48 days in Hawaii & Caribbean Itinerary

48 days in Hawaii & Caribbean Itinerary

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Plan created by another user. Make it yours

Route & dates

1
Honolulu, United States
— 9 nights
2
Lihue, United States
— 8 nights
3
Kailua-Kona, United States
— 7 nights
4
Lahaina, United States
— 5 nights
5
Oranjestad, Aruba
— 4 nights
6
Punta Cana, Dominican Republic
— 5 nights
7
San Juan, Puerto Rico
— 7 nights

9
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.
Escape the urban bustle at Koko Crater Railway Trail and Waimanalo Beach. Relax by the water at Kailua Beach Park and Lanikai Beach. Get out of town with these interesting Honolulu side-trips: Sharks Cove (in Pupukea), Lanikai Pillboxes (in Kailua) and Byodo-In Temple (in Kaneohe). And it doesn't end there: cross one thing off your bucket list with a skydiving experience, see the interesting displays at USS Bowfin Submarine Museum & Park, take in the dramatic scenery at Manoa Falls, and enjoy the sand and surf at Laniakea Beach.

To see ratings, where to stay, traveler tips, and other tourist information, read our Honolulu day trip site.

Palma de Mallorca, Spain to Honolulu is an approximately 25-hour flight. The time zone difference when traveling from Palma de Mallorca to Honolulu is minus 11 hours. Traveling from Palma de Mallorca in June, plan for somewhat warmer nights in Honolulu, with lows around °C. Cap off your sightseeing on the 8th (Thu) early enough to travel to Lihue.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Kailua, Sharks Cove, Swim with Dolphins, Halona Blowhole
Find places to stay Jun 28 — Jul 8:
Highlights from your plan
Koko Crater Railway Trail ©
Koko Crater Railway Trail
Kailua Beach Park ©
Kailua Beach Park
Lanikai Beach ©
Lanikai Beach

8
nights
Lihue, United States

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll enjoy a bit of beach vacationing at Hanalei Beach and Pali Ke Kua Beach (Hideaway s Beach). Discover out-of-the-way places like Wailua Falls and Zipline. You'll find plenty of places to visit near Lihue: Na Pali Coast State Park (in Wainiha), Hanalei Valley Lookout (in Hanalei) and Polihale State Park (in Waimea). There's still lots to do: discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Ke'e Beach, stroll through Shipwreck Beach, and identify plant and animal life at Kilauea Point National Wildlife Refuge.

To find other places to visit, more things to do, maps, and tourist information, read Lihue online driving holiday planner.

You can fly from Honolulu to Lihue in 2.5 hours. In July, daily temperatures in Lihue can reach °C, while at night they dip to °C. Cap off your sightseeing on the 16th (Fri) early enough to travel to Kailua-Kona.

Things to do in Lihue

Parks Outdoors Beaches

Side Trips

Kauai, Poipu, Kapaa, Koloa, Princeville
Find places to stay Jul 8 — 16:
Highlights from your plan
Wailua Falls ©
Wailua Falls
Scuba & Snorkeling
Na Pali Coast State Park ©
Na Pali Coast State Park

7
nights
Kailua-Kona, United States

Kailua-Kona ©
Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Explore hidden gems such as Saddle Road and Fishing Charters & Tours. Get outdoors at Hapuna Beach State Recreation Area and Kayaking & Canoeing. Explore the numerous day-trip ideas around Kailua-Kona: Papakōlea Green Sand Beach (in Naalehu), Punalu‘U Beach (in Pahala) and Royal Kona Coffee Center (in Captain Cook). The adventure continues: enjoy the sand and surf at Manini'owali Beach (Kua Bay), admire the sheer force of Rainbow Falls, appreciate the extensive heritage of Waipio Valley, and take some stellar pictures from Waipiʻo Valley Lookout.

To see where to stay, ratings, traveler tips, and tourist information, go to the Kailua-Kona trip planner.

You can fly from Lihue to Kailua-Kona in 2.5 hours. In July, daily temperatures in Kailua-Kona can reach °C, while at night they dip to °C. Finish your sightseeing early on the 23rd (Fri) so you can travel to Lahaina.

Things to do in Kailua-Kona

Parks Nature Outdoors

Side Trips

Island of Hawaii, Papakōlea Green Sand Beach, Pu'uhonua O Honaunau National Historical Park, Waipiʻo Valley Lookout, Rainbow Falls
Find places to stay Jul 16 — 23:
Highlights from your plan
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Punalu‘U Beach ©
Punalu‘U Beach
Kaloko-Honokohau National Historical Park ©
Kaloko-Honokohau National Historical Park

5
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.
You'll explore the less-touristy side of things at Napili Beach and Makena Beach. Your itinerary includes some good beach time at Kapalua Beach and Ulua Beach. Venture out of the city with trips to Wailea Beach (in Wailea), Kihei (Kamaole Beach Park II & Kamaole Beach Park III) and Iao Valley (in Wailuku). Next up on the itinerary: hike along Kapalua Coastal Trail, let the river carry you with a rafting and tubing tour, fly like a bird with a parasailing or paragliding tour, and stop by Surf Ripper Shave Ice Co.

