Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Boat Rentals
    5. /Private Charter or Rental in San Jose
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Private Charter or Rental in San Jose

    Customize a private outing for up to 9 people

    5.0 stars• 29 reviews

    Duration

    4 or 6 hrs

    Highlights

    Customize a private charter or bareboat rental in San Jose around your group’s plans.

    • Choose a private charter for groups of up to 6 people
    • Rent bareboat for groups of up to 9 people
    • Customize your private outing
    • Gather your group for a charter or rental

    Important details

    • Complete a waiver for private charters
    • Expect a captain fee for bareboat rentals; it is not included in the listed price

    Cancellation Policy

    Private charters require 2 days' notice for a full refund. Reservations made less than 24 hours before departure are nonrefundable. Failure to cancel at least 24 hours before departure results in a full charge. Full refund if the captain cancels the trip.

    Product ID: G8XXMT

    Meeting details

    Hurricane Hole Marina, 5130 Overseas Hwy 1, Key West, FL 33040

    Experience provided by Sun Surf & Sand Charters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Private Charter - 4 Hours

    $850.12

    4 Hours | Up to 6 People

    0

    Private Charter - 6 Hours

    $1,020.36

    6 Hours | Up to 6 People

    0

    Bareboat Rental - 4 Hour

    $1,133.86

    4 Hours | Up to 9 people

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    Our experience with Sun Surf and Sand Charters was exceptional before we ever stepped on the boat. I spoke with Captain Shane prior to booking, and he took the time to answer every question I had—and even a few I didn’t know I should be asking. We booked the Outer Island Sand Bar trip, and it did not disappoint. The entire trip was smooth and relaxed, and Captain Shane took us to three absolutely stunning, incredibly private locations. It felt like we had our own little pieces of paradise. One of the things we appreciated most was that Captain Shane took numerous photos of us throughout the trip. He captured some wonderful memories for us, and that was such an unexpected and thoughtful part of the experience. Captain Shane was also a great local resource. When we asked for recommendations, he happily shared suggestions for restaurants and nightlife all the way from Key Largo to Key West. We absolutely loved this experience. Looking back on our vacation, this was truly the highlight of our time in the Keys. Thank you, Captain Shane, for making the day so memorable and for giving us an experience we’ll remember for years to come!

    Photo of C. Milbert

    C. Milbert

    August 12, 2026

    Review 1 of 1
    5/5

    Our experience with Sun Surf and Sand Charters was exceptional before we ever stepped on the boat. I spoke with Captain Shane prior to booking, and he took the time to answer every question I had—and even a few I didn’t know I should be asking. We booked the Outer Island Sand Bar trip, and it did not disappoint. The entire trip was smooth and relaxed, and Captain Shane took us to three absolutely stunning, incredibly private locations. It felt like we had our own little pieces of paradise. One of the things we appreciated most was that Captain Shane took numerous photos of us throughout the trip. He captured some wonderful memories for us, and that was such an unexpected and thoughtful part of the experience. Captain Shane was also a great local resource. When we asked for recommendations, he happily shared suggestions for restaurants and nightlife all the way from Key Largo to Key West. We absolutely loved this experience. Looking back on our vacation, this was truly the highlight of our time in the Keys. Thank you, Captain Shane, for making the day so memorable and for giving us an experience we’ll remember for years to come!

    Photo of C. Milbert

    C. Milbert

    August 12, 2026

    Great for groups

    24' Sea Fox Boat Rental in Key West
    Boat RentalsUp to 8

    24' Sea Fox Boat Rental in Key West

    Self-guided Key West boating with flexible docking options

    Self-guided Key West boating with flexible docking options
    4.7 • 21 reviews
    $460/ boat
    24' Boat Rental in Key West
    Boat RentalsUp to 8

    24' Boat Rental in Key West

    Flexible Key West boat days with onboard GPS and radio

    Flexible Key West boat days with onboard GPS and radio
    4.7 • 21 reviews
    $460/ boat
    22' Sea Fox Boat Rental in Key West
    Boat Rentals

    22' Sea Fox Boat Rental in Key West

    Take the helm for flexible Key West boating, from a half day to a week

    Take the helm for flexible Key West boating, from a half day to a week
    4.7 • 21 reviews
    $426/ boat

    Nearby activities

    3-Hour Dolphin Watching & Snorkeling Cruise in the Keys
    Dolphin Watching

    3-Hour Dolphin Watching & Snorkeling Cruise in the Keys

    Cruise the Keys waters and watch dolphins, with time to snorkel

    Cruise the Keys waters and watch dolphins, with time to snorkel
    5.0 • 29 reviews
    $158/ person
    3-Hour Key West Sandbar Charter
    Boat Tours

    3-Hour Key West Sandbar Charter

    Cruise to shallow sandbars and glide through mangroves in the Florida Keys

    Cruise to shallow sandbars and glide through mangroves in the Florida Keys
    5.0 • 29 reviews
    $56/ person
    Florida Keys Sunset Charter
    Sunrise and Sunset Tours

    Florida Keys Sunset Charter

    Watch the Florida Keys sunset from the Gulf of Mexico

    Watch the Florida Keys sunset from the Gulf of Mexico
    5.0 • 29 reviews
    $146/ person
    3-Hour Dolphin Watching Charter in San Jose
    Dolphin Watching

    3-Hour Dolphin Watching Charter in San Jose

    Customize a private boat outing around dolphin watching and sandbar time

    Customize a private boat outing around dolphin watching and sandbar time
    5.0 • 29 reviews
    $169/ person
    3-Hour Charter in San Jose
    Yacht Charters

    3-Hour Charter in San Jose

    Shape a private boat outing around your group's interests

    Shape a private boat outing around your group's interests
    5.0 • 29 reviews
    $737
    Florida Keys Sunset Charter
    Sunrise and Sunset Tours

    Florida Keys Sunset Charter

    Watch the Florida Keys sunset from Gulf waters

    Watch the Florida Keys sunset from Gulf waters
    5.0 • 29 reviews
    $623