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A serene landscape featuring mountains, a lake, and a clear blue sky with fluffy clouds.

Discover the World with My Bear Cruise

November 14 2026 to November 21th 2026

Caribbean Bear Cruise 2026 - Join the Fun!

Book Now
Group of men enjoying a sunny pool day holding one man horizontally.

🐻 Welcome to the My Bear Cruise Caribbean Experience


Welcome aboard the My Bear Cruise Caribbean Cruise — the ultimate gathering for bears, cubs, chasers, admirers, and friends seeking an unforgettable Caribbean cruise experience filled with sun, sea, connection, and sheer fun.


This is more than just a cruise; it’s a vibrant floating bear community tailored for men who appreciate a relaxed, friendly, body-positive atmosphere. With incredible destinations, exclusive private events, and nonstop social energy, whether you're cruising solo, with friends, or with a partner, you'll feel completely welcomed and right at home from the moment you step onboard.


Get ready for fantastic music, themed parties, laid-back daytime vibes, exciting nights, and friendships that often extend long after our LGBTQ+ group travel adventure concludes.


🌴 What to Expect on a My Bear Cruise


My Bear Cruise is designed to be fun, social, and pressure-free. You control your pace—party hard, unwind by the pool, explore new ports, or enjoy a little of everything at your leisure.


Onboard, you can expect:


- A friendly, welcoming bear crowd from around the world  

- Daily social meetups and casual gatherings  

- High-energy themed parties and relaxing evening events  

- Poolside lounging, cocktails, and sun-soaked afternoons  

- Private bear-only events exclusively for our group  

- A vibrant, body-positive environment where everyone belongs  


From morning coffee chats to late-night dance floors, there’s always something happening—or if you prefer, just relax and take it easy.


🎉 Private Bear Events & Theme Nights


As part of our exclusive group programming, My Bear Cruise offers private events just for our guests, including:


- Welcome Meet & Greet  

- White Party  

- Pirates of the Caribbean Party  

- Great Gatsby / Roaring 20s Party  

- Pool & Deck Parties  

- Farewell Celebration  


All events are optional—feel free to come dressed up or keep it casual. The only requirement is to have fun and be your true self.


🍽️ What’s Included in Your Cruise


Your cruise fare provides exceptional value, comfort, and entertainment:


Included in your cruise fare:


- Your cruise accommodations  

- All main dining room meals  

- Buffet and casual dining options  

- Entertainment and shows onboard  

- Access to pools, hot tubs, gym, and ship amenities  

- All My Bear Cruise private events and parties  

- Daily activities and social gatherings  


Not included:


- Alcoholic beverages and specialty coffee (beverage packages available)  

- Specialty dining restaurants  

- Shore excursions  

- Spa services  

- Gratuities, taxes, and fees (where applicable)  

- Taxes and fees of $210 not included in the price  


Optional beverage packages and upgrades can be added to enhance your cruise experience.


🗺️ Caribbean Itinerary Highlights


Our Caribbean itinerary perfectly balances beautiful tropical destinations with relaxing sea days—making it the ideal escape. 


Typical itinerary includes:


- Fort Lauderdale, Florida – Easy embarkation and smooth sailing  

- Caribbean Island Ports – Crystal-clear waters, beaches, local culture, and excursions  

- At-Sea Days – Pool parties, relaxing, themed events, and social time  

- Return to Fort Lauderdale – Full of new friendships and unforgettable memories  


Exact ports and times may vary by sailing—full details are listed on the cruise itinerary page.


🐻 Who Should Join My Bear Cruise?


My Bear Cruise is for:


- Bears, cubs, chubs, chasers, admirers, and allies  

- Solo travelers eager to make new friends  

- Couples and groups of friends  

- First-time cruisers and seasoned travelers  


No cliques. No pressure. Just good vibes, amazing people, and an unforgettable week at sea.


⚓ Ready to Sail With the Bears?


If you're searching for a cruise that seamlessly blends community, fun, relaxation, and unforgettable experiences, My Bear Cruise is your perfect destination.


Come for the Caribbean. Stay for the bears. Leave with memories that last a lifetime.


🐻 Welcome aboard.

prices starting at only $599+ per person

Cruise route map from Ft. Lauderdale to Caribbean destinations.

