30 days in Caribbean, South America, Central America & United States Itinerary

30 days in Caribbean, South America, Central America & United States Itinerary

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30 days in Caribbean, South America, Central America & United States Itinerary

Start: Boracay, Philippines
+2
Drive + Fly + Drive:  39​h
1
Varadero, Cuba
— Few hours
Drive:  2​h
2
Havana, Cuba
— 4 nights
Fly:  5​h
3
Montego Bay, Jamaica
— 4 nights
bus:  1​h 30​min
4
Ocho Rios, Jamaica
— 1 night
+2
bus + Fly + shuttle:  5​h 15​min
5
Punta Cana, Dominican Republic
— 4 nights
Fly + foot:  5​h 45​min
6
Caracas, Venezuela
— 1 night
Fly + Drive:  23​h 30​min
7
Dominical, Costa Rica
— 2 nights
+2
Drive + Fly + Drive:  30​h
8
Lahaina, United States
— 4 nights
Fly:  3​h 15​min
9
Honolulu, United States
— 4 nights
+3
Fly + foot + bus + ferry:  21​h 15​min
End: Boracay, Philippines

few
hours
Varadero, Cuba

Varadero ©
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
Kick off your visit on the 9th (Tue): meet the residents at Delfinario and then enjoy the sand and surf at Varadero Beach.

To find maps, other places to visit, and other tourist information, read Varadero itinerary builder.

Boracay, Philippines to Varadero is an approximately 39-hour flight. You'll gain 13 hours traveling from Boracay to Varadero due to the time zone difference. In January, daytime highs in Varadero are 30°C, while nighttime lows are 19°C. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Havana.

Things to do in Varadero

Parks Beaches Outdoors
Find places to stay Jan 9 — 10:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Delfinario ©
Delfinario

4
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, sightseeing, nightlife, museums, and beaches. Your plan includes some of its best attractions: make a trip to Old Havana, steep yourself in history at FINCA VIGÍA, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), and get to know the fascinating history of El Malecon.

To see more things to do, photos, other places to visit, and more tourist information, read our Havana online itinerary creator.

Drive from Varadero to Havana in 2 hours. Alternatively, you can take a bus. In January, daily temperatures in Havana can reach 30°C, while at night they dip to 18°C. Wrap up your sightseeing by early afternoon on the 13th (Sat) to allow time for travel to Montego Bay.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Jan 9 — 13:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

4
nights
Montego Bay, Jamaica

Montego Bay ©
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Change things up with these side-trips from Montego Bay: Tryall Golf Course (in Sandy Bay) and Negril (Mary, Gate of Heaven Catholic Church, Seven Mile Beach, & more). And it doesn't end there: enjoy the sand and surf at Doctor's Cave Beach, stop by Tropicana Jewelers, and steep yourself in history at Rose Hall Great House.

To find ratings, reviews, traveler tips, and more tourist information, use the Montego Bay itinerary planner.

Getting from Havana to Montego Bay by flight takes about 5 hours. Traveling from Havana in January, expect Montego Bay to be a bit warmer, temps between 34°C and 26°C. Finish up your sightseeing early on the 17th (Wed) so you can catcht the bus to Ocho Rios.

Things to do in Montego Bay

Outdoors Parks Beaches

Side Trips

Negril, Tryall Golf Course, Mayfield Falls Jamaica (Original)
Find places to stay Jan 13 — 17:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Mayfield Falls Jamaica (Original)
Mayfield Falls Jamaica (Original)
Rose Hall Great House ©
Rose Hall Great House

1
night
Ocho Rios, Jamaica

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Kick off your visit on the 17th (Wed): take in nature's colorful creations at Shaw Park Gardens & Waterfalls, then take in the dramatic scenery at Blue Hole, and then admire the sheer force of Dunn's River Falls and Park.

To see traveler tips, photos, where to stay, and other tourist information, you can read our Ocho Rios vacation planner.

You can take a bus from Montego Bay to Ocho Rios in 1.5 hours. Another option is to drive. In January in Ocho Rios, expect temperatures between 35°C during the day and 27°C at night. Wrap up your sightseeing by early afternoon on the 18th (Thu) to allow enough time to travel to Punta Cana.

Things to do in Ocho Rios

Parks Nature Beaches
Find places to stay Jan 17 — 18:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
James Bond Beach ©
James Bond Beach
Shaw Park Gardens & Waterfalls ©
Shaw Park Gardens & Waterfalls

4
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Change things up with these side-trips from Punta Cana: Isla Saona (in Parque Nacional del Este) and La Romana (Altos de Chavon & Teeth of the Dog). There's still lots to do: enjoy the sand and surf at Bavaro Beach, don't miss a visit to Jesus Maestro Parish, stop by Don Lucas Cigars, and play a few rounds at Punta Espada Golf Course.

