Anchors Away Sailing Charters

10/06/2026

Great list for all of our Halloween Fun, come see why fall is a great time to be on Hilton Head! And while you’re here… join us for some great sailing!!!

THERE IS SOOO MUCH going on in October; we had to make two posts to cover it all!

🎃👻 HALLOWEEN EVENTS & ACTIVITIES AROUND HILTON HEAD! 👻🎃

Looking for some spooky fun around Hilton Head and Bluffton? From pumpkin patches and trick-or-treating to costume contests, wagon rides, pet parties and even a spooky cruise, there’s plenty happening as we head toward Halloween!

👉 SAVE this post so you have the dates handy and SHARE it with someone looking for Halloween fun!

📅 OCTOBER 23

🎃 Island Rec Pumpkin Patch | 4–7 PM
📍 Shelter Cove Community Park
FREE pumpkins, bounce houses, games and a costume contest!

👻 6th Annual Bluffton Safety Spooktacular | 5–7 PM
📍 Oscar Frazier Park, Bluffton
Tons of family fun, candy, costumes and more!

📅 OCTOBER 24

🧀 Not Halloween, but... Hilton Head Mac & Cheese Festival! | 5–8 PM
📍 Lincoln & South Brewing Company
Take a break from the candy and enjoy some seriously good mac & cheese!

🎃 Halloween Wagon Rides | Starting at 10 AM
📍 Heritage Farm in Sea Pines / Forest Preserve
Celebrate the season with a festive wagon ride through Sea Pines.

📅 OCTOBER 25

👻 Halloween on the Harbour | 1:30–3:30 PM
📍 Harbour Town
Activities, games, trick-or-treating and a Halloween fashion show! Be sure to bring your costumes.

🐶🎃 Hilton Head Humane Halloween Party
📍 10 Humane Way, Hilton Head Island
Music, games, treats and a costume contest for BOTH people and pets!

📅 OCTOBER 29

🍬 Halloween at Coligny
📍 Coligny Plaza
Trick-or-treating plus costume contests for kids, adults, families AND pets!

👻 Old Town Bluffton Trick or Treat | 6–9 PM
📍 Old Town Bluffton
Put on your costumes and head to Old Town for an evening of Halloween fun and trick-or-treating!

📅 OCTOBER 30

📚👻 Haunted Maze of Authors | 6–8 PM
📍 Emry’s Bookshop — 95 Mathews Drive, Suite A5, Hilton Head Island
Costume contest, trick-or-treating, drinks, snacks and a spooky literary twist!

📅 HALLOWEEN — OCTOBER 31! 🎃

🍭 Tanger BOO Bash | 1–3 PM
📍 1414 Fording Island Road, Bluffton
Candy, festive fall fun and your chance to show off your costume in the Wicked Best Dressed Contest!

⛵👻 Salty Dog Spooky Cruise | 5–7 PM
Food, costumes and Halloween fun on the water, including a costume contest!

🧟‍♂️ Haunted Hospital Halloween Party | 9 PM
📍 Rooftop at Poseidon
Looking for some adults-only Halloween fun? Head to the Rooftop for a full night of Halloween chaos with a DJ and costume contest!

🎃 There’s no shortage of Halloween fun around Hilton Head & Bluffton this year!

👉 SAVE this list so you don’t miss your favorites.
👉 TAG someone you want to celebrate Halloween with!
👉 SHARE this post with friends and families visiting the island.
👉 FOLLOW The Best of Hilton Head for more events, things to do, restaurants, discounts and Hilton Head tips.

🌴 www.thebestofhiltonhead.com

Event dates, times and details can change, so we recommend confirming with the event organizer before heading out.

10/02/2026

Lots of great things happening in October, come out and enjoy some of the best sailing we do all year long over the next month in a half!!

🍂 WHAT’S HAPPENING AROUND HILTON HEAD THIS OCTOBER? 🎃

October is packed with festivals, live music, great food, family fun, and Lowcountry culture! Save this post so you don’t miss what’s happening around Hilton Head and Bluffton this month.

📅 OCTOBER 2

🎣 Community Fishing Night | 5–7 PM
📍 Hilton Head Island Fishing Cooperative Park
Hosted by Island Rec. Enjoy an evening of community fishing fun!

🎶 Bluffton Music Series | 5:30–7:30 PM
📍 Buckwalter Place Park
Kick off October with an evening of live music in Bluffton.

