Guest celebrating aboard the charter boat with El Morro fort in the background
Sail or power boat

From $595/ 3 hour trips

Sunset or bay cruise

Private for you and yours. Cruise the stunning waters of Old San Juan Bay full of Caribbean flare, past El Morro Castle, La Fortaleza, the Bacardi Factory and more.

Book NowView Fishing Tours
1 to 6 guests
Free appetizers and local drinks
Every 3 hour trip

How it works

Your bay, your boat, your pace

Your choice of sailing or boating the historical landmarks of Old San Juan, headlined by El Morro Castle. Choose a day outing or a sunset outing with tapas and a drink included for a limited time. Our captain and crew share San Juan's history and Caribbean flare along the way, and up to 6 guests may come aboard.

01

Old San Juan's landmarks

El Morro Castle, La Fortaleza and the Bacardi Factory pass by from the water, a view the walled city does not give you on foot.

02

Day or sunset outing

Pick a daytime cruise or the sunset outing with tapas and a drink included for a limited time.

03

Special requests welcome

Building a memory with your loved ones is the point. Tell us what you have in mind and we will work to make it happen.

04

Departure times

Your choice of departure time, to be confirmed with the captain ahead of your trip.

Two ways to cruise

Choose your vessel

Every private cruise goes out aboard one of two boats. Both carry up to 6 guests and a licensed captain.

Game Day, the 2014 Contender 25 foot center console power boat, near the historic fort on San Juan BayCenter console power boat

Game Day

A 2014 Contender 25T completely refitted in 2023 with new twin Suzuki 150 hp engines, all new electrical components and electronics, and a redesigned center console. The deep-v hull holds steady even in rough conditions, and the T-top keeps the cockpit shaded. Also the perfect vessel for a fish and cook beach day.

Length
25 ft
Guests
6 guests
In service
2014, refitted 2023
Engines
Twin Suzuki 150hp
Hull
Deep-V
Live well
34 gallon
Shade
T-top
Fish boxes
3
Guests
Up to 6
Cruising sailboat with guests aboard near a tropical shoreline at sunset, similar in spirit to Sail La VieMonohull sailboat

Sail La Vie

A 1994 Hunter 37.5 foot Legend monohull, refitted in 2023 with a new main sail, jib sail, running rigging and decking material. Roomy deck space runs bow to stern, with a comfortable aft cockpit and a sugar scoop swim platform. Below deck: a kitchen, one bathroom and two cabins, including an aft queen stateroom and a roomy forward V-berth. Powered by a Yanmar diesel engine for a quiet approach to any anchorage.

Length
37.5 ft
Guests
6 guests
In service
1994 Hunter Legend, refitted 2023
Engine
Yanmar diesel
Sails
Main and jib
Cabins
2
Layout
Aft queen, fwd V-berth
Bathroom
1
Guests
Up to 6

What comes with every trip

Included on all tours

A pro USCG certified licensed captain, fuel, water and a cooler with ice for your use.

  • Pro USCG certified licensed captain
  • Fuel, water and a cooler with ice for your use
  • Free appetizers and local drinks on 3 hour trips
  • Your choice of sailboat or power boat
Book Now

Gratuities are not included.

Guest giving a thumbs up aboard the charter boat with El Morro fort in the background

Good to know

This is a drug free operation for your safety and in compliance with local law. Reservations are first come, first served and subject to confirmation. Deposits are fully refundable if a cancellation is received 30 days prior to a trip, or if the captain cancels for safety or the vessel is not operational.

Ready when you are

Reserve your sunset or bay cruise

From $595 for up to 6 guests. Tell us your date and we will confirm your captain and vessel.

Book NowSee Fishing Tours

USCG certified pro captains. Immediate confirmation.