For the party · Oct 16–24
Fantasy Fest Boat Party
Private and clothing-optional, run only during Fantasy Fest by Bone Island Charters.
| Whole boat, up to 6 | $600 |
|---|
Seasonal guide · Key West · October 16–25, 2026
Fantasy Fest 2026: Boat Parties, Sunset Sails and How to Escape Duval
Fantasy Fest 2026 runs October 16–25. The theme is "Musical Icons and Iconic Musicals," and the parade rolls down Duval Street on Saturday, October 24 at 7 p.m. For ten days the island doubles in population, Duval closes to traffic most nights, and hotels that were booked in March charge what they like.
- Dates
- Oct 16–25
- Parade
- Sat 24, 7 pm
- Sunset
- ~6:50 pm
Here is the part first-timers miss: the festival happens on land after dark. The water is wide open during the day, and a boat is the one place you can escape the crowds, cool off, and still be back on Duval for the night's party. This guide covers what's on, and which boats run during Fantasy Fest with current prices.
Short answer: Book a boat for a daytime slot on the quiet days (Monday–Thursday of festival week) and keep the two big nights, the Masquerade March on Friday the 23rd and the parade on Saturday the 24th, for Duval. Sunset sails on parade night sell out first; private charters on weekday mornings are the last to go.
Our picks
Three boats with festival-week dates open
Checked against each operator's calendar on September 28, 2026. All three still showed open dates for October 24, parade day.
Sunset on a budget
Hula Hank's Tiki Sunset Cruise
A tiki boat with a bar aboard, back at the dock before Duval gets going.
| Adult | $59.95 |
|---|---|
| Child | $49.95 |
For a group of six
3-Hour Private Sandbar Charter
Dolphin Safari's private boat to the sandbar. About $125 each split six ways.
| Whole boat | $749 |
|---|
The festival
Fantasy Fest 2026 at a glance
Dates
Friday, October 16 to Sunday, October 25, 2026.
Theme
Musical Icons and Iconic Musicals.
Parade
Saturday, October 24, 7 p.m., on Duval Street.
Goombay Festival
Opening weekend in Bahama Village: Bahamian food, junkanoo and music. Free and family-friendly.
Masquerade March
Friday, October 23. The Captain Morgan Masquerade March walks from the Key West Cemetery to Duval.
Balls and parties
Pet Masquerade, Headdress Ball and Royal Coronation run across the week. Most signature parties are ticketed, typically $40–$150.
After dark
The last four nights are not for kids. Body paint counts as a costume on Duval after dark.
Dates and the parade time are published by the festival and the Key West Chamber of Commerce; individual party times change year to year, so check fantasyfest.com the week of.
Festival photos via Wikimedia Commons: Parade float at dusk, 2012 by Cayobo, CC BY 2.0; Costume after dark, 2014 by Cayobo, CC BY 2.0; Lit parade float on Duval, 2014 by Cayobo, CC BY 2.0; Night parade float, 2013 by Cayobo, CC BY 2.0; Band on a parade float, 2013 by Cayobo, CC BY 2.0; Skull makeup on parade night, 2014 by Cayobo, CC BY 2.0; Monarch butterfly costume, Masquerade Parade 2023 by Cayobo, CC BY 2.0; Wigs and bright costumes, Locals Costume Parade 2025 by Life's a breeze in the Florida Keys, CC BY 4.0; Popcorn costumes, Locals Costume Parade 2025 by Life's a breeze in the Florida Keys, CC BY 4.0; Costumed group, Locals Costume Parade 2025 by Life's a breeze in the Florida Keys, CC BY 4.0; Parade float and costumes, Locals Costume Parade 2025 by Life's a breeze in the Florida Keys, CC BY 4.0; Costumes on Duval, Locals Costume Parade 2025 by Life's a breeze in the Florida Keys, CC BY 4.0; Giant costume, Locals Parade 2022 by Key West Wedding Photography, CC BY 2.0. Licenses: CC BY 2.0, CC BY 4.0.
After dark
Parade night on Duval
The floats roll after sunset, which is why a daytime or sunset boat and a night on Duval fit together.
Only during the festival
The Fantasy Fest boat party
One operator runs a charter built for the week. It is private, clothing-optional, and cruises the harbor and backcountry with your own group. Six-person max, so it works for a couples' trip or a small crew that wants the party without the sidewalk.