🦐 OCTOBER 2–3 — Beaufort Shrimp Festival
📍 Henry C. Chambers Waterfront Park, Beaufort
Plenty of shrimp, live music, festivities and more along the beautiful Beaufort waterfront.

📅 OCTOBER 3

🍂 The Sandbox Fall Fest & Market | 11 AM–3 PM
📍 The Sandbox
A fun fall celebration and market for the family.

🎶 Fish & Grits Music Festival
📍 Lowcountry Celebration Park
Celebrate Gullah Geechee food, music, art and culture!

🐶 Hounds on the Harbour
📍 Harbour Town
A dog-friendly event featuring fun activities and adoptable dogs from Hilton Head Humane.

📅 OCTOBER 4

🍺 Oktoberfest at Rollers W**e & Spirits
Live music, Bavarian-inspired food, games and Oktoberfest fun!

🐐 OCTOBER 8–9 — Isla J Farms Zoo Sanctuary
Meet and interact with exotic and barnyard animals.

🎨🦐 OCTOBER 9–18 — Bluffton Arts & Seafood Festival
📍 Old Town Bluffton
One of the Lowcountry’s signature fall festivals!

⭐ Street Fest: October 17–18
Enjoy vendors, food trucks, art and plenty to explore throughout Old Town Bluffton.

📅 OCTOBER 10

🍔 Slider Showdown
📍 Lowcountry Celebration Park
Come hungry for a day dedicated to delicious sliders!

📅 OCTOBER 14

🎭 Crescendo Celebration
📍 Shelter Cove Community Park
Celebrate Hilton Head’s vibrant arts and cultural community.

📅 OCTOBER 16

🎻 Symphony Under the Stars
📍 Lowcountry Celebration Park
A special evening under the stars featuring a tribute to Harry Belafonte.

🍺 Top Dawg Oktoberfest | 5–7 PM
📍 Top Dawg Tavern & Pizzeria
Celebrate Oktoberfest with food, drinks and fun.

📅 OCTOBER 17

🇮🇹 Italian Heritage Festival
📍 Honey Horn
Food, entertainment, vendors, kids’ activities and the always-popular grape-stomping contest!

🌴 Gullah Food Festival
📍 Gullah Museum
Experience Gullah culture through food, music and storytelling.

📅 OCTOBER 18

🔥🎸 Rock N Ribs
📍 Coligny Plaza
Barbecue + live music featuring Cowboy Mouth & Cranford Hollow!

OF COURSE, ALL kinds of Halloween happenings, but that will be in a later post!!!

🍁 October is one of the BEST times to be in the Lowcountry!

👉 SAVE this post so you have the list handy.
👉 SHARE it with someone coming to Hilton Head this October.
👉 FOLLOW The Best of Hilton Head for more local events, things to do, restaurants, discounts and Hilton Head tips.

08/08/2026

We would love for one of our great customers to win this Sail!

🍂 YOU HAVE A GREAT CHANCE TO WIN! 🍂

If you've been thinking about entering our Fall Giveaway, now is the time!

Unlike most giveaways, we're choosing SIX different winners, so your chances of winning are much better than a typical online giveaway.

🎉 6 Amazing Prizes
🏆 6 Different Winners
❤️ One of those winners could be YOU!

If you could only win ONE of these incredible local experiences, which would it be?

🎭 Comedy Magic Cabaret – 4 Tickets

🏌️ Pirate's Island Adventure Golf of Hilton Head Island – 4 Tickets

⛵ Anchors Away Sailing Charters – Private Sail for up to 6 People

💆 Fountain Spa- Massage, Facial, & Relaxation Services Hilton Head Island, SC – Island Renewal Facial

🍫 MilkShake Factory – Gourmet Chocolate Bark Box

🎨 Creative Escapes Art Cafe – Large Family Pour

If you won, who would you bring with you? Tag that person below! 👇
Each of the following will give you one entry:

Follow The Best of Hilton Head

❤️ Like the original giveaway post

🔄 Share the original giveaway post

💬 Comment on the original giveaway post with the prize(s) you'd like to win and tag that business.

📅 Winners will be announced Friday, August 14!

Good luck, everyone, and thank you for supporting these incredible local businesses that help make Hilton Head Island such a special place to visit! 🍂❤️

08/04/2026

🍂 FALL GIVEAWAY #1 IS HERE! 🍂

Fall is the BEST time to visit Hilton Head Island... and we're making your trip even better!

