DeLand  is pretty tiny, and the centrally located University Inn (644 N. Woodland Blvd., 386/734-5711, www.universityinndeland.com , from $85 d) will put you across from Stetson and blocks from downtown. With basic clean motel accommodations, it’s nothing fancy, but it puts you within walking distance of most of the town’s sights.
On the opposite end of downtown but still within walking distance of Woodland Avenue’s shops and restaurants is the charming and super-friendly DeLand Country Inn Bed & Breakfast (228 W. Howry Ave., 386/736-4244, www.delandcountryinn.com , from $89 d). Operated by a British couple, the inn has five spacious and bright bedrooms, two of which share a bathroom, and serves up a gut-busting English breakfast that puts the croissants and coffee at many bed-and-breakfasts to shame.
Cress Restaurant (103 W. Indiana Ave., 386/734-3740, main courses from $14) offers contemporary global-inspired cuisine in a fine-dining atmosphere. Chef Hari Pulapaka hails from Mumbai, and his delicate touches of chutneys, peppers, and curries don’t turn the steak, poultry, and seafood dishes at Cress into Indian food, but they do provide plenty of interesting flavor combinations. The inclusion of unusual dishes like ostrich loin and shiitake-infused grits also adds a bit of adventure to the menu, while the abundance of vegetables and herbs from Cress’s organic garden ensure plenty of freshness.
The Abbey (117 N. Woodland Ave., 386/734-4545, 4 p.m.–1 a.m. Mon.–Thurs., 4 p.m.–2 a.m. Fri.–Sat.) offers an excellent selection of imported and microbrewed beers. The classy and comfortable bar area is a great place to get a lesson in Belgian ales, but the sidewalk tables provide an ideal setting to relax and watch small-town DeLand slowly roll by.
Bands from DeLand  and Orlando  frequently perform at Caffe Da Vinci (112 W. Georgia Ave., 386/736-4646, 5 p.m.–2 a.m. Tues.–Fri., noon–2 a.m. Sat.), and the lineups here are often unpredictable; it could be a headbanging metal act or a sensitive singer-songwriter dishing out their tunes onstage. If the band inside isn’t your thing, head to the quaint antique-strewn courtyard area to enjoy your coffee or imported beer.