Photo: Marc Averette / CC BY 3.0, via Wikimedia Commons
Charter portYacht charter in Key West
96 boats available to charter in Key West, U.S.A. — compare motor yachts, catamarans and sailing boats from verified operators.
Verified operatorsCaptained or bareboatConcierge offers in 24hAbout chartering in Key West
Chartering in Key West offers a vibrant blend of historic seaport charm and world-class reef sailing, where you can depart from downtown marinas or upscale Stock Island facilities. Most charters launch from Key West Historic Seaport, Garrison Bight Marina, or Stock Island Marina Village, providing easy access to open ocean and backcountry waters. A day trip reaches the barrier reefs, Man of War Harbor for anchoring, and the shallow flats ideal for snorkeling and fishing.
The setting combines bustling waterfront restaurants with serene coral landscapes, making it perfect for both relaxed cruises and adventurous exploration. Whether you choose a catamaran, sailing yacht, or motor yacht, the waters around Key West deliver clear visibility and diverse marine life.
From Key West, you can sail south to the Florida Reef, anchor at Man of War Harbor, or explore the backcountry flats near Fleming Key. These routes offer unforgettable experiences for families, groups, and solo sailors alike.
Boats available in Key West
Captained or bareboat. Book direct with verified operators.
40 ft (12 m) · 6 guests
1970, 40' Luhrs Sportfishing "Irish Cowboy"
Key West, U.S.A.
From US$1,349 /day
46 ft (14 m) · 12 guests · 2 cabins
2003, 46ft SeaRay | Grand Admiral
Key West, U.S.A.
From US$1,256 /day
22 ft (7 m) · 8 guests
2023, Deluxe Deckboat – Premium Sound & Comfort Seating | Sandbar Ready!
Key West, U.S.A.
From US$651 /day
65 ft (20 m) · 105 guests · 2 cabins
2017, 65' Party Cat for Sunset Dinner Cruise in Key West!
Key West, U.S.A.
Price on request
45 ft (14 m) · 10 guests · 2 cabins
2004, 45ft Sea Ray 420 Grand Admiral – Key West
Key West, U.S.A.
From US$2,325 /day
30 ft (9 m) · 6 guests
1999, Key West Fishing - Packages in listing description
Key West, U.S.A.
From US$930 /day
48 ft (15 m) · 6 guests · 1 cabin
1994, Experience the Florida Keys that few people ever see.
Key West, U.S.A.
From US$1,023 /day
31 ft (9 m) · 6 guests
2020, Key West Fishing Charter...like no other!
Key West, U.S.A.
From US$1,488 /day
50 ft (15 m) · 12 guests · 6 cabins
2020, Luxury 50’ Sailing Yacht! Offering Day, Overnight Sunset Charters
Key West, U.S.A.
From US$3,023 /day
22 ft (7 m) · 10 guests
2024, Tropical Drift - A Key West Private Boat Adventure!
Key West, U.S.A.
From US$977 /day
32 ft (10 m) · 6 guests
2017, Still Dreamin’ – Luxury Belzona 325 Charter
Key West, U.S.A.
From US$1,488 /day
63 ft (19 m) · 41 guests
2004, Ultimate Fishing Charter Experience 63' Blind Squirrel!
Key West, U.S.A.
From US$2,651 /day
38 ft (12 m) · 12 guests · 1 cabin
2019, Ultimate speed, spacious comfort and elegant style... Best Time Ever!
Key West, U.S.A.
From US$1,116 /day
37 ft (11 m) · 6 guests
2011, Enjoy A Key West Fishing Trip on Compass Rose!
Key West, U.S.A.
From US$1,442 /day
25 ft (8 m) · 5 guests
2025, Inshore, Reef, Wreck, Flats Fishing Charter
Key West, U.S.A.
From US$1,209 /day
17 ft (5 m) · 6 guests
2022, AB Inflatables DLX Luxury Sport Runabout
Key West, U.S.A.
From US$5,580 /day
45 ft (14 m) · 6 guests · 3 cabins
1996, Thirsty Lady. All Included! Daily Sails & Lodging! 3bd/3bth
Key West, U.S.A.
From US$989 /day
47 ft (14 m) · 6 guests
1970, The best offshore fishing charter in Key West on 47' Hatteras!
Key West, U.S.A.
