After landing and checking into your luxury Condado hotel, enjoy a leisurely late-morning stroll and coffee at Café Cuatro Sombras followed by a light brunch at the elegant Oceano beachfront restaurant to soak in ocean views. Spend the rest of the morning wandering the tree-lined streets of Condado Lagoon, renting a paddleboard or kayak for a calm glide before returning to freshen up for an easy afternoon in Old San Juan.
Wander into Old San Juan for a relaxed afternoon of discovery, beginning with a guided stroll through the colorful streets to admire the colonial architecture and artisan shops, then stop for a late-afternoon cocktail on the terrace at Punto de Vista Rooftop to enjoy sweeping views of the bay. Follow with a private carriage or walking tour that includes a visit to La Fortaleza grounds and a photo pause at Plaza de Armas, ending with an intimate seaside dinner reservation at the charming Santaella as the sun softens toward evening.
As the sun sets, take a short drive to the waterfront neighborhood of La Perla Promenade for a romantic sunset photo stop, then head to 1919 Restaurant at the Condado Vanderbilt for a refined multi-course dinner featuring Puerto Rican flavors with a modern twist. After dinner, enjoy live jazz and crafted cocktails at the intimate La Factoria Speakeasy in neighboring Santurce for a perfect first-night celebration before returning to your hotel.
Begin your morning with a private guided walking tour through the cobblestone streets, stopping at San Juan Cathedral to admire its historic nave and to learn about the island's Spanish colonial past. Continue to the panoramic ramparts of Castillo San Cristóbal for sweeping city and ocean views, then linger over a leisurely brunch of mofongo and tropical fruit at the charming courtyard of Café El Punto before browsing nearby artisan shops for hand-crafted souvenirs.
After a morning of historic sights, linger into the afternoon with a private art-focused stroll through the gallery-lined Calle San Francisco, stopping to admire contemporary Caribbean works at Galería Botello and tactile crafts at Musa Gallery. Pause for a late lunch and people-watching on the shaded terrace of Princesa Gastrobar, then take a romantic carriage ride toward the waterfront to explore the quiet gardens of Paseo de la Princesa before an early-evening rooftop cocktail at La Terraza de San Juan to watch the light soften over the bay.
As twilight deepens, stroll the lesser-known alleys to discover vibrant murals and stop for pre-dinner drinks at the cozy rooftop bar of El Jibarito to toast with a signature rum cocktail. For dinner, savor a romantic tasting menu at the intimate Marmalade Restaurant & Wine Bar, then finish the night with a moonlit walk along the waterfront to admire the illuminated stone walls of Castillo San Felipe del Morro from outside and a nightcap at the charming Nuyorican Cafe for live music and a relaxed local atmosphere.
Collect your rental SUV from Caribbean Rent A Car in San Juan and set off along PR-2, stopping for a coffee and breakfast of freshly baked pastries at the seaside café Panadería y Pastelería La Preferida in Arecibo. Continue the coastal drive with a detour to stretch your legs at the dramatic cliffs of Cueva del Indio, where you can walk the natural rock terraces and admire the Atlantic surf before resuming the scenic route toward Rincón with panoramic pull-offs perfect for honeymoon photos.
After your coastal morning, detour to the charming seaside town of Aguadilla for a relaxed lunch at La Cambija Seafood Grill, then wander the art-filled plaza and boutique shops along Península de Punta Borinquen. In the late afternoon, stretch your legs with a short, scenic hike to the panoramic lookout at Punta Higuero Lighthouse, watching for surfers and pausing at the nearby sheltered cove Domes Beach for golden-hour photos before checking into your Rincón boutique resort.
Wind down your day with a sunset cocktail at Tamboo Tavern, perched right on the sand where you can watch surfers and unwind to live acoustic music; follow with a fresh seafood dinner at the intimate La Cambija (different location from earlier stops) to sample island ceviches and catch-of-the-day preparations. After dinner, take a short moonlit stroll along Playa María, then retire to your Rincón boutique resort for a couple's nightcap on the terrace or a private spa treatment to relax for tomorrow's west-coast adventures.
