60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

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Route & dates

60 days in Caribbean Itinerary

Start: Toronto, Canada
Fly:  6​h 45​min
1
Cayo Largo, Cuba
— 4 nights
Fly:  12​h 45​min
2
Culebra, Puerto Rico
— 4 nights
Ferry:  6​h 30​min
3
Virgin Islands National Park, U.S. Virgin Islands
— 8 nights
+2
Drive + Fly + Drive:  5​h 45​min
4
Shoal Bay Village, Anguilla
— 6 nights
+2
Ferry + Foot + Fly:  6​h 15​min
5
Palm - Eagle Beach, Aruba
— 5 nights
Fly + Bus:  1​h 45​min
6
Willemstad, Curacao
— 11 nights
Fly:  5​h
7
Providenciales, Turks and Caicos
— 12 nights
Fly:  7​h 45​min
8
Southampton Parish, Bermuda
— 4 nights
Fly:  5​h 30​min
End: Toronto, Canada

4
nights
Cayo Largo, Cuba

Cayo Largo ©
The stress of modern life feels a million miles away when you holiday on Cayo Largo, a small and unspoiled resort island off the coast of Cuba.
Discover out-of-the-way places like Caleta Buena and Sea Turtle Hatchery. Visit Playa Paraiso and Playa Mal Tiempo for some beach relaxation. There's lots more to do: enjoy the sand and surf at Sirena Beach, head off the coast to Cayo Rico, and tour the pleasant surroundings at Playa Blanca Beach.

For reviews, maps, ratings, and more tourist information, go to the Cayo Largo trip planner .

Toronto, Canada to Cayo Largo is an approximately 7-hour flight. You can also do a combination of train and flight. Traveling from Toronto in June, things will get a bit warmer in Cayo Largo: highs are around 36°C and lows about 28°C. Finish up your sightseeing early on the 5th (Wed) so you can travel to Culebra.

Things to do in Cayo Largo

Parks Beaches Outdoors

Side Trip

Caleta Buena
Find places to stay Jun 1 — 5:
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach
Playa Blanca Beach ©
Playa Blanca Beach

4
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
You'll discover tucked-away gems like Tamarindo Beach and Carlos Rosario Beach. We've included these beaches for you: Flamenco Beach and Brava Beach. There's still lots to do: kick back and relax at Zoni Beach, browse the collection at Culebra Public Library, head off the coast to Culebra National Wildlife, and see the interesting displays at Museo Historico de Culebra.

For other places to visit, photos, ratings, and other tourist information, go to the Culebra holiday planning site .

Getting from Cayo Largo to Culebra by combination of flight, shuttle, and ferry takes about 13 hours. Other options: fly; or do a combination of flight and ferry. The time zone changes from Cuba Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. In June in Culebra, expect temperatures between 37°C during the day and 30°C at night. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Virgin Islands National Park.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Jun 6 — 10:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Tamarindo Beach ©
Tamarindo Beach
Carlos Rosario Beach ©
Carlos Rosario Beach

8
nights
Virgin Islands National Park, U.S. Virgin Islands

Virgin Islands National Park ©
The hills, valleys, and tropical rainforest of Virgin Islands National Park tell only half the story, with just as much (if not more) to be found under the sea.
You'll get in some beach time at Cinnamon Bay Beach and Maho Bay. Eschew the tourist crowds and head to Salt Pond Bay and Waterlemon Cay. Get out of town with these interesting Virgin Islands National Park side-trips: Hansen Bay Beach (in East End) and Coral Bay (Drunk Bay Trail & Island Muse Boutique). Next up on the itinerary: enjoy the sand and surf at Trunk Bay, steep yourself in history at Annaberg Sugar Plantation, contemplate the waterfront views at Hawksnest Beach, and see some colorful creatures with a scuba or snorkeling tour.

For where to stay, ratings, traveler tips, and other tourist information, use the Virgin Islands National Park trip builder app .

The Route module can help you plan travel from Culebra to Virgin Islands National Park. In June, daily temperatures in Virgin Islands National Park can reach 37°C, while at night they dip to 30°C. Finish up your sightseeing early on the 19th (Wed) so you can travel to Shoal Bay Village.

Things to do in Virgin Islands National Park

Parks Outdoors Beaches

Side Trips

St. John, Coral Bay, Hansen Bay Beach
Find places to stay Jun 10 — 19:
Highlights from your plan
Trunk Bay ©
Trunk Bay
Cinnamon Bay Beach ©
Cinnamon Bay Beach
Salt Pond Bay ©
Salt Pond Bay

6
nights
Shoal Bay Village, Anguilla

Shoal Bay Village ©
You'll discover tucked-away gems like Shoal Bay and Little Bay. You'll enjoy a bit of beach vacationing at Meads Bay and Rendezvous Bay Beach. Explore Shoal Bay Village's surroundings by going to West End Village (Cove Bay, Limin' Boutique, & more) and The Valley (Cheddie Richardson Carving Studio & Anguilla Watersports).

For where to stay, photos, traveler tips, and tourist information, you can read our Shoal Bay Village trip planner .

The Route module can help you plan travel from Virgin Islands National Park to Shoal Bay Village. In June, daytime highs in Shoal Bay Village are 36°C, while nighttime lows are 30°C. Cap off your sightseeing on the 26th (Wed) early enough to travel to Palm - Eagle Beach.