To see traveler tips, photos, ratings, and more tourist information, use the Lahaina trip planner.

Fly from Kailua-Kona to Lahaina in 4.5 hours. In July in Lahaina, expect temperatures between °C during the day and °C at night. Cap off your sightseeing on the 28th (Wed) early enough to travel to Oranjestad.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailea, Kihei, Kapalua, Parasailing & Paragliding, Ho'okipa Beach Park
Find places to stay Jul 23 — 28:
Highlights from your plan
Napili Beach ©
Napili Beach
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Kamaole Beach Park II ©
Kamaole Beach Park II

4
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Take a break from the city and head to The Butterfly Farm and Fishing Charters & Tours. You'll explore the less-touristy side of things at Arashi Beach and Boca Cataavlina. The adventure continues: kick back and relax at Malmok Beach, see Off-Road Tours, stroll through Donkey Sanctuary Aruba, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

For other places to visit, photos, more things to do, and tourist information, read Oranjestad road trip planner.

Use the Route module to find suitable travel options from Lahaina to Oranjestad. Traveling from Lahaina to Oranjestad, you'll lose 6 hours due to the time zone difference. Expect somewhat warmer evenings in Oranjestad when traveling from Lahaina in July, with lows around °C. Cap off your sightseeing on the 2nd (Mon) early enough to travel to Punta Cana.

Things to do in Oranjestad

Outdoors Parks Tours

Side Trips

Palm - Eagle Beach, Noord, Arashi Beach, Donkey Sanctuary Aruba
Find places to stay Jul 29 — Aug 2:
Highlights from your plan
The Butterfly Farm ©
The Butterfly Farm
Arashi Beach ©
Arashi Beach
Malmok Beach ©
Malmok Beach

5
nights
Punta Cana, Dominican Republic

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.
Explore hidden gems such as Hoyo Azul and Nature & Wildlife Tours. Relax by the water at Juanillo Beach and Public Beach Playa Dominicus. Explore Punta Cana's surroundings by going to Bayahibe (Speed Boats Tours & Scuba & Snorkeling) and Altos de Chavon (in La Romana). Spend the 7th (Sat) exploring nature at National Park of the East. The adventure continues: try to win big at Hard Rock Casino Punta Cana.

To find maps, ratings, and tourist information, read Punta Cana travel planner.

Traveling by combination of flight and shuttle from Oranjestad to Punta Cana takes 7 hours. In August, daily temperatures in Punta Cana can reach °C, while at night they dip to °C. Finish your sightseeing early on the 7th (Sat) to allow enough time to travel to San Juan.

Things to do in Punta Cana

Outdoors Parks Nature

Side Trips

Bayahibe, Altos de Chavon, National Park of the East
Find places to stay Aug 2 — 7:
Highlights from your plan
Scuba & Snorkeling
Juanillo Beach ©
Juanillo Beach
Nature & Wildlife Tours

7
nights
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Eschew the tourist crowds and head to Carabali Rainforest Park and Kayaking & Canoeing. Take a break from the city and head to Canyoning & Rappelling Tours and Palomino Island. Change things up with these side-trips from San Juan: Horseback Riding Tours (in Utuado), Scuba & Snorkeling (in Fajardo) and Zipline (in Rio Grande). There's still lots to do: see the sights as you ascend with a climbing tour, sample the fine beverages at Casa Bacardi Puerto Rico, indulge in some culinary diversions at a local gastronomic tour, and admire the sheer force of Cascada La Mina (La Mina Falls).

To find where to stay, reviews, photos, and other tourist information, read San Juan planning tool.

Fly from Punta Cana to San Juan in 2.5 hours. Alternatively, you can do a combination of bus and ferry. Expect a daytime high around °C in August, and nighttime lows around °C. Finish your sightseeing early on the 14th (Sat) so you can travel back home.

Things to do in San Juan

Tours Outdoors Parks

Side Trips

Fajardo, Horseback Riding Tours, Casa Bacardi Puerto Rico, Zipline, Carabali Rainforest Park
Find places to stay Aug 7 — 14:
Highlights from your plan
Kayaking & Canoeing
Carabali Rainforest Park ©
Carabali Rainforest Park
Zipline

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