Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Gulfport…
    3. /Water Activities
    4. /Sailing
    5. /Gulfport Sunset Sail Charter
    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
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Gulfport Sunset Sail Charter

    Private evening sailing with sunset views across Tampa Bay

    5.0 stars• 25 reviews

    Duration

    3–4 hours

    Ideal For

    Up to 6 people

    Includes

    Captain and crew, onboard amenities

    Highlights

    Sail Tampa Bay aboard SV Cay Michele as the evening sky changes color. Settle in with your own snacks and drinks or optional catered food and drinks.

    • Relax aboard SV Cay Michele through calm, protected waters
    • Watch the sunset across an open horizon
    • Bring your own drinks and snacks to enjoy onboard
    • Listen to your music through the Bluetooth sound system

    What's Included

    • Professional captain and crew
    • Refrigeration
    • Air conditioning
    • Bluetooth sound system

    Important details

    • Arrive 15–20 minutes before departure
    • Complete a waiver for each passenger upon arrival

    Cancellation Policy

    Free cancellation with 24 hours' notice. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    Product ID: Z25CAW

    FAQs

    Bring your own drinks and snacks, or choose optional catered food or drinks for the Luxury Sunset Sail.

    Wear comfortable outdoor clothing. Bring sun protection, any drinks or snacks you want, and gratuity for the crew.

    Meeting details

    4699 Tifton Dr S, Gulfport, FL 33707

    Experience provided by St. Pete Sail Charters

    Related locations

    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

    Four Hour Private Charter

    $1,356

    1-6 Passengers

    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 4
    5/5

    My boyfriend surprised me with the most incredible sailboat trip for my birthday, and it was truly such a beautiful experience! ⛵️🤍 The entire trip was so peaceful and relaxing, and the boat itself was absolutely stunning one of the most beautiful sailboats I’ve ever seen. Noah was an amazing captain! His experience and the way he handled the boat made me feel completely safe and comfortable the entire time. He was also so welcoming and made the whole experience even more enjoyable. The amenities were incredible, too. The seats were so comfortable, there was plenty of space to move around and enjoy different parts of the boat, and having a bathroom and full kitchen onboard was such a nice touch. Everything was thoughtfully designed to make the trip comfortable and relaxing. It was the perfect birthday surprise and such a memorable experience. I couldn’t recommend this sailboat trip enough! 🌊☀️⛵️💙

    Photo of Vic Hamel

    Vic Hamel

    August 15, 2026

    Review 1 of 1
    5/5

    My boyfriend surprised me with the most incredible sailboat trip for my birthday, and it was truly such a beautiful experience! ⛵️🤍 The entire trip was so peaceful and relaxing, and the boat itself was absolutely stunning one of the most beautiful sailboats I’ve ever seen. Noah was an amazing captain! His experience and the way he handled the boat made me feel completely safe and comfortable the entire time. He was also so welcoming and made the whole experience even more enjoyable. The amenities were incredible, too. The seats were so comfortable, there was plenty of space to move around and enjoy different parts of the boat, and having a bathroom and full kitchen onboard was such a nice touch. Everything was thoughtfully designed to make the trip comfortable and relaxing. It was the perfect birthday surprise and such a memorable experience. I couldn’t recommend this sailboat trip enough! 🌊☀️⛵️💙

    Photo of Vic Hamel

    Vic Hamel

    August 15, 2026

    Nearby activities

    4-5 Hour Private Daytime Sail in St. Petersburg
    Sailing

    4-5 Hour Private Daytime Sail in St. Petersburg

    Private daytime sail with dinghy access for island exploring

    Private daytime sail with dinghy access for island exploring
    5.0 • 25 reviews
    $1,356& up
    Treasure Island Sandbar Sailing Charter
    Yacht Charters

    Treasure Island Sandbar Sailing Charter

    Sail to a sandbar with a private yacht as your home base

    Sail to a sandbar with a private yacht as your home base
    5.0 • 25 reviews
    $1,695& up
    Egmont Key Snorkeling Cruise
    Snorkeling

    Egmont Key Snorkeling Cruise

    Snorkel Fort Dade ruins and explore Egmont Key’s shores

    Snorkel Fort Dade ruins and explore Egmont Key’s shores
    4.9 • 764 reviews
    $80/ person
    Private Shell Key Dolphin & Shelling Tour
    Boat Tours

    Private Shell Key Dolphin & Shelling Tour

    Explore Shell Key's shores for shells and Gulf wildlife

    Explore Shell Key's shores for shells and Gulf wildlife
    4.9 • 764 reviews
    $396
    Shell Key Dolphin & Shelling Cruise
    Boat Tours

    Shell Key Dolphin & Shelling Cruise

    Private Shell Key escape for beachcombing, snorkeling and wildlife watching

    Private Shell Key escape for beachcombing, snorkeling and wildlife watching
    4.9 • 764 reviews
    $622
    Shell Key Sunset Cruise From Gulfport
    Boat Tours

    Shell Key Sunset Cruise From Gulfport

    Shell, swim, and watch the Florida sunset from Shell Key Sandbar

    Shell, swim, and watch the Florida sunset from Shell Key Sandbar
    4.9 • 764 reviews
    $64/ person