Bone Island Charters runs it October 16–24. Your boat, your music, your rules on the water. Bring your own drinks and costumes.
| Whole boat, up to 6 | $600 |
|---|
Evenings
Sunset sails during festival week
Sunset in late October is about 6:50 p.m., so a sunset sail gets you back to the dock before the night's events start. These book out early on parade night; the weekday departures are the realistic option if you're deciding now.
Sebago Watersports · Shared
Hula Hank's Tiki Sunset Cruise
A tiki-boat sunset cruise with a bar on board. The cheapest way onto the water at sunset during festival week.
| Adult | $59.95 |
|---|---|
| Child | $49.95 |
Sunset Watersports · Shared
Sunset Sip & Sail
Open bar included. Departs from the Historic Seaport, a five-minute walk from the top of Duval.
| Adult | $69.95 |
|---|---|
| Youth | $39.95 |
Mermaid Charters · Private
Champagne Sunset & Dolphin Watch
A private boat for your group with champagne and a dolphin-watching loop before the sun goes down. Up to six.
| Whole boat | $500 |
|---|
Daytime
Daytime escapes: sandbar and private charters
The sandbars west of Key West are a 20–30 minute run from the seaport and see none of the festival. A morning or midday charter is the reset most people need by day four. Private boats are priced per boat, not per person, so a group of six splits the cost.
Dolphin Safari · Private
3-Hour Private Sandbar Charter
Three hours on a private boat to the Key West sandbar. Six people works out to about $125 each.
| Whole boat | $749 |
|---|
Mermaid Charters · Private
Sandbar Excursion
A private sandbar run with snorkel gear included. Up to six guests.
| Whole boat, up to 6 | $650 |
|---|
Mermaid Charters · Private
Tiki Bar & Boca Chica Sandbar
Tiki bar aboard, a stop at the Boca Chica sandbar and a sightseeing loop. Private, up to six.
| Whole boat, up to 6 | $750 |
|---|
Sunset Watersports · Shared
Sandbar & Kayak Eco Adventure
The per-person option: a shared eco tour to the sandbar with kayaks. Runs every day of the festival.
| Adult | from $129.95 |
|---|---|
| Youth | from $89.95 |
Before you go
Practical notes for festival week
Book boats now
Operators run the same fleet as any other week while the island holds three times the people. Weekend and parade-night slots go first.
Where you board
Most departures are from the Historic Seaport (north end of Duval) or Garrison Bight. Duval closures make driving pointless; walk or use the Duval Loop bus.
Costumes on boats
Operators are relaxed about body paint and costumes on the private charters. Shared sunset sails expect swimwear or clothes.
Weather
Late October is the tail of hurricane season. Operators cancel for weather and refund; your risk is a lost afternoon, not lost money.
Family visit?
Goombay on the opening weekend and any daytime boat are fine for kids. The last four nights on Duval are not.
Questions
Frequently Asked Questions
When is Fantasy Fest 2026?
Fantasy Fest 2026 runs Friday, October 16 through Sunday, October 25, 2026. The parade is Saturday, October 24 at 7 p.m. on Duval Street. The theme is Musical Icons and Iconic Musicals.
Can you do a boat tour during Fantasy Fest?
Yes. Boats run their normal schedules during Fantasy Fest and the water is far less crowded than Duval Street. Daytime sandbar charters and sunset sails both operate all week; one operator runs a dedicated private, clothing-optional Fantasy Fest charter for up to six guests.
How far ahead should I book a Fantasy Fest boat?
As early as you can. The fleet is the same size as any other week while the island holds several times its usual visitors. Sunset sails on parade night (October 24) and the Friday Masquerade March night sell out first; weekday mornings last longest.
Is Fantasy Fest family-friendly?
The opening weekend's Goombay Festival in Bahama Village is family-friendly, and daytime boat tours are fine for kids all week. The final four nights on Duval Street are adults-only in practice.
What is the Fantasy Fest boat party?
It is a private charter run by Bone Island Charters only during Fantasy Fest: your own boat for up to six people, clothing-optional, cruising the harbor and backcountry. It is priced per boat, so a full group splits the cost.
Get on the water before Duval fills up
Parade-night sunset sails go first. Weekday mornings are the easiest to book.
See the three picks