Even on the hottest night of Indian summer, there’s a cooling breeze as you sip strawberry caipirinha coolers under the stars in the funky High Bar on the roof of the Gramercy Park Hotel (the top-of-the-town fantasy of a longtime pal, I confess). True, the eager servers, saronged as if auditioning for Gauguin, seem a bit disorganized, and the Astroturf squishes with every step after a storm. Relax. Just join a savvy crowd, savoring the jeweled spires of Manhattan dressed for evening. Idle over a Georgia-peach mint julep or a Singapore Sling with salmon tartare, lush lobster salad, or a mound of sweetly sticky baby back ribs to share. Drop a ring in her drink, or your keys in his pocket. With the Chrysler Building’s crown aglow over one shoulder, you’ll feel like you own the town.