Things to do in Shoal Bay Village

Parks Beaches Outdoors

Side Trips

West End Village, Anguilla, Sandy Ground, The Valley, Island Harbour
Find places to stay Jun 19 — 26:
Highlights from your plan
Meads Bay ©
Meads Bay
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

5
nights
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Relax by the water at Palm Beach and Malmok Beach. Step off the beaten path and head to Boca Catalina and Donkey Sanctuary Aruba. Get out of town with these interesting Palm - Eagle Beach side-trips: San Nicolas (Baby Beach & Boca Grandi). There's lots more to do: kick back and relax at Eagle Beach, see some colorful creatures with a scuba or snorkeling tour, stroll through Hadicurari Beach, and pause for some serene contemplation at St. Ann's Catholic Church.

To see ratings, reviews, maps, and tourist information, read Palm - Eagle Beach online travel planner .

Traveling by combination of ferry and flight from Shoal Bay Village to Palm - Eagle Beach takes 6.5 hours. Alternatively, you can fly. June in Palm - Eagle Beach sees daily highs of 38°C and lows of 31°C at night. Wrap up your sightseeing on the 2nd (Tue) early enough to travel to Willemstad.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Noord, Santa Cruz, San Nicolas, Oranjestad, Arashi Beach
Find places to stay Jun 26 — Jul 2:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Malmok Beach ©
Malmok Beach

11
nights
Willemstad, Curacao

Willemstad ©
Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Explore hidden gems such as Playa Lagun and Playa Piscado/Playa Grandi. We've included these beaches for you: Playa Kenepa Chiki and Kleine Knip. Change things up with a short trip to Playa Piskado in Sabana Westpunt (about 1h 20 min away). Spend the 6th (Sat) exploring nature at Shete Boka National Park. The adventure continues: head off the coast to Klein (Little) Curacao, tour the pleasant surroundings at Blue Bay Beach, explore the world behind art at Kura Hulanda Museum, and take in the views from Queen Emma Pontoon Bridge.

To find where to stay, traveler tips, maps, and other tourist information, read Willemstad tour itinerary planner .

Do a combination of flight and bus from Palm - Eagle Beach to Willemstad in 2 hours. In July, plan for daily highs up to 38°C, and evening lows to 30°C. Finish your sightseeing early on the 13th (Sat) so you can travel to Providenciales.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trips

Curacao, Playa Piscado/Playa Grandi
Find places to stay Jul 2 — 13:
Highlights from your plan
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Playa Lagun ©
Playa Lagun
Playa Kenepa Chiki ©
Playa Kenepa Chiki

12
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
You'll discover tucked-away gems like Long Bay Beach and Stand-Up Paddleboarding. Visit Grace Bay and Half Moon Bay for some beach relaxation. Spend the 18th (Thu) exploring nature at Chalk Sound. There's much more to do: zoom along the surf with a waterskiing or jet-skiing adventure, stroll through Grace Bay Beach, take a tour by water with Boat Tours & Water Sports, and relax and rejuvenate at some of the top local wellness centers.

For traveler tips, where to stay, and more tourist information, read our Providenciales trip itinerary planning app .

You can fly from Willemstad to Providenciales in 5 hours. You'll gain 1 hour traveling from Willemstad to Providenciales due to the time zone difference. Expect a daytime high around 37°C in July, and nighttime lows around 31°C. Wrap up your sightseeing on the 25th (Thu) to allow time to travel to Southampton Parish.

Things to do in Providenciales

Outdoors Parks Beaches

Side Trip

Smith's Reef
Find places to stay Jul 13 — 25:
Highlights from your plan
Half Moon Bay ©
Half Moon Bay
Grace Bay Beach ©
Grace Bay Beach
Long Bay Beach ©
Long Bay Beach

4
nights
Southampton Parish, Bermuda

Southampton Parish ©
The area's beaches remain the primary reason to holiday in Southampton Parish, with their number and variety providing entertainments and sights to suit a range of tastes.
Eschew the tourist crowds and head to Elbow Beach and Tobacco Bay. You'll enjoy a bit of beach vacationing at Horseshoe Bay Beach and Jobson's Cove Beach. You'll find plenty of places to visit near Southampton Parish: Crystal & Fantasy Caves (in Hamilton Parish) and Bermuda National Trust Museum (in St. George). And it doesn't end there: enjoy the sand and surf at Warwick Long Bay Beach, stroll through Stonehole Bay Beach, enjoy the sea views from Gibb's Hill Lighthouse, and browse the exhibits of Bermuda Aquarium, Natural History Museum & Zoo.

For traveler tips, more things to do, other places to visit, and other tourist information, read Southampton Parish online day trip planner .

You can fly from Providenciales to Southampton Parish in 8 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Expect a daytime high around 34°C in July, and nighttime lows around 29°C. Finish your sightseeing early on the 30th (Tue) to allow enough time to travel back home.

Things to do in Southampton Parish

Parks Beaches Outdoors

Side Trips

Warwick Parish, St. George, Elbow Beach, Bermuda Aquarium, Natural History Museum & Zoo, Crystal & Fantasy Caves
Find places to stay Jul 25 — 30:
Highlights from your plan
Jobson's Cove Beach ©
Jobson's Cove Beach
Church Bay Beach ©
Church Bay Beach
Horseshoe Bay Beach ©
Horseshoe Bay Beach

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