Sunset Sail in Key West with Beverages Included
Run by Floridays
How it compares: Which sunset sail is actually worth it
- Departs Key West
- 1 hour 30 minutes
- Free cancellation to 24 hrs before
from $79 / personprice checked Oct 13
Tours & charters, compared
Golden hour on the water, the reef, the fish and Old Town, compared trip by trip. Each group below starts with the trip its own page would book, then the full comparison. No operator pays to be listed or ranked, and every card says where the trip actually leaves from.
Sunset and the water
A sail at golden hour, wild dolphins watched from a boat, and jet skis and parasails.
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We earn a commission if you book through these links, and no one pays to be listed. Each is the trip its own page picks, or the one trip it lists, not a ranking across pages. How we make money
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Key West Dolphin Watch and Sunset Sail on Catamaran
Run by Honest Eco Kayak and Snorkel
How it compares: Dolphin tours in Key West
- Departs Key West
- 3 hours
- Free cancellation to 24 hrs before
from $117.17 / personprice checked Oct 13
Key West Island Adventure Jet Ski Tour: Bring a Partner for Free
Run by Sunset Watersports
How it compares: Key West jet ski and parasail rules
- Departs Key West
- 1 hour 30 minutes
- Free cancellation to 24 hrs before
from $155.95 / personprice checked Oct 13
Prices and ratings as checked on 13 October 2026.
The full guides
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Departs Key West
Which sunset sail is actually worth it
A dozen boats leave the same harbor at the same hour, and the three worth choosing between run $79 to $117.18. The differences are real and the listings bury them.
3 trips · from $79 Checked -
Departs Key West
Dolphin tours in Key West Watching, not swimming, by season
Key West's dolphins are wild: you watch from a boat, 50 yards off, as NOAA asks. Which trips run all year, which only mid-October to April, and where the swims are.
1 trip · from $117.17 Checked -
Departure varies
Key West jet ski and parasail rules Ages, tests, weather
Jet skis go out as guided tours, drivers from 16 with a parent aboard (14 at Fury), the boating test takes minutes, and Florida law grounds a parasail over 20 mph.
4 trips · from $64.45 Checked
The reef and the fish
Snorkeling the reef off Key West, and fishing from a party-boat seat or a boat of your own.
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We earn a commission if you book through these links, and no one pays to be listed. Each is the trip its own page picks, or the one trip it lists, not a ranking across pages. How we make money
Key West Sailing & Snorkeling: A Reef Adventure
Run by Floridays
How it compares: Snorkeling the reef from Key West, and its rules
- Departs Key West
- 3 hours
- Free cancellation to 24 hrs before
from $79 / personprice checked Oct 15
Gulfstream IV party boat
Run by Gulfstream Fishing, Inc
How it compares: Key West fishing charters
- Departs Key West
- 6 hours
- Free cancellation to 24 hrs before
from $77.87 / personprice checked Oct 27
Prices and ratings as checked between 15 October 2026 and 27 October 2026.
The full guides
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Departs Key West
Snorkeling the reef from Key West, and its rules
The reef is 6 to 8 miles off Key West, at Eastern Dry Rocks, Rock Key and Sand Key. The sanctuary rules, the marked zones, and a 2027 ban that skips these reefs.
1 trip · from $79 Checked -
Departure varies
Key West fishing charters A $77.87 seat or the whole boat
A party-boat seat is $77.87, a private offshore boat $1,200 to $1,600. No license needed aboard, and the reefs off Key West where nobody may fish at all.
4 trips · from $77.87 Checked
On land
Old Town by train or trolley, and the ghost tours after dark.
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We earn a commission if you book through these links, and no one pays to be listed. Each is the trip its own page picks, or the one trip it lists, not a ranking across pages. How we make money
Key West Hop-On Hop-Off Trolley Tour
Run by Historic Tours Of America
How it compares: Conch Tour Train or Old Town Trolley, and what neither says
- Departs Key West
- 1 hour 30 minutes
- Free cancellation to 24 hrs before
from $55.60 / personprice checked Oct 27
Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)
Run by Sloan's Key West Ghost Tours
How it compares: Key West ghost tours
- Departs Key West
- 2 hours
- Free cancellation to 24 hrs before
from $99 / personprice checked Oct 13
Prices and ratings as checked between 13 October 2026 and 27 October 2026.
The full guides
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Departs Key West
Conch Tour Train or Old Town Trolley, and what neither says
The same company runs both. The Conch Tour Train is one 60-minute loop with no hop-off; the Old Town Trolley is 90 minutes, with 13 stops and a day of reboarding.
2 trips · from $45.10 Checked -
Departs Key West
Key West ghost tours Which one takes you to Robert the Doll
Robert the Doll is at Fort East Martello, 3 miles from Duval by the airport. The one tour that goes inside after dark, the trolley ghost tour, and the day visit.
from $39.85 Checked
From Miami
A long day from Miami, and how much of it you spend in Key West.
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We earn a commission if you book through these links, and no one pays to be listed. Each is the trip its own page picks, or the one trip it lists, not a ranking across pages. How we make money
Miami to Key West Day Trip with Activity Options
Run by TRAVEL TO KEY WEST
How it compares: Key West day trip from Miami
- Departs Miami
- 15 hours
- Free cancellation to 24 hrs before
Viator's $49 fare is one way; there and back is $54 for an adult and $51 for a child.
from $54 / personprice checked Oct 30
Prices and ratings as checked on 30 October 2026.
The full guides
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Departs Miami
Key West day trip from Miami 15 hours for 6 on the island
Bus tours from $54 round trip pick up from 6 a.m. and give you about six hours in Key West. Driving, flying, the $6.65 public bus, and what fits.
3 trips · from $54 Checked
Places to stay
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Where to stay in Key West, and the license to check before you pay
Old Town, the Seaport, the south shore or New Town: what each area trades, where Booking.com lists it, and the license to check before you pay a rental.
Places to stay Checked
Photo credits
- A schooner in the light before sunset: Yinan Chen, Public domain
- Parasailing off a Florida beach: Yinan Chen, Public domain
- Staghorn coral on Looe Key reef: Lauren Toth, USGS. Sound Waves Newsletter, Public domain
- The charter fishing docks: Sharon Hahn Darlin, CC BY 2.0
- The Conch Tour Train: Cullen328, CC BY-SA 3.0
- Fort East Martello: Ebyabe, CC BY-SA 3.0
- Driving the Seven Mile Bridge: David Broad, CC BY 3.0
- A conch house porch: Cayobo, CC BY 2.0
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