3 hours · Private
Sunset Sail
Out of the seaport for sunset. Drinks and appetizers can be added.
| ARIA, 42 ft | $1,200 |
|---|---|
| Zodiac, 60 ft | $2,200 |
Editorial spotlight · Historic Seaport, Key West
2026 Conch Shell Awards nomineeBest Sailing Experience
Restless Native
Private sailing catamaran charters out of Key West's Historic Seaport: sunset sails, days on the reef, nights at anchor, and a three-day trip to the Dry Tortugas. Six guests at most, and the boat is yours.
- From
- $1,200
- Tripadvisor
- 5.0
- Guests
- Up to 6
Editorial spotlight. Restless Native Charters is a nominee in the 2026 Conch Shell Awards. They did not pay for this page and had no say in it. We earn a commission when you book through the links here; your price is the same.
The crew
Captain Brad, Captain Maddie and two catamarans
Restless Native runs private charters on two sailing catamarans, the 42-foot ARIA and the 60-foot Zodiac. Every trip is one group, capped at six guests.
Captain Brad Barker runs the company. Guests name him and Captain Maddie in review after review; Maddie is also the cook aboard. The Restless Native name has been on Key West charter boats since 1993.
“Captain Brad is an expert sailor.”
- BB
Owner · Captain
Capt. Brad Barker
- M
Captain · Chef
Capt. Maddie
- L
Captain
Capt. Lailani
The big one
Three days to the Dry Tortugas
A private three-day trip from Key West to Fort Jefferson aboard the Zodiac. The boat has four cabins, each with its own bathroom and shower; three are for guests. The crew cooks every meal, and there is nothing for sale on the island.
Because you sleep aboard, you have the park in the early morning and evening, when the day boats are gone. Restless Native says it holds a permit to guide in Dry Tortugas National Park.
| Whole boat, 3 days, up to 6 | $10,700 |
|---|
They recommend booking before you buy plane tickets; the trip often books up months ahead.
Check AvailabilityThe boats
ARIA and Zodiac
Both boats take up to six guests. On day sails the Zodiac costs $1,000 more for the bigger boat.
SV ARIA
- Type
- Sailing catamaran
- Length
- 42 ft
- Guests
- Up to 6
- Guest cabins
- 3, each with bath
- Boards
- Historic Seaport, Pier C-18
SV Zodiac
- Type
- Sailing catamaran
- Builder
- Fountaine Pajot
- Length
- 60 ft
- Guests
- Up to 6
- Guest cabins
- 3, each with bath
- Boards
- Historic Seaport, Pier D-22
Book it
Every trip is private
Prices are for the whole boat, up to six guests, and were checked against FareHarbor on September 28, 2026.
4 hours · Private
Half Day Sail
Sail, swim and snorkel. Gear, towels and floats are aboard.
| ARIA, 42 ft | $1,400 |
|---|---|
| Zodiac, 60 ft | $2,400 |
6 hours · Private
3/4 Day Sail
Enough time for a reef stop and a long lunch at anchor.
| ARIA, 42 ft | $1,600 |
|---|---|
| Zodiac, 60 ft | $2,600 |
8 hours · Private
Full Day Sail
A full day out of Key West, built around what your group wants to do.
| ARIA, 42 ft | $1,800 |
|---|---|
| Zodiac, 60 ft | $2,800 |
Overnight · Zodiac
Overnight Expedition
Sleep aboard the Zodiac at anchor, in a cabin or under the stars.
| Zodiac, 60 ft | $3,700 |
|---|
Also private: the Epic Sail (from $2,700), and weddings, memorials and custom sails from $5,200 on ARIA or $6,200 on the Zodiac.
Before you go
Know before you go
Where to board
Historic Seaport, 120 Margaret St. ARIA boards at Pier C-18 and the Zodiac at Pier D-22. They suggest parking in the lot next to Cuban Coffee Queen.
What to pack
Soft bags only; hard suitcases don't fit. It's a barefoot boat. Bring a swimsuit, sunscreen, a hat, and a windbreaker for winter sunsets.
Included
Snorkel gear, towels, inner tubes and pool floats.
Add-ons
Drinks and appetizers, a personal chef, Starlink Wi-Fi, an eFoil session and spearfishing.
One house rule
No red wine aboard. It spills, and mixed with salt water it stains like paint.
Photos: Restless Native Charters, used with permission.
Reviews
What guests say
- 5.0Tripadvisor182 reviews
- #49of 397Key West boat tours and water sports on Tripadvisor
Reviewers keep naming the same things: trips shaped around what the group wants, Captain Maddie's cooking, and Captain Brad's sailing and stories, with dolphins and turtles along the way.
Questions
Good to know
How many guests can come?
Up to six per charter on either boat. Every trip is private.
Where do we board?
At the Historic Seaport, 120 Margaret St, Key West. ARIA is at Pier C-18 and the Zodiac at Pier D-22.
Is food included?
On day sails you can bring your own or add drinks and appetizers or a personal chef. On the Dry Tortugas trip the crew provides the meals.
Can we stay overnight?
Yes. The Overnight Expedition on the Zodiac is $3,700, and the Dry Tortugas trip is three days aboard for $10,700.
What is the difference between ARIA and the Zodiac?
ARIA is a 42-foot catamaran and the Zodiac is a 60-foot Fountaine Pajot. Both take up to six guests; the Zodiac costs $1,000 more on day sails.
Sail with Restless Native
Sunset sails leave the Historic Seaport in the evening. Every trip is private.
Check Availability