Get ready to sail on the biggest bear cruise in the Caribbean

Depart 


Saturday, November 14, 2026 Departs at 03:00 PM  


Day 1: Ft. Lauderdale, Florida - Sat, Nov 14 • 03:00 PM  


Day 2: Experience the vibrant atmosphere of Celebration Key, Grand Bahama Island on our Caribbean cruise, Sun, Nov 15 • 08:00 AM - 05:00 PM  


Day 3: At Sea - Mon, Nov 16  


Day 4: Amber Cove, Dominican Republic - Tue, Nov 17 • 09:00 AM - 06:00 PM  


Day 5: Grand Turk, Turks & Caicos - Wed, Nov 18 • 08:00 AM - 06:00 PM  


Day 6: At Sea - Thu, Nov 19  


Day 7: At Sea - Fri, Nov 20  


Day 8: Return to Ft. Lauderdale, Florida - Sat, Nov 21 • 06:00 AM. Join us for an unforgettable Caribbean cruise experience tailored for LGBTQ+ group travel and gay cruises enthusiasts.

Discover the Best Cruises with My Bear Cruise

Meet & Greet Cocktail Party

Pirates of the Caribbean Party

Pirates of the Caribbean Party

Group of men enjoying a meet and greet at sunset.

Welcome Aboard! 🛳️🍸


Gentlemen, it’s time to set sail on an unforgettable Caribbean cruise experience! Whether you’re a seasoned cruiser or stepping aboard for the first time, we’re thrilled to welcome you to this exclusive LGBTQ+ group travel meet-and-greet cocktail party. 

Tonight is all about great conversation, new friendships, and a little sparkle on the high seas. So grab a drink, mix and mingle, and let’s toast to this adventure together! 

The ocean breeze, the clink of glasses, and the laughter of like-minded souls—what more could we ask for? So relax, be yourself, and let’s make memories that last far beyond the horizon.

Cheers to an amazing voyage ahead! 🥂🌊

Pirates of the Caribbean Party

Pirates of the Caribbean Party

Pirates of the Caribbean Party

Four friends dressed as pirates enjoying drinks and smiling.

🏴‍☠️ Pirates of the Caribbean Party


Ahoy, mateys! One night on our Gay Caribbean Cruise, the ship transforms into a high-seas playground for our legendary Pirates of the Caribbean Party—one of the most anticipated theme nights of the week, perfect for those seeking an unforgettable Caribbean cruise experience.


Inspired by the spirit, adventure, and playful mischief of Pirates of the Caribbean, this over-the-top themed party invites you to unleash your inner pirate. Expect a night filled with swashbuckling fun, tropical beats, rum-fueled energy, and plenty of eye candy as our guests bring the theme to life.


Dress the part with pirate hats, bandanas, boots, corsets, vests, leather, stripes, or anything sexy and sea-worthy. Whether you come as a fearless captain, a rogue deckhand, or a cheeky Caribbean pirate, creativity is encouraged—and rewarded with plenty of attention on the dance floor, making this one of the highlights of our LGBTQ+ group travel itinerary.


Our DJs will keep the party going with high-energy music, themed surprises, and nonstop dancing as the night sails on. This is a private gay group event, exclusively for our guests, designed to be fun, flirtatious, and unforgettable.


So grab your crew, raise a glass, and prepare to plunder the dance floor. No rules. No curfews. Just pure pirate fantasy at sea.


🏴‍☠️ Arrr you ready?

70s Costume Party

Pirates of the Caribbean Party

70s Costume Party

Group of happy men at a 70s party.

Welcome to the Ultimate 70s Disco Bash on our Caribbean cruise experience! 🕺🎶🚢


Alright, gentlemen—get ready to step back in time to an era of bell-bottoms, glitter, and funkadelic beats! The ocean may be beneath us, but tonight, we’re soaring straight to Studio 54. Whether you're showcasing your best dance moves or simply here to soak in the electric energy, this is your moment to shine! The drinks are flowing, the disco ball is spinning, and the night is ours to groove.


So channel your inner diva, hit the dance floor, and let’s make this gay cruise party one for the history books. After all, tonight, we’re not just cruising—we’re cruising in style with our vibrant LGBTQ+ group travel! 

Let’s boogie! 🕺🥂✨

White Party

Great Gatsby Party

70s Costume Party

Group of four men dressed in white, smiling, holding drinks.

🤍 White Party at Sea


One of the standout nights on our Gay Caribbean Cruise experience is the unforgettable White Party—a timeless celebration of style, confidence, and pure island energy under the stars.


Inspired by legendary all-white events around the world, our onboard White Party is a private, adults-only evening exclusively for our gay group guests. As the sun sets and the ocean sparkles, the ship comes alive with glowing white attire, sultry beats, and an atmosphere that’s equal parts chic and electrifying.


Dress in your best white look—linen, swimwear, sleek resort wear, bold statement pieces, or daring minimalist styles. From casual coastal elegance to high-fashion fantasy, this is your moment to shine. White is more than a dress code—it’s a vibe.


