12 days in Caribbean Itinerary

12 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

This plan was created by another user. Make it your plan

Route & dates

Start: Chicago, United States
Fly:  7 h 30 min
1
Virgin Gorda, British Virgin Islands
— 2 nights
+2
Fly + Drive + Ferry:  1 h 30 min
2
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
Drive + Fly + Drive:  5 h 15 min
3
Road Town, British Virgin Islands
— 2 nights
Fly:  5 h 30 min
4
Havana, Cuba
— 3 nights
Fly:  2 h
5
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  7 h 15 min
End: Chicago, United States

2
nights
Virgin Gorda, British Virgin Islands

Virgin Gorda ©
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Start off your visit on the 31st (Thu): enjoy the sand and surf at Spring Bay, explore and take pictures at The Baths, and then soothe aching muscles at some of the top local wellness centers. Here are some ideas for day two: explore the striking landscape of Devil's Bay National Park and then get outside with Fusion BVI.

To find more things to do, where to stay, photos, and other tourist information, go to the Virgin Gorda online day trip planner.

Chicago, USA to Virgin Gorda is an approximately 7.5- hour flight. You can also do a combination of flight and ferry. You'll lose 2 hours traveling from Chicago to Virgin Gorda due to the time zone difference. Plan for warmer temperatures traveling from Chicago in December, with highs in Virgin Gorda at 85°F and lows at 76°F. Wrap up your sightseeing on the 1st (Fri) early enough to travel to Virgin Islands National Park.

Things to do in Virgin Gorda

Parks Nature Outdoors
Find places to stay Dec 30 — Jan 1:
Highlights from your plan
Spring Bay ©
Spring Bay
The Baths ©
The Baths
Devil's Bay National Park ©
Devil's Bay National Park

2
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.
Kick off your visit on the 2nd (Sat): hike along Francis Bay Trail, make a trip to Annaberg Sugar Plantation, and then enjoy the sand and surf at Trunk Bay Beach. Get ready for a full day of sightseeing on the 3rd (Sun): explore the gorgeous colors at Leinster Bay, then contemplate the waterfront views at Salt Pond Bay, and then don't miss a visit to Peace Hill Windmill.

For more things to do, maps, photos, and tourist information, use the Virgin Islands National Park road trip planner.

Traveling by combination of flight and ferry from Virgin Gorda to Virgin Islands National Park takes 1.5 hours. Alternatively, you can ride a ferry. In January, daytime highs in Virgin Islands National Park are 84°F, while nighttime lows are 73°F. Finish up your sightseeing early on the 3rd (Sun) so you can travel to Road Town.

Things to do in Virgin Islands National Park

Parks Outdoors Beaches

Side Trip

Peace Hill Windmill
Find places to stay Jan 1 — 3:
Highlights from your plan
Trunk Bay Beach ©
Trunk Bay Beach
Annaberg Sugar Plantation ©
Annaberg Sugar Plantation
Leinster Bay ©
Leinster Bay

2
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. Start off your visit on the 4th (Mon): explore the striking landscape of Sage Mountain National Park and then go for a stroll along the water at Rhone National Marine Park. Get ready for a full day of sightseeing on the next day: explore the gorgeous colors at Smuggler's Cove, then explore the activities along Cane Garden Bay, and then contemplate the waterfront views at Brewers Bay.

To see where to stay, other places to visit, traveler tips, and other tourist information, use the Road Town journey site.

Use the Route module to find suitable travel options from Virgin Islands National Park to Road Town. In January, daily temperatures in Road Town can reach 84°F, while at night they dip to 75°F. Finish your sightseeing early on the 5th (Tue) to allow enough time to travel to Havana.

Things to do in Road Town

Parks Nature Outdoors

Side Trip

Tortola
Find places to stay Jan 3 — 5:
Highlights from your plan
Cane Garden Bay ©
Cane Garden Bay
Sage Mountain National Park ©
Sage Mountain National Park
Brewers Bay ©
Brewers Bay

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: don't miss a visit to Malecón of Havana, appreciate the extensive heritage of Old Havana, take a stroll through Iglesias de San Francisco de Paula, and steep yourself in history at Castillo de la Real Fuerza.

To find ratings, traveler tips, more things to do, and tourist information, go to the Havana online travel planner.

Getting from Road Town to Havana by flight takes about 5.5 hours. Other options: do a combination of ferry and flight. The time zone changes from Atlantic Standard Time to Cuba Standard Time, which is usually a -1 hour difference. Expect slightly colder temperatures when traveling from Road Town in January; daily highs in Havana reach 79°F and lows reach 62°F. Finish your sightseeing early on the 8th (Fri) so you can travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Jan 5 — 8:
Highlights from your plan
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. On the 9th (Sat), kick back and relax at Seven Mile Beach, then sample the fine beverages at Cayman Spirits Co. Distillery, and then stroll through Stingray City Grand Cayman. Get ready for a full day of sightseeing on the 10th (Sun): look for gifts at TAG Heuer Boutique, take in the dramatic natural features at Hell Gift Store, and then try out the rides at Cayman Turtle Centre: Island Wildlife Encounter.

To find photos, traveler tips, reviews, and more tourist information, refer to the Seven Mile Beach route planner.

You can fly from Havana to Seven Mile Beach in 2 hours. Traveling from Havana in January, expect somewhat warmer with lows of 74°F in Seven Mile Beach. Wrap up your sightseeing on the 10th (Sun) early enough to travel back home.

Things to do in Seven Mile Beach

Parks Wildlife Theme Parks

Side Trips

Grand Cayman, George Town, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Jan 8 — 10:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Cayman Turtle Centre: Island Wildlife Encounter ©
Seven Mile Beach ©
Seven Mile Beach

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