Gay Bear Cruises 2027: Every Bear Sailing, Dated

A bear cruise is a group of bears and their admirers sailing together on a regular cruise ship, with their own cocktail hours, pool takeovers, dinners and shore excursions. None of the four bear groups here charters a whole ship, so you share it with other passengers but spend the week with your group. Four companies run bear groups between November 2026 and February 2028, on 16 sailings from the Caribbean to Alaska, the British Isles and the Greek Isles. Every date, ship, fare and status below comes from the operators' own websites, checked on October 23, 2026.

Every bear cruise, November 2026 – February 2028

BearCruise

BearCruise is run by Dan Howell Travel. Its groups run from about 100 to as many as 400 guests, and its Bear Benefits page lists pre-cruise parties, daily meetups, an almost-daily late-afternoon pool and hot-tub takeover followed by a cocktail hour, a reserved section of the main dining room on some ships, and private group shore excursions, including catamaran trips on Caribbean sailings. BearCruise staff sail with the group.

Its 2027 sailings:

• MayDaze (May 6–10, Virgin Voyages' Valiant Lady from Miami, with Key West and Bimini).
• British Isles (August 5–15, Norwegian Star from Southampton): $2,110 per person, taxes and fees included; gratuities of $20 per person per day are extra.
• 15th Anniversary Boston to San Juan (October 20–29, Celebrity Summit): about $1,089 per person, taxes included. BearCruise calls this a guideline quote from March 2026, not a guaranteed price.
• New Year's sailings on Virgin's Scarlet Lady (December 30, 2026 – January 4, 2027) and Valiant Lady (December 30, 2027 – January 3, 2028, per the page header; its day-by-day list gives December 28 – January 2).

BearCruise also brings a bear group onto VACAYA's February 14–21, 2027 Caribbean charter on Celebrity Beyond; you book through VACAYA and name BearCruise as your agency. On Virgin sailings, fares are priced per cabin in Virgin's own booking system.

BearCruise says about a quarter of its guests travel solo. It doesn't match roommates itself; solo travelers find each other through its Facebook group, and BearCruise then splits the booking.

Bears On Deck

Bears On Deck sails Celebrity Constellation round trip from San Juan, March 6–13, 2027, calling at St. Thomas, St. Maarten, Antigua, St. Lucia and Barbados. Fares are by inquiry only, through a form on its site, and it says they include the Classic Beverage Package, basic Wi-Fi and gratuities.

Adventure Bears

Adventure Bears, hosted by Laz Cabrera, runs smaller bear groups with reserved group dining every night on its Princess sailings (at least two hosted group dinners are planned on its Virgin sailing), private group events and a T-shirt. Its 2027 sailings:

• Alaska Denali Explorer (May 15–25, Discovery Princess from Vancouver, plus three land nights): $1,493 per person for the cruise, taxes included.
• Greek Isles Odyssey (October 3–10, Virgin's Scarlet Lady from Athens): $1,673 per person, plus a required $100 hosted-experience fee.
• Western Mediterranean (October 17–24, Sun Princess, Barcelona to Rome): $2,441 per person, taxes included.
• Eastern Caribbean with Puerto Rico (November 21–28, Sky Princess from Fort Lauderdale): $1,544 per person, taxes included.

Its December 2026 Rhine and December 2027 Christmas markets river cruises were sold out.

Arno's Bear Cruises

Arno's Bear Cruises started in 2009 as a bear cruise; it now describes its groups as LGBTQ vacations open to friends and family. His 2027 Caribbean sailing on Royal Caribbean's Symphony of the Seas from Galveston (January 31 – February 7) starts at $729 per person, tax included. His Beef Dip Mexico sailing on Navigator of the Seas from Los Angeles (January 28 – February 4, 2028) starts at $625. His September 2027 Greece, Cyprus and Egypt group block is sold out.

More options for bears

Big all-gay charters welcome bear groups too: BearCruise's group on VACAYA is one example. For older gay men, Daddy Cruises lists 14 group sailings between December 2026 and early March 2028. Filter our sortable table of every 2027 gay cruise to compare them all, or read our guides to Atlantis and VACAYA.

Frequently asked questions

What is a bear cruise?

A group of bears sailing together on a regular cruise ship, with private parties, meetups, dinners and shore excursions. You share the ship with other passengers.

How much does a bear cruise cost?

On October 23, 2026, 2027 bear sailings started at $729 per person, tax included (Arno's Caribbean sailing from Galveston), followed by Boston to San Juan with BearCruise (about $1,089 with a non-refundable deposit, a March 2026 guideline quote) and Adventure Bears' Alaska cruise ($1,493).

When is the next BearCruise?

BearCruise's New Year's sailing on Virgin's Scarlet Lady leaves Miami on December 30, 2026. After that come its group on VACAYA's February 14–21, 2027 Caribbean charter (VACAYA lists it as sold out, with a waitlist) and MayDaze from Miami, May 6–10, 2027.

Are bear cruises good for solo travelers?

BearCruise says about a quarter of its guests travel solo, and it helps solo travelers find roommates through its Facebook group.