San Juan is one of the best places in the Caribbean to start a cruise, and we've made it easy to get there from Toronto with everything bundled into one all-in price. Our cruise packages include your return flight, your cruise fare, and all taxes. No surprises at checkout.
The Southern Caribbean is a different experience than the more common Eastern or Western routes. You're venturing further south into the islands: think St. Lucia, Barbados, Grenada, Aruba, and Curaçao, where the landscapes are more dramatic, the reefs are pristine, and the crowds are noticeably thinner. These are the itineraries that seasoned Caribbean cruisers tend to prefer.
Why Sail from San Juan?
Flying into San Juan (SJU) from Toronto is a short, direct flight, usually around four hours. No overnight journeys or awkward connection layovers. And Old San Juan itself is worth arriving a day early for: the cobblestone streets, the colorful colonial buildings, El Morro fortress, and the food scene around La Placita are all worth your time before you even step onboard.
What's Included
Every package you'll find on this page includes:
- Return flights from Toronto (YYZ) to San Juan (SJU)
- Your cruise fare in your chosen stateroom category
- All taxes and port fees
We show you the total cost per person, so what you see is what you pay
Choosing Your Ship and Cruise Line
We currently offer sailings on several cruise lines departing San Juan, ranging from mainstream to luxury. Here's a quick honest take:
- Royal Caribbean (Rhapsody of the Seas, Vision of the Seas) — Great value for couples and families. These ships are mid-sized and very manageable, not overwhelming like the mega-ships, while still offering solid dining, entertainment, and itineraries that go deep into the Southern Caribbean.
- Celebrity Cruises (Celebrity Constellation) — A step up in polish and cuisine. The Constellation is a classic ship with a refined atmosphere. Great pick if you want a slightly more upscale feel without going full luxury.
- Norwegian Cruise Line (Norwegian Prima) — Norwegian's Freestyle Dining is a genuine perk if you hate fixed dining times and prefer flexibility. Prima is one of NCL’s newer ships with impressive design and specialty dining options.
- Princess Cruises (Crown Princess) — A solid, well-rounded ship. Particularly popular with Canadian travellers. The MedallionClass technology simplifies embarkation and onboard ordering.
- Disney Cruise Line (Disney Dream) — If you're travelling with kids, this is a league of its own. The character experiences, kids' clubs, and family programming are unmatched. Prices are higher, but families consistently say it's worth it.
- Windstar Cruises (Star Pride) — A boutique luxury option for travellers who want something intimate. A small ship with exceptional service, that can get into ports the big ships can't reach.
- Virgin Voyages (Valiant Lady) — Adults only (18+), and different from anything else out there. All dining is included, the vibe is lively and design-forward, and the entertainment is more eclectic. A great pick for couples who want something fresh.
- Oceania (Allura) — If food is your main event, Oceania is hard to beat. Their culinary program is exceptional, and the onboard atmosphere is relaxed and sophisticated.
Southern Caribbean Ports You'll Visit
Depending on your itinerary, Southern Caribbean sailings from San Juan typically include a mix of these destinations:
- St. Maarten — Half French, half Dutch, and completely charming. Great beaches and excellent duty-free shopping in Philipsburg.
- St. Lucia — One of the most naturally beautiful islands in the Caribbean. The Pitons are bucket-list territory. If your itinerary includes Soufriere, don't skip it.
- Barbados — Feels more polished than many islands. Bridgetown has great rum shops, the east coast beaches are spectacular, and the island is easy to navigate independently.
- Grenada — The "Spice Isle" is one of the Caribbean's hidden gems. Grand Anse Beach is gorgeous, and the St. George's harbour is one of the prettiest port settings you'll see.
- Aruba — Sunny, dry, and reliably beautiful. Eagle Beach is consistently rated among the best beaches in the world. Perfect if you just want to relax.
- Curacao — Willemstad is one of the most photogenic cities in the Caribbean. The Dutch colonial architecture and pastel-painted waterfront are genuinely stunning.
Practical Tips for Toronto Travellers
A few things worth knowing before you book:
Arrive in San Juan a day early if you can. Flights from Toronto to San Juan do occasionally face delays, and missing your departure is a painful (and expensive) experience. A pre-cruise night at a San Juan hotel is inexpensive insurance, and you get to enjoy the city.
Travel insurance is a must. We offer it, and our agents can walk you through options. Cruises and medical emergencies outside Canada are a combination that requires proper coverage.
You'll want a full Canadian passport with at least six months validity beyond your travel dates.
Book shore excursions in advance for popular ports. Aruba and Barbados in particular book up quickly for the highly sought tours.
Talk to One of Our Agents
Our agents have sailed these itineraries personally. They know which stateroom categories offer the best value, which ships have the best dining, and which San Juan hotels make the best pre-cruise stay.
You can call us, reach out via our online chat, or simply search the packages above and let the price grid do the talking. Either way, we're here when you're ready.
MyPortfolio Call Us Open Menu 
