53 days in Caribbean, Central America & United States Itinerary

53 days in Caribbean, Central America & United States Itinerary

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Route & dates

53 days in Caribbean, Central America & United States Itinerary

Start: Orlando, United States
Fly:  4​h 45​min
1
East End, U.S. Virgin Islands
— 5 nights
+2
taxi + Fly + taxi:  1​h
2
Road Town, British Virgin Islands
— 5 nights
Drive:  5​h 30​min
3
Anegada, British Virgin Islands
— 4 nights
Drive + Fly:  10​h
4
Basseterre, St. Kitts and Nevis
— 5 nights
Fly:  7​h 15​min
5
Montserrat, Montserrat
— 3 nights
ferry:  1​h 45​min
6
St. John's, Antigua and Barbuda
— 3 nights
Fly + Drive:  3​h 30​min
7
Roseau, Dominica
— 3 nights
ferry:  2​h
8
Fort-de-France, Martinique
— 3 nights
Fly + Drive:  11​h 30​min
9
Choiseul, St. Lucia
— 5 nights
Drive + Fly:  11​h 15​min
10
Kingstown, St. Vincent and the Grenadines
— 2 nights
Fly + taxi:  1​h
11
St. George's, Grenada
— 3 nights
Fly + Drive:  15​h 30​min
12
La Fortuna de San Carlos, Costa Rica
— 7 nights
Fly:  9​h 15​min
13
Orlando, United States
— 1 night
End: Orlando, United States

5
nights
East End, U.S. Virgin Islands

St.
Venture out of the city with trips to Maho Beach (in Cruz Bay) and Virgin Islands National Park (Trunk Bay & Annaberg Sugar Plantation). And it doesn't end there: kick back and relax at Magens Bay, stroll through Honeymoon Beach, discover the deep blue sea with a scuba or snorkeling tour, and observe the fascinating underwater world at Coral World Ocean Park.

For ratings, where to stay, photos, and more tourist information, you can read our East End trip planner .

Orlando, USA to East End is an approximately 5-hour flight. The time zone changes from Eastern Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. Expect somewhat warmer weather when traveling from Orlando in January: highs in East End hover around 84°F, while lows dip to 73°F. Wrap up your sightseeing on the 20th (Mon) early enough to travel to Road Town.

Things to do in East End

Outdoors Parks Beaches

Side Trips

Virgin Islands National Park, St. Thomas, Charlotte Amalie, Maho Beach, Magens Bay
Find places to stay Jan 15 — 20:
Highlights from your plan
Scuba & Snorkeling
Magens Bay ©
Magens Bay
Trunk Bay ©
Trunk Bay

5
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. Road Town is known for wildlife, adventure, nature, museums, and parks. Your plan includes some of its best attractions: stroll through Cane Garden Bay, enjoy the sand and surf at Long Bay Beach, head off the coast to Sandy Cay, and go for a stroll along the water at Rhone National Marine Park.

For where to stay, ratings, more things to do, and more tourist information, go to the Road Town trip planner .

You can do a combination of taxi and flight from East End to Road Town in an hour. Alternatively, you can ride a ferry. In January, plan for daily highs up to 84°F, and evening lows to 75°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to Anegada.

Things to do in Road Town

Parks Outdoors Beaches

Side Trips

Tortola, British Virgin Islands, Soper's Hole
Find places to stay Jan 20 — 25:
Highlights from your plan
Cane Garden Bay ©
Cane Garden Bay
Sage Mountain National Park ©
Sage Mountain National Park
Brewers Bay ©
Brewers Bay

4
nights
Anegada, British Virgin Islands

Anegada ©
The only inhabited island of the British Virgin Islands to be formed of coral and limestone, rather than volcanic activity, Anegada offers flat terrain at odds with the primarily mountainous islands that sit close to it.
Anegada is known for beaches, wildlife, outdoors, nature, and adventure. Your plan includes some of its best attractions: get outside with Loblolly Bay, explore the gorgeous colors at Horseshoe Reef, kick back and relax at Loblolly Beach, and stroll through Flash of Beauty.

For traveler tips, photos, more things to do, and tourist information, refer to the Anegada online trip itinerary builder .

You can drive from Road Town to Anegada in 5.5 hours. Expect a daytime high around 84°F in January, and nighttime lows around 75°F. You'll set off for Basseterre on the 29th (Wed).

Things to do in Anegada

Parks Outdoors Beaches
Find places to stay Jan 25 — 29:
Highlights from your plan
Horseshoe Reef ©
Horseshoe Reef
Loblolly Bay ©
Loblolly Bay
Loblolly Beach ©
Loblolly Beach

5
nights
Basseterre, St. Kitts and Nevis

Basseterre ©
Basseterre, estimated population 13,000 in 2011, is the capital of the Federation of Saint Kitts and Nevis in the West Indies. Take a break from Basseterre with a short trip to Pinney's Beach in Charlestown, about 1h 05 min away. And it doesn't end there: explore the striking landscape of Brimstone Hill Fortress National Park, explore and take pictures at Timothy Hill, tour the pleasant surroundings at Cockleshell Beach, and enjoy the sand and surf at South Friars Beach.