For maps, where to stay, other places to visit, and other tourist information, refer to the Punta Cana vacation trip planner.

Getting from Ocho Rios to Punta Cana by combination of bus, flight, and taxi takes about 5.5 hours. The time zone difference when traveling from Ocho Rios to Punta Cana is 1 hour. In January in Punta Cana, expect temperatures between 33°C during the day and 25°C at night. Wrap up your sightseeing on the 22nd (Mon) early enough to travel to Caracas.

Things to do in Punta Cana

Outdoors Parks Golf

Side Trip

La Romana
Find places to stay Jan 18 — 22:
Highlights from your plan
Saona Island ©
Saona Island
Bavaro Beach ©
Bavaro Beach
Altos de Chavon ©
Altos de Chavon

1
night
Caracas, Venezuela

Caracas ©
Tropical weather, great food, and memorable jungle surroundings seem like all the ingredients Caracas needs to become a must-see destination.
To see maps, other places to visit, photos, and tourist information, refer to the Caracas travel itinerary planner.

Use the Route module to find suitable travel options from Punta Cana to Caracas. While traveling from Punta Cana, expect a bit warmer days and about the same nights in Caracas, ranging from highs of 37°C to lows of 22°C. Finish up your sightseeing early on the 23rd (Tue) so you can travel to Dominical.

Things to do in Caracas

Historic Sites
Find places to stay Jan 22 — 23:
Highlights from your plan
Iglesia de San Francisco ©
Iglesia de San Francisco

2
nights
Dominical, Costa Rica

Dominical ©
The laid back beachfront town of Dominical has been transformed from a sleepy fishing village into a surfer haunt of some repute.
Kick off your visit on the 24th (Wed): explore the striking landscape of Parque Nacional Manuel Antonio and then stop by Mama Toucan's Natural and Organic Food Store. Here are some ideas for day two: get the adrenaline pumping with an extreme tour and then stroll through MidWorld Costa Rica.

To find more things to do, maps, reviews, and more tourist information, refer to the Dominical itinerary planner.

The Route module can help you plan travel from Caracas to Dominical. Due to the time zone difference, you'll gain 2 hours traveling from Caracas to Dominical. Wrap up your sightseeing on the 26th (Fri) early enough to travel to Lahaina.

Things to do in Dominical

Tours Adventure Outdoors

Side Trip

MidWorld Costa Rica
Find places to stay Jan 24 — 26:
Highlights from your plan
MidWorld Costa Rica ©
MidWorld Costa Rica

4
nights
Lahaina, United States

Lahaina ©
Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Explore the numerous day-trip ideas around Lahaina: Haleakala Crater (in Haleakala National Park), Wailea Beach (in Wailea) and Iao Valley State Monument (in Wailuku). The adventure continues: enjoy the sand and surf at Ka'anapali Beach, stop by Glass Mango, take in the architecture and atmosphere at Maria Lanakila Catholic Church, and admire nature's wide array of creatures at Maui Ocean Center.

To see other places to visit, photos, more things to do, and tourist information, read Lahaina travel itinerary planner.

The Route module can help you plan travel from Dominical to Lahaina. Traveling from Dominical to Lahaina, you'll gain 4 hours due to the time zone difference. In January, plan for daily highs up to 30°C, and evening lows to 22°C. Cap off your sightseeing on the 31st (Wed) early enough to travel to Honolulu.

Things to do in Lahaina

Parks Beaches Outdoors

Side Trips

Wailuku, Wailea Beach, Haleakala Crater
Find places to stay Jan 27 — 31:
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Maui Ocean Center ©
Maui Ocean Center
Ka'anapali Beach ©
Ka'anapali Beach

4
nights
Honolulu, United States

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Explore the numerous day-trip ideas around Honolulu: Kailua Beach Park (in Kailua) and Haleiwa (Waimea Bay & Sunset Beach Park). There's lots more to do: appreciate the history behind USS Arizona Memorial, kick back and relax at Kapiolani Regional Park, stroll the grounds of National Memorial Cemetery of the Pacific, and take a memorable drive along Makapu'u Point.

To see where to stay, photos, more things to do, and more tourist information, you can read our Honolulu trip builder.

You can do a combination of bus and flight from Lahaina to Honolulu in 3.5 hours. In January in Honolulu, expect temperatures between 31°C during the day and 22°C at night. Finish your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Makapu'u Point, Kailua Beach Park
Find places to stay Jan 31 — Feb 4:
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

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