May is a great time to visit. Weather should be really nice if you come early in the month (can get hot later in the month).
Staying in downtown Charleston is always a treat, but expensive. We always stayed just across the bridge in Mount Pleasant at Old Village Post House - the inn is very quaint, has great service, and a great restaurant with a lovely outdoor courtyard. And very reasonable rates.
Old Village Post House Inn | Mount Pleasant, SC. If you prefer to stay in Charleston, The Governor's House is reasonable (for downtown Charleston) and a great location with awesome breakfasts on their beautiful porch -
Charleston, SC Historic Bed & Breakfast (B&B) - Weddings - Business Venue | Governor's House Inn
Old Village Post House is in a beautiful part of Mount Pleasant -
www.thecassinagroup.com/the-old-village. Walk around the streets after dinner. It's also an easy walk to Shem Creek from there for a drink on the water and dolphin viewing!
Bars & Restaurants on Shem Creek, South Carolina
Shem Creek food (my opinion) is just "ok", so I would eat elsewhere and just go for drinks. There is a catamaran you can take out of Shem Creek (docked right in front of Red's) -
PALMETTO BREEZE - AquaSafarisAquaSafaris.
Take a walk on Pitt Street during the day and poke into the shops. It's a throwback to yesteryear - Out of Hand is a favorite.
https://shopoutofhand.com/. Grab lunch at the Village Bakery - excellent food (it's more than just sweets) -
Village Bakery and Cafe | Mount Pleasant, SC, then take a short walk to the Pitt Street Bridge -
Pitt Street Bridge Review at ExploreCharleston.net - for great views. Walk around the Old Village to view the homes which are to die for - and water views - some of the paths lead to benches where you can sit and enjoy the view and breeze. Check out Alahambra Hall and walk around the town green, see the old buildings, and read the plaques to get a sense of the history. The ones about Hugo are particularly interesting.
Venture over to Sullivan's Island one day (15 min from OVPH or downtown Charleston) and have lunch at Poe's Tavern (named after Edgar Allen Poe) - one of the best casual places with great atmosphere and great burgers. Also outdoor dining -
Poe's Tavern – Sullivan's Island, Charleston, South Carolina. Take in Fort Moultrie -
https://www.nps.gov/fosu/learn/histo...t_moultrie.htm - and then walk the beach. If you're still there @ dinner time, try The Obstinate Daughter for dinner -
HOME - The Obstinate Daughter.
Spend a day in Charleston, but first stop in at the Visitor Center in Mount Pleasant at Patriot's Point (99 Harry Hamlin Blvd - follow signs to Waterfront Park). Grab some brochures, check out the Sweetgrass Basket Center, walk Waterfront Park for some great views, then head to Charleston Harbor Resort (just down the road) and catch the Charleston Water Taxi into the city. It's the best way to get into the city - you can enjoy being on the water, relax, not worry about parking, and get a great view of Charleston from the water - all for only $10 -
Ferry Service | Charleston Water Taxi.
Others can chime in for great lunch spots, but if you want water views try Fleet Landing -
Fleet Landing. It's an easy walk from where the water taxi drops you off and from there to City Market. Spend the day walking around the historic district, visit Rainbow Row, walk along The Battery, visit the stalls at City Market, stroll along King Street for shopping, then have a drink at one of the rooftop bars - maybe Pavilion Rooftop Bar -
Pavilion Bar before taking the water taxi back to Mount Pleasant.
Head over to Daniel Island one night for dinner (15 min from Mt Pleasant or downtown Charleston). Go early before dinner, and check out Smythe Park (2364 Daniel Island Drive) -
Smythe Park - Daniel Island. Park and take a walk in the park, around the lake, and read and learn about the history of the island. On your way back from Smythe Park to dinner, you'll drive by the Volvo Car Stadium (161 Seven Farms Dr) - on your left in the center of town where the annual Volvo Open Tennis Tournament is held (women's pro tennis) and concerts are held (including by our beloved local Darius Rucker from Hootie and the Blowfish) throughout the summer - it's an awesome open air venue.
For dinner, eat at Sermet's Courtyard - on a side street lined with gorgeous old Live Oaks which will be lit up. Great food and atmosphere - outdoor courtyard -
Sermet’s Courtyard – Sermet’s Southernterranean & Sermet’s Courtyard Restaurants. After dinner, walk down to the waterfront (at the bottom of the street), and walk the trail along the water.
Those are just what I consider some highlights and things we did during our scouting trips to the area. There are lots more things to do and see. We have yet to get to any of the plantations, but those are certainly worth a visit as is Boone Hall in Mt. Pleasant.
Obviously if you are here for scouting purposes, you'll want to visit and spend time in the towns/neighborhoods you are interested in living in, as they are all very different, and are not going to be like downtown Charleston or Old Village unless you have mucho bucks! My favorite communities are Mt Pleasant and Daniel Island -
http://danielisland.com/island-living/parks - but there are many great areas depending on your budget, wants and needs.
Have fun!