49 days in Caribbean & Hawaii Itinerary

49 days in Caribbean & Hawaii Itinerary

Created using Inspirock travel planner

Make it your trip
Fly
1
Punta Cana, Dominican Republic
— 3 nights
Fly
2
Culebra, Puerto Rico
— 4 nights
Fly to Vieques, Taxi to Isla de Vieques
3
Isla de Vieques, Puerto Rico
— 4 nights
Fly
4
Simpson Bay, St. Maarten-St. Martin
— 4 nights
Fly
5
Palm - Eagle Beach, Aruba
— 2 nights
Fly
6
George Town, Cayman Islands
— 3 nights
Fly
7
Havana, Cuba
— 3 nights
Fly
8
Ocho Rios, Jamaica
— 3 nights
Fly
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Seven Mile Beach, Cayman Islands
— 2 nights
Fly
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Little Cayman, Cayman Islands
— 2 nights
Unknown
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Santo Domingo, Dominican Republic
— 2 nights
Fly
12
San Juan, Puerto Rico
— 6 nights
Fly
13
Honolulu, United States
— 6 nights
Fly to Toronto, Train to Niagara Falls

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Punta Cana, Dominican Republic

— 3 nights
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.
Your day by day itinerary now includes Runners Adventures. Next up on the itinerary: head off the coast to Saona Island, look for gifts at Manuel cigarros, make a trip to Jesus Maestro Parish, and enjoy the sand and surf at Bavaro Beach.

To find maps, ratings, other places to visit, and tourist information, refer to the Punta Cana trip itinerary builder app.

New Delhi, India to Punta Cana is an approximately 23-hour flight. The time zone difference when traveling from New Delhi to Punta Cana is minus 9.5 hours. While traveling from New Delhi, expect a bit cooler days and about the same nights in Punta Cana, ranging from highs of 36°C to lows of 29°C. Wrap up your sightseeing on the 2nd (Fri) to allow time to fly to Culebra.

Things to do in Punta Cana

Outdoors · Parks · Adventure · Tours

Side Trip

Culebra, Puerto Rico

— 4 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and nature. Your trip includes some of its best attractions: stroll through Flamenco Beach, step off the mainland to explore Culebrita, kick back and relax at Brava Beach, and identify plant and animal life at Wildlife Areas.

For more things to do, ratings, reviews, and tourist information, refer to the Culebra trip planner.

Traveling by flight from Punta Cana to Culebra takes 7.5 hours. Alternatively, you can do a combination of bus, ferry, and taxi; or do a combination of bus, ferry, shuttle, and taxi. August in Culebra sees daily highs of 37°C and lows of 31°C at night. Cap off your sightseeing on the 6th (Tue) early enough to travel to Isla de Vieques.

Things to do in Culebra

Outdoors · Parks · Beaches · Tours

Isla de Vieques, Puerto Rico

— 4 nights

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Isla de Vieques is known for beaches, nature, and adventure. Your trip includes some of its best attractions: enjoy the sand and surf at Balneario Sun Bay, take in the waterfront at Mosquito Pier, stroll through Playa Media Luna, and expand your understanding of the military at Camp Garcia.

To see maps, where to stay, traveler tips, and tourist information, you can read our Isla de Vieques road trip planning app.

Traveling by combination of flight and taxi from Culebra to Isla de Vieques takes 3.5 hours. Alternatively, you can do a combination of flight, car, and ferry; or ride a ferry. In August, daytime highs in Isla de Vieques are 36°C, while nighttime lows are 30°C. Finish up your sightseeing early on the 10th (Sat) so you can catch the flight to Simpson Bay.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife

Simpson Bay, St. Maarten-St. Martin

— 4 nights
Simpson Bay offers luxury resort living and good access to the main areas of the island.
Simpson Bay is known for wildlife, adventure, and nightlife. Your trip includes some of its best attractions: kick back and relax at Dawn Beach, stroll through Cupecoy Bay Beach, explore the activities along Mullet Bay Beach, and don't miss a visit to Frontstreet.

