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2026 Activities Guide

Villa with saltwater pool, golf, firepit...

Summary:Windward Village 109The Space:Located on the eighth hole of the golf course, this amazing townhome is an ideal getaway for your Hilton Head hideaway. Savor close by access to a seasonal, saltwater pool, a 27-hole golf course, and hiking and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Driessen Beach Park

The postcard-worthy Driessen Beach Park is a little hard to find, and for most Hilton Head Island regulars, that's a very good thing. Seldom crowded, with plenty of parking spaces to go around, this relatively expansive park has plenty of room to...

Near Shipyard Beach | Pool, Bikes + Full...

Southwind II at Shipyard puts you in the kind of Hilton Head setting people hope to find, where golf and nature vistas replace busy roads. Shipyard Beach is about 0.8 miles away, and Coligny Beach Park is roughly 2.5 miles out for dining, shopping...

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

Nothing beats an ice-cold beverage while relaxing on the beach. Nothing is worse than reaching for an icy drink and finding your cans swimming. Coolers are essential for family days on the sand. A good modern cooler will keep food and drinks fresh...

Tropical Waterfront Oasis

Feel true island luxury in this handsomely modernized four bedroom, five bathroom lagoon-front getaway, ideally positioned on one of the widest stretches of the spectacular 11-mile lagoon system in Palmetto Dunes. Just a short walk to Palmetto...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Day Rental

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: 1 Day description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Additional Fees - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free (1 lock per 2 bikes) About - Perfect for a day...

Eleven Day Electric Bike Rental

duration: 11 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Afternoon Half Day Sail Trip On Seas the Moment - Our Newest Boat
Book online
$1,203.60 - $1,450.00

duration: 4 Hour 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 we can...

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...

Jet Ski Rental

Timberlake Marina

Book online
$250.00 - $700.00

duration: 4.5 or 8.5 Hours min_age: 23 group_size: Maximum capacity is 2 people description: There’s nothing quite like a day on Lake Murray—wide open water, sunshine reflecting off the surface, and miles of shoreline waiting to be explored. At...

Three Hour Private Inshore Charter

max_age: 99 group_size: Up to 6 guests description: Spend a day fishing Hilton Head Island waters with Captain John aboard the Sweet Pea, a 29 ft World Cat outfitted with modern electronics, tackle and an enclosed head for comfort. This inshore...

Shrimping

May River Excursions

Book online
$325.00 - $425.00

description: *Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6...

Hilton Head Plantation Kayak Club May River Kayak Tour

meeting_point: Outside Palmetto Bluff

One Week Bike Rental

Wheelz of Hilton Head

Book online
$50.00 - $210.00

description: One Week Bike Rental Rates Duration 7 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...

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...

Sail Sumo

H2O Sports

Book online
$350.00 - $450.00

duration: 1.5-2 hours cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: 1-6 people description...

Pony Rides - Montage Guests

Longfield Stables

Book online
$170.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

Bunny Eggspress      (28 March & 4 April)

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Easter each year. Riders will board the train for a 3-mile trip to the event area. We will stop the train...

Lunar Paddle at The Landing

Saluda Lake Landing

Book online
$8.00 - $60.00

duration: 2 hrs cancellation_summary: Cancellations made 48 hours or more before the event are eligible for a full refund. Cancellations made within 48 hours of the event are nonrefundable, but your ticket can be transferred to a future paddle...

Seven Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 7 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...

1.5 Hour Dolphin Tour
Book online
$15.00 - $500.00

duration: 1.5 hour tour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Lowcountry Marsh Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if reschedule cannot be arranged. meeting_point: 59 Shelter Cove Lane, Hilton Head Island, SC description: Join us along the Lowcountry...

Playing Lesson

Palmetto Dunes Golf Academy

Book online
$195.00 - $745.00

description: Duration & Rates - 2 hours - Price varies. Please call to get pricing. About Play with the Pro & learn as you go. Videos, photos & instruction notes are included. - When: Seasonal - by appointment only & course availability ...

Two day bike rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

duration: 2 days cancellation_summary: No refunds or rainchecks. meeting_point: your address min_age: 1 max_age: 99 description: Forest Beach Surf & Cycle offers two-day bike rentals on Hilton Head Island with options for kids and adults across a...

2 Hour Lane Rental

Palmetto Axes

Book online
$45.00

description: Hit the Bullseye! Duration 2 Hours About Enjoy hurling axes as your friends or family marvel in your skills. Team up to see who the best pair is or compete individually in a winner take all (the glory and bragging rights...

Holiday Market

Coastal Discovery Museum Hilton Head

Book online
$45.00

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.

