We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Pensacola, FL/
    3. Water Activities/
    4. Sailing/
    5. The Locals Island Charter
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    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

    Reserve in minutes with flexible 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

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Gallery image
    Gallery image 2
    Gallery image 3

    The Locals Island Charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter

    From$1,344incl. taxes and fees

    Duration

    6 hours

    Ideal For

    Up to 6 people

    Includes

    Lunch, Soft drinks, Gear

    Highlights

    Sail from Bayou Chico across Pensacola Bay to anchor near Fort McRee and a secluded beach. Enjoy swimming, paddleboarding, sightseeing, and lunch on a private 6-hour charter.

    • Sail to Fort McRee and a secluded beach
    • Anchor for swimming and paddleboarding
    • Watch for dolphins and local marine life
    • Learn a bit of Pensacola history
    • Explore spots only accessible by boat
    • Bring your own beverages and snacks

    What's Included

    • Soft drinks, light sandwiches, ice and water
    • Paddleboards, snorkel gear, sunscreen, life vests and towels

    Things to know

    Arrive 15 minutes before departure. Guests who plan to swim or paddleboard must sign a swim waiver. Wear non-marring deck or athletic shoes; no smoking on board; the charter is weather dependent and may be canceled for safety.

    Cancellation policy

    Provide 48 hours' notice for a full refund. If weather or captain-determined circumstances do not permit the charter, the full price is refunded.

    Meeting location

    Day Break Marina, 811 South R St, Pensacola, FL 32501

    Experience provided by Wine Down Sailing
    Experience provided by Wine Down Sailing

    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 (650) 414-7338

    Reference #GYXQ26

    Private Sail

    $1,344

    Up to 6 people

    0

    *Price includes taxes and fees

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

    Search all experiences

    Discover what we've curated for you

    5.0 stars• 16 reviews

    Review summary

    5.0
    Excellent
    16 reviews•Google Maps

    Captain Steve and Melissa have created something truly special here. Guests consistently rave about feeling like friends rather than customers from the moment they step aboard, with several reviews mentioning the warm, welcoming atmosphere that makes even nervous sailors feel completely at ease. The boat itself gets top marks for being immaculate, comfortable, and beautifully maintained. Steve's sailing expertise and communication skills shine through in every review, with guests appreciating his responsiveness and flexibility in planning their trips. The sunset and moonlit cruises seem to be the most popular offerings, with travelers loving the peaceful, intimate experience on the water. Multiple guests mention spotting dolphins and enjoying the stunning views of Pensacola Bay and Perdido Key. What really sets them apart is the personal touches: custom charcuterie boards, birthday cakes, help with surprise proposals and engagement photos. This feels less like a commercial operation and more like sailing with knowledgeable friends who genuinely care about making your celebration memorable. First-timers and repeat customers alike can't wait to book again.

    What people are saying

    Review 1 of 5
    5/5

    I truly would give this business 20 stars if I could. The owner, Cpt. Steve, was wonderful at communicating and was there to guide, answer questions and stay in touch. But he also went all the extra miles. We truly felt like friends the moment we stepped on the boat. Yes the boat was beautiful, spotless clean and we never felt like we couldn't enjoy. If you are interested in a smaller family feel atmosphere to enjoy the beauty and peaceful moments this is the one to book. It was our 48th Anniversary and it made all the memories we were hoping to make become reality. We definitely will be booking again and YES I HIGHLY RECCOMEND!!!!

    Photo of MARTHA WING

    MARTHA WING

    June 5, 2025

    Review 1 of 1
    5/5

    I truly would give this business 20 stars if I could. The owner, Cpt. Steve, was wonderful at communicating and was there to guide, answer questions and stay in touch. But he also went all the extra miles. We truly felt like friends the moment we stepped on the boat. Yes the boat was beautiful, spotless clean and we never felt like we couldn't enjoy. If you are interested in a smaller family feel atmosphere to enjoy the beauty and peaceful moments this is the one to book. It was our 48th Anniversary and it made all the memories we were hoping to make become reality. We definitely will be booking again and YES I HIGHLY RECCOMEND!!!!

    Photo of MARTHA WING

    MARTHA WING

    June 5, 2025

    Nearby activities

    Thumbnail

    Pensacola Bay Inshore Fishing Charter, Private

    From$636
    Thumbnail

    Private Dolphin Tour in Pensacola

    $424
    Thumbnail

    Pensacola Gulf Private Offshore Fishing Charter

    From$636
    Thumbnail

    Private Shark Fishing Charter in Pensacola

    $530
    Thumbnail

    Dessert Madness: Walking Dessert Tour

    From$39/ person
    Thumbnail

    Ghosts and Graveyards Tour of Pensacola

    From$37/ person