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. /Sailing
    5. /Key West Valentine's Sunset Sail
    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
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Key West Valentine's Sunset Sail

    Celebrate Valentine’s Day with cocktails, passed appetizers, and a sail through Key West waters

    5.0 stars• 375 reviews

    Duration

    2 hours

    Includes

    Cocktails, wines & appetizers

    Highlights

    Celebrate friendship and love aboard the Argo Navis with Valentine’s Day cocktails, appetizers, bubbly on embarkation, and attentive service at your seat. Cruise the waters where the Atlantic Ocean meets the Gulf of Mexico as wind, waves, and conversation set the soundtrack.

    • Sip bubbly on embarkation and Valentine’s Day specialty cocktails
    • Savor six rounds of handmade passed appetizers served at your seat
    • Cruise where the Atlantic Ocean meets the Gulf of Mexico
    • Relax aboard a 75-foot wind-driven vessel with space to enjoy the view

    What's Included

    • Valentine’s Day specialty cocktails
    • Bubbly on embarkation
    • Premium wines
    • Florida craft beers and Miller Lite
    • Nonalcoholic drinks, including sodas, sparkling water, and nonalcoholic beer
    • Six rounds of passed appetizers
    • Blankets

    Important details

    • Arrive at the dock 15 minutes before departure for check-in and a safety briefing
    • Bring an ID if you plan to drink alcohol
    • Boarding involves a ramp and a few steps; the restroom is reached by four steep steps
    • Public sails are smoke-free

    Cancellation Policy

    Cancel at least 48 hours before sailing for a full refund. Cancellations within 48 hours are not refunded. Sails run rain or shine unless weather is unsafe; if the operator cancels, reschedule at no extra charge or receive a full refund. A minimum of 6 passengers is required; if not met, reschedule or receive a full refund.

    Product ID: ET5437

    FAQs

    Tell the crew at boarding about food allergies or dietary restrictions. They will do their best to accommodate them.

    Boarding the Argo Navis involves a ramp and a few steps. The restroom level is reached by four somewhat steep steps, more like a ladder. Crew can assist travelers who are somewhat ambulatory.

    The six rounds of passed appetizers provide a few bites while you enjoy the sail, but may not replace dinner. Plan accordingly.

    Meeting details

    Ocean Key Resort Marina, 0 Duval Street, Key West

    Experience provided by Hindu Charters - Argo Navis

    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

    Over 21

    $170.25

    0

    Under 21

    $170.25

    Ages 12 - 20

    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

    Review summary

    5.0
    Excellent
    375 reviews•Google Maps
    344
    2
    1
    0
    1

    If you're weighing sunset cruise options in Key West, this one consistently rises to the top. The vibe skews relaxed and upscale rather than loud and crowded, which is a deliberate choice the crew leans into. Reviewers frequently mention crew members Carol, Kyle, Sidney, and Captain Andy by name, which says a lot about how personally invested the staff are in making guests feel taken care of. The open bar gets high marks across the board, with generous pours and thoughtfully crafted cocktails. Food is generally praised, though a small handful of guests found the appetizers a little underwhelming compared to the rest of the experience. The boat itself is described as spacious, clean, and comfortable, with enough room to actually move around and enjoy the sunset rather than feeling packed in. Repeat visitors are a real pattern here, with several reviewers mentioning they've come back for brunch, holiday cruises, and even weddings. That kind of loyalty is usually a reliable signal. If a peaceful, well-run evening on the water sounds appealing, this is a strong choice and as more than a few reviewers put it, tip the crew.

    What people are saying

    Review 1 of 4
    5/5

    This was our favorite experience in the Keys! The crew is amazing! Very engaging and attentive. Food and drinks were great! And they keep the number of guests on the boat low! 20/10 recommend!

    Photo of Bobby Lee

    Bobby Lee

    September 2, 2026

    Review 1 of 1
    5/5

    This was our favorite experience in the Keys! The crew is amazing! Very engaging and attentive. Food and drinks were great! And they keep the number of guests on the boat low! 20/10 recommend!

    Photo of Bobby Lee

    Bobby Lee

    September 2, 2026

    Nearby activities

    Sunday Brunch & Swim Cruise in Key West
    Sailing

    Sunday Brunch & Swim Cruise in Key West

    Brunch, drinks, and a swim stop aboard a Key West sail

    Brunch, drinks, and a swim stop aboard a Key West sail
    5.0 • 375 reviews
    $153/ person
    Key West Ghost & Voodoo Pedicab Tour
    Ghost and Haunted

    Key West Ghost & Voodoo Pedicab Tour

    Explore Key West's supernatural stories from a cozy pedicab

    Explore Key West's supernatural stories from a cozy pedicab
    5.0 • 18 reviews
    $157& up
    Key West History & Culture Walking Tour
    Historical Tours

    Key West History & Culture Walking Tour

    Walk Key West’s landmarks with local insight from Kino Sandals to the Southernmost Point

    Walk Key West’s landmarks with local insight from Kino Sandals to the Southernmost Point
    5.0 • 18 reviews
    $57/ person
    Perfume Making Class in Key West
    Aromatherapy

    Perfume Making Class in Key West

    Create your own fragrance in a guided Key West perfume class

    Create your own fragrance in a guided Key West perfume class
    4.8 • 50 reviews
    $138/ person
    Golf Simulator Session in Key West
    Golf and Mini Golf

    Golf Simulator Session in Key West

    Play 1,700+ virtual courses with real-time swing data

    Play 1,700+ virtual courses with real-time swing data
    4.5 • 640 reviews
    $51/ person
    Key West Bike Tour: Historic Old Town Landmarks
    Bike Tours

    Key West Bike Tour: Historic Old Town Landmarks

    Explore Key West's iconic landmarks with a local guide on two wheels

    Explore Key West's iconic landmarks with a local guide on two wheels
    4.9 • 523 reviews
    $58/ person