Find deals on 16 top-rated, price matched, things to do close to $500+ around Portland and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.

Half Day Private Boat Charter From Portland
Portland, Maine, United States
5.0 (16)
from $650
Mysteries & Maritime: Cape Anne, Ma: Exclusive Private Tour
Portland, Maine, United States
5.0 (3)
from $330
Camden, Rockland, Pemiquid, And Belfast Exclusive Private Tour
Portland, Maine, United States
5.0 (1)
from $350
New Hampshire White Mountains Exclusive Private Tour
Portland, Maine, United States
5.0 (4)
from $375
MONHEGAN at sunset hour
Likely to sell out
Much loved
Private Sunset Charter On A Vintage Lobster Boat With Drinks
Portland, Maine, United States
4.9 (37)
from $408
M/V MONHEGAN at Portland Head Light
Likely to sell out
Maine Fall Foliage Private Lobster Boat Cruise With Local Drinks
Portland, Maine, United States
4.6 (10)
from $381
“essence Of Portland: Private Tour: Lighthouses And Nature
Portland, Maine, United States
4.9 (27)
from $350
Central Coastal Maine Private Day Tour
Portland, Maine, United States
4.5 (14)
from $325
Lobster Roll by the Ocean
6 Hours Private Lighthouses And Kennebunkport Tour In Portland
Portland, Maine, United States
4.8 (9)
from $715
“coastal Gems: Exclusive Private Tour To Maine’s South Coast & Nh
Portland, Maine, United States
5.0 (2)
from $325
MONHEGAN is equipped with a finely finished wooden table in between cushioned "booth style" benches
Likely to sell out
Much loved
Private Sightseeing Charter On A Vintage Lobster Boat With Drinks
Portland, Maine, United States
4.9 (51)
from $381
Sightseeing Boat Tour In Portland's Casco Bay Bird's Eye Maine
Portland, Maine, United States
5.0 (2)
from $385
Portland Tall Ship Private Charter On Casco Bay
Portland, Maine, United States
New
from $1,041
2 Hours Sunset Private Charter On Heart's Desire In Casco Bay
Portland, Maine, United States
New
from $650
2-hour Private Morning Charter On Heart's Desire In Casco Bay
Portland, Maine, United States
New
from $500
Portland Headlight at Fort Williams Park
Private Portland Lighthouses And Kennebunkport Tour - 12 Pax
Portland, Maine, United States
New
from $1,550