We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Edgartown, MA/
    3. Water Activities/
    4. Boat Tours/
    5. Private Sunset Cocktail Cruise

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
    Greetwell

    Trusted by leading vacation properties and hotels, Greetwell helps travelers feel at home wherever they go. Enjoy curated experiences that carry you from the comfort of your stay into the heart of the local community.

    Safe & Secure Payments

    Guest Support

    • Help Center
    • (650) 414-7338
    • [email protected]

    Company

    • About
    • Nominate Providers
    • Hospitality Partners
    © 2025 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Private Sunset Cocktail Cruise

    Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group

    From$2,595

    Ideal For

    Up to 18 people

    Includes

    Private boat, Licensed captain

    Highlights

    Set sail on a private evening cruise through the scenic waters around Cape Cod and Martha's Vineyard. Watch the sun dip below the horizon while you relax with your group of up to 18 guests.

    1. Marvel at vibrant sunset colors over the islands
    2. Relax on a spacious vessel reserved just for your group
    3. Sip favorite beverages as gentle breezes surround you
    4. Capture stunning photos from the open deck
    5. Enjoy attentive service from a licensed captain

    What's Included

    1. Private boat charter
    2. Experienced U.S. Coast Guard-licensed captain

    Arrive at the dock at least 15 minutes before departure; the boat may leave without late guests. Parking is limited at all pickup points, so plan ahead. Maximum capacity is 18 passengers.

    Cancellation policy

    50% deposit is fully refundable up to 7 days before the cruise. Within 6 days the deposit is non-refundable unless the cruise can be rescheduled. A full refund is provided for mechanical issues or if the captain cancels due to bad weather.

    Meeting location

    50 Dock St, Edgartown, MA 02539

    Experience provided by Plan Sea Adventure Charters
    Experience provided by Plan Sea Adventure 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 (650) 414-7338

    Reference #H68DJH

    Private Charter Cruise

    $2,595

    Up to 18 passengers

    1

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    5.0 stars• 169 reviews

    Review summary

    5.0
    Excellent
    169 reviews•Google Maps

    Captain Dave and his crew consistently deliver exceptional charter experiences that work beautifully for groups of all sizes, from intimate family outings to bachelorette parties of 12-13 people. Reviewers rave about the attentive, friendly service and how Dave makes everyone feel welcome while sharing fascinating local history about Martha's Vineyard and the Elizabeth Islands. The boat is well-equipped and comfortable, with fun extras like cannon shooting and opportunities for guests to take the helm. What really sets this operation apart is the crew's ability to blend education with entertainment. Even self-described non-boat people found themselves completely at ease thanks to the crew's expertise and the smooth sailing experience. Common highlights include swimming stops, port tours, sunset viewing, and visits to spots like Cuttyhunk with its spectacular lookout views. Crew members like Molly, Ben, and Roy get regular shoutouts for being knowledgeable and accommodating, making special occasions truly memorable. <similarity_check> This summary takes a "strengths-first" approach with a focus on the crew's versatility with different group types. It uses straightforward, descriptive language and emphasizes the educational aspect alongside entertainment value. The structure flows from general service quality to specific differentiators to crew recognition. </similarity_check>

    What people are saying

    Review 1 of 5
    5/5

    Plan Sea was an amazing experience for my bachelorette party. Captain Dave and Molly were incredible and so accommodating. I highly recommend booking for your next trip to the Vineyard if you want to make it a truly memorable and special experience. Something I’ll remember for a lifetime. Thank you!

    Photo of Marilyn Buck

    Marilyn Buck

    August 31, 2024

    Review 1 of 1
    5/5

    Plan Sea was an amazing experience for my bachelorette party. Captain Dave and Molly were incredible and so accommodating. I highly recommend booking for your next trip to the Vineyard if you want to make it a truly memorable and special experience. Something I’ll remember for a lifetime. Thank you!

    Photo of Marilyn Buck

    Marilyn Buck

    August 31, 2024

    Nearby activities

    Thumbnail

    Electric Townie Beach Cruiser Rental

    $240
    Thumbnail

    21ft Boston Whaler 210 Dauntless Boat Rental

    $2,000
    Thumbnail

    Three Hour Martha's Vineyard Island Tour

    $65/ person