For other places to visit, reviews, more things to do, and more tourist information, you can read our Simpson Bay trip maker site.

Traveling by flight from Isla de Vieques to Simpson Bay takes 6 hours. In August, plan for daily highs up to 36°C, and evening lows to 31°C. Finish your sightseeing early on the 14th (Wed) so you can fly to Palm - Eagle Beach.

Things to do in Simpson Bay

Outdoors · Parks · Beaches · Wildlife

Side Trips

Palm - Eagle Beach, Aruba

— 2 nights
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kick off your visit on the 15th (Thu): stroll through Eagle Beach and then enjoy the sea views from California Lighthouse. On your second day here, contemplate the long history of Antilla Shipwreck and then enjoy the sand and surf at Palm Beach.

To see more things to do, photos, and other tourist information, read Palm - Eagle Beach trip planning tool.

Fly from Simpson Bay to Palm - Eagle Beach in 7.5 hours. In August, daytime highs in Palm - Eagle Beach are 39°C, while nighttime lows are 32°C. Finish your sightseeing early on the 16th (Fri) so you can fly to George Town.

Things to do in Palm - Eagle Beach

Beaches · Parks · Outdoors · Historic Sites

Side Trip

George Town, Cayman Islands

— 3 nights
George Town is a city situated on Grand Cayman island of the Cayman Islands. Go for a jaunt from George Town to Bodden Town to see Mission House about 36 minutes away. Next up on the itinerary: stroll through Stingray City Grand Cayman, enjoy the sand and surf at Rum Point, get a new perspective on things with Boat Tours & Water Sports, and take in nature's colorful creations at Queen Elizabeth II Botanic Park.

For maps, photos, more things to do, and other tourist information, refer to the George Town road trip planner.

You can fly from Palm - Eagle Beach to George Town in 9.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Palm - Eagle Beach to George Town. In August, daily temperatures in George Town can reach 38°C, while at night they dip to 31°C. Wrap up your sightseeing on the 19th (Mon) to allow time to fly to Havana.

Things to do in George Town

Outdoors · Parks · Tours · Wildlife

Side Trips

Havana, Cuba

— 3 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Tropicana has been added to your itinerary. Start off your visit on the 20th (Tue): steep yourself in history at El Morro, get to know the fascinating history of Malecón of Havana, then appreciate the extensive heritage of Old Havana, and finally get a taste of local nightlife at Tropicana. Keep things going the next day: take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), then make a trip to Plaza de la Catedral, then make a trip to Plaza de Armas, and finally contemplate the long history of Old Square (Plaza Vieja).

To find reviews and more tourist information, go to the Havana online travel planner.

You can fly from George Town to Havana in 5 hours. Traveling from George Town in August, plan for little chillier nights in Havana, with lows around 26°C. You'll have a few hours on the 22nd (Thu) to wrap things up before traveling to Ocho Rios.

Things to do in Havana

Historic Sites · Museums · Nightlife

Ocho Rios, Jamaica

— 3 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Ocho Rios is known for nature, wildlife, and adventure. Your trip includes some of its best attractions: admire the sheer force of Dunn's River Falls and Park, get in on the family fun at Rainforest Adventures, take in the architecture and atmosphere at Our Lady of Fatima Catholic Church, and head outdoors with Outdoor Activities.

To find traveler tips, more things to do, other places to visit, and tourist information, refer to the Ocho Rios trip planner.

Getting from Havana to Ocho Rios by flight takes about 5.5 hours. Traveling from Havana in August, Ocho Rios is somewhat warmer at night with lows of 30°C. Cap off your sightseeing on the 25th (Sun) early enough to catch the flight to Seven Mile Beach.

Things to do in Ocho Rios

Outdoors · Parks · Tours · Theme Parks

Seven Mile Beach, Cayman Islands

— 2 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Seven Mile Beach is known for wildlife, beaches, and spas. Your trip includes some of its best attractions: tour the pleasant surroundings at Seven Mile Beach, get close to the beloved marine mammals with a swim-with-the-dolphins experience, look for gifts at Cayman Scents, and see the vivid underwater world at Kittiwake Shipwreck & Artificial Reef.