Gingham Tablecloth, Bibs & Wipes
Book online
$12.95

Reptiles for Kids

Coastal Discovery Museum Hilton Head

Book online
$7.00

description: Come and meet some of the coolest critters around! ___________________________________ Duration 30 minutes ___________________________________ About Come and meet some of the coolest critters around…REPTILES! Meet and get to...

4.5 Hour Deep Sea Fishing Aboard the Drifter
Book online
$75.00 - $1,000.00

duration: 4.5 hours cancellation_summary: 48 hours meeting_point: 86 Helmsman Way. Please meet at the flag pole at the right side of the marina. pricing: Adults $85 Children 12 and under $75 description: This fishing trip will travel to an...

Museum Closed Today

Coastal Discovery Museum Hilton Head

Book online
$75.00 - $1,000.00

Sunrise Kayak Tour

Lowcountry Watersports

Book online
$45.00

duration: 1.5 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 pricing: * $45 - Adult ...

Lowcountry Lake Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if unable to reschedule meeting_point: 100 Jarvis Park Rd Hilton Head Island, SC US 29926 description: Join us at Jarvis Creek Park on...

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...

Paint the Pony - Montage Guests
Book online
$170.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

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...

12 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$85.99 - $171.99

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...

Phone Dry Bag

Lowcountry Watersports

Book online
$12.95

PB Private Freshwater Kayak Fishing

meeting_point: Palmetto Bluff, Bluffton description: *We have pioneered kayak fishing on the east coast!* ___________ About This is one of the fastest growing sports and is offered in the Inland Waterway Trails at Palmetto Bluff. The Hobie Pro...

PB Family Fishing - 10 Passenger
Book online
$1,195.00 - $1,320.00

meeting_point: Palmetto Bluff, Bluffton description: Fishing Fun for the Whole Family! _____________ This trip includes everything you need: Bait and tackle U.S. Coast Guard licensed captain and fishing guide Licensing Iced cooler ___ This trip...

Day with a Native - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

duration: 3 to 8 hours description: Choose from a range of half‑day to full‑day coastal excursions tailored to your interests—fish, hunt for shark teeth and fossils, crab like a local, paddle with dolphins in uncrowded areas, birdwatch, or...

Dolphins & Donuts

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours before the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 max_age: 99 group_size: 48 accessibility: Ramp...

Brunch Under Sail

BC2 - Island Head

Book online
$19.99 - $89.00

duration: 2 Hours meeting_point: Broad Creek Marina 18 Simmons Rd. description: A Luxury Brunch Sailing Experience Step aboard our luxury catamaran for a truly elevated morning on the water. Brunch Under Sail is a two-hour sailing experience...

Tubing and Dolphin - 12 max

meeting_point: Hilton Head Island, SC description: Family Fun With Nature, Tubing and Exploring! --- Join us for a boating and tubing tour through the Lowcountry waters! Watch for birds and dolphin through the salt marsh ecosystem and get behind...

DIG Mitchelville Archaeology Camp

Historic Mitchelville Freedom Park

Book online
$10.00 - $150.00

duration: June 22–26 | 8:30 AM–1:30 PM daily cancellation_summary: No Cancellations Available min_age: 13 max_age: 18 group_size: Max 20 Campers description: What did freedom look like — and what did it leave behind? At Dig Mitchelville...

Pilates for Pink — A Breast Cancer Donation Class

duration: 1.5 Hours meeting_point: Broad Creek Marina group_size: Maximum 12 guests description: An exclusive one-day event hosted by HHI Pilates Club. Enjoy a 90-minute pilates session on the water aboard Bonjour. 100% of the proceeds will be...

Two Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$115.99 - $160.99

description: Single Kayak Full Day Rental: $115.99 ________________________________ Double Kayaks or Canoes Full Day Rental: $160.99

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

description: Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy...

Six Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 6 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...

Revolutionary War Lecture Series

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: 1 hour cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. min_age: 13 group_size: 60 description: Join us for "Revolutionary Reflections", a...

Small Group Tasting

Honey & Thistle

Book online
$7.00

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...

Bike Rental • Six Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 6 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

HH Seafood Festival: Private Fireworks Cruise: Up to 6 guests

description: Enjoy an evening on a private sunset dolphin cruise from Shelter Cove Marina and watch the firework display from the best seat in the house. Six, Twelve and Sixteen passenger boats available. Departing Saturday February 26th from ...

Three Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$165.00 - $393.00

description: Enjoy miles and miles of scenic bike paths Duration 3 Weeks 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...

