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Boston for couples

Rediscover love in Boston with our curated experiences and tours tailor-made for couples. Be it something adventurous or romantic, we’ve got you covered.
Couple enjoying a playful moment on a European city street.

Top things to do

Boston Tea Party Ships & Museum
Boston Tea Party Ships & Museum
from $35
Boston Whale Watching Cruises
Boston Whale Watching Cruises
from $46

Top experiences in Boston

Free cancellation
Reenactment of Boston Tea Party debate with actors in period costumes inside a historic room.
Museums
Boston Tea Party Ships & Museum Tickets
from
$35
Boston Tea Party Ships & Museum Tickets. Rated 4.8 out of 5 from 160 ratings.From $35
Free cancellation
Liberty Star docked at Boston Harbor with crew preparing the ship.
Sightseeing Cruises
Boston: Sunday Pastry & Prosecco Sail on Boston Harbor
$80.25
Boston: Sunday Pastry & Prosecco Sail on Boston Harbor. Rated 0 out of 5 from 0 ratings.From $80.25
Free cancellation
Boston skyline at sunset with boats on the water.
Sightseeing Cruises
Boston Harbor Sunset Cruise
from
$56.35
Boston Harbor Sunset Cruise. Rated 4.7 out of 5 from 17 ratings.From $56.35
Free cancellation
Boston downtown skyscrapers viewed from Seaport District on a winter evening.
Sightseeing Cruises
Boston: Sunset Tall Ship Harbor Cruise
from
$77.04
Boston: Sunset Tall Ship Harbor Cruise. Rated 0 out of 5 from 0 ratings.From $77.04
Free cancellation
Boston skyline from the harbor with Liberty Fleet tall ship docked in foreground.
Sightseeing Cruises
Boston: Tall Ship Harbor Cruise Tickets
from
$37.45
Boston: Tall Ship Harbor Cruise Tickets. Rated 0 out of 5 from 0 ratings.From $37.45

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How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

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We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind

We've served 48 million+ guests and we are here for you

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Happy customers across 10,000+ experiences

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