Our DJs keep the energy flowing with a mix of dance, house, and party anthems while the dance floor fills with smiling faces, new friendships, and unforgettable moments. Whether you’re dancing until late, enjoying cocktails with friends, or simply soaking in the ambiance, the White Party is where memories are made during this incredible LGBTQ+ group travel experience.


Elegant. Sexy. Iconic. The White Party is a signature event you won’t want to miss.


🤍 Come dressed in white. Leave glowing.

Great Gatsby Party

Great Gatsby Party

Great Gatsby Party

Four men in vintage formal attire at a party.

🥂 The Great Gatsby / Roaring 20s Party


Step back in time and into a world of glamour, excess, and timeless style at our Great Gatsby / Roaring 20s Party—one of the most elegant and high-energy nights on the Gay Caribbean Cruise. This exclusive Caribbean cruise experience invites you to dress to impress and celebrate in true 1920s fashion, inspired by the lavish parties and Jazz Age decadence of The Great Gatsby. Think champagne towers, jazz-inspired beats, art-deco flair, and a dance floor filled with confidence and charisma.


Gentlemen are encouraged to channel classic Gatsby style with tailored suits, suspenders, bow ties, vests, pinstripes, fedoras, or slick vintage looks. Feel free to add a modern twist—this is about elegance with attitude. The goal? Look sharp, feel bold, and own the night.


As the music builds and the energy rises, our DJs blend vintage vibes with modern dance tracks to keep the party roaring well into the night. Surrounded by like-minded travellers, this private LGBTQ+ group travel event is all about indulgence, connection, and unforgettable moments at sea.


This is your night to dress up, stand out, and live a little dangerously—just like Gatsby would.


🥂 A little party never killed nobody.

Farewell Party

Great Gatsby Party

Great Gatsby Party

Four men enjoying a farewell cocktail hour and dance.

🌅 Farewell Party – Until We Sail Again


As our incredible gay cruise experience in the Caribbean comes to an end, we gather one last time for our Farewell Party—a heartfelt celebration of friendships made, memories shared, and moments we’ll never forget.


This special evening is all about connection, reflection, and celebration. After a week filled with laughter, themed parties, tropical destinations, and unforgettable nights at sea, the Farewell Party gives us a chance to slow down just enough to appreciate the journey we’ve shared together as part of this LGBTQ+ group travel.


Join your fellow cruisers for cocktails, music, and relaxed vibes as we toast to new friendships, inside jokes, epic dance floors, and the magic that happens when an amazing group of people comes together. It’s a night filled with smiles, hugs, photos, and plenty of “we’ll definitely stay in touch.”


Our DJs set the perfect soundtrack—uplifting, celebratory, and nostalgic—creating an atmosphere that’s joyful, emotional, and full of gratitude. Whether you’re dancing, chatting, or simply soaking it all in, this final gathering is the perfect way to close out an extraordinary week of our Caribbean cruise experience.


It may be the last party of the cruise…

but it’s never goodbye.


🌅 Until we sail again.

D J RICHI RICH

D J RICHI RICH

D J RICHI RICH

DJ mixing music at a club with headphones and a cap.

Get Ready to Dance with DJ Richi Rich on Your Next Caribbean Cruise Experience! 🎧🔥


Prepare to turn up the energy because we have a special guest onboard tonight—none other than the iconic DJ Richi Rich from Fort Lauderdale, Florida! Known for his electrifying mixes, high-energy beats, and unparalleled ability to keep the crowd moving, DJ Richi Rich has been setting dance floors on fire across the country. Whether he’s spinning classic anthems, deep house grooves, or the hottest hits, one thing’s for sure—tonight’s party is about to be legendary.


So grab a drink, hit the dance floor, and let DJ Richi Rich take us on a musical journey we won’t forget. This is not just a party; this is an experience that epitomizes LGBTQ+ group travel on a gay cruise! Let’s make some noise for DJ Richi Rich! 🕺🥂🎶

Explore the Caribbean with My Bear Cruise

Two men unlocking a hotel room door with a digital panel.

Optional add-ons enhance your Caribbean cruise experience. Purchase these features individually, or elevate your journey with a Princess Plus or Princess Premier package. Both packages include some of the most popular options at a great value, perfect for anyone, including those looking for gay cruises or LGBTQ+ group travel opportunities.


Enjoy an array of beverages including beer, wine, cocktails, specialty coffees, sodas, and a juice bar. Stay connected with Wi-Fi, enabling you to share your adventures with friends back home.