Nightly Rental.   Premium 6 Passenger Electric

meeting_point: PICK UP AND DROP OFF AT RENTAL ADDRESS ONLY description: About 48 volt electric golf cart with 2026 Lithium Battery. Equipped with seat belts, extended top, LED headlights (high and low beam), turn signals, horn, and digital...

Sport Crabbing Adventure
Book online
$10.00 - $1,000.00

description: Join us for a Sport Crabbing Adventure! Duration 1 hour 45 minutes Tour About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on vacation! Well …...

Sips, Small Bites, Starlite, and Sinatra

Kennington Family Winery

Book online
$50.00

duration: 2 Hours min_age: 21 group_size: Maximum 30 Guests description: **Join us for an evening of wine, the Synergy Twins and the stars!** *Dates for this event are: 9/4 and 9/18, event starts at 7pm.* We hope to see you...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time Each Way 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 description: Hilton Head -> Daufuskie Island...

Private Fishing Charters

Performance Fishing Charters

Book online
$525.00 - $1,400.00

description: Hilton Head’s premiere fishing charter! Duration 3-8 Hour Rentals **Up to 4 people** Possibility for 5 with children About Located on Hilton Head Island, your charter will be guided by Captain John Cloyd, a USCG...

13 Day Rental

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 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...

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...

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

Hilton Head Seafood Festival Daufuskie Island History Experience

description: Step Back in Time on Daufuskie Island Tucked between Hilton Head and the mainland, and accessible only by boat, Daufuskie Island is often described as “the other side of the river” — a hidden gem where time seems to stand still...

Thirteen Day Bike Rental

Wheelz of Hilton Head

Book online
$80.00 - $160.00

description: Thirteen Day Bike Rental Rates Duration 13 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...

Fishing Charters

Hilton Head Inshore Charters

Book online
$425.00 - $1,200.00

description: Let's Adventure! About Inshore and nearshore fishing trips. Fun for the whole family. Targeting redfish, speckled trout, jack crevalle, tarpon, cobia, sharks, and more!

Deck the Porch

Brice Herndon Draft Horse and Carriage Company

Book online
$15.00

description: Group Carriage Rides Climb aboard and stroll through our beautiful town as we harness in some of our Christmas magic. Travel along historic Hampton Street in Walterboro, known as the Front Porch of the Lowcountry and enjoy the twinkle...

Solaris - Sunset Cruise

Vagabond Cruise

Book online
$595.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates...

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...

Camellia Care

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $12.00

description: Do you love the Lowcountry’s winter rose? Come and learn how to grow and care for camellias from Coastal Discovery Museum’s Manager of Horticulture, Wendy Dickes. Learn how to choose from the over 20,000 varieties of camellias, be...

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...

All Day Kayak Rentals

Crooked Creek Kayaks

Book online
$80.00 - $100.00

duration: 8 Hours description: Unguided access begins with personalized, concierge-style recommendations designed to help you move with Jarvis Creek’s ever-changing tidal currents. Before you launch, our team will walk you through ideal routes...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Donuts with Dads

Saluda Lake Landing

Book online
$17.00 - $22.00

duration: 10am-8pm max_age: 101 group_size: 300 description: Celebrate Father’s Day Weekend at The Landing with coffee, fishing, lake days, and family memories made by the water. Join us for Donuts With Dads: Father’s Day Fish-a-Thon at Saluda...

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton...

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...

Sunset Dolphin Cruise
Book online
$45.00 - $55.00

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane pricing: $45 for children 12 and younger $55 for 13 and over description: Looking for a memorable evening on the water? Our Sunset Dolphin Cruise in Hilton Head...

Dolphin Cruise

Reel Native Fishing Charters

Book online
$65.00

description: See Dolphins Up Close! Duration 2 hours About We're committed to providing a stress-free experience to both new and returning clients. More info Minors must be accompanied by adults

Private Gullah Heritage Trail Tour Requests

Gullah Heritage Trail Tours

Book online
$28.00

description: *Gullah people are known for preserving more of their African linguistic and cultural heritage than any other African-American community in the United States.* ___________________________________ Duration 2.5 hours...

Pony Rides - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

Cooler and Ice

Lowcountry Watersports

Book online
$15.00

One Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

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.

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

description: *Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* ___________________________________ Rates are per private charter **2 Hours** - $375*-Only Recommended for Small Children* **3 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...

Two Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$35.99

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.

Private Dolphin Tour

Cross Island Cruises

Book online
$279.00

duration: 90-105 minutes meeting_point: 68 Helmsman Way group_size: Maximum 6 people pricing: $269 total, for up to 6 passengers per boat. No hidden fees! description: On a private dolphin tour, guests can expect a personalized and up-close...