Top North America Sailing Trips

632 Results
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff …More

Bacalar, Mexico

Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff...

4 hours Free Cancellation
5.0 (78)
from
$237
Platinum Private Catamaran Sailing Tour

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April …More

Cabo San Lucas, Mexico

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April...

2 hours Hotel pickup offered Free Cancellation
4.9 (12)
from
$237
Los Cabos Seasonal Whale Watch and Snorkel Tour

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the …More

Likely to Sell Out
Likely to Sell Out
San Jose del Cabo, Mexico

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the...

4 hours Hotel pickup offered Free Cancellation
4.9 (19)
from
$239
Sailing Charter

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend …More

Likely to Sell Out
Likely to Sell Out
Port Angeles, USA

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend...

1 to 3 hours Free Cancellation
5.0 (9)
from
$240
Private sailing tour of Bacalar Lagoon

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a …More

Bacalar, Mexico

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a...

3 hours Free Cancellation
5.0 (432)
from
$240
Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based …More

Maui, USA

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours Free Cancellation
5.0 (95)
from
$243
2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

Likely to Sell Out
Likely to Sell Out

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation
5.0 (17)
from
$245
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249
Private Guided Sunset and Eco Tour up to 6 Passengers

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation
5.0 (81)
from
$250
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours Free Cancellation
4.8 (37)
from
$250
Polynesian Canoe Sunset Sail

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (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 (128)
from
$250
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and …More

Likely to Sell Out
Likely to Sell Out
Long Beach, USA

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and...

1 hour
4.6 (8)
from
$255
Nāpali Sunset Dinner Sail

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...

4 to 5 hours Free Cancellation
4.8 (563)
from
$264
Sailboat with Shade Private Adventure in Bacalar

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our …More

Bacalar, Mexico

Join us on an exciting sailing adventure. Learn about the Lagoon and the art of moving with wind. We explore mangroves, shoreline and Cenotes. Our...

3 hours 30 minutes Free Cancellation
5.0 (22)
from
$264
Bimini or Grand Bahama Island Day Cruise

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear...

12 hours Free Cancellation
3.7 (24)
from
$265
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation
5.0 (135)
from
$269
Private - Bacalar sailing across the mesmerizing waters

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon …More

Tulum, Mexico

Bacalar is an idyllic town set on an enchanting inland lagoon, immersed in nature, with a presence of colonial history & pirates. We embark upon...

12 hours Hotel pickup offered Free Cancellation
5.0 (5)
from
$274
Bacalar - Gourmet Tour in Private Catamaran with Cocktails Included

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich …More

Bacalar, Mexico

During this experience you will try star dishes from the best restaurants in the area aboard a comfortable private boat. You will enjoy a rich...

4 hours Free Cancellation
5.0 (22)
from
$275
Private Sailing Excursions, Nice Spacious Sailboats

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island, …More

Bacalar, Mexico

Bacalar's lagoon is explored by sailboat with up to six guests, giving families and friends space to tailor the trip. Sail to cenotes, Bird Island,...

4 hours Free Cancellation
4.9 (33)
from
$275
Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation
5.0 (6)
from
$276

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Discover North America