Start your day with a leisurely beachfront breakfast at The Beach House Restaurant overlooking calm morning swells, then stroll the powdery sand of Calzada Beach to collect shells and watch local fishermen bring in their catch. Mid-morning, drive a short way to the secluded coves around Punta Borinquen Natural Reserve for a gentle coastal hike and a snorkeling stop at Shacks Beach to discover vibrant reef life before returning to your boutique resort for a couples' poolside massage.
Spend a leisurely afternoon driving the coastal stretch to Tres Palmas Marine Reserve for world-class snorkeling among coral gardens, then pause at Maria's Beach (a quieter local cove distinct from earlier spots) for a seaside picnic with gourmet takeout from The Beach House Deli. Later, head to the cliffside bar at The Lighthouse at Punta Higuero to watch surfers carve the swells while sipping rum-forward cocktails, and finish with a romantic beachfront dinner at Shipwreck Bar & Grill as the sky turns golden.
As night falls, savor a romantic beachfront aperitivo at The Lazy Parrot Inn's Sunset Lounge, then stroll hand-in-hand to the dramatic headland at Tres Palmas Lookout to watch the sky blush over distant surf breaks. For dinner, indulge in a candlelit tasting of Caribbean-fusion cuisine at The English Rose Restaurant and finish with nightcaps under the stars at Coco's Rooftop Bar, where soft live music and ocean breezes set a perfect honeymoon mood.
Begin with an early drive inland to the cooler cloud-forest trails of Toro Negro State Forest, where you'll tackle the verdant Tetas de Cerro Gordo loop to enjoy panoramic ridgeline views and hidden waterfalls-pack sneakers, trekking poles, and a picnic from Rincón Market. After the summit, descend toward the coast for a restorative dip and tidepool exploration at the secluded Gozalandia falls and river pools, then return to your boutique Rincón hotel for a late-morning couples' soak or light brunch.
After a morning in the highlands, drive toward the coast for a breezy cliffside walk along Playa Sucia and explore the dramatic limestone overlooks at Caja de Muertos viewpoint (short scenic detour), followed by a gourmet seaside picnic from Rincón Farmer's Market on the sheltered sands of Corcega Beach. Later, join a guided coastal ecology stroll at Punta Higuero Nature Preserve to learn about native flora and watch for shorebirds, then return to your boutique resort in time for a sunset cocktail on the terrace.
After a day of highland trails, unwind with a late-afternoon drive to Playa Ojo de Agua for a soothing shoreline walk and a private seaside picnic delivered by Rincón Gourmet Provisions, watching pelicans and the last light on the cliffs. Later, enjoy a romantic farm-to-table dinner at 7 Seas Restaurant & Lounge with locally caught fish and mountain-grown sides, then finish the night with a moonlit stroll and cocktails at the intimate beachfront bar The Dock at Villa Cofresi, where soft waves and distant lighthouse beams set a tranquil honeymoon mood.
Depart Rincón after an early coffee and pastry from Panadería La Ceiba and take the scenic drive east, stopping for a coastal stretch and a short nature walk at Piñones Boardwalk to sample local fritters and fresh coconut water from a seaside kiosk. Continue toward Ceiba with a leisurely harbor-side brunch at La Estación in Fajardo, then stroll the marina to arrange a relaxed ferry check-in and an afternoon luggage drop at the boutique yacht-style Hacienda Sarria B&B or similar near the Ceiba Ferry Terminal to set up a smooth transfer to Vieques tomorrow.
Explore the gentle seaboard near Ceiba with a late-afternoon visit to the botanical paths and coastal viewpoints of Reserva Natural Cabezas de San Juan, then enjoy an island-inspired seafood lunch at the waterfront El Bohío de la Marina to sample fresh ceviche and local tapas. Afterward, take a relaxed harbor-side stroll through Marina Puerto del Rey, pop into the boutique shops of Paseo del Mar, and return to your lodging for an early-evening check-in and luggage prep for tomorrow's ferry to Vieques.
As the day cools, dine al fresco at El Guateque del Mar, a hidden waterfront bistro known for grilled lobster and chef's tasting plates paired with island wines, then wander the nearby tidal pools at Playa Escondida for a quiet sunset stroll away from the larger crowds. After dinner, enjoy a nightcap and live acoustic music on the terrace of Casa del Mar Rooftop, where the view toward the ferry terminal and twinkling harbor lights sets a calm, anticipatory mood for your morning transfer to Vieques.
