Cheese Competition

meeting_point: 2nd Annual Amateur Pimento Cheese Competition description: Does your pimento cheese have what it takes to win "South Carolina's Best Pimento Cheese" title? Registration **$25 per entry** - This fee includes entry into the...

Private Lesson with Samm Wolfe

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

meeting_point: Arthur Hills Course description: About Samm Wolfe, General Manager of the Arthur Hills Golf Course Samm Wolfe has been a member of the Palmetto Dunes staff since 1986 and a teaching professional since 1988. Entertaining and affable...

Critter Meet and Greet

Coastal Discovery Museum Hilton Head

Book online
$10.00

description: Drop by the Museum for this casual Meet & Greet to learn about the alligators, snakes, and a few other fun critters that share Hilton Head Island with us. Take this opportunity to see animals up close, gets hands-on and hold a critter...

Beach Comber & Vanishing Island

Dolphin Discoveries Hilton Head

Book online
$69.75 - $395.00

duration: 3 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Nine Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$70.74 - $168.39

description: Enjoy miles and miles of scenic bike paths Duration 9 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

8 Day Rental

Island Life Rentals and Tours

Book online
$36.00 - $255.00

duration: 8 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Multi Day Destination sail with Overnight Stay

Anchors Away Sailing Charters

Book online
$1,275.00 - $1,425.00

meeting_point: Hilton Head Island, SC description: *Multi-Day sail to a destination of your choosing* Stay onboard the boat overnight at the dock Duration Up to you!

Carolina HydroFly Parties

Carolina Hydrofly

Book online
$800.00 - $1,600.00

description: Private Party About Enjoy a 4 or 8 Hour Group Lesson. Can have up to 8 people (Half day) & 16 people (Full day) in your party. - Includes 10 minutes of instruction time, fuel, life jacket, and helmet **What's Included** ...

Beach Bum

Hilton Head Helicopter Tours

Book online
$109.00

duration: 20 miles description: This helicopter tour follows Hilton Head’s most active stretch of beaches to Coligny Beach, the island’s popular beach park. Pilots keep the flight low along the shoreline for close-up views of surf and potential...

Tuesday Fireworks and Sunset Sport Crabbing Adventure

description: Join us for a Seasonal Summertime Firework and Sunset Sport Crabbing Adventure Duration 2.5 hours About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing...

Sunset Creek Cat Tour

Lowcountry Watersports

Book online
$120.00 - $159.00

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours prior to the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 max_age: 99 group_size: 2 people per...

PVT Shark Tooth 6p

description: Discover Shark Tooth Island! ___ Description Enjoy a boat cruise from Hilton Head Island through the back waterways to Shark Tooth Island (near Savannah, Georgia) where you can hunt for shells, shark teeth and other ocean...

Half Day Flats Fishing (4 Hrs)

Green Heron Adventures

Book online
$550.00

meeting_point: Beaufort and Hilton Head/Bluffton, SC description: Duration 4 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target...

Mighty Mako

Mighty Mako

Book online
$350.00 - $550.00

description: **From the backwater creeks to where ocean waters meet (and sometimes further), Mighty Mako Sport Fishing Charters provides a rewarding and memorable outing on the water.** - - - - - - - Rates: - 2 Hour Charter: $350 (afternoon...

Weekend 10:30am-6:15pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekend 10:30 am to 6:15 pm- Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Bike Rental • Five Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 5 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

21 Day Rental

Island Life Rentals and Tours

Book online
$75.00 - $555.00

duration: 21 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$80.99 - $161.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Gingham Tablecloth, Bibs & Wipes
Book online
$12.95

Beach Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

description: Everything you need for a fun and comfortable day at the beach! Duration 24 Hours About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later...

Sunset Cruise

Island Time Charters

Book online
$350.00 - $450.00

The most spectacular views and vivid colors! Duration 2 or 3 Hours About This Sunset Cruise allows access to the best locations in the Low Country to enjoy the breathtaking views. With the sunset on one side of the boat and a view of the...

Dolphin & Nature Cruise

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

meeting_point: Broad Creek Marina description: *Opportunity to see bottlenose dolphins, river otters and special species of birds! March through October.* ___________________________________ Duration 1.5...

PVT Shark Tooth 12p

description: Discover Shark Tooth Island! ___ Description Enjoy a boat cruise from Hilton Head Island through the back waterways to Shark Tooth Island (near Savannah, Georgia) where you can hunt for shells, shark teeth and other ocean...

Strand Feeding Tour

Cross Island Cruises

Book online
$329.00

description: Join your Captain on a private excursion in the back waters of the salt marsh as we look for dolphins strand feeding. Duration 2 Hours Rates **Private Charter:** $329 About Get up close and personal watching these amazing...

