From Private Boat Tours to Oysters on the Dock & Sunset Dinners in Bluffton and Hilton Head Island
Kayaking and paddleboarding typically trend the highest when considering water adventures in the Lowcountry. But in Bluffton and Hilton Head Island, there is a lot more to life on the water besides a paddle and life vest. Here, the waterways are woven into everyday life — whether that means a private boat tour, tying up at a dockside restaurant for fresh oysters or watching the sky melt into shades of gold and pink during a sunset cruise.
If you’re dreaming about coastal living (or if you’re already enjoying it), these experiences show what it really means to live in a place where the tide sets the pace.
Bluffton: Slow Rivers and Big Views
Bluffton’s charm lives along the May River, where it’s quiet, winding, and endlessly scenic. A private boat tour here isn’t about rushing from point A to point B. It’s about cruising past shrimp boats, gliding through salt marshes and spotting dolphins surfacing just a few feet from the bow.
Many locals love using private charters for relaxed afternoons with visiting friends or family. It’s a low-key way to showcase the area while enjoying cool drinks, sea breezes and stories from captains who know every bend in the river.
If you want a relaxed way to explore the marshes and river life, local guided tours are a standout choice:
- May River Excursions — A popular Bluffton tour that takes you down the May River with a captain who knows all the bends, birds, and hidden coves worth seeing. These small-group tours are ideal for visitors, families, or anyone who wants photos without doing the rowing.
- Palmetto Bluff Waterway Tours — Just minutes from Bluffton proper, Palmetto Bluff offers stunning water tours through its private waterways. These captained excursions give a peaceful, up-close look at marsh life, herons in flight, and gorgeous Lowcountry sunsets above the May River and beyond.
- Custom Charters — Many local captains will tailor trips to your group’s vibe, whether it’s dolphin watching at golden hour or a leisurely cruise with drinks and snacks aboard.
After a few hours on the water, many Bluffton boaters plan their cruise around a waterfront meal — and it’s easy to see why.
Captains from May River Excursions and private charters operating through Palmetto Bluff Conservancy Tours frequently point guests toward May River restaurants where you can dock, dine, and linger a little longer.
Popular stops include:
- The Bluffton Oyster Company – A longtime waterfront favorite known for oysters, peel-and-eat shrimp, and relaxed dockside seating.
- FARM Bluffton – Located directly on the May River with dock access and an elevated take on Southern coastal cuisine.
- Captain Woody’s Seafood Bar – Casual, laid-back, and perfect for cold drinks and oysters.
Consider timing a late-afternoon cruise so it rolls effortlessly into dinner — stepping off the boat, grabbing a table by the water, and watching the sky turn shades of peach and gold as the day winds down.
It’s the kind of simple luxury that defines Bluffton living: boat ride first, oysters second, sunset always included. And then there are the sunsets. Bluffton sunsets feel personal. Whether you’re anchored mid-river or sitting on a dock with a glass of wine, the sky puts on a nightly performance that never gets old.
Hilton Head Island: Coastal Cruises, Harbour Views & Sunset Dinners
For Hilton Head Island, water adventures lean a little more toward “choose your own adventure.” Private boat charters range from dolphin tours and sandbar hopping to leisurely coastal cruises around iconic marinas and inlets.
A favorite local ritual? Plan an early evening cruise that ends with dinner at a waterfront restaurant. Pulling into a marina as the sun sets, lights flicker on along the docks, and music drifts from nearby patios feels like vacation, even when it’s just a Tuesday.
Sunset dinner cruises are another island staple. Picture fresh seafood, a cool ocean breeze, and panoramic views of the shoreline as day fades into night. It’s one of those experiences that quickly becomes a tradition.
Sunset & Dinner Cruise Options
- Vagabond Cruise – A local institution since 1968, Vagabond offers classic Sunset Dinner Cruises and dolphin sightseeing cruises aboard the Spirit of Harbour Town, with chef-prepared meals and unbeatable views of Calibogue Sound.
- Island Head – Known for its Sunset Hibachi Dinner Cruise, this company combines an interactive dinner experience with a relaxed evening on the water as the sun dips over Hilton Head.
- Outside Hilton Head Dinner Cruises – Known for themed experiences like the Lowcountry Boil Dinner Cruise, this option pairs classic coastal cuisine with scenic evening views (often departing from Shelter Cove Marina).
Private & Customized Sunset Cruises
- Hilton Head Boat Tours – Offers flexible sunset charter options that you can tailor — perfect for a pre-dinner cruise before tying up at a dockside restaurant.
- Salty Dog Happy Hour Cruise – A popular charter out of Harbour Town and South Beach marinas that’s ideal for a sunset or happy hour cruise before dinner ashore.
- Solaris / Luxury charters – For a more upscale, private sunset cruise, companies around Shelter Cove and Harbour Town offer bespoke charters with gourmet meals and skyline views as you cruise into golden hour.
Just beyond the beach vibes, you’ll find one of Hilton Head’s most peaceful water adventures at Saltmarsh Paddle Tours, where guided excursions through the island’s tidal creeks and salt marsh estuaries bring you face-to-face with Lowcountry wildlife. These hour-and-a-half kayak and SUP tours — led by experienced local naturalists — glide through Broad Creek and surrounding marshes in search of bottlenose dolphins, herons, blue crabs, and even the occasional sea turtle, all while you learn about the unique ecosystem that makes Hilton Head’s waterways so special. Reservations are available throughout the day, and the serene scenery makes this a favorite for families, couples, or anyone who wants a slower-paced adventure on the water.
Just a short waterway ride from Bluffton’s marshy creeks
Cast Away Charters delivers a quintessential Lowcountry adventure on the salt — whether your crew is chasing tailing redfish or cruising into a sunset. This family-friendly charter company takes care of everything from licenses and gear to local expertise, making it easy for beginners and seasoned anglers alike to reel in Redfish, Trout, Flounder, Cobia and more against scenic tidal backdrops.
Beyond classic fishing trips, Cast Away’s offerings include fan-favorite experiences like “Hook ‘n Cook,” where you catch the day’s haul and either have it prepared locally or enjoy it fresh ashore, sunrise and sunset cruises for a more relaxed shoreline view, shark-themed outings, fly-fishing sessions, and even nature-focused odysseys that let you soak up the region’s rich ecosystem.
It’s one of those outings that blends adventure, saltwater culture, and community in a way only the Sea Islands can — perfect for visitors and locals craving a day on the water with a real coastal twist.
Thinking About Life on the Water?
Homes with private docks, community marinas, or easy boat access offer more than convenience, they unlock an entirely different way of living. From spontaneous sunset cruises to oyster nights on the dock, your backyard can become your favorite destination.
If you’re curious about neighborhoods that make this lifestyle possible, reach out to Delcher & Delcher. Click here to fill out a contact form. We love helping buyers discover homes that fit not just their needs, but the lifestyle they’ve always imagined.