Catch the morning ferry from Ceiba and, upon arrival, stop by Malecon de Isabel II for a coffee and a chance to stretch your legs while admiring the colorful waterfront houses; then head to Villa Cofresí Beach for a gentle swim and shelling on quieter sands. After a seaside dip, check in at your boutique hotel (think Sueño del Mar or El Blok Hotel) and arrange a private guided snorkeling excursion to Mosquito Bay's neighboring coral flats or a short boat trip to the pristine Sun Bay lagoon for a relaxed, romantic first-afternoon introduction to Vieques' turquoise waters.
After settling in, take a late-afternoon drive to Playa Caracas (Red Beach) for calm swimming and a shaded picnic-pick up gourmet sandwiches and local pastries from Isabel's Gourmet beforehand for a beachside feast. Follow with a relaxed horseback ride along the shoreline departing from Cabalgatas Vieques, finishing at the clifftop lookout above Sun Bay Nature Reserve to watch the light soften over the water before returning to your boutique hotel for a sunset cocktail.
As twilight falls, savor a seafood-forward dinner at El Quenepo, where ocean-facing tables and a tasting of local fish paired with Puerto Rican wines set an intimate mood. After dinner, take a moonlit stroll through the lantern-lit lanes of Isabel II Malecon to enjoy street musicians and stop for a creamy rum cocktail at Bananas Bar, then return to your boutique hotel for a private rooftop soak under the stars.
Begin with a sunrise paddle and shallow-water snorkeling session at Bahía de la Chiva (Blue Beach) where calm shallows reveal colorful reef fish and nurse sharks in the early light, then stop for a seaside café con leche and pastries at the charming Café del Sol in Isabel II. Mid-morning, join a private eco-tour to explore the island's lesser-known coastal habitats-look for sea turtles from the lookout at Playa Mansa before returning for a relaxed beachside brunch of lobster empanadillas at El Edencito Bistro.
Head to Playa La Chiva (Blue Beach) East for a sheltered snorkel among shallow coral gardens, then enjoy a gourmet beach picnic from Isabel's Gourmet on the sand while watching for rays. Later, join a guided island-trail horseback ride departing from Caballos del Sol that winds past secluded coves to the dramatic cliffs above Playa Grande, where you'll pause for golden-hour photos before returning to your hotel.
As the sun dips, enjoy a romantic seafood tasting at El Blok Rooftop featuring daily ceviche and island-inspired small plates while you watch boats glide past the harbor. After dinner, take a guided night walk through Tres Palmas Coastal Trail to listen for nocturnal birds and admire phosphorescent shoreline glimmers, then finish with cocktails and live acoustic music at Duffy's Jazz Bar before returning to your boutique hotel for a starlit soak.
Wake slowly with a barefoot breakfast on the terrace of El Quenepo's garden cafe, then head to the sheltered tidepools of Playa Negra for serene shallow-water exploring and tidepool life-bring water shoes and a snorkeling mask to spot colorful blennies and crustaceans. Mid-morning, enjoy a private farm-to-table cooking demo and tasting at Finca La Luna, where you'll learn to prepare a classic Puerto Rican breakfast using island-grown coffee and tropical fruit, then return to your boutique hotel for a light siesta or couples' spa treatment to conserve energy for the glowing bay tonight.
Spend a calm, sunlit afternoon exploring the eastern shore with a visit to Playuela (Gaviao Beach) for a secluded swim and cliffside photos, then drive inland to stroll the fragrant paths of Hacienda Tamarindo for a guided coffee and cacao tasting paired with tropical pastries. Later, unwind at Malecon Isabel II with a waterfront cocktail and light bites at Bokwa Bar & Bistro before returning to your hotel to prepare for the luminous bay tour at dusk.
As dusk deepens, take a private guided boat transfer from Esperanza Pier to the famed Mosquito Bay for an intimate bioluminescence tour-your captain will anchor in a quiet channel so you can drift and gently dip your fingers into the glowing water while the natural light show swirls around you. After the bay, return to shore for a late-seafood supper at La Estación Vieques or a romantic beachfront tasting at El Quenepo's outdoor terrace, then finish the night with a slow walk along Playa Negra beneath the stars before returning to your boutique hotel.