Fireworks Cruise

Island Time Charters

Book online
$425.00

Duration 2 Hours About This Fireworks Cruise provides a front row seat to one of our Island's most popular events! Enjoy the sunset while dolphin watching and taking in the beauty of the salt marsh ecosystem then stay on board with the best...

Weekday 9:30am-3:30pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekday - Golf Cart Rental 9:30am - 3:30pm *Must have valid Driver's License to rent a cart.*

Two Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$345.00 - $525.00

description: Golf Cart Rentals! Duration 2 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

PB Heritage Shuttle

meeting_point: Palmetto Bluff description: Roundtrip shuttle from Palmetto Bluff to Harbour Town by boat for the Heritage Golf Tournament. Please call Reservations at 843-686-6996 for private options. Limited spots available.

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: Duration 3 Hours About Learn the secrets of Hilton Head’s history and the fascinating stories that bring it to life. This 3-hour expert guided tour takes you to five nearby historic sites in an air-conditioned bus. You will...

4 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours...

Private Sunset Sail

BC2 - Island Head

Book online
$1,400.00 - $4,400.00

duration: 2-6 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Baby Gear Rental Package • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$190.00 - $235.00

description: Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 48 Hours About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby...

Lighthouse Admission

Harbour Town Lighthouse

Book online
$8.00

description: Climb Through Time & Explore The History of the Island! Duration All Day Admission Open everyday 10 a.m. to sundown. About Climb 114 steps as you travel through Hilton Head Island history. Explore the Island’s rich history...

Kayak Rentals (Please call if unsure about booking a Guided Tour versus a Kayak Rental)

description: Kayak unguided if you have kayaking experience. We will go over the area with you, tell you about the dolphins favorite spots to hang out and answer any questions that a you have before departure. Of course our guided tours are...

SPECIAL / Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$200.00 - $250.00

duration: 1.75 hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. max_age: 1000 group_size: Up to 6 guests accessibility: Two, 8" steps down into...

Vanishing Island Expedition™ - Three Hour

Island Life Rentals and Tours

Book online
$65.00 - $780.00

duration: 3 Hours group_size: 12 - 14 Max description: Our Three-Hour Beach Combing Expedition to "Vanishing Island™" starts at The Old Oyster Factory docks near the top of Broad Creek. As we glide through the Lowcountry Salt Marsh, you'll watch...

Four Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$645.00 - $935.00

description: Golf Cart Rentals! Duration 4 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

One Week Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$59.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Sunset Beach Photography

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations may be rescheduled or fully refunded if no suitable time is found meeting_point: 64 Bradley Beach Road, Hilton Head Island, SC 29928 description: Want to commemorate a special...

Sunset Dolphin Tour

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 1 max_age: 99 group_size: Maximum 48...

One Week Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$225.99 - $299.99

description: Single Kayak Full Day Rental: $225.99 ________________________________ Double Kayaks Full Day Rental: $299.99

Happy Hour Cruise

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane pricing: $75 per adult (adults only) description: Set sail for the perfect start to your evening with Outside Hilton Head’s adults-only Happy Hour Cruise aboard...

Ohana Low Country Paddle Festival VIP Cruise

description: Saturday, September 6th 8:30-11 am Meets at: Rowing and Sailing Center at Squire Pope Community Park 137 Squire Pope Rd, Hilton Head Island SC 29926 The cruise will include: -Custom Pickney Island circumnavigation on the luxury...

Stella

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

Luxury Pontoon Rental with Fireworks Experience

description: Fireworks Pontoon Party Boat Rental and private VIP box for Harbourfest Fireworks Show! Captain your own adventure as you head out on a 2-hour self-guided cruise on a luxurious Bentley pontoon boat. Return to Shelter Cove Marina no...

Seas The Moment Public Afternoon Sail

Anchors Away Sailing Charters

Book online
$120.00

meeting_point: Hilton Head Island, SC description: *Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with...

PB Full Moon Kayak Nature Tour
Book online
$115.00 - $230.00

description: *Explore the Lowcountry waters by the light of the moon!* __________ About A beautiful and serene nature tour, in the moonlight, along the pristine May River. No kayak experience is necessary. _________ Duration 2 hours

Baby Gear Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $175.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 7 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

PB Private Pedego Tour
Book online
$130.00 - $425.00

meeting_point: Palmetto Bluff

Glow in the Dark Splatter Party! - Basic
Book online
$45.00 - $550.00

duration: 1.5 hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: It’s your invite to light up the night and vibe out with your crew! Experience the thrill of our glow-in-the-dark parties...

Valentine's Day Carriage Rides

Brice Herndon Draft Horse and Carriage Company

Book online
$100.00

description: A Fairytale Valentine's Day: Take Your Sweetheart on a Magical Carriage Ride. We will start from the north side of Union Point Park . Each ride is approximately 18 to 20 minutes long. The carriage will comfortably hold 4 adults and...

