We've Got Your Bliss!!
The November 2026 Bliss Cruise is the BIGGEST cruise of the year with 6000 people. It has been SOLD OUT for months BUT TOM'S HAS YOUR CABIN!
Tom’s Trips Cruise Collection:
Your Lifestyle Family: Now At Sea
Tom’s Trips has been a leader in lifestyle resort travel for over 30 years, and now we’re bringing that same trusted experience, our signature hosted group energy, personal service, to our curated collection of lifestyle cruises.
With concierge-level support, experienced hosts, and a community-first approach, Tom’s Trips Cruise Collection is designed to make your vacation easier, more exciting, and more connected from sign-up through sailing.
Just like we help level up your Hedonism II vacation from booking to the beach, we’re here to help make your cruise experience smoother, more social, and more memorable from booking to boarding.
When you travel with Tom’s Trips, you’re not just booking a vacation — you’re joining a lifestyle travel family.
From Land to Sea: Tom's Trips is A Name You Can Trust
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This is the same award-winning Tom’s Trips you know and trust for over 30 years— now at sea.
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#1 Lifestyle Travel Agent by the Annual Lifestyle Awards
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98% Guest Satisfaction
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3 time ASN Award winner for Best Adult Travel Agency
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4 time Annual Lifestyle Award winner
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Top 50 Jamaica Travel Specialist by the Jamaica Tourist Board for nine consecutive years.
Why Book With Tom's?
The Tom's Experience:
Hosted Events:
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Our dedicated hosts are here to help you feel connected from the start.
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Add-on activities and special plans help turn your cruise into a full experience. Enjoy on ship hosted events, group experiences, and extra touches designed for our lifestyle family.
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We help make your cruise experience easier, smoother, and more fun.
Concierge Level Support
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Need help? Call, text, email, or WhatsApp us or visit our support page.
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From sign-up to sea, we’ve got your back.
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Don’t call the cruise ship. Call Tom’s.
* No extra fees - you get the full Tom's experience and support at no additional cost *
- Join the Tom's Family at Sea -
Upcoming Cruises
November 9 - 16, 2026 - 7 Nights - Curacao & Aruba
Wonder of the Seas
HOSTED BY TOM AND BUNNY!
Join the Tom's Trips family plus 6000 lifestylers on one of the largest and most amazing cruise ships in the world. This ship has been sold out for months, but Tom's has a small room block availalbe.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
In Wonderland, curiosity is rewarded and nothing unfolds the way you expect. This couple's only lifestyle cruise is a full ship takeover aboard Wonder of the Seas, one of the world's largest cruise ships. As you wander through eight unique neighborhoods, find hidden corners and discover the energy changing daily and nightly, each moment and experience will be a surprise.
Prepare for a milestone in lifestyle history. We're taking over the most magnificent super-ship for the largest lifestyle event on the planet. This isn't just a cruise, it is a 6,000-guest floating wonderland of freedom, connection and pulse-pounding excitement. With 18 decks of luxury and 8 distinct "neighborhoods" to explore, Wonderland 2026 is the ultimate playground for couples who want everything, all at once.
April 18 - 24, 2027 - 6 Nights - Cabo Rojo & LabadeeCelebrity Silhouette
Bask in the glow of the radiant Celestial Cruise, a six-night voyage where desire rises with the sun and temptation lingers long after dusk. This star-kissed sailing invites couples to explore new horizons, orbit each other a little closer and surrender to moonlit magic beneath endless skies. From golden dawns to electric nights under the constellations, every moment is designed to shimmer, seduce and leave you glowing long after the final sunset.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
February 19 - 25, 2028 - 6 Nights - Cozumel & Costa Maya
Mariner of the Seas
Mardi Gras Cruise. Masks on, inhibitions off. . Let the beads drop and the boundaries disappear!
Sailing out of New Orleans for the first time, this couples-only lifestyle cruise blends big energy and revelry with one of the world's most iconic celebrations. Departing the Saturday before Mardi Gras 2028 and returning on the Friday just before Fat Tuesday, this perfectly timed sailing puts you right at the center of it all. Join us for a sexy, immersive carnival experience filled with sensual encounters and tropical escapes to Cozumel and Costa Maya. If you've ever wanted to experience Mardi Gras, this is your moment. It is festive, indulgent and designed to keep the party flowing from embarkation to the final night... and after, with a hotel takeover in the heart of Mardi Gras. This will be a one-of-a-kind landmark event for the Bliss community.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
February 24-28, 2027 - 4 nights - Cozumel
Celebrity Summit
A thrilling 5-day Mexican getaway full of energy and something exciting to come.
Hosted by Paul and Jennie
Our February Fiesta Cruise is the perfect escape for couples craving a little winter heat with a whole lot of spice. Departing from Tampa, this four-night getaway blends sun-fueled sea days, sultry nights and a high-energy social vibe that makes it easy to find your rhythm and your people. Expect tequila-fueled temptations, salsa under the stars and enough Latin fever to melt the chill right off the season. Trust us, this cruise is going to be muy caliente and this fiesta will deliver.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
November 8 - 15, 2027 - 7 Nights - St. Maarten & St. Kitts Saints & Sinners Cruise
Seven Nights. The World's Largest Ship. No Limits.
Wonder of the Seas
Get ready to give in to your most wicked desired on the Saints + Sinners Cruise. Departing from Miami for seven lust-fueled nights, this full-ship takeover invites you to choose your halo or your horns and sail boldly between the heavenly and the sinful. Expect sunlit indulgence worthy of a saint, after-dark mischief that would make the devil blush and an atmosphere where every couple decides just how virtuous or how deliciously sinful their journey will be.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
April 08 - 13, 2028 - 5 Nights - Grand Turk & Labadee
Celebrity Summit Cruise
New port. New energy. Same irresistible chemistry.
Spring arrives with a fresh kind of energy and this sailing is designed to match it. Set aboard the revitalized Celebrity Summit, this Bliss Cruise brings together open-minded couples for a week of connection, discovery and high-energy escape. With a new destination in Grand Turk and a return to the sexy, indulgent shores of Labadee, this itinerary blends exploration with signature Bliss moments that build from day to night. The details are still unfolding, but one thing is certain. Each sailing continues to evolve, becoming more immersive, more elevated and more unforgettable than the last. This is your chance to be part of it.
Enjoy clothing-optional pools and decks, optional excursions, icebreakers and meet & greets, lifestyle seminars, play areas and a dungeon, evening entertainment, pool and dance parties, themed costume nights, and all meals included.