After your return to the capital, ease into the morning with a restorative couples' treatment at Spa Botánico in Santurce-choose a signature coffee-and-cocoa scrub to celebrate island flavors-and follow with a light brunch of tropical bowls and artisanal coffee at the nearby Caficultura. Spend the last hours hunting for refined keepsakes at The Mall of San Juan for designer finds or wander the elegant boutiques along Calle del Cristo in Old San Juan for handcrafted jewelry and local art, then collect luggage from your hotel and head to the airport feeling relaxed and perfectly curated for your flight home.
Drive or taxi to the elegant boutique district of Miramar for a relaxed late-afternoon appetizer at Trade Wind Bar & Bistro, then browse curated homewares and island fragrances at Tesoros PR for last-minute luxury gifts. If you prefer pampering, book a signature couples' mani-pedi and scalp ritual at SOAK & Savor Spa in Condado before a light seaside coffee at Café Comunión to savor your final ocean view and collect your luggage feeling renewed for your flight home.
For a graceful final evening, enjoy an intimate sunset sail from San Juan Bay Marina aboard a private catamaran with champagne and hors d'oeuvres while you toast your honeymoon and watch the city lights come alive. After disembarking, savor a last-night tasting at the chef-driven 1919 Wine & Dine Room (distinct from earlier venues) featuring seasonal Puerto Rican ingredients, then cap the night with a digestif and live piano at the elegant Hotel El Convento Bar, returning to your hotel relaxed and ready for your morning transfer.
| Place / Activity | Cost |
|---|---|
| Café Cuatro Sombras (coffee) | $5 |
| Oceano (brunch per person) | $35 |
| Condado Lagoon paddleboard/kayak rental | $30 |
| Old San Juan guided stroll (private, per person) | $40 |
| Punto de Vista Rooftop (cocktail) | $12 |
| Private carriage or walking tour incl. La Fortaleza grounds (per person) | $50 |
| Plaza de Armas (visit) | Free |
| Santaella (intimate seaside dinner per person) | $65 |
| La Perla Promenade (sunset photo stop) | Free |
| 1919 Restaurant (multi-course dinner per person) | $150 |
| La Factoría Speakeasy (drinks, live jazz) | $20 |
| Private guided walking tour Old San Juan (day 2, per person) | $45 |
| San Juan Cathedral (visit) | Free |
| Castillo San Cristóbal (entry) | $10 |
| Café El Punto (brunch per person) | $20 |
| Galería Botello (gallery visit) | Free |
| Musa Gallery (gallery visit) | Free |
| Princesa Gastrobar (late lunch per person) | $30 |
| Carriage ride toward waterfront (per person) | $25 |
| Paseo de la Princesa (walk) | Free |
| La Terraza de San Juan (rooftop cocktail) | $12 |
| El Jibarito (rooftop drink) | $10 |
| Marmalade Restaurant & Wine Bar (tasting menu per person) | $120 |
| Nuyorican Cafe (nightcap/live music) | $15 |
| Caribbean Rent A Car (rental SUV per person estimate, 8 days split between 2) | $200 |
| Panadería y Pastelería La Preferida (coffee & pastry) | $6 |
| Cueva del Indio (visit) | Free |
| La Cambija Seafood Grill (lunch per person) | $30 |
| Península de Punta Borinquen (walk/shops) | Free |
| Punta Higuero Lighthouse (lookout visit) | Free |
| Domes Beach (visit) | Free |
| Tamboo Tavern (sunset cocktail per person) | $18 |
| La Cambija (dinner per person) | $40 |
| Playa María (moonlit stroll) | Free |
| The Beach House Restaurant (breakfast per person) | $25 |
| Calzada Beach (visit) | Free |
