Caribbean

Bob's Groups

Bob Family Newfoundland Tour
Bob Family Newfoundland Tour

from $3,993.00 CAD Jul 11 - Jul 20 , 2026

We invite you to join Pat and Mary and a local guide on a 10 Day curated journey around Newfoundland, one of Canadas most unique and beautiful provinces we can call our own. learn more

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Discover Alaska In Style - Celebrity Summit
Discover Alaska In Style - Celebrity Summit

from $3,039.00 CAD Aug 07 - Aug 14 , 2026

Experience the raw beauty of Alaska paired with the modern luxury of Celebrity Summit on this unforgettable 7-night southbound journey. From towering glaciers to charming frontier towns, this is Alaska at its most breathtaking. learn more

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Bob Family Come Back Celebrity Cruise November 2026
Bob Family Come Back Celebrity Cruise November 2026

from $3,076.00 Nov 08 - Nov 15 , 2026

Join us for our Bob Family COME BACK Private Caribbean Cruise Group departing from the beautiful city of Miami on Sunday, November 8th for one week on... learn more

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Southern Caribbean Jan 29th 2027 Virgin Voyages
Southern Caribbean Jan 29th 2027 Virgin Voyages

from $6,014.00 CAD Jan 29 - Feb 06 , 2027

Come sail the Southern Caribbean Islands with us! This 8-night San Juan voyage spends a day sailing to your first stop, Oranjestad, Aruba — the happiest island in... learn more

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Slovenia to Venice with Uniworld
Slovenia to Venice with Uniworld

from $5,519.20 CAD May 27 - Jun 06 , 2027

Begin your journey in Ljubljana, the picturesque capital of Slovenia, and explore the countryside on your way to board the S.S. Venezia for a blissful sailing of... learn more

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Africa Safari Spring 2027
Africa Safari Spring 2027

from $13,595.00 Apr 21 - May 08 , 2027

South Africa, Zimbabwe, and Botswana - Safari and Tour 18 Days/17 nights - 3 Countries Inclusions in the tour: 4* to 4.5* Class hotel accommodation as per itinerary, based on... learn more

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Alaska June 18 2027 Celebrity Edge
Alaska June 18 2027 Celebrity Edge

Jun 18 , 2027

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Coming Soon
Newfoundland again June 2027
Newfoundland again June 2027

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Coming Soon
Alaska July 9-16 2027 Celebrity Solstice
Alaska July 9-16 2027 Celebrity Solstice

Jul 09 - Jul 16 , 2027

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Coming Soon
Bob Family 12 Night British Isles
Bob Family 12 Night British Isles

from $5,878.20 Aug 08 - Aug 20 , 2027

Come join us in Amsterdam to board the Celebrity Eclipse for 12 nights in the British IslesExplore tranquil landscapes, wander through art-filled streets, and savor culinary delights... learn more

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Bob Family 11-Day Celebrity Cruise Canary Islands & Portugal
Bob Family 11-Day Celebrity Cruise Canary Islands & Portugal

from $5,863.00 Sep 25 - Oct 06 , 2027

We invite you to join us on an 11-night exceptional journey aboard the next-generation Edge Class ship, the Celebrity Apex, in an Infinite Edge Veranda. We will... learn more

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Croatia Sailing Yacht Bike and Barge Fall of 2027
Croatia Sailing Yacht Bike and Barge Fall of 2027

from $3,129.00 EUR Oct 08 , 2027

Looking for an active vacation adventure like no other? This boat and cycle journey is the perfect escape. Aboard a charming motor yacht, you’ll explore one of... learn more

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Bob Family Caribbean Nov 6 2027 Celebrity Apex
Bob Family Caribbean Nov 6 2027 Celebrity Apex

Nov 06 - Nov 13 , 2027

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Coming Soon
Japan March 2028
Japan March 2028

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Coming Soon
*All prices quoted in Canadian Dollars unless otherwise stated

FAQs

Bob Groups are curated group departures — cruise and land vacations — organized by Bob Family Travel that anyone can join. Rather than travelling with strangers, you travel with a vetted community of like-minded people, led by an experienced Bob Family Travel advisor. Current group trips range from Alaska cruises aboard Celebrity Edge, to Caribbean sailings with Virgin Voyages, to an Africa safari, a Japan cultural tour, and active adventures in Croatia and Newfoundland. Most trips are priced per cabin, so you can join as a couple, solo, or with friends.

Yes. Solo travelers are welcome on Bob Group trips. Some trips offer single-supplement options or single cabins specifically for solo travelers. Traveling in a group is one of the best ways to travel solo — you have the independence to do your own thing at port, but a built-in community for dinners, excursions, and shared moments onboard. Many of our most loyal solo travelers have met lifelong friends on Bob Group departures. Contact us to ask about single cabin availability on any specific trip.

Group cruise bookings unlock several benefits that independent bookings can't access: group cabin rate discounts negotiated with the cruise line, dedicated group dining times so your group eats together, onboard group amenities (welcome cocktail parties, onboard credit, and sometimes complimentary cabins for trip leaders), a dedicated advisor managing all logistics, and the social experience of travelling with people who share your interests. Bob Groups also include exclusive pre-trip briefings and insider access that solo bookings don't receive.

Browse the current Bob Group departures on this page. Each listing shows the destination, ship, dates, starting price, and availability status. Click "Join This Group" on the trip you're interested in to start the enquiry, or visit our Join The Family page to register as part of the broader Bob Family Travel community. Our advisors will follow up to walk you through cabin options, pricing, deposit requirements, and what's included in your specific group departure.

Our current and upcoming Bob Group trips cover a wide range: Alaska (Celebrity Edge June 2027 and Celebrity Solstice July 2027), the Caribbean (Virgin Voyages Southern Caribbean January 2027 and Celebrity Apex November 2027), the British Isles (Celebrity Eclipse August 2027), the Canary Islands and Portugal (Celebrity Apex September 2027), Newfoundland (June 2027), Croatia (sailing and cycling, October 2027), Africa Safari (spring 2027), and Japan (March 2028). New trips are added regularly — join the community to be notified first.

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