Bossytravell HalloweenSingles Cruise 2026

Bossy Travel’s 2026 Halloween Singles Cruise

“Sail Into the Spooky Season with Style, Flirtation & Fun!”

October 25–31, 2026 | 6Nights | Departing from Miami, FL

Get ready for an unforgettable adventure at sea where ghoulish glam meets grown-up getaway! Bossy Travel invites you to join our 2026 Halloween Singles Cruise, exclusively curated for fabulous singles who crave connection, excitement, and a bit of costume magic.

This 6-night cruise combines all the energy of Halloween with the relaxed luxury of tropical cruising. Whether you’re looking for love, laughter, or just a wickedly good time, this is your chance to mix, mingle, and party with like-minded travelers while exploring stunning Caribbean destinations.

Destinations Include:

• Grand Turk: A haven of history and heavenly beaches

This 6-night sojourn starts in Miami and spends a day sailing to the beach-ladened city of Grand Turk, followed by a day of outdoor adventure, self-care, or utter relaxation on the beaches of Puerto Plata. Spend one more day at sea sailing to Bimini, home of our famous Beach Club at Bimini, where you can sunbathe, swim in the enormous pool, and sip perfect cocktails before returning to Miami.

Always Included LuxuryOver $1000 in value. The luxury you deserve — without the nickel & diming from the others. Look (far) beyond the headline rate.

WiFi

Browse, post, and stay connected on board.

Tips & Gratuities

We take care of our Crew. You just enjoy.

All Dining

20+ eateries with Michelin-star chef curated menus.

Soda & Water

Non-pressed juices, teas, and drip coffee, too!

Fitness Classes

Yoga, meditation, cycling, HIIT classes, and more!

Entertainment

Jaw-dropping shows? Always included.

Who Should Join:

Solo travelers, open-hearted adventurers, and singles of all ages (21+) ready to celebrate Halloween in a one-of-a-kind way—on the open sea! LGBTQ+ friendly, confidence-boosting, and drama-free.

Don’t Miss the Boat!

Space is limited—and this is Bossy Travell’s most anticipated singles event of the year. Grab your costume, pack your sass, and get ready to sail spooky with us.

Reserve Your Cabin Today at BossyTravell.com

Info: BossyTravell’s 2026 Halloween Singles Cruise

“Sail Into the Spooky Season with Style, Flirtation & Fun!”

October 25–31, 2026 | 6 Nights | Departing from Miami, FL


Get ready for an unforgettable adventure at sea where ghoulish glam meets grown-up getaway! Bossy Travell invites you to join our 2026 Halloween Singles Cruise, exclusively curated for fabulous singles who crave connection, excitement, and a bit of costume magic.


This 7-night cruise combines all the energy of Halloween with the relaxed luxury of tropical cruising. Whether you’re looking for love, laughter, or just a wickedly good time, this is your chance to mix, mingle, and party with like-minded travelers while exploring stunning Caribbean destinations.

Also check out other Trips & Adventurous Activities in Miami, Workshops in Miami, Health & Wellness events in Miami.