| Punta Borinquen Natural Reserve (hike/snorkel, guided snorkel per person) | $35 |
| Shacks Beach snorkeling (rental/snorkel per person) | $20 |
| Couples' poolside massage (per person estimate) | $75 |
| Tres Palmas Marine Reserve snorkeling (per person guided) | $50 |
| Maria's Beach (picnic) | Free |
| The Lighthouse at Punta Higuero (cocktail) | $15 |
| Shipwreck Bar & Grill (dinner per person) | $35 |
| The Lazy Parrot Inn's Sunset Lounge (aperitivo) | $12 |
| The English Rose Restaurant (tasting dinner per person) | $60 |
| Coco's Rooftop Bar (nightcap) | $12 |
| Toro Negro State Forest - Tetas de Cerro Gordo (park visit) | Free |
| Gozalandia falls (entry/parking fee) | $5 |
| Playa Sucia / Caja de Muertos viewpoint (visit) | Free |
| Rincón Farmer's Market (picnic supplies) | $20 |
| Punta Higuero Nature Preserve guided ecology stroll (per person) | $30 |
| Playa Ojo de Agua (walk) | Free |
| 7 Seas Restaurant & Lounge (dinner per person) | $45 |
| The Dock at Villa Cofresi (cocktails/nightcap) | $15 |
| Panadería La Ceiba (coffee & pastry) | $6 |
| Piñones Boardwalk (walk & snacks) | $10 |
| La Estación (brunch per person) | $30 |
| Reserva Natural Cabezas de San Juan (visit) | $5 |
| El Bohío de la Marina (lunch per person) | $25 |
| Marina Puerto del Rey / Paseo del Mar (stroll) | Free |
| El Guateque del Mar (dinner per person) | $45 |
| Casa del Mar Rooftop (nightcap) | $12 |
| Ceiba to Vieques ferry (one-way per person) | $2.50 |
| Malecon de Isabel II (coffee) | $5 |
| Villa Cofresí Beach (visit) | Free |
| Sueño del Mar / El Blok Hotel (boutique hotel per person per night estimate) | $200 |
| Private guided snorkeling excursion (per person) | $80 |
| Sun Bay (boat trip / entry) | $15 |
| Playa Caracas (Red Beach) (visit) | Free |
| Isabel's Gourmet (picnic sandwiches per person) | $15 |
| Cabalgatas Vieques (horseback ride per person) | $70 |
| Clifftop lookout above Sun Bay (visit) | Free |
| El Quenepo (dinner per person) | $70 |
| Bananas Bar (rum cocktail) | $12 |
| Sunrise paddle and snorkeling at Bahía de la Chiva (per person rental/guide) | $60 |
| Café del Sol (coffee & pastry) | $6 |
| El Edencito Bistro (brunch per person) | $25 |
| Playa La Chiva East snorkeling (rental) | $20 |
| Caballos del Sol (guided horseback per person) | $75 |
| El Blok Rooftop (seafood tasting per person) | $50 |
| Tres Palmas Coastal Trail night walk (guided) | $25 |
| Duffy's Jazz Bar (drinks/live music) | $15 |
| Playa Negra (tidepool visit) | Free |
| Finca La Luna cooking demo & tasting (per person) | $60 |
| Playuela (Gaviao Beach) (visit) | Free |
| Hacienda Tamarindo coffee & cacao tasting (per person) | $35 |
| Bokwa Bar & Bistro (cocktail & light bites) | $25 |
| Private guided boat transfer to Mosquito Bay (bioluminescent tour per person) | $90 |
| La Estación Vieques (dinner per person) | $45 |
| El Quenepo's outdoor terrace (beachfront tasting) | $70 |
| Spa Botánico (couples' treatment per person) | $120 |
| Caficultura (brunch per person) | $20 |
| The Mall of San Juan (shopping visit) | Free |
| Calle del Cristo boutiques (shopping) | Free |
| Trade Wind Bar & Bistro (appetizer per person) | $20 |
| Tesoros PR (shopping) | Free |
| SOAK & Savor Spa (mani-pedi per person) | $60 |
| Café Comunión (seaside coffee) | $6 |
| San Juan Bay Marina private catamaran sunset sail (per person) | $150 |
| 1919 Wine & Dine Room (final tasting per person) | $150 |
| Hotel El Convento Bar (digestif/live piano) | $18 |
| Estimated Total (per person) | $3809.50 |