Is San Juan LGBTQ-friendly?

Book in Condado or Ocean Park, not Isla Verde. In March, Isla Verde's beach towers fill with spring-break groups and bachelorette parties, and the pool decks get loud by noon. Ocean Park is different: the guesthouses along Calle Santa Ana and McLeary Avenue are small, often gay-owned, and quiet after 10pm, and at night you hear the surf through louvred shutters. Many Condado rooms date from the 1960s and are narrow, so on Trip.com filter for a king room with an ocean view rather than a plain 'double'. La Concha Renaissance on Ashford Avenue has bigger rooms with balconies over the beach, and its front desk books two men or two women into one bed without a second question.

Split your first full day. The history buff should be at Castillo San Felipe del Morro for the 9am opening, because by mid-morning, passengers from the Old San Juan cruise piers crowd the ramps and the limestone heats up. San Juan is reading 28°C with 81% humidity this week, which feels closer to 33°C on the open esplanade, so carry water. The El Morro ticket also covers Castillo San Cristóbal, a 20-minute walk east along Calle Norzagaray. Meanwhile, the food lover heads to the Plaza del Mercado in Santurce for batidas, crisp alcapurrias and strong Puerto Rican coffee at the market stalls. Meet at 4pm at the Cathedral of San Juan Bautista on Calle del Cristo, where Ponce de León is entombed, then walk down to the Paseo de la Princesa as the bay turns orange.

Dinner is where couples overspend. Marmalade on Calle Fortaleza is the anniversary pick, with a tasting menu that tends to run above US$100 a head before wine; when you book, ask for a table away from the entrance and the bar. For less ceremony and better food per dollar, Jose Enrique on Calle Duffaut in Santurce serves fried whole snapper and garlicky mofongo, and on Fridays the wait can stretch past an hour. Afterwards, La Factoría on Calle San Sebastián has a salsa room and a quieter wine bar behind its unmarked doors, and the crowd is a mix of gay and straight couples; two men dancing bachata there at 1am draw no stares.

For a sunset sail on San Juan Bay, pull quotes from both Viator and GetYourGuide before booking. Most boats leave the Old San Juan waterfront around 5pm and run roughly US$70 to US$100 per person. Any boat advertising an open bar and a DJ is worth skipping in spring, when those boats fill with bachelorette groups. For two people, a better evening is the bioluminescent kayak trip on Laguna Grande in Fajardo, about an hour east. Check the moon first: near a full moon the glow fades to almost nothing, but the tours still run and still charge. Leave your last morning free for a swim off Ocean Park, about 15 minutes from Luis Muñoz Marín airport.