We're excited to kick off the first of TWO Fall Giveaways, featuring over $1,200 in amazing local experiences and prizes! 🎉

🎁 6 lucky winners will each receive ONE incredible prize!

🏆 Choose from:

🎭 Comedy Magic Cabaret – 4 Tickets for an unforgettable "Fun, Not Filthy" night of comedy, magic, and audience participation.

🏌️ Pirate's Island Adventure Golf of Hilton Head Island – 4 Tickets for a round of family-friendly mini golf at one of Hilton Head's favorite attractions.

⛵ Anchors Away Sailing Charters – A Private Day Sail for up to 6 people aboard a beautiful sailing yacht. Relax, spot dolphins, and experience Hilton Head from the water.

💆 Fountain Spa- Massage, Facial, & Relaxation Services Hilton Head Island, SC – An Island Renewal Facial, a deep-cleansing treatment designed to cleanse, exfoliate, extract, and moisturize your skin for a fresh, vibrant complexion. Includes a relaxing scalp, neck, and shoulder massage (50 minutes).

🍫 MilkShake Factory – A delicious Gourmet Chocolate Bark Box of your choice.

🎨 Creative Escapes Art Cafe – A Large Family Pour where you'll create a beautiful piece of fluid art to take home.

🍁 HOW TO ENTER

✅ Follow The Best of Hilton Head

❤️ Like this post

🔄 Share this post

💬 Comment which prize(s) you'd like to win AND tag that business.

Feel free to comment for multiple prizes! Each prize you're interested in can be entered with its own comment.

Example:
"I'd love the Private Sail! Away Sailing Charters"

or

"Comedy Magic Cabaret!"

📅 Winners will be announced Friday, August 14!

👀 And don't forget... this is only Giveaway #1!

Stay tuned because Giveaway #2 is coming soon with even MORE incredible local prizes!

Good luck everyone, and thank you for supporting these amazing local businesses that help make Hilton Head Island such a special place to visit! ❤️🍂 Be sure to check out www.thebestofhiltonhead.com for top things to do, places to stay, eat and so much more!

07/23/2026

Very cool! Worth the visit to Savannah

07/15/2026

We may not have the best moves… but we have a lot of fun taking people out sailing!!!

07/01/2026

Reposting but great information!

Heading to the island to celebrate the 4th of July? Here are the events that are happening around the island. Most events are FREE to attend - There is a nominal fee per vehicle to get into Sea Pines.

Kicking off on July 3rd - Bluffton's Independence Day Celebration at Martin Family and Dubois Parks featuring carnival games, bounce houses, food concessions, live music from the Parris Island "Dirty Boots" Brass Band with fireworks display around 9 PM at Oyster Factory Park and Wright Family Park.

Events on the 4th
42nd Annual Firecracker 5000 starting at 8 am. This is the island's largest and oldest 5K and family fun walk. Starting at 70 Honey Horn Drive - Must pre-register https://www.hiltonheadfirecracker5000.com/

Harbour Town Parade (8:30AM - 10:30AM) A festive, patriotic parade through Sea Pines Resort led by Woody the Clydesdale, Participants are encouraged to decorate bicycles, wagons and pets.

Harbour Town Carnival (10AM - 11:30AM) located under the Liberty Oak, featuring games, a water balloon toss, tie-dye, and a watermelon eating contest.

Salute from the Shore (Approx 1:30PM) Military flyover of F-16s and vintage warbirds along the SC coastline (Best viewing from any Hilton Head beach, including Sea Pines Beach Club.

Shelter Cove Harbour Fest (6:00PM - 10PM) A massive Independence Day celebration featuring Shannon Tanner's patriotic shows (6:30PM & 8PM), Cappy the clown (6pm-9pm) and fireworks over Broad Creek at 9 pm - Be prepared to get there early and stay late as this always brings large crowds and traffic

Harbour Town Fireworks Extravaganza (approx. 9PM): Fireworks over Harbour Town Lighthouse and Calibogue sound in Sea Pines. Come early and enjoy a Gregg Russell special concert under the Liberty Oak from 8:30 to 9:30PM

OFF ISLAND -
Beaufort / Port Royal
Sands Beach (Port Royal) - Festivities take place throughout the evening with fireworks starting around 9pm

Savannah
John P Rousakis Riverfront Plaza for live music across multiple outdoor stages, food venders and activities throughout the afternoon with a massive fireworks display choreographed to patriotic music over the Savannah River starting around 9PM