To see traveler tips, where to stay, and other tourist information, use the Basseterre trip app .

The Route module can help you plan travel from Anegada to Basseterre. In January, plan for daily highs up to 84°F, and evening lows to 73°F. Finish your sightseeing early on the 4th (Tue) so you can travel to Montserrat.

Things to do in Basseterre

Parks Outdoors Wildlife

Side Trips

St. Kitts, Clay Villa Plantation House & Gardens, Pinney's Beach
Find places to stay Jan 30 — Feb 4:
Highlights from your plan
Brimstone Hill Fortress National Park ©
Pinney's Beach ©
Pinney's Beach
Frigate Bay ©
Frigate Bay

3
nights
Montserrat, Montserrat

Montserrat ©
The Caribbean island of Montserrat can divide its history into two main parts: before 18th July 1995, and after.
Montserrat is known for childrens museums, wildlife, nature, beaches, and museums. Your plan includes some of its best attractions: look and learn at Montserrat Volcano Observatory, hike along Runaway Ghaut Trail, see the interesting displays at Montserrat National Trust, and enjoy the sand and surf at Woodlands Beach.

To see photos, ratings, and more tourist information, read Montserrat planning site .

The Route module can help you plan travel from Basseterre to Montserrat. Finish up your sightseeing early on the 7th (Fri) so you can travel to St. John's.

Things to do in Montserrat

Parks Outdoors Trails
Find places to stay Feb 4 — 7:
Highlights from your plan
Soufriere Hills Volcano ©
Soufriere Hills Volcano
Montserrat Volcano Observatory ©
Montserrat Volcano Observatory
Woodlands Beach ©
Woodlands Beach

3
nights
St. John's, Antigua and Barbuda

St. John's ©
The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Here are some ideas for day two: get engrossed in the history at Betty's Hope, then explore the striking landscape of Nelson's Dockyard, and then stop by Silver Chelles.

Plan my St. John's trip by asking Inpirock to come up with tips and suggestions.

Traveling by ferry from Montserrat to St. John's takes 2 hours. Expect a daytime high around 82°F in February, and nighttime lows around 72°F. Finish up your sightseeing early on the 10th (Mon) so you can travel to Roseau.

Things to do in St. John's

Parks Nature Historic Sites

Side Trips

English Harbour, Scuba & Snorkeling, Gilly Gobinet Art
Find places to stay Feb 7 — 10:
Highlights from your plan
Nelson's Dockyard ©
Nelson's Dockyard
Shirley Heights ©
Shirley Heights
Betty's Hope ©
Betty's Hope

3
nights
Roseau, Dominica

Roseau ©
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
You'll find plenty of places to visit near Roseau: Morne Trois Pitons National Park (Boiling Lake & Emerald Pool Nature Trail). Next up on the itinerary: take in the dramatic scenery at Trafalgar Falls, tour the pleasant surroundings at Champagne Beach, discover the deep blue sea with a scuba or snorkeling tour, and examine the collection at Roseau Museum.

For traveler tips, other places to visit, ratings, and tourist information, go to the Roseau trip app .

Traveling by combination of flight and car from St. John's to Roseau takes 3.5 hours. Wrap up your sightseeing on the 13th (Thu) early enough to ride a ferry to Fort-de-France.

Things to do in Roseau

Parks Nature Outdoors

Side Trips

Morne Trois Pitons National Park, Screw's Sulphur Spa
Find places to stay Feb 10 — 13:
Highlights from your plan
Boiling Lake ©
Boiling Lake
Emerald Pool Nature Trail ©
Emerald Pool Nature Trail
Trafalgar Falls ©
Trafalgar Falls

3
nights
Fort-de-France, Martinique

Fort-de-France ©
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Here are some ideas for day two: browse the exhibits of La Savane des Esclaves, look for gifts at Grand Marche, then admire the landmark architecture of Schoelcher Library, then contemplate in the serene atmosphere at St. Louis Cathedral, and finally take in nature's colorful creations at Jardin de Balata.

To see maps, photos, reviews, and tourist information, go to the Fort-de-France journey website .

Traveling by ferry from Roseau to Fort-de-France takes 2 hours. Alternatively, you can do a combination of taxi and flight. In February in Fort-de-France, expect temperatures between 84°F during the day and 72°F at night. Finish up your sightseeing early on the 16th (Sun) so you can travel to Choiseul.

Things to do in Fort-de-France

Historic Sites Outdoors Wildlife

Side Trips

La Savane des Esclaves, Habitation Clement
Find places to stay Feb 13 — 16:
Highlights from your plan
St. Louis Cathedral ©
St. Louis Cathedral
Jardin de Balata ©
Jardin de Balata
La Savane des Esclaves ©
La Savane des Esclaves

5
nights
Choiseul, St. Lucia

Choiseul ©
Get out of town with these interesting Choiseul side-trips: Castries (Diamonds International, Holy Trinity Anglican Church, & more).