From US$1,535 /day
Boat types & prices in Key West
Live availability from verified operators; day rates converted to USD.
| Boat type | Available | From (per day) |
|---|---|---|
| Yacht | 26 | $561 |
| Fishing boat | 23 | $558 |
| Catamaran | 22 | $186 |
| Boat | 16 | $632 |
| Sailing yacht | 7 | $823 |
| Mega yacht | 2 | $6,975 |
Find your perfect boatWhere do yacht charters depart from in Key West?
Most charters depart from Key West Historic Seaport (downtown), Garrison Bight Marina, or Stock Island Marina Village. Garrison Bight is a one-stop hub with fuel, bait, and repairs, while Stock Island offers easier parking and quicker open-ocean access for larger yachts.
Key West Bight Marina is also a popular downtown option, located in the historic seaport district with direct access to vibrant shops and restaurants.
What day-trip routes and anchorages are best near Key West?
The top day-trip routes include sailing to the Florida Reef for snorkeling, anchoring at Man of War Harbor, and exploring the backcountry flats near Fleming Key. The barrier reefs rival the Bahamas, offering crystal-clear water and breathtaking coral formations.
These routes are ideal for 3–5 hours of daily sailing, allowing you to fully enjoy snorkeling, fishing, and sunset views without stress.
When is the best sailing season and weather window in Key West?
Key West offers year-round sailing with warm temperatures and consistent sunshine, making it a top-tier destination in any month. The best weather windows typically occur from late spring through early fall, when winds are mild and seas are calm.
Summer months bring higher humidity but excellent conditions for reef exploration and backcountry adventures.
What licence or skipper rules apply for yacht charters in the U.S.A.?
In the U.S.A., bareboat charters require a valid boating licence or certification, while crewed charters include a professional captain. For private '6-pack' charters, the limit is 6 guests, and '12-pack' yachts allow up to 12 passengers.
Inspected Passenger Vessels, often large catamarans, can carry 30 to 100+ guests for events like bachelorette parties or wedding cruises.
How do I get to Key West for my yacht charter?
The nearest airport is Key West International Airport (EYW), with a rough transfer time of 10–15 minutes to downtown marinas. For larger yachts, Stock Island departures are preferred due to easier parking and quicker open-ocean access.
Public transport and shuttles are also available from the airport to Key West Bight Marina and Garrison Bight.
Key West yacht charter — FAQ
How much does a boat rental in Key West cost?
From around $875 per day for catamarans, sailing yachts, or motor yachts.
What is the best time to sail in Key West?
Year-round sailing is possible, with optimal conditions from late spring to early fall when winds are mild and seas are calm.
Do I need a licence to charter a bareboat in Key West?
Yes, bareboat charters require a valid boating licence or certification; crewed charters include a professional captain.
What are the top day-trip routes from Key West?
Sail to the Florida Reef for snorkeling, anchor at Man of War Harbor, and explore the backcountry flats near Fleming Key.
Is Key West suitable for family or group charters?
Yes, with options for 6–12 guests on private charters and 30–100+ guests on inspected passenger vessels for events.
Which marina is best for larger yachts in Key West?
Stock Island Marina Village is preferred for larger yachts due to easier parking and quicker open-ocean access.
Boat types
Browse by boat type
From RIBs and motorboats to catamarans and crewed superyachts.
YachtYacht charters
Luxury cruising with full crew
8–16 guests ·
from $480/day
CatamaranCatamaran rentals
Stable, spacious, perfect for groups
10–12 guests ·
from $280/day
SailboatSailboat rentals
Wind, sails and slow island hopping
6–10 guests ·
from $130/day
MotorboatMotorboat rentals
Fast day cruises without the captain
4–10 guests ·
from $90/day
Nearby ports
More charter ports in U.S.A.
Compare departure points and fleets across the coast.
Other destinations
Popular charter destinations
Compare nearby coasts and plan your next charter.
USABoat rentals in Miami
Sun, skyline and sandbar weekends
USA ·
from $145/hour
SpainBoat rentals in Ibiza
Formentera day trips and sunset cruises
Spain ·
from $220/hour
UAEBoat rentals in Dubai
Marina skyline & Palm Jumeirah cruises
UAE ·
from $180/hour
CroatiaBoat rentals in Split
Island hopping in the Adriatic
Croatia ·
from $130/hour
Request offers
Find a boat