Top Sailing Vacations in Hawaii | Trips, Rentals & Lessons

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Hawaii Sailing Adventures | Honolulu, Hawaii | Sailing

Hawaii Sailing Adventures

Honolulu, Hawaii

From $600

Cinderella Sailing Charters | Wailuku, Hawaii | Sailing

Cinderella Sailing Charters

Wailuku, Hawaii

Honolul Sailing Company | Honolulu, Hawaii | Sailing

Honolul Sailing Company

Honolulu, Hawaii

From $60

Hawaii Glass Bottom Boat | Honolulu, Hawaii | Sailing

Hawaii Glass Bottom Boat

Honolulu, Hawaii

From $35

Makana Charters | Waimea, Hawaii | Sailing

Makana Charters

Waimea, Hawaii

Waikiki Yacht Charters | Honolulu, Hawaii | Sailing

Waikiki Yacht Charters

Honolulu, Hawaii

Pacific Boats and Yachts | Kailua Kona, Hawaii | Sailing

Pacific Boats and Yachts

Kailua Kona, Hawaii

Hawaiian Sailing Canoe Adventures | Paia, Hawaii | Sailing

Hawaiian Sailing Canoe Adventures

Paia, Hawaii

Blue Dolphin Charters | Eleele, Hawaii | Sailing

Blue Dolphin Charters

Eleele, Hawaii

Pacific Yacht Management LLC | Honolulu, Hawaii | Sailing

Pacific Yacht Management LLC

Honolulu, Hawaii

Hawaii Yachts | Honolulu, Hawaii | Sailing

Hawaii Yachts

Honolulu, Hawaii

Maui Yacht Charters | Kailua Kona, Hawaii | Sailing

Maui Yacht Charters

Kailua Kona, Hawaii

Alli Nui Sailing Charters | Kailua Kona, Hawaii | Sailing

Alli Nui Sailing Charters

Kailua Kona, Hawaii

North Shore Catamaran | Haleiwa, Hawaii | Sailing

North Shore Catamaran

Haleiwa, Hawaii

Wa'akaulua Sailing Excursions | Pahala, Hawaii | Sailing

Wa'akaulua Sailing Excursions

Pahala, Hawaii

Kaahele Hawaii | Hilo, Hawaii | Sailing

Kaahele Hawaii

Hilo, Hawaii

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More Sailing in United States (show all)

Day Sailing & Custom Charters On The Schooner Olad | Camden, Maine | Sailing

Day Sailing & Custom Charters On The Schooner Olad

Camden, Maine

From $57

Rainy Lake Houseboats premier houseboat rentals | International Falls, Minnesota | Sailing

Rainy Lake Houseboats premier houseboat rentals

International Falls, Minnesota

From $260

Custom Sailing Charters from Rockland, Maine | Rockland, Maine | Sailing

Custom Sailing Charters from Rockland, Maine

Rockland, Maine

From $30

Emerald Isle Sailing Charters | Deer Harbor, Washington | Sailing

Emerald Isle Sailing Charters

Deer Harbor, Washington

From $229

Sailing Charters At Compass Sailing, Llc | Savannah, Georgia | Sailing

Sailing Charters At Compass Sailing, Llc

Savannah, Georgia

From $499

Sail Channel Islands | Oxnard, California | Sailing

Sail Channel Islands

Oxnard, California

From $195

Delaune Sailing Charters | Mandeville, Louisiana | Sailing

Delaune Sailing Charters

Mandeville, Louisiana

From $450

Sailing Alaska | Auke Bay, Alaska | Sailing

Sailing Alaska

Auke Bay, Alaska

From $440

Sail Selina Ii | Saint Michaels, Maryland | Sailing

Sail Selina Ii

Saint Michaels, Maryland

From $75

Sailing in Arizona | Peoria, Arizona | Sailing

Sailing in Arizona

Peoria, Arizona

From $185

Top Listings in United States (show all)

Mt. Baker Lodging Cabins At Mount Baker Washington | Maple Falls, Washington | Vacation Rentals

Mt. Baker Lodging Cabins At Mount Baker Washington

Maple Falls, Washington
Vacation Rentals

From $99

Africa Tours | Philadelphia, Pennsylvania | Sight-Seeing Tours

Africa Tours

Philadelphia, Pennsylvania
Sight-Seeing Tours

From $1,475

Cruzan Yacht Charters, Inc. | Miami, Florida | Yacht Charters

Cruzan Yacht Charters, Inc.

Miami, Florida
Yacht Charters

From $950

Timberpine Lodge | Adel, Iowa | Vacation Rentals

Timberpine Lodge

Adel, Iowa
Vacation Rentals

From $375

Maine's Best Vacation Value Poland Spring Resort | Poland Spring , Maine | Hotels & Resorts

Maine's Best Vacation Value Poland Spring Resort

Poland Spring , Maine
Hotels & Resorts

From $145

Everglades Day Safari | Fort Myers, Florida | Eco Tours

Everglades Day Safari

Fort Myers, Florida
Eco Tours

From $199

Cielito Lindo Travel Agency Llc | Indio, California | Car & Van Shuttle Service

Cielito Lindo Travel Agency Llc

Indio, California
Car & Van Shuttle Service

From $65

Florida Van Rentals - Passenger & Wheelchair Vans | Orlando, Florida | Car Rentals

Florida Van Rentals - Passenger & Wheelchair Vans

Orlando, Florida
Car Rentals

From $71

Fun fishing Charter Williamsburg Virginia | Williamsburg, Virginia | Fishing Trips

Fun fishing Charter Williamsburg Virginia

Williamsburg, Virginia
Fishing Trips

From $300

The Isle au Haut Mail Boat - Puffin Cruises | Stonington, Maine | Cruises

The Isle au Haut Mail Boat - Puffin Cruises

Stonington, Maine
Cruises

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Also in Hawaii

Accommodations

Bed & Breakfasts in Hawaii

Bed & Breakfasts (22)

Campgrounds & RV Parks in Hawaii

Campgrounds & RV Parks (3)

Hotels & Resorts in Hawaii

Hotels & Resorts (223)

Vacation Rentals in Hawaii

Vacation Rentals (88)

Youth Hostels in Hawaii

Youth Hostels (27)

Adventure Travel

ATV Riding & Jeep Tours in Hawaii

ATV Riding & Jeep Tours (1)

Bike Tours in Hawaii

Bike Tours (11)

Hiking & Trekking in Hawaii

Hiking & Trekking (25)

Horseback Riding & Dude Ranches in Hawaii

Horseback Riding & Dude Ranches (10)

Kayaking & Canoeing in Hawaii

Kayaking & Canoeing (19)

Sailing in Hawaii

Sailing (16)

Scuba Diving & Snorkeling in Hawaii

Scuba Diving & Snorkeling (51)

Skydiving in Hawaii

Skydiving (2)

Fishing & Hunting

Fishing Trips in Hawaii

Fishing Trips (43)

Hunting Trips in Hawaii

Hunting Trips (2)

Health & Wellness

Health Spas & Retreats in Hawaii

Health Spas & Retreats (8)

Nature & Wildlife

Eco Tours in Hawaii

Eco Tours (14)

Whale Watching in Hawaii

Whale Watching (2)

Wildlife & Safari Tours in Hawaii

Wildlife & Safari Tours (3)

Top Sailing Vacations in Hawaii | Trips, Rentals & Lessons

Browse incredible sailing vacations & trips in Hawaii, take a lesson or rent your own sail boat. Browse our sailing options in Hawaii and plan your vacation. Also of Interest: boat charter | charter sailing | charter yacht | private sail | private sailing |

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