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2026 Activities Guide

Family-Friendly Home w/Private Pool, Scr...

Gloucester 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Harbour Town

The unique waterfront community of Hilton Head's Harbour Town features a world of activities that are sure to wow and engage visitors of all interests, all while providing a spectacular view of the neighborhood's "harbor," and the adjoining...

Tuscan-Style Waterfront Retreat!

Welcome to your Mediterranean dream home! A beautiful Tuscan-style getaway ideally located along the relaxing 11-mile lagoon. This extravagant residence features four cavernous bedrooms, a additional bunk room, and a entirely air-conditioned private...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Hilton Head, SC Fishing Guide

Hilton Head Island, South Carolina is a popular vacation destination known for its pristine beaches, lush forests, and abundant wildlife. But did you know that it's also one of the best places to go fishing in the Southeast? Whether you're a...

Totally Updated Three Bedroom Golf Cours...

An astounding example of rental villa perfection! This marvelous three bedroom villa has been completely refreshed from the walls in and redesigned with materials of the highest quality with no expense spared and an extraordinary attention to...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
PB Private SUP Instruction
Book online
$75.00 - $325.00

meeting_point: Palmetto Bluff, Bluffton description: *Get on the water with one of our custom kayak tours & classes* Outside Palmetto Bluff has a professional staff of Instructors ready to help you enjoy the fun, fitness and beauty of the...

Santa’s Twilight Express

The South Carolina Railroad Museum

Book online
$27.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual twilight holiday ride. Santa walks through the train and comes to you—no lines! As we travel down the tracks, the...

Nine Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $295.00

description: Electric Bike Rental Duration 9 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...

2.5 Hour Firework Tour

Hilton Head Island Tours

Book online
$425.00

description: *Learn about our Coastal Ecology on our 2hr Private Crabbing Excursion!* ___________________________________ Rates **Private Charter** - $425.00 *(Up to 6 passengers)* ***All ages welcome! | Maximum of 1200...

Five Hour Private Nearshore Charter

max_age: 99 group_size: For up to 6 guests description: Fish the productive waters around Hilton Head Island with Captain John aboard the Sweet Pea, a fully equipped 29 ft. World Cat. Depending on the season, your trip may target cobia, bull...

Two Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

description: Enjoy miles and miles of scenic bike paths Duration 2 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...

Family Fishing

Outside

Book online
$495.00 - $625.00

meeting_point: Hilton Head Island, SC description: Family, Fishing, Fun! This 3-hour private Hilton Head Island fishing charter is great for families with kids and beginners! Catch and release only. Our family fishing charters include boat, bait...

Sunset Cruise - One Hour

Island Life Rentals and Tours

Book online
$40.00 - $250.00

duration: 1 Hour cancellation_summary: 24 Hours in advance group_size: 12 to 14 description: See dolphins up close! About Our one hour Sunset Cruise is a great introduction to Hilton Head Island's beautiful salt marsh environment and dolphin...

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...

Small Group Tasting

Honey & Thistle

Book online
$895.00

duration: 1 Hour min_age: 21 group_size: 6-10 people 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...

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

Echaw Creek Tour

Nature Adventures Outfitters

Book online
$52.00 - $104.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Bike Rental • Four Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 4 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Hilton Head Yacht Cruise

Salt Shaker Charter LLC

Book online
$3,750.00 - $6,600.00

duration: 4 - 8 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Your Cruise, Completely Customized! At Salt Shaker Charter, every cruise is tailored to you. From intimate getaways to...

Beach Discovery Walk

Hilton Head Island Recreation Association

Book online
$5.00 - $24.00

duration: 1.5hrs meeting_point: Fish Haul Beach Park group_size: Up to 25ppl description: Explore the amazing beach front eco-system from the tides to the shoreline and all the creatures that call this home!  You’ll be amazed by what we...