To find ratings, more things to do, maps, and tourist information, use the Choiseul itinerary planner.

Explore your travel options from Fort-de-France to Choiseul with the Route module. In February in Choiseul, expect temperatures between 84°F during the day and 75°F at night. Cap off your sightseeing on the 21st (Fri) early enough to travel to Kingstown.

Things to do in Choiseul

Parks Nature Outdoors

Side Trips

St. Lucia, Soufriere, Castries
Find places to stay Feb 16 — 21:
Highlights from your plan
Pigeon Island National Park ©
Pigeon Island National Park
Marigot Bay ©
Marigot Bay
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens

2
nights
Kingstown, St. Vincent and the Grenadines

Kingstown ©
Kingstown is the capital, chief port, and main commercial centre of Saint Vincent and the Grenadines. Kingstown is known for parks, historic sites, shopping, wildlife, and beaches. Your plan includes some of its best attractions: take in nature's colorful creations at Botanical Gardens, contemplate in the serene atmosphere at St. George's Cathedral, admire the striking features of St. Mary's Cathedral of the Assumption, and take in the awesome beauty at La Soufriere Cross Country Trail.

To find traveler tips, where to stay, and other tourist information, read our Kingstown online journey planner .

The Route module can help you plan travel from Choiseul to Kingstown. February in Kingstown sees daily highs of 84°F and lows of 75°F at night. Cap off your sightseeing on the 24th (Mon) early enough to travel to St. George's.

Things to do in Kingstown

Parks Historic Sites Nature

Side Trips

St. Vincent, Dark View Falls
Find places to stay Feb 22 — 24:
Highlights from your plan
Botanical Gardens ©
Botanical Gardens
Montreal Gardens ©
Montreal Gardens
Wallilabou River ©
Wallilabou River

3
nights
St. George's, Grenada

St. George's ©
The capital of the Island of Spice, St.
Start off your visit on the 25th (Tue): contemplate the long history of Fort George and then stroll through Grand Anse Beach. Get ready for a full day of sightseeing on the next day: discover the deep blue sea with a scuba or snorkeling tour, admire the sheer force of Annandale Falls, then examine the collection at Grenada National Museum, and finally pause for some photo ops at Underwater Sculptures.

To find ratings, maps, more things to do, and more tourist information, read our St. George's road trip planner.

Do a combination of flight and taxi from Kingstown to St. George's in an hour. Alternatively, you can do a combination of ferry and flight; or ride a ferry. February in St. George's sees daily highs of 85°F and lows of 74°F at night. Wrap up your sightseeing by early afternoon on the 27th (Thu) to allow time for travel to La Fortuna de San Carlos.

Things to do in St. George's

Outdoors Parks Beaches

Side Trip

Grand Anse Beach
Find places to stay Feb 24 — 27:
Highlights from your plan
Grand Anse Beach ©
Grand Anse Beach
Annandale Falls ©
Annandale Falls
Market Square ©
Market Square

7
nights
La Fortuna de San Carlos, Costa Rica

Set against the backdrop of the imposing Arenal Volcano, La Fortuna de San Carlos offers visitors a chance to explore diverse natural landscapes and sample some delicious local produce.
Explore La Fortuna de San Carlos' surroundings by going to Poas Volcano (in Poas Volcano National Park) and Jardins da Cachoeira de La Paz (in Vara Blanca). And it doesn't end there: take in the natural beauty of Tabacon Hot Springs, get impressive views of Arenal Volcano, scramble along the landscape with a canyoning and rapelling tour, and identify plant and animal life at Proyecto Asis.

To see photos, traveler tips, other places to visit, and more tourist information, refer to the La Fortuna de San Carlos road trip planning app .

Explore your travel options from St. George's to La Fortuna de San Carlos with the Route module. The time zone difference moving from Atlantic Standard Time to Central Standard Time is minus 2 hours. On the 6th (Fri), wrap the sightseeing up by early afternoon so you can travel to Orlando.

Things to do in La Fortuna de San Carlos

Parks Nature Outdoors

Side Trips

Arenal Volcano National Park, Jardins da Cachoeira de La Paz, Poas Volcano
Find places to stay Feb 27 — Mar 6:
Highlights from your plan
River Rafting & Tubing
Tabacon Hot Springs ©
Tabacon Hot Springs
Arenal Volcano
Arenal Volcano

1
night
Orlando, United States

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Start off your visit on the 7th (Sat): find something for the whole family at Walt Disney World Resort.

To see ratings, maps, reviews, and tourist information, read Orlando online journey planner .

Getting from La Fortuna de San Carlos to Orlando by flight takes about 9.5 hours. Other options: do a combination of shuttle and flight; or drive. Traveling from La Fortuna de San Carlos to Orlando, you'll lose 1 hour due to the time zone difference. In March, daily temperatures in Orlando can reach 78°F, while at night they dip to 58°F. Wrap up your sightseeing on the 7th (Sat) to allow time to travel back home.

Things to do in Orlando

Theme Parks
Find places to stay Mar 6 — 7:
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort

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