Casa Marina Sosua Trademark By Wyndham Ai
All-InclusiveSosua
Dominican Republic
From Toronto (YYZ)VAT · Direct flightDeparts Wed, Sep 23
- 7 nights
- Room Gardenview
- Flights incl.
From
$929
per person · taxes incl.
or $77/mowith FlexPay
Caribbean
All-Inclusive · Flights Included · 82 destinations · Direct flights from Canada
All-Inclusive · Flights Included
Vacation Deals in Caribbean
Live deals across Caribbean — updated daily
Flying from
3.4 (2,763)
Playabachata Hotel
All-InclusivePuerto Plata
Dominican Republic
From Toronto (YYZ)VAT · Direct flightDeparts Wed, Sep 16
- 7 nights
- Room King
- Flights incl.
From
$939
per person · taxes incl.
or $78/mowith FlexPay
Catalonia Yucatan Beach
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)VAT · Direct flightDeparts Mon, Oct 5
- 4 nights
- Comfort Room
- Flights incl.
From
$939
per person · taxes incl.
or $78/mowith FlexPay
Bluebay Grand Esmeralda Riviera Maya
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)VAT · Direct flightDeparts Mon, Oct 5
- 4 nights
- Promo Room
- Flights incl.
From
$939
per person · taxes incl.
or $78/mowith FlexPay
Bahia Principe Explore Coba
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)VAT · Direct flightDeparts Mon, Oct 5
- 4 nights
- Junior Suite Superior
- Flights incl.
From
$959
per person · taxes incl.
or $79/mowith FlexPay
Viva Maya By Wyndham
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)VAT · Direct flightDeparts Mon, Oct 5
- 4 nights
- Superior Room
- Flights incl.
From
$959
per person · taxes incl.
or $79/mowith FlexPay
Vik Hotel Arena Blanca
All-InclusivePunta Cana
Dominican Republic
From Toronto (YYZ)VAT · Direct flightDeparts Thu, Sep 17
- 5 nights
- Superior Gardenview
- Flights incl.
From
$969
per person · taxes incl.
or $80/mowith FlexPay
Catalonia Riviera Maya
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)VAT · Direct flightDeparts Mon, Oct 5
- 4 nights
- Premium Room
- Flights incl.
From
$979
per person · taxes incl.
or $81/mowith FlexPay
Destinations
Explore Caribbean
82 destinations to choose from
Mexico16 destinations
Dominican Republic8 destinations
Costa Rica7 destinations
Belize6 destinations
Jamaica5 destinations
Bahamas3 destinations
Panama2 destinations
St Vincent And The Grenadines2 destinations
Anguilla1 destination
Antigua and Barbuda1 destination
Argentina1 destination
Aruba1 destination
Barbados1 destination
Bermuda1 destination
Bonaire1 destination
Cayman Islands1 destination
Colombia1 destination
Curacao1 destination
Grenada1 destination
Guadeloupe1 destination
- Pointe a Pitre
Honduras1 destination
Martinique1 destination
- Fort de France
Nicaragua1 destination
Peru1 destination
Puerto Rico1 destination
Saint Lucia1 destination
Salvador1 destination
St Maarten1 destination
Turks And Caicos1 destination
Handpicked · Verified reviews
Hotels in the Caribbean
5-Star
All-InclusiveWyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Bridgetown
3.9(1,567)
- All-inclusive
- Beach
- Pool
- Spa
From
$512/ night
All-Inclusive
All-InclusiveOcean Allure Costa Mujeres - Adults Only - All Inclusive
Cancun
5.0
- All-inclusive
- Beach
- Pool
- Spa
From
$437/ night
All-Inclusive
All-InclusiveSandos CancãºN All Inclusive - Adults Only
Cancun
4.9(11,223)
- All-inclusive
- Beach
- Pool
- Water Park
From
$307/ night
All-InclusiveThe House, Barbados, An Autograph Collection All-Inclusive Resort - Adults Only
St. James
5.0
- All-inclusive
- Beach
- Pool
- Water Park
From
$1,162/ night
5-Star
5-StarDreams Vista Cancun Golf & Spa Resort - All Inclusive
Cancun
4.4(1,710)
- Beach
- Pool
- Water Park
- Water Slide
From
$520/ night
At a glance
Everything you need to know about Caribbean
The Caribbean is Canada's classic winter escape — hundreds of islands from Cuba and Jamaica to the Dominican Republic and the Lesser Antilles, each with its own beaches, culture and all-inclusive resorts.
CaribbeanClimate
Climate
25–31°C, sunniest Dec–Apr
JanDec
PeakShoulderAvoid
Tropical. Dry, sunny winters; Atlantic hurricane season peaks Sep–Oct.
Currency
Varies by island (USD widely accepted)
US dollars are accepted across most Caribbean resorts
Entry
Mostly visa-free
Canadians travel visa-free to most Caribbean nations with a valid passport
Language
English, Spanish & French
Top Experiences in Caribbean
EverywhereWhite-sand beaches
Turquoise water and palm-lined sand from the Bahamas to Barbados.
Snorkel & diveCoral reefs
World-class reefs off Belize, the Bay Islands and the Grenadines.
Food & musicIsland culture
Reggae, salsa, colonial old towns and some of the world's best rum.
Essential info for Canadian travellers
Passport: A valid Canadian passport is required. Canadians travel visa-free to most Caribbean nations with a valid passport.
Travel insurance: Provincial health plans don't cover medical emergencies abroad — comprehensive travel insurance is essential.
Power & plugs: Type A/B outlets at 110–120V, same as Canada. No adapter needed at most resorts.
Money: Resorts run largely cashless; bring a credit card plus some small bills for tips and local vendors.
Best time to visit Caribbean
Dec – AprPeak season
Dry, sunny and warm — the most popular time for Canadians.
May – AugShoulder season
Hotter and more humid, with fewer crowds and lower prices.
Sep – OctLow season
Peak of the Atlantic hurricane season; watch forecasts.
Where to stay
Where to stay in Caribbean
Caribbean offers a range of bases — here's how to choose the right area for your trip.
Mexico & Riviera Maya
Western Caribbean
The biggest, most accessible all-inclusive beaches with Mayan day trips.
Best for
- Families
- All-inclusive
- Beach
Greater Antilles
Cuba · DR · Jamaica
Large islands with the widest resort choice and strong value.
Best for
- Value
- Families
- Beach
Lesser Antilles
Aruba · Barbados · St. Lucia
Smaller, characterful islands for couples and quieter escapes.
Best for
- Couples
- Boutique
- Quiet
● Book with confidence
Your Caribbean escape awaits
Compare live packages with flights from Toronto, Montreal, Calgary & Vancouver.
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Good to know
Caribbean travel FAQ
Everything Canadian travellers ask before booking
Do Canadians need a visa for Caribbean?
Mostly visa-free. Canadians travel visa-free to most Caribbean nations with a valid passport.
How long is the flight from Canada to Caribbean?
Approximately ~3–6h from Toronto. Times vary by gateway and season.
When is the best time to visit Caribbean?
December to April offers the driest, sunniest weather. The summer months are hotter but quieter and better value.
What currency should I bring?
Varies by island (USD widely accepted). US dollars are accepted across most Caribbean resorts.
Do I need travel insurance?
Yes — it's strongly recommended. Provincial health plans don't cover medical emergencies abroad.
Are all-inclusive resorts worth it in Caribbean?
For most Canadians, yes — meals, drinks and activities are bundled at a strong fixed price, making budgeting easy.