The southernmost point in the continental United States, where the highway finally runs out and the pace drops to almost nothing.
Key West is not like the rest of Florida, and everyone who goes figures that out within about an hour. It is closer to Havana than to Miami, and it feels it. Conch houses with wraparound porches, roosters wandering the sidewalks, and a sunset that the whole island stops to watch.
The Overseas Highway getting there is half the trip. Forty-two bridges strung across open water, including the Seven Mile Bridge, with the Atlantic on one side and the Gulf on the other.
Once you are there it is a walking town. Duval Street, Mallory Square at sunset, Hemingway's house and its six-toed cats, the Truman Little White House, and the buoy at the southernmost point that everyone queues up to photograph.
This one is paced easy on purpose. Key West does not reward rushing.
Forty-two bridges across open water, including the Seven Mile Bridge. The drive down is genuinely part of the trip.
Conch architecture, Duval Street, and the Southernmost Point buoy. Compact and walkable, which is exactly what you want.
The whole island turns out for it, street performers and all. It is a nightly ritual and it does not get old.
The Hemingway Home with its famous cats, and the Truman Little White House where a president came to rest.
The complete day-by-day, hotels, meals, inclusions, and pricing are being finalized. Send me a note and I will get them to you the moment they are set, and put you first in line.
Yes. This one is open to everyone. Bring him along, bring a friend, bring the whole family.
Soon. This departure is still being finalized. Send me a note or call me at 931-801-9900 and you will hear the moment pricing and the full itinerary are set.
Not a thing. Asking for information is just asking. No deposit, no obligation, and it helps me size the trip.
No, but sharing brings the cost down. I am glad to match you with a roommate from the group.
I recommend it on every trip, and I recommend buying it at deposit rather than waiting. The pre-existing condition waiver window closes early, and once it does I cannot reopen it.
Pricing and the full itinerary are being finalized. Send me a note and you will hear first, with no deposit and no obligation.
Button not opening your email? Write to frances@tripsunlimited.com or call 931-801-9900.
No deposit required to ask · Travel insurance recommended at deposit.
Browse our full lineup of trips, day adventures, and members-only gatherings.
See All Trips →