Make your Seven Mile Beach itinerary with Inspirock to find out what to see and where to go.

You can fly from Ocho Rios to Seven Mile Beach in 4.5 hours. Expect a daytime high around 38°C in August, and nighttime lows around 31°C. Finish your sightseeing early on the 28th (Wed) so you can fly to Little Cayman.

Things to do in Seven Mile Beach

Wildlife · Outdoors · Parks · Tours

Side Trips

Little Cayman, Cayman Islands

— 2 nights
The smallest and undeniably quietest of the Cayman Islands, Little Cayman is truly little in terms of its population, with fewer than 200 permanent residents, almost all of whom work in the tourism industry.
Start off your visit on the 29th (Thu): see the vivid underwater world at Bloody Bay Wall, take in the spiritual surroundings of Little Cayman Baptist Church, and then explore the gorgeous colors at Point of Sand.

To see maps, other places to visit, ratings, and more tourist information, you can read our Little Cayman trip maker.

You can fly from Seven Mile Beach to Little Cayman in 2.5 hours. August in Little Cayman sees daily highs of 37°C and lows of 32°C at night. Wrap up your sightseeing by early afternoon on the 30th (Fri) to allow time for travel to Santo Domingo.

Things to do in Little Cayman

Parks · Wildlife · Beaches · Nature
Highlights from your trip

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, nature, and shopping. Your trip includes some of its best attractions: make a trip to Zona Colonial, browse the exhibits of Columbus Lighthouse (Faro A Colon), explore the striking landscape of The 3 Eyes National Park, and admire nature's wide array of creatures at National Aquarium.

To see traveler tips, photos, more things to do, and more tourist information, read our Santo Domingo trip itinerary maker website.

Explore your travel options from Little Cayman to Santo Domingo with the Route module. Due to the time zone difference, you'll lose 1 hour traveling from Little Cayman to Santo Domingo. Finish your sightseeing early on the 2nd (Mon) to allow enough time to fly to San Juan.

Things to do in Santo Domingo

Parks · Nature · Historic Sites · Zoos & Aquariums

San Juan, Puerto Rico

— 6 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Explore San Juan's surroundings by going to Museo de Arte de Ponce (in Ponce) and El Yunque Rain Forest (in El Yunque National Forest). Next up on the itinerary: stroll through Condado Beach, get to know the fascinating history of Old San Juan, scramble along the landscape with a canyoning and rapelling tour, and savor the flavors at Food & Drink.

To find other places to visit, maps, more things to do, and tourist information, you can read our San Juan online tour itinerary planner.

Getting from Santo Domingo to San Juan by flight takes about 3 hours. Other options: ride a ferry. In September, daytime highs in San Juan are 38°C, while nighttime lows are 30°C. Wrap up your sightseeing by early afternoon on the 8th (Sun) to allow enough time to fly to Honolulu.

Things to do in San Juan

Outdoors · Tours · Parks · Historic Sites

Side Trips

Honolulu, United States

— 6 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day by day itinerary now includes Mai Tai Bar at Royal Hawaiian Hotel as well as Royal Star Hawaii Deluxe Tours. Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Haleiwa (Sunset Beach Park & Waimea Bay) and Kailua Beach Park (in Kailua). There's much more to do: contemplate the long history of USS Arizona Memorial, kick back and relax at Waikiki Beach, browse the different shops at Ala Moana Center, and head outdoors with Outdoor Activities.

For maps, traveler tips, ratings, and tourist information, read Honolulu trip itinerary tool.

You can fly from San Juan to Honolulu in 17 hours. The time zone difference moving from Atlantic Standard Time to Hawaii-Aleutian Standard Time is minus 6 hours. September in Honolulu sees daily highs of 36°C and lows of 28°C at night. Wrap up your sightseeing by early afternoon on the 15th (Sun) to allow time for travel back home.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.