Transat Cayman Islands Vacation Packages: New Porter Airlines Service from Toronto | Book by May 10, 2026
- Boarding Pass Travel
- 5 days ago
- 5 min read
These Transat Cayman Islands vacation packages are available thanks to a new partnership between Transat and Porter Airlines, with Economy Class flights operated by Porter from Toronto departures only, and all vacation package details and inclusions managed by Transat. Five properties are on offer for a December 11, 2026 departure — from a 3-star studio suite to The Ritz-Carlton Grand Cayman — with 7-night packages starting from $2,489 CAD per person.
Every package includes one checked bag and one carry-on.
Book by May 10, 2026 while early availability lasts.
Why Grand Cayman Stands Out
Grand Cayman consistently ranks among the Caribbean's most refined travel destinations — and it offers a genuinely different experience from the all-inclusive resort circuit.
Seven Mile Beach is one of the Caribbean's finest: Calm turquoise water, powder-white sand, and a beach that stretches for miles with no rough surf — it's among the most consistently praised stretches of sand in the entire region
World-class diving and snorkelling: The Cayman Islands sit on an oceanic wall with some of the most dramatic underwater topography in the Caribbean; Stingray City is one of the world's most famous marine encounters
A sophisticated food and culture scene: George Town and the Seven Mile Beach corridor have a restaurant and bar scene that punches well above the island's size — this is a destination where dining out is part of the experience
Five properties across four star levels: The lineup covers the full range from comfortable 3-star value to the Ritz-Carlton's 5-star standard — meaningful choice for different budgets and expectations
New Porter Airlines service from Ontario: This partnership opens Grand Cayman to Porter's network for the first time — a new routing option that expands access for travellers in Toronto beyond the traditional Air Canada and WestJet options
Transat Cayman Islands Vacation Packages Deal Breakdown
All five packages depart from Ontario on flights operated by Porter Airlines in Economy Class, with all vacation package details and inclusions managed by Transat Tours Canada. Every package includes return Economy Class flights, 7 nights of hotel accommodation, one checked bag, and one carry-on per person. All prices are in CAD, per person, based on double occupancy.
Book by May 10, 2026. Travel agency fees may apply.
⚠️ These packages are exclusively available from Toronto. No departures available from other provinces.
⚠️ Grand Cayman transfers are not included. Airport-to-hotel transfers must be arranged and paid for independently. Grand Cayman's Owen Roberts International Airport is close to the Seven Mile Beach corridor but transfer arrangements are the guest's responsibility.
The Sunshine Hotel & Suites
Stars: ⭐⭐⭐
Room: Studio Suite
Meal plan: EP
Departure: Friday, December 11, 2026
Duration: 7 nights
Price: From $2,489 CAD per person
Hampton by Hilton Grand Cayman
Stars: ⭐⭐⭐
Room: Standard King Bed
Meal plan: Breakfast only
Departure: Friday, December 11, 2026
Duration: 7 nights
Price: From $2,539 CAD per person
Grand Cayman Marriott Resort
Stars: ⭐⭐⭐⭐
Room: Island View Room — King Bed
Meal plan: EP
Departure: Friday, December 11, 2026
Duration: 7 nights
Price: From $3,689 CAD per person
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Stars: ⭐⭐⭐⭐
Room: Island View Room — 2 Double Beds
Meal plan: EP
Departure: Friday, December 11, 2026
Duration: 7 nights
Price: From $4,159 CAD per person
The Ritz-Carlton Grand Cayman
Stars: ⭐⭐⭐⭐⭐
Room: Room Garden View King
Meal plan: EP
Departure: Friday, December 11, 2026
Duration: 7 nights
Price: From $4,939 CAD per person
All prices per person, based on double occupancy. Subject to availability and change without notice. Book by May 10, 2026.
Why Book Through Boarding Pass Travel
Five Grand Cayman properties across four star levels — and the right one depends on what kind of trip you're planning. The Sunshine Hotel & Suites and Hampton by Hilton are well-positioned value options — clean, comfortable, and close to Seven Mile Beach without the Marriott or Westin price point. The Grand Cayman Marriott and Westin are full-service resort properties directly on or adjacent to Seven Mile Beach with the amenities to match. The Ritz-Carlton is in a category of its own — one of the most acclaimed luxury properties in the Caribbean with a level of service and setting that justifies the premium for the right traveller. We'll help you choose the right fit.
This is a new Porter Airlines routing to Grand Cayman — and it opens up access from Ontario in a genuinely useful way. Porter's network from Ontario gives travellers in Toronto, Hamilton, and surrounding cities a new flight option to Grand Cayman that wasn't previously available through this supplier. The Transat package structure wraps around Porter's flights seamlessly — one booking, one package, one point of contact for service.
Transfers need to be arranged before you arrive — Grand Cayman is not a resort corridor with obvious ground transport. Owen Roberts International Airport is compact and manageable, but arriving without pre-arranged transfers means navigating taxi options at arrival. We'll coordinate those arrangements as part of the booking so you're collected on arrival without any uncertainty.
December 11 in Grand Cayman is peak Caribbean season — book early for the best property choice. December is one of the most popular months to visit Grand Cayman — school holidays, warm weather, and the island's busiest dining and social season all converge. All five properties on a single departure date means availability at the more popular 4 and 5-star options will move quickly. Booking in May for December travel gives you the best selection.
IMPORTANT DETAILS
All prices are in CAD, per person, based on double occupancy, Economy Class air, departing from Toronto only. Book by May 10, 2026. Applicable to Toronto departures only — no other provinces available. Flights operated by Porter Airlines (Canada) Ltd or Porter Airlines Inc in Economy Class. All vacation package details and inclusions managed by Transat Tours Canada. One checked bag and one carry-on per person included. Grand Cayman airport-to-hotel transfers are not included and are the guest's responsibility. Travel agency fees may apply. Subject to availability at time of booking and subject to change without notice. For full terms and conditions, visit transat.com.
DISCLAIMER
Boarding Pass Travel is not responsible for errors or omissions in this post. All pricing, availability, and promotional details are provided by Transat Tours Canada and are subject to change without notice. We strongly recommend the purchase of comprehensive travel insurance to protect your vacation investment. Boarding Pass Travel is a TICO-registered travel agency in Ontario, Canada. Packages are offered by Transat Tours Canada Inc., registered as a travel wholesaler in Ontario (Reg. #50009486) with offices at 5915 Airport Road, Suite 910, Mississauga, ON L4V 1T1; and in Quebec (Reg. #754241) with offices at 300 Léo-Pariseau Street, Suite 200, Montreal, QC H2X 4C2. Ask your travel professional for full details and current pricing.
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