Sunset & Fireworks Dolphin Tour

Lowcountry Watersports

Book online
$15.00 - $59.99

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 1 max_age: 99 group_size: Maximum 48...

Memberships

The South Carolina Railroad Museum

Book online
$20.00 - $400.00

pricing: - **Family (4 People) Membership:** $50.00 - **Individual Membership:** $30.00 - **Senior (62+) Membership:** $25.00 description: When you join as a member of the South Carolina Railroad Museum, you’re ensuring our museum and railway are...

PB Electric Bike Rentals
Book online
$20.00 - $400.00

meeting_point: Palmetto Bluff

DI 4 Hour Ultimate Lowcountry Day

meeting_point: Daufuskie Island, SC description: *Customized adventures are the best way to see and do the Lowcountry!* Description Designed for the family or small group interested in experiencing an authentic day in coastal Carolina. We...

Two Month Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$250.99 - $431.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Private Morning Sail and Dolphin watch on Knot The Office
Book online
$315.00 - $395.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 passengers accessibility: Limited Handicap accessibility, Please call us to ensure we...

PB Private Daufuskie Island Tour - 6 passenger

description: *Catch a glimpse into a fascinating chapter of Lowcountry history* --- Description Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This trip provides a glimpse into a...

Black & Blue Fishing Charters

Black & Blue Charters

Book online
$425.00 - $1,700.00

description: Black & Blue Duration & Rates **Three Hour Fishing Charter** - $625.00 *Will catch mostly sharks* **Four Hour Fishing Charter** - $750.00 *Most popular for families* **Five Hour Fishing Charter** - $900.00 *Catch your...

Pony Rides

Daufuskie Marsh Tacky Society

Book online
$10.00

description: Duration 10 minutes About Do you have a child that's either totally horse crazy or slightly horse curious who would delight in a chance to sit in the saddle? Allow us to provide a memorable, confidence building experience while...

Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $950.00

description: This trip is great for kids or anyone who wants a little taste of Lowcountry fishing! **If you don't see a time on the calendar that works for you, text us at 843-422-5438 to see if we can accommodate you!** Duration 2 to 6...

Blue Angel Airshow Harbor Cruise

Charleston Water Taxi

Book online
$65.00 - $75.00

duration: 1.5 Hours description: Departure is from Charleston Harbor Resort & Marina, A Dock. Guests are welcome to bring their own drinks (no glass bottles permitted). Please plan to arrive at least 30 minutes early to allow time for parking at the...

2-Hour Day Sail

BC2 - Island Head

Book online
$19.99 - $49.99

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Private Sunset & Fireworks Cruise - 16p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Holiday Market

Coastal Discovery Museum Hilton Head

Book online
$1,095.00

description: Holiday Market - November 25,2025 10AM- 1PM We will have local authors and artists on site as well as food tastings. Buy a special gift for your special someone for the holidays.

One Hour Sunset/Dolphin Cruise

Lowcountry Cowboy Fishing Charters

Book online
$40.00

duration: 1 hour meeting_point: Lowcountry Cowboy Fishing Charters description: Hilton Head has a ton of dolphins, and we wont come back to the dock until you see some! The sunsets are world class too! It's the perfect way to spend an hour enjoying...

Boomerang Private Charter Fishing
Book online
$540.00 - $640.00

meeting_point: Palmetto Bay Marina description: Rate **Three Hour** - $540 **Four Hour** - $630 About The Boomerang 2 is a comfortable 28 foot Parker center console that is powered by two brand new Suzuki outboards. We specialize in fun...

Stand Up Paddle Board Rental

Forest Beach Surf & Cycle

Book online
$60.00 - $200.00

description: Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island SUP rentals

Three Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$40.00 - $150.00

description: Electric Bike Rental Duration 3 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

SC Pimento Cheese Festival Merch
Book online
$2.00 - $18.00

Adopt-a-Dolphin

Coastal Discovery Museum

Book online
$50.00 - $100.00

description: About Sixty percent of all adoption money goes directly to the scientists who are studying these magnificent mammals and helps fund interns studying these dolphins, boat fuel, and supplies needed for the Marine Sensory and...

Trail Rides Experience - Palmetto Bluff Members

duration: 1.5 hours meeting_point: Longfield Stables Trail Barn min_age: 8 group_size: Up to 5 people description: Embark on an unforgettable experience through the scenic Lowcountry of Palmetto Bluff. Our expertly guided rides take you through...

Pirate Cruise

Pirates HHI

Book online
$10.00 - $39.99

duration: 1.5 Hours cancellation_summary: Full Refunds are issued with 48 hours advanced notice meeting_point: 86 Helmsman Way, Hilton Head, SC 29928 - Check In at the Lowcountry Watersports Office to the left of Black Marlin Restaurant pricing...