53 days in Caribbean, Central America & United States Itinerary

53 days in Caribbean, Central America & United States Itinerary

Created using Inspirock vacation maker

Plan created by another user. Make it yours

Route & dates

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

5
nights
East End, U.S. Virgin Islands

St.
Change things up with these side-trips from East End: Virgin Islands National Park (Trunk Bay Beach & Annaberg Sugar Plantation) and Maho Bay Beach (in Cruz Bay). Next up on the itinerary: kick back and relax at Magens Bay, stroll through Sapphire Beach, see some colorful creatures with a scuba or snorkeling tour, and make a trip to Main Street.

To find photos, more things to do, traveler tips, and tourist information, refer to the East End road trip planning tool.

Orlando, USA to East End is an approximately 7.5-hour flight. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. While traveling from Orlando, expect somewhat warmer days and much hotter nights in East End, ranging from highs of °F to lows of °F. Finish your sightseeing early on the 20th (Mon) to allow enough time to ride a ferry to Road Town.

Things to do in East End

Outdoors Parks Beaches

Side Trips

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

5
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. Step out of Road Town to go to West End and see Soper's Hole, which is approximately 30 minutes away. There's still lots to do: contemplate the waterfront views at Cane Garden Bay, take in nature's colorful creations at J.R. O'Neal Botanic Gardens, stroll through Nanny Cay, and explore the wealth of natural beauty at Sage Mountain National Park.

For reviews, ratings, more things to do, and more tourist information, you can read our Road Town road trip website.

Traveling by ferry from East End to Road Town takes 1.5 hours. Expect a daytime high around °F in January, and nighttime lows around °F. Cap off your sightseeing on the 25th (Sat) early enough to catch the ferry 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, and outdoors. Your plan includes some of its best attractions: see the vivid underwater world at Horseshoe Reef, head outdoors with Loblolly Bay, kick back and relax at Cow Wreck Beach, and stroll through Flash of Beauty.

To see ratings, photos, and other tourist information, go to the Anegada journey builder tool.

Getting from Road Town to Anegada by ferry takes about 2 hours. In January in Anegada, expect temperatures between °F during the day and °F at night. You will leave 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 Beach ©
Loblolly Beach
Loblolly Bay ©
Loblolly Bay

5
nights
Basseterre, St. Kitts and Nevis

Basseterre ©
When in Basseterre, make a side trip to see Pinney's Beach in Charlestown, approximately Charlestown away.

For reviews, ratings, photos, and tourist information, use the Basseterre road trip app.

Explore your travel options from Anegada to Basseterre with the Route module. January in Basseterre sees daily highs of °F and lows of °F at night. 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 ©
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 wildlife, nature, and parks. Your plan includes some of its best attractions: take in panoramic vistas at Montserrat Volcano Observatory, browse the exhibits of Montserrat National Trust, get impressive views of Soufriere Hills Volcano, and tour the pleasant surroundings at Rendezvous Beach.

To find maps, other places to visit, photos, and other tourist information, refer to the Montserrat day trip website.

You can do a combination of flight and ferry from Basseterre to Montserrat in 5 hours. Wrap up your sightseeing on the 7th (Fri) to allow time to 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
Jack Boy Hill Viewing Facility ©
Jack Boy Hill Viewing Facility

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.
Get ready for a full day of sightseeing on the next day: take an in-depth tour of Betty's Hope, thenexplore the striking landscape of Nelson's Dockyard, and then stop by Silver Chelles.

For where to stay, ratings, more things to do, and tourist information, read our St. John's trip tool.

Traveling by ferry from Montserrat to St. John's takes 2.5 hours. In February, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Roseau.

Things to do in St. John's

Nature Parks Wildlife

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.
Venture out of the city with trips to Morne Trois Pitons National Park (Boiling Lake & Emerald Pool Nature Trail). There's still lots to do: admire the sheer force of Trafalgar Falls, stroll through Champagne Beach, take in the spiritual surroundings of St. Patrick's Roman Catholic Cathedral, and surround yourself with nature on a nature and wildlife tour.

Planning Roseau trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by flight from St. John's to Roseau takes 3.5 hours. Cap off your sightseeing on the 13th (Thu) early enough to catch the 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, stop by Grand Marche, admire the striking features of Schoelcher Library, thentake in the spiritual surroundings of St. Louis Cathedral, and finally take in nature's colorful creations at Jardin de Balata.

To find traveler tips, reviews, more things to do, and more tourist information, read our Fort-de-France travel route planner.

You can ride a ferry from Roseau to Fort-de-France in 3 hours. Another option is to fly. In February, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 16th (Sun) to allow enough time to travel to Choiseul.

Things to do in Fort-de-France

Historic Sites Wildlife Tours

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 ©
You'll find plenty of places to visit near Choiseul: Castries (Diamonds International, Holy Trinity Anglican Church, &more).

To find where to stay, reviews, more things to do, and tourist information, use the Choiseul trip planner.

The Route module can help you plan travel from Fort-de-France to Choiseul. In February in Choiseul, expect temperatures between °F during the day and °F at night. Wrap up 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
Rodney Bay ©
Rodney Bay

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, and shopping. Your plan includes some of its best attractions: admire the natural beauty at Botanical Gardens, don't miss a visit to Layou Village, contemplate the long history of Fort Charlotte, and take your sightseeing to a higher altitude at La Soufriere Cross Country Trail.

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

Explore your travel options from Choiseul to Kingstown with the Route module. In February in Kingstown, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 24th (Mon) early enough to travel to St. George's.

Things to do in Kingstown

Parks Nature Historic Sites

Side Trips

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

3
nights
St. George's, Grenada

St. George's ©
The capital of the Island of Spice, St.
On the 25th (Tue), contemplate the long history of Fort George and then kick back and relax at 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, thentake in the dramatic scenery at Annandale Falls, thenexamine the collection at Grenada National Museum, and finally examine the collection at Underwater Sculptures.

You can plan St. George's trip in no time by asking Inspirock to help create your itinerary.

You can fly from Kingstown to St. George's in 5.5 hours. Alternatively, you can ride a ferry. In February, daily temperatures in St. George's can reach °F, while at night they dip to °F. On the 27th (Thu), wrap the sightseeing up by early afternoon so you can 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
Market Square ©
Market Square
Annandale Falls ©
Annandale Falls

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.
Venture out of the city with trips to Poas Volcano (in Poas Volcano National Park) and Jardins da Cachoeira de La Paz (in Vara Blanca). Next up on the itinerary: witness a stunning natural landmark at Tabacon Hot Springs, hike along Arenal Natura Ecological Park, take a memorable tour with Tours, and contemplate the geological forces at Arenal Volcano.

To see reviews, photos, other places to visit, and other tourist information, you can read our La Fortuna de San Carlos driving holiday planning app.

The Route module can help you plan travel from St. George's to La Fortuna de San Carlos. Traveling from St. George's to La Fortuna de San Carlos, you'll gain 2 hours due to the time zone difference. 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, Poas Volcano, Jardins da Cachoeira de La Paz
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.
Kick off your visit on the 7th (Sat): discover the magic at Walt Disney World Resort.

To see where to stay, maps, traveler tips, and tourist information, go to the Orlando trip planning app.

Traveling by flight from La Fortuna de San Carlos to Orlando takes 10.5 hours. Alternatively, you can drive. You'll lose 1 hour traveling from La Fortuna de San Carlos to Orlando due to the time zone difference. March in Orlando sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 7th (Sat) to allow enough 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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