Top North America Sailing Trips

633 Results
Sunday Brunch Sail in Greenport

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see …More

Long Island, USA

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see...

2 hours Free Cancellation
5.0 (10)
from
$175
Private Sailing on the Miami Bay - Biscayne Bay

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Cool Shore Excursions Beneteau stylish vessels in the company of experienced, but mostly fun, well …More

Likely to Sell Out
Likely to Sell Out
Miami, USA

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Cool Shore Excursions Beneteau stylish vessels in the company of experienced, but mostly fun, well...

4 to 12 hours Free Cancellation
5.0 (67)
from
$175
Full-Day El Cielo Snorkel Tour in Cozumel with Transportation and Lunch

You will discover an underwater world. Admire the colorful variety of fish and the different forms that the coral reef has. El Cielo reef is …More

Punta Sam, Mexico

You will discover an underwater world. Admire the colorful variety of fish and the different forms that the coral reef has. El Cielo reef is...

9 hours Hotel pickup offered Free Cancellation
from
$175
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red …More

Big Island of Hawaii, USA

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red...

4 hours 30 minutes Free Cancellation
4.9 (590)
from
$179
Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along …More

Big Island of Hawaii, USA

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

4 hours 30 minutes Free Cancellation
4.9 (480)
from
$179
Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours Free Cancellation
4.9 (59)
from
$179
Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation
5.0 (18)
from
$180
Luxury Sailboat Tour at Sunset in Los Cabos + Snacks + Premium Drinks

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and …More

Cabo San Lucas, Mexico

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and...

3 hours Hotel pickup offered Free Cancellation
5.0 (13)
from
$180
Pirate Ship Premium Dinner Cruise with Show

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing …More

Puerto Vallarta, Mexico

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing...

4 hours Free Cancellation
4.7 (31)
from
$181
Private Sailing between Mangroves

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with …More

Bacalar, Mexico

Within the activities of this tour, it will be bird watching, sailing in an ecological way without motor. We will swim in the places with...

3 hours Free Cancellation
5.0 (111)
from
$182
Okanagan Lake Sailing Tour from Penticton & Naramata BC

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We …More

Kelowna & Okanagan Valley, Canada

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We...

4 hours Free Cancellation
5.0 (51)
from
$183
Super ATVs and Romantic Dinner Combo, with transport & dinner

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you …More

Punta Sam, Mexico

Would you like to give your partner the best birthday or anniversary gift during the holidays? Join us in this great adventure that takes you...

13 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$184
Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink …More

Portland, USA

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink...

3 hours Free Cancellation
5.0 (2)
from
$185
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hours Free Cancellation
5.0 (713)
from
$189
Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours Free Cancellation
4.8 (109)
from
$189
Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets …More

Maui, USA

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets...

2 hours Free Cancellation
5.0 (2)
from
$189
ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink

Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty of the beach. We are the ultimate vacation …More

Mazatlán, Mexico

Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty of the beach. We are the ultimate vacation...

5 hours Hotel pickup offered Free Cancellation
3.0 (2)
from
$189
Private Tour: Bacalar Lagoon Tour Sailboat or Pontoon Adventure

Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you choose the elegance of a sailboat or the comfort of …More

Costa Maya, Mexico

Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you choose the elegance of a sailboat or the comfort of...

5 hours Free Cancellation
5.0 (4)
from
$190
Private sailing tour in the seven colors lagoon in Bacalar

You will enjoy a wonderful tour visiting the highlights of the Bacalar Lagoon. Harnessing the power of nature, you will navigate to the Pirates' Channel, …More

Bacalar, Mexico

You will enjoy a wonderful tour visiting the highlights of the Bacalar Lagoon. Harnessing the power of nature, you will navigate to the Pirates' Channel,...

3 hours Free Cancellation
4.9 (21)
from
$193
Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide …More

Bacalar, Mexico

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide...

4 hours Free Cancellation
5.0 (44)
from
$193

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