**Princess Plus**

$70 per person/day

This package includes drinks, bottled water, specialty coffee, and a juice bar offering a wide selection of non-alcoholic soft drinks alongside premium Lavazza coffees. You can savor cocktails, wine, and beer priced up to $15 each, plus a 25% discount on bottles of wine. Boost your immunity and energy with power shots from the unlimited juice bar. Gratuities are included, and Wi-Fi is available for 1 device per guest. MedallionNet® Max delivers our highest performing Wi-Fi service for texting, sharing, streaming, and video chatting.


**Princess Premier**

$105 per person/day

With this premier package, you get unlimited premium drinks, bottled water, specialty coffee, and juice bar access. This includes top-shelf spirits and craft cocktails priced up to $20 each. Enjoy Wi-Fi for 4 devices per guest, powered by MedallionNet® Max for seamless communication and entertainment. Gratuities are also included.


Enhance your experience with options like dining at award-winning specialty restaurants, thrilling shore excursions, luxury spa services, and exclusive access to The Sanctuary. We also offer laundry services and celebrations tailored for romance and wedding packages. 


The Princess Standard fare includes:

- MedallionClass® experience allowing effortless, personalized cruising: your stateroom unlocks as you approach, offering next-level service while easily connecting with family and friends on board.

- Entertainment featuring Broadway-style shows, live music, movies, themed activities, game shows, and entertainers.

- A delectable dining experience with multicourse options, buffets, pizza, burgers, hot dogs, soft-serve ice cream, pastries, and desserts.

Discover the World with My Bear Cruise

Inside

Deluxe Balcony

Ocean View

Modern hotel room with a comfortable bed and wooden accents.

Inside Cabin


Experience the best of the Caribbean cruise experience starting at only $599+ per person. For those planning a memorable getaway with friends, our inside cabins are perfect for LGBTQ+ group travel. 


Choose from options including inside forward starting at $609pp+, aft cabins at $6579.00pp+, and midship accommodations at $889.00pp+. Don’t miss out on an incredible journey tailored for all travelers, including those who cherish gay cruises.

Ocean View

Deluxe Balcony

Ocean View

Luxury cruise ship bedroom with king-size bed and ocean view window.

Experience the stunning Caribbean cruise with ocean views starting at only $679.00+ per person. For an unforgettable LGBTQ+ group travel adventure, consider our obstructed view options at $739.00 per person, or enjoy the beauty of a non-obstructed view for just $799.00 and $849.00+. Join us for a memorable gay cruise that makes the most of your journey.

Deluxe Balcony

Deluxe Balcony

Deluxe Balcony

Modern cruise ship stateroom with bed and balcony.

Deluxe Balcony from $799+ per person offers an ideal Caribbean cruise experience, perfect for those seeking adventure and relaxation. For a more luxurious stay, the Premium Deluxe option is available at $1059.00+ per person. Additionally, the Cove Balcony starts from $799+, making it a great choice for gay cruises and LGBTQ+ group travel while enjoying stunning views at sea.

Mini Suite

Owner's Suite

Deluxe Balcony

Modern and cozy hotel room with elegant lighting and neutral tones.

Mini Suite


Starting at only $1279.00+ per person


Midship $1139.00


Sanctuary Mini-Suite $2899+ pp

The perfect choice for your Caribbean cruise experience, our accommodations are ideal for LGBTQ+ group travel and feature the exclusive Princess Premier® Package.

Suite

Owner's Suite

Owner's Suite

Bright hotel room with king-sized bed and modern decor.

Suite


Signature Suite  $3794.00+pp


Princess Premier® Package Included


Experience the ultimate Caribbean cruise experience tailored for all travelers, including those seeking gay cruises and LGBTQ+ group travel options.

Owner's Suite

Owner's Suite

Owner's Suite

Modern hotel suite with bedroom and living area.

Vista Suite


$4799.00+pp


Includes the Princess Premier® Package for an unforgettable Caribbean cruise experience, perfect for LGBTQ+ group travel and gay cruises.

Grand Suite

Grand Suite

Grand Suite

Modern living room with sofa and dining table.

Grand Suite


$5499.00=pp


Experience the ultimate Caribbean cruise experience with the Princess Premier® Package included, perfect for those seeking memorable gay cruises and LGBTQ+ group travel opportunities.

Sky Suite

Grand Suite

Grand Suite

Modern hotel suite with bedroom and living area.

Sky Suite


$10,934.00+pp


Experience the ultimate Caribbean cruise experience with the Princess Premier® Package included, perfect for LGBTQ+ group travel and unforgettable gay cruises.

Contact Us

Drop us a line!

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All prices for this gay group cruise are per person based on double occupancy. Please note that taxes and fees of $210 are not included in the price. Prices may change at any time without notice, offering you the best Caribbean cruise experience tailored for LGBTQ+ group travel.

My Bear Cruise - Gay Cruises & Group Travel

+15617030064

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