While your on the Island - be sure to check out these companies for some great family fun around your holiday celebration! Find these and more at www. The Best of Hilton Head . Com
Anchors Away Sailing Charters
Hilton Head Boat Tours - Dolphin Tours and Sunset Cruises
Hilton Head Helicopter Tours
Escape Island HHI
Creative Escapes Art Cafe
Island Explorer - Hilton Head Island Dolphin and Nature Tours
MilkShake Factory
Sea Monkeys Watersports
Pirate's Island Adventure Golf of Hilton Head Island
Comedy Magic Cabaret
Hilton Head Nannies
Hilton Head Boat Rentals and Sales
Avocado Bikes

If you are planning to head out on the water for the weekend - Please note, several professional companies that do this daily, choose not to operate for safety reasons on the 4th of July. Please be Extra careful and safe out there, and ENJOY YOUR HOLIDAY WEEKEND!!!!!

06/23/2026

Hope you get to experience July on Hilton Head Island. It is something special! With so much to do, you will need to book a relaxing Sunset Sail 😁 Happy July!!!

There is no better time to be on the Island in July. There are a TON of FREE family-friendly events all month long. Check out our site for more information or to find top-rated things to do, places to eat, places to stay, and so much more!!!

06/17/2026

Only a few days until Father's Day! Give him the gift of a true sailing experience. Purchase your gift card now and receive a discounted rate! Call us today at (843)278-9553

06/15/2026

Heading to the island to celebrate the 4th of July? Here are the events that are happening around the island. Most events are FREE to attend - There is a nominal fee per vehicle to get into Sea Pines.

Kicking off on July 3rd - Bluffton's Independence Day Celebration at Martin Family and Dubois Parks featuring carnival games, bounce houses, food concessions, live music from the Parris Island "Dirty Boots" Brass Band with fireworks display around 9 PM at Oyster Factory Park and Wright Family Park.

Events on the 4th
42nd Annual Firecracker 5000 starting at 8 am. This is the island's largest and oldest 5K and family fun walk. Starting at 70 Honey Horn Drive - Must pre-register https://www.hiltonheadfirecracker5000.com/

Harbour Town Parade (8:30AM - 10:30AM) A festive, patriotic parade through Sea Pines Resort led by Woody the Clydesdale, Participants are encouraged to decorate bicycles, wagons and pets.

Harbour Town Carnival (10AM - 11:30AM) located under the Liberty Oak, featuring games, a water balloon toss, tie-dye, and a watermelon eating contest.

Salute from the Shore (Approx 1:30PM) Military flyover of F-16s and vintage warbirds along the SC coastline (Best viewing from any Hilton Head beach, including Sea Pines Beach Club.

Shelter Cove Harbour Fest (6:00PM - 10PM) A massive Independence Day celebration featuring Shannon Tanner's patriotic shows (6:30PM & 8PM), Cappy the clown (6pm-9pm) and fireworks over Broad Creek at 9 pm - Be prepared to get there early and stay late as this always brings large crowds and traffic

Harbour Town Fireworks Extravaganza (approx. 9PM): Fireworks over Harbour Town Lighthouse and Calibogue sound in Sea Pines. Come early and enjoy a Gregg Russell special concert under the Liberty Oak from 8:30 to 9:30PM

OFF ISLAND -
Beaufort / Port Royal
Sands Beach (Port Royal) - Festivities take place throughout the evening with fireworks starting around 9pm

Savannah
John P Rousakis Riverfront Plaza for live music across multiple outdoor stages, food venders and activities throughout the afternoon with a massive fireworks display choreographed to patriotic music over the Savannah River starting around 9PM

While your on the Island - be sure to check out these companies for some great family fun around your holiday celebration! Find these and more at www. The Best of Hilton Head . Com
Anchors Away Sailing Charters
Hilton Head Boat Tours - Dolphin Tours and Sunset Cruises
Hilton Head Helicopter Tours
Escape Island HHI
Creative Escapes Art Cafe
Island Explorer - Hilton Head Island Dolphin and Nature Tours
MilkShake Factory
Sea Monkeys Watersports
Pirate's Island Adventure Golf of Hilton Head Island
Comedy Magic Cabaret
Hilton Head Nannies
Hilton Head Boat Rentals and Sales
Avocado Bikes

If you are planning to head out on the water for the weekend - Please note, several professional companies that do this daily, choose not to operate for safety reasons on the 4th of July. Please be Extra careful and safe out there, and ENJOY YOUR HOLIDAY WEEKEND!!!!!