A Maid of Honor HQ three-day sample
Cobblestone Old City, La Factoría cocktails, and El Yunque rainforest — Caribbean without leaving US soil.
San Juan, PR carries 7 bachelorette-friendly nightlife venues and 8 curated daytime activities in this guide. The 3-day sample below anchors Friday at Marmalade Restaurant & Wine Bar and Saturday night at La Factoría.
Build her own San Juan weekend — free →Personalize this around the bride in about 60 seconds. No credit card.
The three days
Day 1 · Friday
Day 2 · Saturday
Day 3 · Sunday
The shortlist
One of the world's 50 best bars — six rooms inside a colonial building, each with its own concept, cocktail menu, and vibe.
Old San Juan stalwart with creative Latin cocktails and a patio that draws a cosmopolitan mix of locals and visitors.
Legendary Old San Juan dive bar — pinball machines, local rum, and walls covered in decades of graffiti. No frills, maximum soul.
Chef Peter Schintler's Old San Juan tasting menu is Puerto Rico's most refined dining experience — reserve well in advance.
Late-night tacos and natural wine in a colonial dining room — the post-Factoría meal the group didn't plan but desperately needed.
Chef Jose Santaella's modern take on Puerto Rican cuisine in the Mercado de Santurce — creative, rooted, and consistently excellent.
Questions bridesmaids ask
Three days — fly in Friday afternoon, do the big dinner + nightlife Friday night, the signature daytime activity plus another dinner Saturday, and a late brunch Sunday before wheels up. Two nights works for drive-in groups; four only if the bride wants a full resort day.
Six to ten bridesmaids is the sweet spot — big enough for a proper reservation, small enough to share one rental home and one group dinner table without splitting the party.
Lock lodging four to six months out, dinners six to eight weeks out, and the headline activity once the group flight count is confirmed. San Juan lodging tightens fast in peak wedding season (April–June and September–October).
Budget $550–$1,100 per bridesmaid for a three-day weekend in San Juan, PR — that covers a shared rental home, two big dinners, one activity, and nightlife. Upgrading to a boutique hotel or a private chef pushes the per-person into $1,200–$1,800.
No — the destination guide at /san-juan lists every venue. This page is a three-day sample itinerary you can hand to the bridesmaids on day one. The AI planner at /plan builds a fully personalized weekend around the bride.
This is the shared sample. The AI planner personalizes every hour around the bride — parallel tracks for the pregnant friend and the sober bridesmaid, a trip terms sheet for the group chat so nobody gets a Venmo surprise, and every venue lifted from the real San Juan catalog. Free. No card.
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