Best Things to Do in the Lowcountry in May 2025

Events, Breakfast Spots, Rosé Picks & Real Estate Tips with The Cobb Group

Looking for fun things to do in Hilton Head, Bluffton, Beaufort, Charleston, or Savannah this May? We’ve got your complete guide to Lowcountry events, eats, lifestyle inspiration, and real estate tips—curated by local experts at The Cobb Group, brokered by eXp Luxury Realty. Allison Cobb & her team know this area like the back of their hands and are excited to share all that May has to offer. 


???? What to Expect This May

  • Weather: High 70s to low 80s, breezy and beautiful

  • Sunset: After 8 PM—ideal for dockside dining and evening strolls

  • Garden Tip: Plant tomatoes, peppers, basil & okra this month

  • Lunar Note: Full Flower Moon rises on May 12


???? May 2025 Events & Festivals in the Lowcountry

Bluffton
  • Mayfest (May 10) – Art, food, and the Ugly Dog Contest

  • Bluffton Sunset Party (May 17) – Music and food trucks along the river

  • Farmers Market – Every Thursday in Old Town

Hilton Head Island
  • Hilton Head Art Festival (May 23–25) – Shelter Cove

  • Gregg Russell Concerts (May 22–24) – Family fun under the Liberty Oak

  • Music & Taste on the Harbour – Thursdays in May

Beaufort
  • A Taste of Beaufort (May 2–3) – Local bites + live music

  • Original Gullah Festival (May 23–25) – Culture, heritage, and art

  • Memory Matters Gala (May 22) – An evening of giving back

Charleston
  • Spoleto Festival USA (May 23–June 8) – Theater, opera, jazz & more

  • The Prosecco Party (May 17) – Rooftop bubbles at The Salty Dog Café

Savannah
  • SCAD Sand Arts Festival (May 2) – Epic sand sculpture on Tybee Island

  • Roddy Ricch Wine Dinner (May 14) – Perry Lane Hotel

  • Street Music on Paris Avenue (May 17 & 31) – Free live music in Port Royal


☕ Top Breakfast Spots in Bluffton & Hilton Head Island

Watusi Café – Try the coconut French toast or shrimp & grits at Coligny Beach
Social Bakery – Marina views and a pain suisse you’ll dream about
Palmetto Bay Sunrise Café – Crab cake benedict + cozy patio blankets

???? Explore More Local Breakfast Favorites


???? Rosé All May

The Lowcountry was made for sipping rosé. Here’s where we’re stocking up and toasting the season:

  • Rollers Wine & Spirits – Boutique bottles, chilled and ready

  • Wine Time Bluffton – Charming, curated, and perfect for porch sipping

  • Michael Anthony’s Market Café – Pair rosé with gourmet snacks

  • Blade & Board and Board & Basket – Charcuterie that elevates your glass

  • Nantucket’s Meat & Fish Market – For wine, cheese, and all the extras

???? Want pairings, tips, and more rosé spots?
???? Read the Full Rosé Season Blog


???? Selling a Home with Pets? Here's What Buyers Want

We adore our furry family members—but not every buyer does. Here’s how to make your home show-ready when you have pets:

  • Remove pet beds, toys, and bowls

  • Deep clean and neutralize odors

  • Repair pet-related wear and tear

  • Arrange for pets to be off-site during showings

???? Read More Pet-Smart Staging Tips


???? Featured Listing: 80 Peninsula Drive | Moss Creek

 3 Beds | 2.5 Baths | First-Floor Living | Lagoon Views - Hilton Head Island

Tucked on a quiet cul-de-sac in Moss Creek, this beautifully updated home features:

  • Open kitchen with granite counters + island

  • Long lagoon views from a spacious back deck

  • Great room with fireplace + tons of natural light

  • Community access to golf, marina, fitness & more

???? Call Allison Cobb at 843-338-7256
???? View the Full Listing


???? Worth the Drive: Summer Events in Savannah

Savannah’s just an hour away—and full of reasons to visit this summer:

June:

  • Dog Days Music Fest (June 13–15)

  • Juneteenth Fine Arts Festival (June 21)

  • Heritage Fire Savannah (June 29)

July:

  • Savannah Waterfront Fireworks (July 4)

  • Tybee Island Fireworks (July 4)

August:

  • Savannah VOICE Festival (August 7–17)

All Summer:

  • Plant Riverside Summer Series

???? Explore Our Full Savannah Summer Guide


???? Community Spotlight: 100 Women Giving Back to the Lowcountry

Join us Monday, May 20th at 6 PM at Chow Daddy’s in Bluffton (on the patio!) for our next giving event.

We meet six times a year. Three charities pitch. One walks away with a $10,000 donation.

Everyone’s welcome to attend—even if you’re not yet a member! Join us!

“No one has ever become poor by giving.” - Anne Frank

???? Learn More About 100 Women Giving Back


???? Buying, Selling, or Just Exploring?

We know the Lowcountry inside and out. Whether you're planning a move, exploring neighborhoods, or just looking for your next great restaurant—we’re here for it all.

???? Request a home valuation
???? View listings or connect with an agent


???? Questions About the Lowcountry?

Whether you're curious about real estate, need dining recommendations, or want to know the best local events, Allison Cobb with The Cobb Group at eXp Luxury Realty is here to help.

???? Call or text 843-338-7256
???? Contact Us
???? www.TheCobbGroup.com

Let’s make your Lowcountry life even better.

Written by Allison Cobb

The author assumes no responsibility or liability for any errors or emissions in the content of this blog. The information provided on is an “as is” basis with no guarantee of completeness, accuracy, usefulness, or timeliness.

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