Hilton Head Yacht Cruise/Anchor/Swim

Salt Shaker Charter LLC

Book online
$4,250.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: An Evening Aboard Salt Shaker: Gourmet Dining Meets Sunset Serenity! Aboard Salt Shaker, every moment is...

Private Sunset & Fireworks Cruise - 12p

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...

13 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 Days 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 self pick up and drop off available...

Fishing Charter

Reel Native Fishing Charters

Book online
$350.00 - $1,150.00

description: Let's get out on the water and makes some memories that will last a lifetime! Rates & Duration - 2 Hour Charter • $350 - 3 Hour Charter • $475 - 4 Hour Charter • $575 - 5 Hour Charter • $700 - 6 Hour Charter • $875 - 8...

Four Hour Private Inshore/Nearshore Charter

group_size: Up to 6 guests description: Experience inshore to nearshore fishing around Hilton Head Island aboard the 29ft World Cat "Sweet Pea." Fish for seasonal species such as cobia, bull reds, king mackerel, tarpon, and sharks while an...

Gift Card

Island Skiff Adventure Tours

Book online
$800.00

Guided Tours

Historic Mitchelville Freedom Park

Book online
$10.00

duration: Approximately 45min description: Step back in time and immerse yourself in the rich history of the first self-governed town of formerly enslaved people in America. At Historic Mitchelville Freedom Park, our guided tours offer visitors an...

Four Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$600.00

description: Duration 4 Hours ___________________________________ About *Most Popular* Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, King Mackerel, Cobia, Triple Tail, Sharks! (Species Depend On Season, Tide ...

Holiday Market

Coastal Discovery Museum Hilton Head

Book online
$600.00

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.

Beginners Rowing

Hilton Head Island Recreation Association

Book online
$100.00

duration: 4 Weeks • 1 Day Per Week meeting_point: Rowing and Sailing Center min_age: 12 max_age: 18 group_size: Up to 12 Campers description: Learn the basics of rowing. We use 1-4 person shells (boats) and will teach participants basic sculling...

Gift Card

Anchors Away Sailing Charters

Book online
$100.00

description: Purchase a gift card for a friend!

Dolphin Strand Feeding Expedition

Dolphin Discoveries Hilton Head

Book online
$395.00 - $445.00

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 - Hilton Head, SC | Meet at the end of the...

PB Private Stand Up Nature Walk
Book online
$95.00 - $325.00

description: *Stand-up paddleboarding is easy to learn, a fantastic workout, and lots of fun!* _____________ _____________ About Take a naturalist guided stand up paddle tour of the coastal salt marsh. An unbelievable perspective! ...

Private Charter to Daufuskie

Daufuskie Difference

Book online
$350.00

meeting_point: Hilton Head description: Now Offering Private Boat Charters for Hilton Head Island. Get outside and enjoy a Dolphin Nature Cruise, Brunch or Lunch, or any of our other great Charter Options.

Family Game Night at The Landing

Saluda Lake Landing

Book online
$350.00

duration: 3 hours max_age: 101 group_size: 50 description: Looking for a night of laughs, friendly competition, and quality time with family and friends? ????✨ Join us at Saluda Lake Landing on Sunday, October 19th from 5–8 PM for Fun Family...

12 Day Rental

Island Life Rentals and Tours

Book online
$48.00 - $335.00

duration: 12 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...

Two Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$380.00

description: Duration 2 Hours ___________________________________ About Learn about fishing, catch sharks and other species and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

6 Day Rental

Island Life Rentals and Tours

Book online
$30.00 - $215.00

duration: 6 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...

Cooler and Ice

Lowcountry Watersports

Book online
$15.00

Body Board Rental

Forest Beach Surf & Cycle

Book online
$40.00

description: Rent with us! Duration 1 week About Forest beach surf & cycle is your source for Hilton Head Island body board rentals!

Go Try Archery

Hilton Head Island Recreation Association

Book online
$30.00

duration: 2 Hours meeting_point: Mid-Island Tract group_size: Up to 30 people description: Take aim at Hilton Head's first-ever Try Archery Event! Outdoor Rec's USA Archery certified instructors will provide you with basic instructions to try...

