A Maid of Honor HQ Guide
Back Bay rosé brunches, boutique-hotel spa afternoons, and drag-show Sundays
Boston's bachelorette lane is the Newbury spa, a Sunday drag brunch at ClubCafé, and rosé dinners at Contessa on top of The Newbury.
Three full weekends at three price points in about 60 seconds. Trip terms sheet included.
What to do
boat cruise • 2 hours
Sunset harbor cruise with skyline views and drinks
brewery tour • 1.5 hours
Tour and tastings at Harpoon's Seaport taproom
escape room • 1 hour
Top-rated escape rooms in Downtown Crossing
boat cruise • 1.5 hours
Iconic amphibious vehicle tour through streets and into the Charles River
food tour • 3 hours
Walking tour through Boston's Italian quarter with tastings
go karts • 2 hours
Upscale bowling, billiards, and arcade in the Seaport
spa • Half day
Boutique-hotel spa with garden-facing treatment rooms
photoshoot • 1.5 hr
Iconic footbridge + swan boats + cobblestone for golden-hour portraits
Where to go out
club • unhinged • $$$
Multi-level Theater District mega-club with rotating DJs
cocktail bar • chill • $$$
No-menu craft cocktail bar in Fort Point — tell the bartender your mood
rooftop • balanced • $$$
Seaport rooftop with harbor and skyline panoramas
club • unhinged • $$$
Two-floor Seaport nightclub with VIP bottle service
Dress code: Upscale casual; no athletic wear
comedy club • balanced • $$
Hilarious improv shows in the North End
lounge • balanced • $$$
Upscale supper club and lounge in Downtown Crossing
Dress code: Smart casual
drag show • unhinged • $$
Boston's longest-running drag venue in Bay Village
rooftop • balanced • $$$$
Top-floor rooftop with the Public Garden view — champagne nights
Where to eat
Seafood • $$$ • Best for: dinner
Tiny North End spot with the best lobster roll in Boston
Bakery/Dessert • $ • Best for: late-night
Legendary North End cannoli shop — the Boston must-do
Seafood • $$$ • Best for: group-dinner
Industrial-chic Fort Point seafood and craft beer spot
Mediterranean/Cafe • $$ • Best for: brunch
Instagram-worthy brunch with shakshuka and pastries
Pizza • $$ • Best for: dinner
North End brick-oven pizza since 1926
Seafood • $$ • Best for: dinner
Casual waterfront seafood shack on the Fort Point Channel
Mexican • $$ • Best for: group-dinner
Funky Back Bay Mexican with killer margaritas
French • $$$ • Best for: brunch
Back Bay brasserie — Sunday brunch + rosé all day
Where to stay
boutique-hotel • Max 2 guests
Converted Charles Street jail with upscale bar scene and Beacon Hill location
hotel • Max 2 guests
Modern Seaport hotel with rooftop terrace and compact smart rooms
airbnb • Max 10 guests
Full houses in Southie near waterfront bars and restaurants
boutique-hotel • Max 2 guests
Rock-and-roll themed hotel steps from Fenway Park
airbnb • Max 10 guests
Brownstone condos in Boston's most walkable neighborhood
Three full weekends at three price points in about 60 seconds. Real venues from the list above, parallel tracks for the pregnant friend and the sober bridesmaid, and a trip terms sheet for the group chat so nobody gets a Venmo surprise. Free. No card.
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