14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

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Route & dates

14 days in Caribbean Itinerary

Start: Austin, United States
Fly:  7​h 45​min
1
Havana, Cuba
— 2 nights
Fly:  7​h 45​min
2
Road Town, British Virgin Islands
— 2 nights
Drive:  9​h
3
Virgin Gorda, British Virgin Islands
— 2 nights
Fly:  1​h
4
Maho, St. Maarten-St. Martin
— 3 nights
Fly:  3​h 15​min
5
Castries, St. Lucia
— 2 nights
Fly:  27​h
End: Dubai, United Arab Emirates

2
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Kick off your visit on the 20th (Mon): enjoy the sand and surf at Santa Maria del Mar, then don't miss a visit to Plaza de Armas, then enjoy the sand and surf at Playas de Este, and finally wander the streets of Christopher Columbus Cemetery (Cemetario de Colon). On the next day, get to know the fascinating history of Malecón of Havana and then make a trip to Plaza de la Catedral.

To see traveler tips, more things to do, and tourist information, use the Havana itinerary builder site .

Austin, USA to Havana is an approximately 8-hour flight. You can also do a combination of car and flight; or do a combination of bus and flight. The time zone difference moving from Central Standard Time (CST) to Cuba Standard Time (CST) is 1 hour. When traveling from Austin in January, plan for somewhat warmer days in Havana, with highs around 30°C, while nights are much warmer with lows around 19°C. Wrap up your sightseeing by early afternoon on the 21st (Tue) to allow enough time to travel to Road Town.

Things to do in Havana

Parks Outdoors Beaches
Find places to stay Jan 19 — 21:
Highlights from your plan
Plaza de la Catedral ©
Plaza de la Catedral
Santa Maria del Mar ©
Santa Maria del Mar

2
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. On the 22nd (Wed), explore the activities along Brewers Bay, then see the vivid underwater world at Smuggler's Cove, and then explore the activities along Cane Garden Bay. On your second day here, glide peacefully along the water with some of the best stand-up paddleboarding in the area.

Plan trip to Road Town with our itinerary maker to find out where to go and what to do.

Getting from Havana to Road Town by combination of flight and ferry takes about 8 hours. Other options: fly. Due to the time zone difference, you'll lose 1 hour traveling from Havana to Road Town. Traveling from Havana in January, Road Town is a bit warmer at night with lows of 28°C. Wrap up your sightseeing by early afternoon on the 23rd (Thu) to allow enough time to drive to Virgin Gorda.

Things to do in Road Town

Outdoors Parks Beaches

Side Trip

Tortola
Find places to stay Jan 21 — 23:
Highlights from your plan
Smuggler's Cove ©
Smuggler's Cove
Cane Garden Bay ©
Cane Garden Bay
Brewers Bay ©
Brewers Bay

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.
Kick off your visit on the 24th (Fri): explore the activities along Savannah Bay, then explore the striking landscape at The Baths, and then tour the pleasant surroundings at Spring Bay. Get ready for a full day of sightseeing on the 25th (Sat): get a dose of the wild on a nature and wildlife tour.

To find traveler tips, more things to do, and tourist information, use the Virgin Gorda travel itinerary planner.

You can drive from Road Town to Virgin Gorda in 9 hours. Expect a daytime high around 34°C in January, and nighttime lows around 28°C. Wrap up your sightseeing by early afternoon on the 25th (Sat) to allow time for travel to Maho.

Things to do in Virgin Gorda

Outdoors Parks Beaches
Find places to stay Jan 23 — 25:
Highlights from your plan
The Baths ©
The Baths
Spring Bay ©
Spring Bay
Nature & Wildlife Tours

3
nights
Maho, St. Maarten-St. Martin

Maho ©
Take a break from the city and head to Maho Beach and Orient Bay Beach. Your itinerary includes some good beach time at Dawn Beach and Mullet Bay Beach.

Discover how to plan a Maho trip in just a few steps with Inspirock's itinerary builder.

Fly from Virgin Gorda to Maho in an hour. Alternatively, you can do a combination of ferry and flight. In January, daily temperatures in Maho can reach 33°C, while at night they dip to 28°C. Wrap up your sightseeing on the 28th (Tue) to allow time to fly to Castries.

Things to do in Maho

Outdoors Parks Beaches

Side Trips

Sint Maarten, WAKE N' GLISSE, Speed Boats Tours, Orient Bay Beach
Find places to stay Jan 25 — 28:
Highlights from your plan
Maho Beach ©
Maho Beach
Orient Bay Beach ©
Orient Bay Beach
Speed Boats Tours

2
nights
Castries, St. Lucia

Castries ©
The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
On the 29th (Wed), enjoy the sand and surf at Reduit Beach and then head off the coast to Pigeon Island National Park. On the 30th (Thu), you'll have a packed day of sightseeing: take a tour by water with Boat Tours & Water Sports, stop by Diamonds International, and then take a stroll through Rodney Bay.

To see ratings, other places to visit, and other tourist information, use the Castries road trip tool .

Fly from Maho to Castries in 3.5 hours. Expect a daytime high around 33°C in January, and nighttime lows around 27°C. Finish your sightseeing early on the 30th (Thu) to allow enough time to travel back home.

Things to do in Castries

Parks Nature Outdoors

Side Trip

St. Lucia
Find places to stay Jan 28 — 30:
Highlights from your plan
Reduit Beach ©
Reduit Beach
Pigeon Island National Park ©
Pigeon Island National Park
Rodney Bay ©
Rodney Bay

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