Bee Inspired: Celebrating World Bee Day in the Lowcountry

Coastal Discovery Museum Hilton Head

Book online
$10.00

duration: 1.5 cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: To mark...

Family Golf Class

Palmetto Dunes Golf Academy

Book online
$1,690.00

Duration & Rates - Three days, two hours of private lessons daily - $1,690 per family About The Family Golf School is a custom program of golf instruction designed to fit a family's needs and skill level. The schedule is flexible, allowing time...

Behind-the-Scenes Series

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $20.00

meeting_point: Coastal Discovery Museum description: Take a peek behind the scenes at the Coastal Discovery Museum and get an up-close look at various areas of the museum and Honey Horn grounds with an experienced staff member. These exclusive tours...

Private Lesson with Edward Sires

Palmetto Dunes Golf Academy

Book online
$110.00 - $550.00

About Edward Sires A Charleston, S.C., native, Edward Sires caddied for Ryder Cup Captain Tom Lehman in 1982 and 1983. He earned a Class A certificate from the PGA in 1997 and has taught the James Island High School Golf Team from 2002 to 2006. He...

Trail Rides Experience - Montage Guests

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...

Two Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$110.00 - $262.00

description: Enjoy miles and miles of scenic bike paths Duration 2 Weeks About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals - please select during...

Six Day Bike Rental

Wheelz of Hilton Head

Book online
$48.00 - $96.00

description: Six Day Bike Rental Rates Duration 6 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect getting...

Birthday Parties and Private Events
Book online
$75.00 - $275.00

Give your child their best birthday yet! Rates - **Party Package Option A (includes 10 guests in the base price)** - $275 - **Party Package Option B (no guests included in the base price)** - $75 **Please contact us directly at 843-835-5912...

Private Sunset Cruise (Up to 14 Passengers)
Book online
$549.00 - $899.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers description: The private sunset...

PB 2 Hour May River Kayak Nature & History Paddle

meeting_point: Palmetto Bluff, Bluffton description: On this casual tour, you'll explore the local creeks with a naturalist guide. No kayak experience is necessary. Duration 2 hours Meeting Location - This activity will meet at the Paddle...

Palmetto Bluff

Flip Flop Charters

Book online
$625.00 - $750.00

Beautiful Scenery Duration - 3 hours - 4 hours About Nestled on the scenic May River is Palmetto Bluff, an idyllic community on 20,000 acres. Within the community is an extensive nature preserve, private residences, a hotel, several...

Shark Fishing Aboard the Drifter
Book online
$60.00 - $70.00

duration: 30 minutes (travel time) cancellation_summary: 48 hours meeting_point: 86 Helmsman Way. Please meet at the flag pole at the right side of the marina. group_size: Number of passengers is limited pricing: * Adults: $70 * Children 12 and...

PB Palmetto Bluff Pedego Bike Tour

meeting_point: Palmetto Bluff, Bluffton description: About There is no better way to discover Palmetto Bluff than on a comfortable seat of a Pedego electric bike. Pedego electric bikes allow riders to travel farther and faster, and breeze through...

General Admission

Bee City Zoo

Book online
$17.00 - $19.00

Come explore our honeybee farm, interactive zoo, gift shop, cafe, nature trail, & nature center! Duration General Admission tickets are good for an *entire* day at the zoo! Please note you can always purchase tickets the day of your visit at...

Private Sunset Sail and dolphin watch on Seas The Moment - newest vessel

duration: 2–2.5 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure...

11 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$45.00 - $315.00

duration: 11 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...

Marriott Vacation Club Dolphin Eco

meeting_point: Hilton Head Island, SC description: Outside Hilton Head’s Dolphin Eco Tour is one of the most popular tours on Hilton Head Island, providing an unforgettable experience for nature lovers, families, and anyone looking for a fun and...

One Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Blue Granite Express

The South Carolina Railroad Museum

Book online
$19.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Guests enjoy a narrated 90-minute trip through Fairfield County countryside. Seating on the train is on board an open-air car, allowing easy viewing as...

Saint Helena Sunset Sail

Otter Sailing Adventures LLC

Book online
$375.00

description: There's nothing like experiencing the magic of a sunset under sail in the beauty of the St Helena sound Duration 2 hours About Private Sailing Charter - Price Per Group (up to 6) There's nothing like experiencing the...

21 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$75.00 - $555.00

duration: 21 Days cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

Powerboat Dolphin and Monkey Adventure

Otter Sailing Adventures LLC

Book online
$300.00

duration: 2 hours meeting_point: Saint Helena Island SC (exact location will be emailed) description: Hop on our 17’ Boston Whaler powerboat for an amazing low country adventure where we explore the creeks and rivers of the Saint Helena Sound...

One Week Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$41.99

description: Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Curator's Tour

Coastal Discovery Museum Hilton Head

Book online
$41.99

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg and...

One Week Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99

description: Rate 7 Day Rental: $149.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration One Week (7 Days)

Face Painting

Coastal Discovery Museum Hilton Head

Book online
$10.00

duration: 2 meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: Join us for a colorful and creative Face Painting experience! From fierce sharks to magical butterflies, our talented artist will bring Lowcountry critter...

One Week Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$225.99 - $350.00

description: Single Kayak Full Day Rental: $275 ________________________________ Double Kayaks Full Day Rental: $375

Two Day Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$29.99

description: The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

Daylight Bike Rental

Wheelz of Hilton Head

Book online
$20.00 - $45.00

description: Half Day Bike Rental Rates Duration 4 hours Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Three Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$660.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a...

Hilton Head Yacht - Lunch Cruise

Salt Shaker Charter LLC

Book online
$4,250.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Midday Magic Aboard Salt Shaker: Sunshine, Sea Breezes & a Delicious Lunch on the Water! Aboard Salt Shaker, every moment is...

Gift Cards

Shelter Cove Marina Boat Rentals

Book online
$4,250.00

Reptile Meet & Greet

Port Royal Sound Foundation

Book online
$10.00

description: Meet and greet the reptiles in the Maritime Center. Duration 1 Hour About Join our Naturalists for an educational program about the reptiles of the Lowcountry. This program will teach you what makes a reptile a reptile along...

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

Beaufort Lands End Paddling

Book online
$40.00 - $60.00

duration: 1.5-2 hours meeting_point: Russ Point Boat Landing, Sea Island Pkwy & Fripp Island Bridge (across from Nature Center) description: Join us for a one-of-a-kind kayak adventure, perfectly timed with the high-tide, offering exclusive access...

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

5 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$27.00 - $195.00

duration: 5 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...

Guided Paddleboard Tour

Island Head- Hilton Head Harbor

Book online
$40.00

description: *Be one with the water* ___________________________________ Rates **Person:** $40 *Ages 12+* ___________________________________ Duration 1 hour ___________________________________ About Stand Up Paddleboarding focuses on...

Family Shell Hunt & Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75 - $319.00

duration: 1.75 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...

Full Day Flats Fishing (8 Hrs)

Green Heron Adventures

Book online
$850.00

meeting_point: Beaufort or Hilton Head/Bluffton, SC description: Duration 8 Hours About Full day trips give you the opportunity to fish and experience the full range of our 8.5 foot average tide swings. For anglers interested in a full day of...

Two Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$42.99 - $85.99

description: Two Day Rental Rates: - 16” Kids Beach Bike: $42.99 - 20” Kids Beach Bike $42.99 - 24” Youth Beach Bike: $42.99 - 26” Bike w/ Child Seat: $57.99 - 26” Mens Beach Bike: $42.99 - 26” Unisex Beach Bike: $42.99 - 12" Balance...